I rushed to rip the headphones out of my ears.

“You’re working hard,” she said.

She was right. I’d been there for two hours, deep in what I thought was going to be this week’s piece. It was about the importance of walking the walk rather than just talking the talk. You’ll probably still read it one day.

What I didn’t expect was that she would become the piece.

Her name is Elizabeth, and what started as a polite exchange turned into an hour-long conversation I absolutely needed.

Does any of it matter?

When we think about legacy, it’s never an easy conversation.

The more I speak with people older than me, the more I realize it doesn’t actually get easier with age. I used to think that clarity comes later. Naively, I thought that at some point in your 40s, 50s, or 60s, you would finally settle into knowing what it was all for. But I’ve come to learn it’s a constant question throughout a life:

Did it make a difference?

Did it matter?

What is my impact?

Elizabeth told me a bit about her story. She is in her 60s and has spent some time in the Canadian judicial system. As we spoke, she was clutching a copy of Women Who Woke Up the Law: Inside the Cases That Changed Women’s Rights in Canada by Karin Wells. Unfortunately, her exposure has led her to see how broken the system is. However, rather than seeing what is broken and simply wishing things were different, she has been advocating for more diverse and disability-inclusive voices in Canadian law.

Her work is rooted in a simple but radical idea: when you build for the most excluded people, you make the whole system better for everyone.

This resonates deeply with my own work in health equity. It shouldn’t require a business case to help the people who need it most. It shouldn’t require justification to be preventative rather than reactive. And yet — it does.

Elizabeth put it perfectly: sometimes it feels like pushing a boulder up a hill, only to watch it roll back half a kilometre. The people doing the hard work of changing systems are always tired. That’s the cost of the fight, but it’s also why we need more people to get in it.

The invisible impact

When Elizabeth reflected on her own legacy, she admitted that there were moments, especially recently, when she felt like she had “expired”.

She kept repeating, in reflection on her life: What was it all for?

And yet, there are so many people he work has impacted that she will never know. h

In the book she was reading, she explained that even lost cases eventually had enough impact to change laws. For example, The Famous Five:

“Led by Emily Murphy, Alberta’s first female judge, a group of Alberta women who came to be known as the “Famous Five” challenged a part of the Constitution that had prevented women from being appointed to the Senate.

The prevailing attitude: men were the only “qualified persons” who could be appointed to the Senate.

Murphy was outraged. She had been subject to sexism since 1916. On her first day on the bench, a lawyer challenged one of her rulings. As a woman, Murphy wasn’t a “person,” so how could she be expected to be taken seriously as a judge? It was a recurring argument she heard throughout her legal career.

In 1927, Murphy and four other women leaders in Alberta (Henrietta Muir Edwards, Nellie McClung, Louise McKinney, and Irene Parlby) asked the Supreme Court of Canada whether the British North America Act’s (BNA) section 24 included women in its definition of “persons.” Five weeks later, the Supreme Court reached a verdict in Edwards v Canada, the official name of the case. Its conclusion? Under Canadian law, women were not “persons.”

The Famous Five (Emily Murphy, Henrietta Muir Edwards, Nellie McClung, Louise McKinney, and Irene Parlby) were undaunted. They took their case to the Judicial Committee of the Privy Council in London, England, which was then the last avenue of appeal. On October 18, 1929, it overruled Canada’s Supreme Court, opening the door for some women to be appointed to the Senate and clearing the way for further advancing women’s rights. October 18 has come to be known as Persons Day.”

The Famous Five eventually won, but for many people, their impact comes to light long after they are gone.

How many of these people did they know they impacted, or would impact when they died? Not all get the privilege of knowledge.

That’s the thing about purposeful work: you rarely get to see the full shape of what you’ve built.

Some of your greatest impacts live in people you’ll never know you helped, so you just have to keep doing the good work anyway.

It’s all fun and games in the end

At the end of our conversation, after all the weight of legacy, justice, and exhaustion, Elizabeth told me what she’s planning to have on her tombstone.

A smile crept over her face as she said:

I laughed out loud right there in the coffee shop.

I knew I couldn’t keep Elizabeth to myself. All of you had to know her.

In that very moment, she taught me a wonderful lesson: you can hold the serious and the joyful at the same time. You can fight hard for a better world and still find reasons to laugh at the absurdity of it all.

She encouraged me to tell all my young friends to continue picking up the fight for all the boulders the people before us have been pushing up the hill, because the work isn’t done yet.

If you already have the mindset of wanting to make the world better, you’re already winning.

So, find your boulder and the people who inspire you to continue pushing forward.

Maintain the momentum of all the work that has come before you. Every moment you continue, it becomes more visible.

As we sit and consume headlines, as we begin to question our stamina to advocate for the causes we care about, as everything just feels… heavy.

Exhaustion is often a result of fighting over a cause you deeply care about. It’s different from feeling tired. It feels heavier. The weight of the system, in addition to the effort to fight against it, can feel insurmountable. When I chat with friends, I often compare it to trying to steer a cruise ship. It takes a long time. Sometimes, it’s such a long time that you’ve got to find ways to love the small wins.

Right as I was in the middle of the darkest weeks of February, questioning whether I had the strength to move forward in fighting for systemic change with the causes I deeply cared about, I came across Dr. Rachel Gifford.

More specifically, I came across the piece she co-authored with Peter Halliwell, “So You Want To Fight The System?”

The piece highlights their work with The School for Moral Ambition, whose mission statement is:

The School emerged from a desire not only to talk about a better world but also to take action towards one. In a world where people often stop after “talking the talk”, it was refreshing to read Rachel and Peter’s work in “From the Field”, in which they describe their experiences as Moral Ambition fellows trying to solve the world’s toughest problems.

Rachel and Peter spoke directly to the people who sometimes, to their own chagrin, find out that systems haven’t changed, well, because they’re pretty difficult to move, but not impossible:

“Five months into working inside organizations dedicated to challenging entrenched power and reshaping public policy, what’s become clear is this: moral ambition rarely stalls because people don’t care enough. It stalls because caring people operate inside systems specifically designed to minimise risk, slow decision-making, and avoid conflict with entrenched, well resourced counterparts.

Systems that have learned - sometimes the hard way - to avoid failure. Legal caution, political compromise, reputational anxiety, resource constraints, human burnout: these aren’t abstract and these systems didn’t emerge arbitrarily.

They’re the result of past efforts, losses, and gut wrenching moments when something almost worked and then didn’t.”

Rachel went on to write about her experience with pragmatism in the food system and titled it, “Care about them, just don’t talk about them.”

I needed to learn about how Rachel was turning talk into action in her own life as a fellow, as well as the change that she was trying to make within food systems.

So, I sat down in the wee hours of the morning to interrupt Rachel’s lunch break in the Netherlands, peppering her with questions on how we find the energy to keep fighting the system.

Moving towards the decision-maker’s chair

Dr. Rachel Gifford works as an Assistant Professor at Maastricht University, the Netherlands’ youngest and most international university.

However, she didn’t plan to start a career in academia.

When we spoke about her journey, Rachel outlined that her pursuit in life started with two goals:

1. Education, get a college degree (something that hadn’t been done in her family before)

2. Try to make the world a better place

She worked in direct service with vulnerable communities, in crisis settings, in organizations that ran on almost nothing and tried to do almost everything. Unfortunately, this is not a rare story within much of the direct service delivery, non-profit, and charitable sectors. Many of the constraints you face daily result from decisions made further upstream. Rachel reflected on this time,

“You’re working directly with people, and you see them in crisis, and you see them struggling, and you see the potential solutions that are not coming down the pipeline, and you see policymakers and politicians making decisions that are slashing budgets and that are actively going against the work that people on the ground are trying to do to help their communities and one another.”

The work was meaningful, but, as we discussed further, Rachel has always been keenly aware of how best to allocate her resources to make the biggest impact.

This voice in the back of her head eventually led her to a crossroads:

“I thought: I could become a manager in third sector work, or I could maybe go back to school and become a policymaker and be the one making the decisions. And so I did that.”

She never expected academia to be the destination, but she found a PhD position, applied, and stayed.

Then, the fellowship posting for the School for Moral Ambition landed in front of her and activated something she’d been suppressing in research: her activist nature. Rachel outlined the electricity she has felt in the room with other fellows:

“There was a recognition of my idealist nature, and a more activist, rebellious nature, which has kind of been lying a bit dormant in academia. Being around these people and seeing genuine interest in making a change, diving into these areas, and trying our best. The people that I work with at my host organizations are also just so open, so welcoming, so much energy for animals, ultimately, for making change, for doing what they consider to be the right thing.

What has surprised me is how very energizing it is. Even when things are really to the wire, and something needs to be dealt with, I find that kind of electric.”

Rachel’s fellowship woke something back up. When you are surrounded by people each day choosing to do what they think is right, there becomes a vicarious cycle of energy. Of realizing that what was missing to try to create change was the people in the room who are willing to continue to say, “this isn’t right, but let’s make it so.”

“Where are the animals?”

In her From the Field piece, Rachel reflects on a moment a few weeks into the fellowship training, where she asked, what she thought was an obvious question,

“I remember just after a couple of days thinking: I’m sorry, but where are the animals? We’re talking about the environment, and it’s very important, and this is one of the main angles. But at the core of this, even if the environment was fine, we are here because of the animals.”

She was reassured that they had a whole day dedicated to discussion about animal welfare, but as her work progressed, she came to understand why she needed a broad perspective on food systems. In policy spaces, leading with animal welfare can shut down conversations that leading with climate or food security keeps open.

Pragmatism is the price of a seat at the table.

She outlined that in the policy room, you find the argument that moves the people there. You speak their language. You don’t demand they meet you at your level of moral urgency; you find the door they’re already near and you open it.

“A win is a win. It doesn’t matter if it’s my organization or me. If you can plant the seeds, get to the table, get people to engage in a conversation, to care about the issue; if you have to use a different framing, at the end of the day, if the outcome is the outcome, and the outcome is making life better for animals. It doesn’t matter how you get there.”

Joy as fuel, not reward

There’s a phrase Rachel heard that she keeps coming back to: joy is an act of resistance.

As we were chatting, she unpacked it in a way that I hadn’t heard it framed before:

“I think the joy is connecting with people and remembering that they’re part of the community. For me, what is motivating about the fellowship is just being in community with people. To have those moments. Check-ins that also try to have some fun built in.”

When you work on addressing heavy issues, like trying to rewire systems that are, as Rachel put it, built to persist rather than fail, it can be very difficult to find the fun in the day-to-day.

However, Rachel reminded me, and I hope all of us, that joy isn’t the reward you get when you win. Joy is how you stay in the fight long enough to have a chance at winning.

Rachel talked about cynicism in the space because there are always ups and downs when trying to make a change:

“I think it’s really important to avoid becoming cynical or bitter, because that’s also just giving a victory to the system, or trying to bring you down.”

People have been trying to change things for a really long time, but it’s really complex. The resources are really scarce, so how can we make the most of our time here?

How can I make the most of my time here and support these organizations that are strapped for budget and trying to do everything as best they can with limited staff?

I think that working in those spaces and being creative is one way that you can do that.

…

But the mobilization of engaged people, you know, who actually create change. It’s also the systems that are pushing up against that that are going to impact whether or not that’s possible.”

When I asked Rachel about how we can stay engaged, say mobilized when things get dark, she outlined:

“I think being in a community of people, and being in conversation with other people, and having outlets like this, to talk about it and to be frustrated together, but say, okay, ‘you can be frustrated, but don’t let it kill your motivation, or distract you from the kind of like purpose at hand, which is to have impact.’

I don’t want to give part of that energy to being bitter or cynical about things, because that’s also not going to do anybody any good.

It’s about finding a way back to the joy. Sometimes you just need to go dance, or talk to a friend, or be reminded of the small victories.

If you think about how much energy and how many resources there are being pushed against any change, that’s huge.”

As we ended our call, I slumped back into my desk chair, feeling, well, even more refreshed when I first read “From the Field”. The thing is, if it feels tough to fight the system, it’s because it is. There’s a reason why it is THE system. However, instead of ignoring the effort it takes to create change, give yourself time to ground yourself in what you can control, and find ways to fill your cup.

When in doubt, dance. Talk. Sing. Do what feels good to use your joy as fuel.

Something spoke to me on a level I honestly can’t describe. It was authentic. It was clear. It feels like the treasure chest at the dentist’s office, or a Where’s Waldo book, somehow re-awakening this childlike wonder you thought had been left to the void.

A cold DM and a few weeks later, I was sitting across from the fool herself, ready with a pen and paper to understand how one can convey an experience so real, so genuine, so fun. A skill that too many of us have forgotten how to do, and the importance of living it authentically.

So, everyone, it’s my pleasure to introduce you to Rithika.

Does your work reflect who you are?

Most of the time, we spend our lives insisting that ambition, or the idea of doing good, or what is externally recognized as good, is enough.

People ask you your values, and you’re able to regurgitate the ones that used to grace elementary school awards: respect, integrity, and making a positive impact. But when you are asked to define these values and why they’re important, they may feel like you’re wearing a stranger’s shoes. They’re nice, but they’re not actually yours.

When hearing Rithika’s story, we started there and the moment she decided to find values that were authentically hers:

“I didn’t have a really solid understanding of who I was. I had these values, but they were vague. It was things like, ‘I want to do something good for the world and people.’ Also, I grew up very privileged, so I didn’t have to worry much about money, sacrifice, or compromise. I could just ask: what’s the most honourable life to live, and landed on one where you make the biggest impact in the world.”

But as Rithika reflected more, she realized that there was a difference between things that sound right and what actually is deep down inside, what you want. She continued,

“The value of helping people and wanting to make the world a better place is still there, but now I think about how I want to do that, and I can articulate it more clearly. Yes, working in tech directly helps people, but I wanted to focus more on creating art that moves others.

As I understand myself better, I also understand those values better, and I keep asking myself, ‘How can this be the most authentic version of who I am as a company?”

That’s ultimately how she built Rithika is a Fool (RIAF), by asking again and again, how can I show up as my most authentic self?

The beautiful thing about Rithika’s work is the fact that it is inherently hers to the point that I felt like I knew her before I met her.

How can we genuinely show up as ourselves? And when we do, will the universe truly reward us? Isn’t that what we’re all seeking?

Often, we find ourselves trapped within the barriers of what we believe is the right image of ourselves. The “right” job, with the “right” title, and the “right” salary. It feels like a strange pyramid scheme where we pursue other people’s ambitions, so deeply invested in what appears good that we forget what truly feels good and lose sight of who we really are in the first place.

How shocking, how devastating, but how interesting that this is a pattern that we’ve not only normalized but also actively celebrated.

If you’re constantly waiting for external validation to define who you are, you’re looking in the wrong place. When we focus too much on who people are, why they act a certain way, and how they interpret us, we give them unnecessary power. Rithika and I bonded over how difficult it is to remove the mask and genuinely be ourselves, she noted:

“I just want to show up as who I am. Even if you don’t think I am smart and cool, I’m now more proud that I simply show up as myself, and I’m less proud of how you think about me and how I present myself. With the company, it’s kind of the same idea. If anyone visits my website or the studio, I want them to think, ‘that’s so Rithika - that’s her embodied concept.’

I believe every decision can be creative. Most companies don’t put in the effort to treat every small thing as a creative choice because they’re honestly too busy, and it costs too much to put that much effort into every detail. But I think artists do - like painters who have one shade of a bird, one painting of a thousand birds. If they don’t like it, they redo the whole thing. I’m trying to do that.”

There’s a desire to do things quickly, and you have the tools readily available. But that deep passion and dedication to your work allow you the time to make it perfect, to truly represent who you are. To create art, instead of just producing an output.

Finding your inner knowing

Learning to trust yourself is probably one of the most valuable aspects of growing up as an adult, but it doesn’t come easily. How did Rithika create this filter to achieve such a unique mix of excellence and taste? Interestingly, she mentioned that her grief played a significant role in it. Rithika’s father passed away last year from cancer. I recommend reading her piece A Daughter’s Witness. It is one of the most beautiful pieces I’ve ever come across on Substack.

Rithika and I discussed her experience with grief:

“I think there are a few things at play: one is probably grief. Going through it was particularly tough after my dad passed last year; I suffered a lot, and it was difficult. I just feel like the idea that we can all die — not in a melancholy way, but in a kind of peaceful way — is always in the back of my mind: ‘We could die’. Why would I try to be anything other than what I am?”

Funnily enough, I’ve resonated with this quite a bit because I, too, believe that death and the fact that life is always fleeting create that sense of urgency. It’s very easy to settle into a routine and not actively think about what you’re doing each day. Rithika then shared how her specific reflections on her dad’s death actually served as a way to continue to build her faith in herself and her confidence to make this leap into a more creative path actively.

It was a lot tied to my dad’s passing in a weird way because I couldn’t imagine a world where he’s not in my life. Maybe not him specifically, but just his love in my life.

There’s this quote that goes, ‘Any love I’ve ever given to you is yours to keep,’ and I kept feeling his love, seeing him and others in front of me. I’m sure it was always there, but perhaps it was more about the person I love so much. He helped me become more confident in myself when I thought about it, and it was my dad’s doing - his love made me who I am. So I don’t have to feel narcissistic when I say I should be myself in this world, and I can be successful as me. I was raised this way. I was given all of this to be me, so why wouldn’t I continue doing that to honour those who brought me here?”

You owe it to yourself and to the ones you love to live authentically. Every single day that you live in alignment with yourself is a way of honouring those you cherish. They took the time, like a piece of art, to shape and mould you as a person. Let them adore you in all of your glory.

Kill (some of) your darlings

On her Substack, Rithika talks about her experience of having too many darlings in her piece, the New Dream.

To define our “darlings”, Rithika takes us back to an experience that she had with her English teacher in high school. Quoting directly from her piece:

“I’m remembering this writing advice that my English teacher gave me in high school -

“Kill your darlings.”

It means that you should eliminate any part of your writing - storylines, characters, chapters, or words - that doesn’t serve your story. No matter how beautiful it might sound or how hard you worked to craft it, if that piece of writing doesn’t meaningfully serve the story, you must kill it. I’m proud of how I’ve learned to select and work on my projects. I adore the impact they have on me and the people I’m close to. But they don’t allow me to make an impact at scale. It doesn’t meaningfully serve my story. Time to kill my darlings.”

When we discussed this, I found it really interesting. When Rithika felt something wasn’t deep enough, she had to dismiss it because it didn’t align with her story. She said,

“I think there were a lot of things that I thought were darlings, but really, I was doing it from not a super authentic place.

Now I think that I’m better at identifying what my real darlings are and what is really authentic to me, and it’s a lot less because it’s not based on what I want to seem smart or anything like that. And I feel like I just wanna have more faith to get everything. Let’s start working on it. And it’s just faith. I just have faith that I will do it or meet the people that will help me do it to get to everything that I want to do.”

Having this faith and leaning into what serves your story can be difficult, but they are the only way to discover your true path. In a way, the universe begins to reward you when you start to focus on your own unique adventure. The path reveals itself as you walk it. You just need to gather enough faith, delusion, or whatever you want to call it to lace up and take the leap.

Ambition can be of service to others

I was curious about the people Rithika chose to surround herself with. Her family and her background with her dad inspired her to live more authentically and to view following your dreams as something you can genuinely do to honour the people in your life. She said something really beautiful about her friends:

“In a way, you need to find people who see you beyond what you can see yourself.”

When speaking about the success she hopes to have with her studio, she wasn’t just seeking personal success; she wanted a way to make her friends’ lives bigger. She said,

“I want to be able in five years or something to take them to a movie premiere or something because I want to make my friends’ lives bigger. I want to give back to them in that sense. And they’re part of the thing we talked about earlier, which is doing things to honour your friends and the people who believe that you should feel that you want to give back to them. That’s also really good motivation.”

And this is the thing: the way we define ambition is something I believe we’re doing very wrong. Right now, ambition is often seen as:

I, as an individual, have achieved the highest level of success.

There’s talk now about the first zero-person billion-dollar companies, but we forget that life isn’t a game to be won, but rather a dinner to be shared.

If you reach these stars, these arbitrary measures of success, what will you do with them? I think we forget what our time on this Earth is truly for.

What are you doing this for? Is it freedom?

What do you want and why?

The more we ask these questions, the further we move away from the conditioned notions of success we’re told to pursue. Instead, we begin to connect with our inner knowing and the life we want to build, and share it with those we love, whether they are physically with us or we are living their love every day.

That’s why I love Rithika’s mission; the way she’s framing up her life, the way that she’s doing this because it isn’t just for her.

She’s actively motivated by doing more for others, honouring her father, enriching her friends’ lives, and genuinely being able to dance around the room while thinking about what she’s doing.

That’s true freedom.

That’s love.

That’s life.

It’s not just about you; it’s about everyone. So, go chase it. Find the people you want to uplift and live the big life you can proudly say on your deathbed: “Hell yeah, I did this.”

Making career decisions based on joy is a deeply personal indicator because it reflects your true choice to dedicate your life’s work to something that brings love, life, and happiness to yourself and others.

So why not commit to something genuine to you, rather than something you think you should do?

Having fun should be your calling.

Maybe that’s the place where you can discover how you truly want to spend this life and honour the people who brought you here.

I hope you enjoyed this new version of “The Rule of 52” for 2026: 52 Coffees!

A huge thank you to Rithika for participating this week :)

Check out Rithika’s website at rithikaisafoolcom & her Substack here

What made Haley pause, as she explained in her Substack, San Francisco’s Story of Inevitability, wasn’t the idea of the startup itself but rather the lack of reflection, acknowledgment, or understanding of the consequences of this organization’s mission in the initial DM “pitch”.

As Haley describes it,

“What she was offering me was not simply a role at a startup, but participation in a process whose consequences have already been decided. They were moving forward in building this company simply because the technology could exist, but they have yet to feel the need to reflect on and name these consequences.”

How many times have you heard the word “inevitable” in 2026?

Before this year, ‘inevitability” was associated with life’s certainties like death and taxes. Now, it’s often linked to the most disruptive technology humanity has faced: AI.

AI is becoming integral to our professional and personal lives. There’s constant pressure to keep pace with its rapid progress, with experts urging us to: Move! Upskill! Or risk falling behind! This message, even as I write, feels overwhelming.

Media coverage on this topic often floods us with information, leaving little room for pause, reflection, or slowing down. The common view tends to see taking time to think as a waste, which intensifies the fear of falling behind. We are living in a constant state of overwhelm, with an urgency to begin but uncertainty about how, when, or why to move forward.

Nevertheless, it’s more important than ever to identify leaders who are engaged in entrepreneurship, AI, and San Francisco, yet who also make time to reflect, question, and critique the industry’s core assumptions. I am excited to share my conversation with one such founder, Haley Moller, as we discuss one of the most important questions of our era:

How and where do we draw the line between “I can build something” and “I should build something”?

Building Because We Can

There has been an interesting shift from entrepreneurship as a “risk” to entrepreneurship as a “way of stability” over the last few years.

As the job market has become more difficult for new grads to enter, and there has been a rise in younger founders quitting school to move to San Francisco, romanticizing entrepreneurship for its outward look of “cool”. I recommend reading Sam Kriss’ piece “Child’s Play” to understand some of the influencer Founders and the landscape in which they’ve gained their popularity.

Now that the concept is widely known, anyone can learn to “vibe code.” With Sycophantic AI models, where Large Language Models (LLMs) often prioritize user approval over accuracy, truth, or critical thinking, individuals can quickly become trapped in an echo chamber. They may promote their ideas at all costs, forgetting essential questions to ask when beginning a project.

• Why am I doing this?

• Who or what will this impact?

• How will I mitigate that impact?

When I asked Haley about the startup culture she’s immersed in while building Socra Education, she didn’t soften the reality:

“What’s going on right now is that we are building these things because we can, a lot of the time, and it’s not because we should. They may say they’re doing it to keep humanity safe, but I think another real motivation is a sense of curiosity.”

Curiosity as an entrepreneur is important, but Haley and I chatted about how it can stop too early. Often, we become fixated on how to build (what’s possible), never arriving at what happens after it’s built. Haley explained her thoughts on this:

“I think it’s an inability to question what’s being built and to question their own motivations.

The story I told at the beginning of my piece about this classmate of mine, whom I didn’t know, but who reached out to me on LinkedIn. What bothered me was not even the technology itself, per se, but that she didn’t even say anything about, ‘and, you know, I acknowledge we’re taking people’s jobs, and we’re going to be figuring out how we can re-employ these people in a different capacity.’ It’s just like a complete lack of awareness.

I want to be clear that I understand people need to innovate and that sometimes people are going to be displaced. Still, I think we, as a society, need to be aware of what’s happening and ready to find solutions for the people it’s affecting.”

We can never foresee all the consequences of our actions, especially the impacts of the innovations we aim to create to advance society. However, that does not mean we should go forward mindlessly. We must understand that innovation, or startups in general, do not exist in a vacuum. If we are consistently prioritizing profit over all else, prioritizing economic viability without questioning what future we are building towards, then we are heading towards a very scary world, filled with tools we don’t need, or worse, tools that could actively cause us harm.

Your Private Accounting

Haley spoke about the practice of private accounting in her Substack:

“There was once an unfashionable idea that self-respect involved a private accounting—not only of what you did, but of what you knew you were doing at the time. That kind of reckoning cannot be outsourced or priced into a round. One of its few outward signs is the ability to say, simply, I could do this, but I won’t.”

The idea of limitlessness is both exhilarating and intimidating. It suggests that anything is possible but neglects to consider that some things we might prefer not to pursue. If we approach every idea assuming that because it can be done, it will be done, and view the consequences as unavoidable, we reduce our ability to stop, adapt, or question ourselves when heading towards a morally questionable decision.

Beyond the mortgage-broker AI example, another instance of the choice between integrity and profit occurred over the weekend. Dario Amodei, CEO of Anthropic, challenged the Pentagon and President Trump’s unrestricted access to Claude, opposing its use for mass surveillance of Americans and fully autonomous weapons. Within hours, Sam Altman of OpenAI stepped in and negotiated a deal with the Pentagon. While Anthropic took a principled stand and faced consequences, OpenAI seized the opportunity to surpass its competitor.

Amodei took a stand, risking his commercial viability and financial gains, because he believed it was the right thing to do. That is integrity.

However, having overwhelming, blinding conviction, a willingness to overlook or bypass potential consequences of actions, and access to this technology, as demonstrated by OpenAI, led to greater financial success.

Even if we genuinely believe in our ideas and work, doing so without properly assessing the consequences makes them more perilous. This act of blinding ourselves with our conviction is also something Haley highlighted during our discussion, where she drew the line between self-belief and conviction.

“Conviction is different from belief. Conviction involves so much more emotion, is really bodily, carries a lot more momentum, and it can be a wonderful thing when applied to the right concept. But I think it can also be quite blinding.”

When we become blind to the consequences of our actions, we forget that we are responsible to ourselves, those we serve, and those affected by our innovations.

As a builder herself, Haley is part of a group whose innovation will have consequences. However, what sets Haley apart from the person with the AI voice mortgage sales company in her DMs is her willingness to think about and sit with the uncertainty of her actions. Haley is willing to actively reflect, build with purpose, and take the time to consider what impact her startup might have on the future. She noted:

“I can’t predict all of the consequences of my actions. My tool could have unforeseen consequences that I’m not aware of right now. I think it’s tricky, as someone who’s building, because you can sort of delude yourself into believing that you know exactly what you’re putting out into the world.” Haley continued:

“What’s important is having strong personal values and the ability to step back if things start going in a direction that you don’t personally approve of, even if it means loss of profit or revenue.”

At the end of the day, no one has a crystal ball. Even if you have an idea of how things will play out for you and the people you will affect through your innovation, you also need to maintain your integrity, even if that means sacrificing potential upside, whether professional, financial, or personal. If your innovation risks crossing a moral boundary, you should be equipped to address or abandon it rather than ignore the issue until the consequences become too great to ignore.

Be a Good Ancestor

Haley’s “why” for building Socra reaches far beyond a mission statement:

“When people ask me what my primary motivation is in building this company, my honest answer is, of course, I want a job, and I want to provide, and I want to create something useful. But I have known since I was young that I wanted to be a parent.

I am truly building this for my own future children and all future children with the hope that this can help solve a genuine problem.”

Haley can picture in her mind’s eye who she is building for. She has her moral compass and feels a sense of urgency and duty to ensure that this rollout is done properly. She looks inevitability in the face and asks, how can we change the course of this innovation’s impact, and how can I use my skills, right now, to do that?

“The way that we choose to introduce AI to children is going to be extremely important in terms of determining how they turn out as adults, their ability to think critically, their ability to write for themselves, and their confidence in their own voice.

This is the tool that I want my kids to have, and that’s why I’m doing this.”

We are at a critical juncture, where the world feels overwhelming, and the tools are emerging faster than ever. As we race to go faster and achieve more, there must still be time to ask why and how, and truly reflect on what future you want.

Consider how you will explain to future generations the decisions you made that will affect the future they must face.

I’ll leave you with an interesting image from UNDP that illustrates the scale of the unborn generations who will come after us on Earth.

It is easy to get caught up in where we are today, trying to take all that we can for ourselves, but we must understand that the decisions we make today will impact the unborn generations ahead of us.

So, ask yourself, what decisions are you making today to be a good ancestor?

I hope you enjoyed this new version of “The Rule of 52” for 2026: 52 Coffees! A huge thank you to Haley for participating this week :)

Check out Haley’s organization, Socra Education here and subscribe to her Substack below:

Haley’s Substack

My personal Substack

By Haley Moller

The text came across Erin’s phone as she was preparing for the inaugural Climate Coffee event in Toronto. She was puzzled by the question, sent in from a student eager to join the conversation with people working in or interested in climate spaces.

She responded, “Of course you’re allowed,” but the question stayed with her, as it piqued her interest. Erin isn’t someone who asks for permission.

People often rule themselves out before anyone even has a chance. The funny thing is, most of the time, they never would have been ruled out at all.

Erin has spent her career building the connective tissue between people who have something to offer and the spaces that need them, often before either side knows it. At the Green Growth Lab, she identifies high-potential climate solutions and links them with the resources they need early, so founders don’t spend years building something nobody will pay for. The logic is the same whether she’s texting a student or vetting a startup: don’t wait for people to find their way in, they’re in.

“People get really intimidated by it. I do think a lot of students kind of rule themselves out, even though startups love students because they’re energized and eager to volunteer. They need them.”

The barriers people imagine aren’t the ones she sees, since she’s actively looking for ways to make what may seem impossible… possible (like recycling textiles in Canada!!! what!!!). So, the more you hang around Erin, the more you start to realize the gap between what you want to do and what you can do is a matter of your own self-imposed limitations.

The Honest Cost

Even after you shed your self-imposed limitations, permission is just the entry point. There are real costs associated with actively choosing the founder path.

Erin doesn’t romanticize this. After five years building Impact Zero from the ground up, she’s clear-eyed about what the path actually looks like.

“Don’t think this is a ‘rainbows and butterflies’ path. It’s really, really stressful.” She pauses. “But the fulfillment is certainly there, which is what is so troubling.”

Stress and fulfillment often go hand in hand. If you want something so deeply, the stress of making sure the execution works is critical to function at such a high level of excellence; doing things independently and doing them well.

A part of what makes it harder is the standard most founders quietly hold themselves to, which Erin calls “The Unicorn Trap.” This trap is the idea that unless your startup reaches a billion-dollar valuation, you haven’t really made it. It’s a benchmark so rare it’s almost fictional, and yet it shapes how founders measure themselves.

Erin fundamentally rejects this framing of success as a position of her values. Working immersed in the circular economy, she knows that the world has limited resources, which, on a fundamental level, means not every startup can become a unicorn. However, that does not diminish the lives and success that can be created for founders who choose this path. A lot of people can genuinely build a meaningful life around their passion without even reaching unicorn status.

What keeps Erin going isn’t the accolades or metrics. However, she is a highly decorated and successful founder, having been named to Forbes 30 Under 30, launched or relaunched 65 climate startups, supporting 250 climate founders in the Toronto community, and reaching over 10,000 people keen to support the creation of a circular economy.

However, her true calling to her work each day comes from something a bit more difficult to manage:

“I have the problem of making my job my entire personality, but I think it happens even more when it’s your passion, too. For evenings, weekends, I’m not working on it because of anxiety; I’m working on it because I’m literally obsessed with it. It adds a layer of stress, but it’s still fun.”

At the end of the day, for those truly living their passion, the honest cost isn’t necessarily the hours or the stress, but the obsession that follows with pursuing it. The work never stops because you don’t want it to. The fun comes from actively building your dreams each day and creating a world where you want to thrive.

Avoid the Apathy

There’s a version of this story that creates the wrong kind of pressure. You read about someone like Erin and suddenly feel like you should be quitting your job by Monday.

But Erin would push back on that.

I reflect on the people who are interested in sustainability, or rather, just making a big change. The real problem isn’t moving too slowly. It’s the slow drain of giving up on the idea entirely.

Both Erin and I reflected on the many times we’ve seen this happen within the corporate sustainability space. Someone passionate, genuinely energized by the scale of the climate problem, takes the sensible job at the big company. It seems like the best route at the time, stable salary, a recognizable name, in an ESG-reporting role, doing what they can within the constraints they’re given.

Then, slowly, their day-to-day starts to warp their perspective of the change that is possible, as well as their own role in making it. That’s when the apathy creeps in. The enthusiasm dulls, you do “what you can” and start muttering little corporate mantras of “it is what it is”.

Erin reached that point in her career, the moment when she realized that there is a limit to what you can do inside of a big corporation, she decided to think outside of it, off the side of her desk. It is what can give us all the momentum to stay connected to the cause and start inching towards a future where we can feel comfortable going full into our passions. That’s the move she recommends to people who don’t feel comfortable:

“If you really can’t take the risk, don’t become a founder straight away. But early-stage startups, you could DM a founder, ‘Hey, I love what you’re working on. Can I do this volunteer thing?’ And that can be your passion outlet, and you find fulfillment after hours. That’s a completely valid way of existing, and probably the best of both worlds.”

We can exist in both arenas, but the key is not to lose the excitement or the power you have to change the world. Don’t lose your intrigue, your excitement, or your sense of how much you think you can make a difference. Apathy doesn’t do anyone any favours, especially the future we are trying to build. You, once again, are allowing yourself to stay connected to what you care about without blowing up your life and refusing apathy.

Find the Third Door

When we reflect on the barriers that keep people out of startup culture, it often boils down to salary, prestige, and the expectations aligned with “winning” in a job market. Erin wanted to set the record straight:

“Entry-level jobs at some of the well-known consulting firms, you can get paid the same or more at a climate startup, because they’re relying on people absolutely chomping at the bit to have that name on their resume.” She paused and smiled,

“If only they didn’t care so much about the LinkedIn announcement.”

There’s a book called The Third Door by Alex Banayan, built on a simple premise: there’s always a third way in, past the line and past the VIP entrance, but you just have to be willing to find it. What Erin is pointing at is that the Third Door, the one that doesn’t have the lines of people eager to have a specific name on their resume, is wide open and ready for you to enter.

So the real question is: if you had no way of telling anyone what you did, no post, no LinkedIn update, no name to drop, what would you actually be doing? Remove every avenue for external validation. What genuinely fuels your fire?

That answer is your third door.

If you’re in Toronto and still looking for an entrance into your third door, Erin has made it a little easier to find. She has expanded Climate Coffee, an informal morning meetup for anyone curious about climate tech, sustainability, and impact, started in Barcelona and now runs it once a month in Toronto at the Centre of Social Innovation.

As we wrapped up our conversation, I asked Erin if she had any last advice for someone interested in getting started in a purpose-led career:

“Come and show up, even if they’re not ready, or they feel like they’re not ready, because they probably are more ready than they think.”

So, give yourself permission to show up in rooms before you feel ready, and we’ll see you this Thursday.

I hope you enjoyed this new version of “The Rule of 52” for 2026: 52 Coffees! A huge thank you to Erin for participating this week :)

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The next Climate Coffee is THIS THURSDAY - check it out here: https://climatecoffee.notion.site/Climate-Coffee-Toronto-2e9437e431d780879f42edd5f26cdea9

As Gabe recounted the story across from me in a bustling cafe in Kensington Market, he reiterated:

“Clearly, it was her second day, at best. She was learning the menu, you know? Whatever, everyone has to start, right?

He went on to discuss that his mom was clearly frustrated throughout the meal. When the bill came, she picked up the pen.

“I’m gonna tip her a little lower,” she declared to Gabe.

“Mom, she’s training. Give her a break.”

“I’m gonna tip her a little lower.”

Gabe watched her write in the amount. Then, as they got up to leave, he pulled out his wallet, took out a few bills and placed them on the table. On the bottom of the receipt, deliberately making a point in front of his mother, he wrote:

He recounted his rationale as,

“I was not going to let her misery block my desire to be kind and bring joy to people.”

Gabe is one of those people who radiate warmth whenever he walks into a room. When I reflected on how we met, I found it hard to pinpoint exactly how we met. It was a mishmash of interactions, friends of friends, and, over time, we also became friends.

He’s the kind of person who, when you invite him, will always show up. He has this energy and a smile that easily lights up the room. He’ll chat with you in the hallways and make anyone he meets feel a sense of belonging. When we sat down for coffee, I immediately started thanking him for his support with my writing. Throughout the past 52 weeks, he has been one of those people who messages me directly with kind, insightful comments on my work.

We often forget how far those small comments go, and they especially gave me the motivation I needed when I needed a bit more encouragement.

When Gabe expressed interest in writing more in 2026, I wanted to ensure he received the recognition he deserved as one of my 52 Coffees. He had shared a list of key topics in a note titled “write that down!” (love it), and one topic caught my attention.

What a line.

Of course, we had to start there, so he took me back to that day in the restaurant, which sparked his reflection on this topic.

“Get real…”

I opened up our coffee chat by asking what he was thinking about when he typed those words into his notes app:

“I was thinking a lot about my relationship with goodness and wonder, and how it’s been like time and time again, I’ve been encouraged, maybe unintentionally, more intentionally, but encouraged to squash it.”

Gabe reflected on how being naive was often used as an insult growing up. His upbringing was somehow encouraging him to anticipate the other shoe to drop, that one day he’ll realize that “the world does not work like this.”

Now, as an adult, when he disagrees with his mom, Gabe is defensive of his naivety, as it is no longer something he has; he is actively choosing to be a good person.

“Stop saying that I am a good person and a good kid, like it’s a bad thing,” he told his mom once.

“Stop saying like my goodness is something that I should be ashamed of.

This theme of “goodness” piqued my interest. We all have different definitions, or rather, expectations of what qualifies someone as “good”. Often, this misalignment is quite revealing of your upbringing, as well as of who you decide to surround yourself with and why.

So, I asked Gabe to define the qualities that would constitute a “good” person, and he had specifics in mind: kindness, honesty, and compassion.

However, he doesn’t just recite these values because they sound nice; he actively lives them every day. Even if that means actively choosing to see the best in people, even when it puts him at risk of being taken advantage of.

“I would rather go to bed happy knowing that I did what is right by me than trying to be objectively right. If someone’s gonna screw me over, I would rather go to bed happy and at peace than to go to bed trying to be ‘right’”

Don’t let the cynicism win.

When we hear the word “vindictive,” the overwhelming reaction is that it comes from a place of aligning that with attributes of someone who is “evil”. A vindictive villain in our childhood novels, or the person who is trying to get one over on someone who once hurt them

If you are vindictive, you want revenge. But is revenge always bad?

My conversation with Gabe had me questioning that assumption. He was using these attributes of vindictiveness to enforce fairness or make things right.

Gabe’s mom’s concern, he knows, comes from a place of love. She doesn’t want people to take advantage of him, to make a fool of him. The restaurant scene wasn’t just about being kind to the waitress. It was about refusing to let cynicism win.

His actions were vindictive in a way that he wanted to show that kindness, and showing it consistently, was a form of resistance against negativity. A way to demonstrate that you can be good, find the good in people, and that will continue to serve you going forward. It was getting back at a worldview that had spent his whole childhood telling him that caring too much was a weakness.

Gabe outlined, quite frankly,

“If you absorb misery so often that it becomes part of you, or you believe it’s part of your personality, there’s no escaping it. It’s literally always gonna follow you.”

“You’re creating it every day.”

What if we take revenge by demonstrating that good can be done? To be leaders of joy, instead of those who fall into the trap of assuming the worst in each other, to bring us all down instead of each other up.

What if wearing your heart on your sleeve, despite getting burned, was an act of resilience?

A heart on your sleeve is a badge of honour

In a world where it is easier to be silent, pessimistic, and cold, wearing your heart on your sleeve is an act of resistance.

By putting your faith in another person, you are giving them the chance to show up as a better person, rather than undermining them or assuming who they already are.

These days, Gabe helps his friends the way he wishes someone had helped him. When someone is stuck in a spiral, wallowing in their feelings, they’ve learned to be blunt. He told me he often uses the one-liner:

“It’s not your fault, but it is your responsibility.”

He continued on:

“It’s not your fault that all these things are piling up, and it’s stressful, and you’re in a bad spot, but it is your job to move in the direction of picking yourself up. You don’t need to pick yourself up today or tomorrow, but you need to shuffle in that direction at least.”

He’s become the friend who brings jokes and humour to serious moments, who lets people feel everything, and then helps them move forward. He refuses to let people stay stuck in a cycle of cynicism, since he’s actively choosing a different path from the negative environment he grew up in.

He’s choosing what is somewhat of a radical alternative: choosing to believe the best in people, even when you’ve been taught it’s naive.

There’s something defiant about wearing your heart on your sleeve when the world keeps telling you to guard it.

When Gabe wrote the waitress an encouraging note in front of his mom, he was making a statement.

His vindictiveness stems from a refusal to see the worst in others for his own protection.

It’s balancing the seriousness with the silliness, striking a balance between the easy route to rationality and “real”, while keeping the child-like wonder that makes each day full of joy and potential.

As we wrapped up our chat, Gabe said,

“Everything requires a balance of seriousness and silliness. As you grow up, it’s really easy to lose that sense of silliness, because you’re just beaten down time and time again from a variety of directions. It can be work, it can be a relationship, it could be your family, or maybe your hobby. You stagnate and you don’t know how to find momentum again. It’s so easy to get lost in the seriousness that you can forget how important and how beneficial it is to be silly.

The through line there is, it’s important to know when you have to be an adult about things, but let your inner child follow you through life. Honour that kid inside of you.”

I end each coffee chat with a reflection on the future. Gabe had a simple yet beautiful one-line reflection,

“I hope the person I am today is someone kid me would think is cool,”

I’ve been thinking about that line a lot since we finished our lattes and walked back out onto the slushy Toronto streets. It seems simple, but truly, the two people you should be appealing to with your decisions are your child self and the person at the end of your life.

It’s not about what your parents want, or what you “think” you should.

So, I’m leaving you with a question this week: what would make the kid version of you proud?

What can you do to honour them this week?

Gabe knows his answer: Showing up with his whole heart anyway, even when, especially when, it would be easier not to.

What a beautiful act of defiance.

I hope you enjoyed this new version of “The Rule of 52” for 2026: 52 Coffees! A huge thank you to Gabe for participating this week :) Check out more of his reflections on Medium!

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“I have someone you definitely should sit down with.”

These second-degree connections, these introductions that seem so serendipitous, the look into someone else’s life you care about, by getting connected into their outer web, bring me so much joy.

As soon as I sat down to chat with Kenzie, she taught me so many key learnings from her ambitious work, demonstrating how fun can be a catalyst to executing on ambition; I immediately knew why she sprang to mind for 52 Coffees.

Kenzie was willing to take on an extreme feat: profiling 365 Women in 365 Days, a project she did in partnership with her best friend, Paige, that emerged from the pandemic in 2021. 365 days. They did not miss one. Even reflecting on it, Kenzie reiterated multiple times that she’s not sure how they ever thought it was possible, let alone actually accomplished it.

But that’s the thing about finding the people that drive you both personally and professionally, who are willing to throw out a big ambition and actually execute on it with you. Together, we discussed what that partnership has grown into over the last five years and the lessons Kenzie hopes to take into the next five.

Just start.

When something feels fun, you don’t overthink whether you’re ready. That’s what struck me about Kenzie’s story.

When the right person asks you to do something ridiculous together, the question isn’t “am I ready?” It’s “I’m game, are you?”

There is always a way to rationalize out of that “CRAZY IDEA.”

But here’s the thing: when you’re doing it with someone who makes it fun, you don’t rationalize your way out. You rationalize your way in. So, when Kenzie’s best friend Paige came to her with a “CRAZY IDEA” in 2020, instead of worrying about the logistics, or the appearance, or the outward interpretation, Kenzie met it with a “I’m game”.

She recalled this moment with me:

“Paige and I were always super collaborative at university - writing essays together, working on projects. We had these inspiring feminist professors, and we carried that into the real world after graduation.

When lockdown happened, Paige was in New Zealand, and I was back in the States. She came to me with this idea: what if we started posting stories about women we know? We can write their stories and celebrate the people in our lives. So I was like, you know, I’m game.”

That single decision would be the origin story of 365 Days, 365 Women, a whirlwind year in 2021 in which Paige and Kenzie set out to interview 365 women in 365 days, living on opposite sides of the globe. 365 days is a wild feat for two people to take on, but the two best friends were encouraged by the interest in celebrating the stories of women everywhere.

I asked Kenzie whether it ever really set in just how big an undertaking this project would be:

“I think taking on 365, we didn’t really understand what we were getting into. So I think that was kind of fun. Looking back, I’m like, why did we think that we could do that?”

Even after accomplishing this goal, Kenzie reflected on how ambitious it was. Where did this confidence around the possibility come from? So I asked, “How did you find the courage to take that leap?”

“All shout out to Paige. She was just like, I really want to do this. Are you game? Sometimes you gotta have people around you who just say, “let’s take the first step.”

Having some type of vision is crucial, even if it evolves. With something daunting, this is the end goal for now. What’s the first step I can take in that direction?”

Paige wasn’t on the call with Kenzie and me, but I could feel the respect and care that Kenzie carried, as 365 was a true partnership between the two.

How often do we reflect on our lives and realize what could have been different if we didn’t meet that person, didn’t feel those words of encouragement, didn’t have someone in our corner saying:

“Yes, you can.”

That is the importance of having people around you who don’t question whether it is possible, but stand beside you to figure out, “how can we make this happen?”

Be selective with your surroundings.

Potential is just that, potential, until you act on it.

It feels really good to have “good potential” or “high potential” or whatever your teachers used to tell you. But the thing about ambition is that it can easily fizzle out. Sometimes, by telling people your goal before acting on it, you can actually make yourself less likely to achieve it.

Kenzie’s story isn’t just about having supportive people around you. It’s about finding someone who transforms what’s possible by making it genuinely enjoyable.

As Kenzie reflected on the times with Paige, there were so many examples where they held each other up to achieve the feat of 365:

“I’d say, I have to post this late. If I draft it, will you post it now? It was so collaborative. Moving that collaboration into uncharted territory might have ruffled some feathers, but we truly enjoy collaboration. It’s a core part of our friendship. And just understanding that this is supposed to be fun - continuing to keep that in mind.”

I was so interested in understanding how Kenzie and Paige managed such a feat, but the theme was clear: 365 was made possible because Kenzie had Paige and Paige had Kenzie.

This trust in each other transcended their working relationship and spilled over into the profiles they posted. Kenzie describes:

“The last question we asked [for each of the 365 profiles] was: What does womanhood mean to you? Seeing the variety of answers over the years impacted my perception. There’s no one definition of womanhood. Women would say, ‘I don’t think my story is that interesting. I’m just a mom of three.’ And then their story was crazy - wow, you actually underwent so much.

Understanding what other people have gone through, how they’ve carried themselves, what they’ve still been able to achieve - that’s changed me through this project.

And the trust. These women didn’t have to share their stories with strangers online, but they decided to. They’d submit their answers, we’d edit for Instagram, but then they trusted us to write their intro. We’d run it by them. Trust is something I’ve learned and appreciated through the project.”

They were able to keep the fun in sharing what can be scary: sharing work publicly. Especially the stories of strangers publicly, included an added layer of ensuring each piece is represented with love, respect, and care.

Instead of seeing each post as a daunting task, Kenzie and Paige together demonstrated that 1+1 can equal 11. For these two, partnership transformed their sense of their own capabilities and enabled them to execute an impossible task without losing the joy in the process.

Where is the fun?

If you’re starting something and asking this question, you may be running into an issue.

Most of the time, we think we need to go into a “monk mode” or channel an unrealistic “grindset” to achieve something great. But, if we take a look around, some of the most successful projects were born out of a genuine love for celebrating or solving problems in partnership with people you care about.

When I asked Kenzie where she wanted to be 5 years from now:

“I hope my future self is doing things I would be proud of now, but also isn’t taking life too seriously. Sometimes when I get really wrapped up in work stuff, I forget to have fun. Travelling, doing things I actually love, and spending time with people. I hope that I, in five years, will still be prioritizing that and reminding myself that it’s not that serious.”

When we look at the inspiring people, the people who have achieved the unimaginable, executed on a dream, and done what they want, it is easy just to think that we need to shut down, “grind” and get to that end state. What we often forget is the importance of the journey and of enjoying it.

Another cliché is “do what you love and never work a day in your life”.

When talking to Kenzie, 365 was not work, but instead a celebration of genuine stories and a way to continue strengthening the bond with her best friend. Besides the personal and professional accomplishments, they are just symptoms of the overall mission to do something worth sharing, to challenge, and to build something beautiful.

Isn’t that a wonderful way to frame up opportunity?

A way to enjoy time with friends together.

What if success isn’t defined in what you are traditionally confining it to right now?

What if success could be building something beautiful with someone you love?

Maybe the question isn’t what you would do if you weren’t afraid. Maybe it’s: who would make the pursuit of the impossible feel like an adventure?

Check out Kenzie and Paige’s work at www.365days365women.com

4 coffees out of 52 for 2026.

A year and 4 weeks into posting a Substack every Tuesday.

And it was at this point, I realized I have a problem.

It was at this very point in time, sitting on my couch, with the darkness of a cold, Canadian winter night (6pm, obviously) in February, stressing over my next post of 52 Coffees, that I realized the source of the stress was not my self-imposed deadlines themselves.

It was that I’d built my own cage that I had forced myself into and forgot that I, too, held the key.

Structure is both a blessing and a curse. In times of self-deprecation, where I feel out-of-control or behind or lost, I ground to a schedule. A long, rigorous series of commitments…and if I’m honest, wayyyy too many commitments.

Maybe I can blame my teenage self for picking long-distance running as my sport of choice, where the constant of my tumultuous times of growing up always had the baseline of my shoes hitting the pavement for at least 10 hours every week.

Grounding to a number, whether it be number of slices of cake skipped, workouts hit, mornings without a snooze, Substacks written, the proof, for my own self, has always been in the pudding. I consider myself valuable when I can quantify success. I can write it down in a little bullet journal, or on my little calendar, and say: ah yes, I am worthy.

However, there comes a time with anything, that’swe begin to over-indulge. This is when we enter the “lost in the sauce” portion of our scheduled programming.

Turns out, we were trained on quantifying the validation of our existence.

When the quantification of success feels good, like gold stars on your 4th grade math test, or straight As on your report card, you start to look for more arbitrary “challenges” to fill this gap. Give me more more more. Tell me I’m good! Tell me I did it! Tell me I’m everything I should be!

It may sound pathetic, but it is simply the internal monologue we are trained to seek out for the entirety of our 2+ decades in formal education and then are shocked that it is our default.

You look for more and more opportunities to prove your worth, until you’re left in the middle of self-imposed deadlines, feeling muzzled by your own commitments.

It isn’t fun anymore!

Because it’s all just for the arbitrary metrics.

Isn’t this just the cost of our cage?

Relentless discipline without reflection can get you speeding in a direction, realizing you forgot why you got in the car in the first place.

We lose autonomy. We lose silliness. We lose the actual reasons we started things.

What would you be doing if you did not have to report, not to adhere to a schedule?

Would you be more creative?

This is exactly the pattern I’ve realized on to Substack.

I miss leaning into bleed onto a page in a way that brings peace. To connect. To create something that feels alive.

Grit and commitment are important skills, don’t get me wrong. When structure becomes a cage, when we’re cutting pieces off ourselves just to fit into our own frameworks, we’ve lost the plot.

So let yourself out.

The Rule of 52 is a way to build self-trust. To bring rigor to passion. To move from a place of “I wish” or “maybe in another life” to “I can, I did, and I am proud.”

So let this piece serve as a reminder that structure doesn’t have to be a cage. It can be a container that holds space for the work while leaving room for breath, for deviation, for the ideas that emerge between the lines. You have permission to break the process. To change it. To flip it up-side-down and try something new.

You should actively try to, as it likely is going to bring out better, more creative, and hell, probably more fun parts of yourself.

Give yourself permission to step outside of what is inherently “the right thing” or the “what you should”. Remember your autonomy. Remember silliness should be an active part of your day-to-day life. Understanding what fun is to you and how to curate it is probably one of the most underrated, and most important things to figure out in your life.

Success doesn’t always need to be quantified. You cannot derive self-worth from an arbitrary metric. Your worth comes from finding out and enjoying who you truly are.

The cage door is open. You built it. You can walk out of it whenever you’re ready.

Super excited to mix in a few solo pieces in addition to the 52 Coffees project because I MISS YOU my lovely readers and excited to connect on a bunch of topics rambling around in my head after the coffee chats :)

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We don’t smile as often in the hallways of our apartments.

We don’t know our neighbours.

We keep contained within our own walls of convenience.

But that doesn’t mean we want to be treated that way.

How often are we sitting beside strangers when we both crave connection but don’t take the opportunity?

It reminded me of my piece from January 2025, “Why are we experiencing more loneliness?”, where I outlined:

“Maybe the solution is more straightforward: organizing more opportunities to bring people together for casual conversations and connections. But then I started asking an even deeper question: Do people want casual discussions anymore, especially with strangers?

While that idea in isolation may sound odd or uncomfortable, these serendipitous conversations can increase our sense of belonging and community. Discomfort, after all, is something we can avoid in today’s world, but should we? I’d argue no.”

The winter blues brought up similar reflections this January as well. Fewer degrees and a couple extra feet of snow will do that to you. But then, I stumbled upon a video of someone doing trivia on a TTC bus.

For those unfamiliar, the TTC is Toronto’s (somewhat infamous) transit system. It has iconic red streetcars, red fabric-covered seats (seriously, why fabric????), and everyone who’s lived in Toronto long enough has a story about it. But here’s what the TTC isn’t: a place where strangers talk to each other.

The TTC is silent. A crowd of people avoiding eye contact, staring at phones, especially since they added 5G service in 2023. Before phones, it was newspapers. Transit has never been a place to strike up a conversation. It’s point A to point B, nothing in between.

Which is precisely what made @itsmagneticmj’s TTC trivia stop me in my tracks. He was someone actively choosing discomfort, walking up to strangers in one of the least social spaces.

I needed to meet him. I needed to know why and how he was getting up the courage to make these first moves.

One cold DM and one cold walk to a Toronto WeWork later, I was sitting across from the man himself, Minjae.

The Man Behind the Message

Most of Minjae’s content is him going up to strangers, giving them a compliment or a quick well-wish.

It often begins with someone being shocked, silent, or taken aback, but it can end with a smile, a quick conversation, and a genuine “thank you”. You can read more about Minjae’s impact in his interview with CTV here.

When I cold DM’d Minjae to participate in 52 coffees, I had a slight concern in the back of my head: “Is this guy actually confident, or is this a facade?”

Any doubt was quickly squandered as soon as we met face to face. Minjae had an immediate warmth. In how he spoke, chatted, and toured me around the WeWork, I immediately knew there was no separation between who he was for the internet and who he was as a person.

I kicked off our conversation over coffee by asking Minjae if he’s always been able to talk to strangers with ease, and he said:

“I would say I got that gene from my grandpa. He was a really social guy and was really well-connected back in Korea. So I’ve always had that since I was a baby, and throughout elementary, high school, and university.”

Like many of us after leaving the structure of education, Minjae went down a winding road to find himself. He detailed his journey, including setbacks in the corporate world, attempts at various entrepreneurial ventures, overcoming personal challenges, and building confidence through self-improvement.

I was curious about Minjae’s ability to find the grit and resilience to keep picking himself back up after these setbacks. He said he knew he was a dreamer and a stable life didn’t attract him initially, but he soon realized that stability was a necessary precursor to a healthy mentality. He went on to describe a key turning point,

“It just started hitting me, because I started becoming self-aware of how it was affecting my family and how they view me, not just myself. I started realizing I was putting them through a lot of stress because they just want the best for me.”

When your decisions start affecting other people, it influences how you start showing up. For Minjae, this meant seriously nurturing what was beginning to grow: his social media following. He was diligent and consistent, and he chose to show up, even on days when he didn’t feel as confident as he exuded.

His ability to get back up and start again is ultimately what has led to some of his most viral content. As of today, he has amassed over 200k followers across platforms. These are huge metrics, but they are not what keep Minjae going; instead, he is driven to show up and share positivity in the Toronto community and beyond.

The Politeness Trap

We’ve normalized something strange: we’re all craving connection, but we’ve convinced ourselves that initiating it would be a burden.

Minjae’s content is a mirror for his own self-confidence, but is also a mirror for all of us. The content is straightforward: kind gestures to strangers. However, in our world where connection is fulfilled through our online communities, in-person serendipitous conversation is few and far between.

We may default to thinking it’s that damn phone, but really, I think it’s because we are scared to be a burden to other people. We assume silence equals politeness, that holding back shows respect for others’ boundaries.

Annaliese Todd calls this “the politeness trap” in her piece about the disappearing “small favour economy”:

“Our current social norms have created ‘the politeness trap.’ We’ve become so concerned with not imposing on others that we’ve actually made it harder to form meaningful connections. When we refuse to ask for help or offer it spontaneously, we’re inadvertently signalling that we don’t trust others to set their own boundaries. But here’s the thing: people generally want to help.”

Take 30 seconds to scroll through Minjae’s comment sections, and you’ll see what people are actually craving:

“I hope someone gives me this energy,”

“I wish I had the confidence to do this.”

People aren’t bothered by his acts; they’re actively craving a part of it in their lives, too.

Minjae’s sincerity is what makes it work. When I asked Minjae how he stays authentic while building a social media following, he said the data shows you which content performs well. It’s easy to lean into its patterns; however, whenever he tried to replicate what worked, whether consciously or subconsciously, it would fall flat. When the sincerity is gone, the message no longer resonates.

This matters because we’ve grown up in a world where vulnerability and community have been co-opted by corporations trying to market to us. That’s why some moments feel icky, why content feels weird, why we go into experiences expecting sincerity and leave feeling empty. We can sense when a connection is transactional.

Breaking these norms requires showing up without expectation. Small steps, such as offering a compliment, making eye contact, or initiating a brief chat, actively build trust and connection by rejecting the idea that conversation is a burden. These simple actions can serve as practical ways for readers to foster authenticity and community in their daily lives.

Pouring From a Full Cup

Putting yourself out on social media opens you up to being perceived by a massive audience, but in some ways, it can feel safer than putting yourself out there in front of strangers face-to-face.

I asked Minjae, “Have you learned more about being perceived from getting out of your comfort zone virtually or in person?”

His answer surprised me, as it wasn’t just one or the other, but the act of being perceived in both settings just taught him one thing: the importance of the relationship with himself.

When he first started posting content, and people reacted positively, they’d say things like “I love what you’re doing, I think it’s hilarious.” Minjae reflected that this reaction often gave him pause. From his perspective, he was just exuding confidence and charisma, not trying to be funny.

Through this journey of being perceived, he has learned to hold others’ perspectives without letting them define him. To stay true to himself and still show up authentically, regardless of how others might perceive it. They’re entitled to their own opinion, and that’s okay. For Minjae, this confidence was earned. He knows the work he put in to build his ability to show up and talk to strangers, to give without expecting return, and that is what he grounds his work in.

I asked Minjae for advice on how to improve confidence and begin this journey of giving back to the community, for both his audience and mine.

Surprisingly, his first recommendation was “take care of your health.” He noted that he can only show up authentically because he takes care of himself.

His recommendation made me think of the metaphor we often use about relationships and self-care: pouring from a full cup. To give without expecting anything in return, you need the energy, resources, and mental capacity to care for others without burning out. You cannot effectively support, love, or help others if you are physically or emotionally depleted yourself.

We see Minjae complimenting strangers on the TTC and think it’s just about confidence or extroversion. However, the foundation is much more practical: he has built a life that fills his cup, so he can pour out the excess to others who need it.

Maybe that’s where the rest of us need to start.

If we want to break the silence, to reject the politeness trap, to create the serendipitous connections we’re all craving, we first need to return to that small favour economy to fill ourselves up, so then we can continue to give.

Each day is an opportunity to put back out into the universe, and as Minjae has exemplified, these efforts compound over time.

As we finished our talk, Minjae said, “Good things take time, but great things can happen all at once,” and although he is in the moment of receiving the great, he doesn’t want to lose the mindset that brought him here.

Throughout this journey, he hopes to stay grounded, show up as himself, and continue the mission he started: giving to others without expecting anything in return.

Take some inspiration from Minjae this week. What can you do to share positivity with a stranger? Could you contribute to the small favour economy?

Introduce yourself to your neighbours?

We’re all human. We need connection. I sincerely believe that we miss each other. We miss the ease that connection once had before it was more “normal” to be silent.

So, make the first move this week. Not out of desire to get something in return, but rather out of deep care for another person that you wish to create some solidarity with.

Thank you so much to Minjae for taking a chance on a stranger and my project 52 Coffees! If you’re interested in getting involved, email me at bykstubbs@gmail.com :)

It began as a “like my status for a tbh,” and now it’s delivered to us through algorithmic feeds and LinkedIn “I’m happy to announce” posts that we all collectively cringe at… and then proceed to post.

However, it is not our curated Instagram profiles, but rather our self-confidence, our conviction, and our “aura” that truly sets us up to foster genuine connections out in the wild.

We spend so much time shaping our online personas that we forget how vital it is to nurture our in-person skills, such as charisma and conversational abilities.

I realized how far these skills can take us into new rooms and open new opportunities, whether personal or professional, when I met the 52 Coffee’s guest this week, Megan.

Authenticity through self-conviction

You know that feeling when you’re at a party or a networking event, you’ve had a few conversations, met some people who chat a lot, and others that, well, you’re mostly leading the discussion with.

It reaches a point late at night when you're starting to feel that wave of exhaustion. You feel compelled to sit down. Depleted.

That was me last Friday night. I was out on the town at a local networking event. There was a deep hum of conversation spreading across the restaurant, with people from all walks of life crammed together in the dim orange light coming from the neon bar rail.

At one point, someone shouted, “Oh, look, the Easter Bunny is here!”, only to realize it was not, in fact, the Easter Bunny, but a massive life-sized Labubu.

I can’t make this up.

It was about that time of night when I was about to sneak back into the dark January evening, as I made my way through the crowd, and I eventually said a quick “Hello!” in passing.

I didn’t expect much from the conversation until we moved beyond the pleasantries, and I found myself captivated. Megan quickly introduced herself and immediately began matching my energy. She was charismatic, confident, and genuinely engaged in our brief chat. As the waves of people moved around the room, we eventually lost sight of each other. '

However, even after I had sat down for dinner on the other side of the restaurant, I couldn’t shake the feeling of a pull towards her. I quickly ran back in and asked for her number so we could grab a coffee… the first of the 52 conversations I would have with someone who could be considered a stranger.

When we sat down to officially get to know each other on a casual Sunday afternoon at a cafe, her energy was just as contagious.

We chatted about lots of things until it was time to deep-dive into the topic she hoped to share for 52 Coffees: authenticity.

Megan shared how habits like meditation, journaling, and setting boundaries can help build self-trust and authenticity, encouraging the audience to see these as achievable steps. Often, especially in the age of social media, the expectation is to share constantly, which can negatively affect how we present ourselves in certain situations. Megan specifically spoke about:

“I don’t necessarily think you bring your whole authentic self to work. There’s always a different persona you adopt in different environments. There’s times that you don’t want to fully bring 100% because you want to protect some of your own likes, dislikes, experiences.”

It’s interesting to think about how we can protect our own taste. It reminded me of a Substack I read recently called “Your Taste Should be Private”, which succinctly sums up the difference between our innate taste and the taste that is a product of the Recommendation Economy:

“The difference between Personal Taste and Public Taste. Personal Taste is dependent on something you might not even be totally aware of, an essential relationship, irreplicable but imitable. At the same time, Public Taste is an attribute aggregated from social and personal values. Public Taste is what the Recommendation Economy runs on—it insists upon itself. Personal Taste is what makes something interesting. Public Taste is saying you get your haircut at Shizen. Personal Taste is some guy named Peyton asking his friend Marta, who is cutting his hair, not to make him look like “the kid from Holes.” Public Taste is what feeds the algorithm, but Personal Taste is what feeds the soul.”

So, are you feeding your soul? Or are you being fed your “Taste” through a curated algorithmic feed and assuming it is something you believe in yourself?

With the rise of LLMs that feel like a friend recommending things to you (especially as the vocal capabilities become more seamless!), it becomes harder and harder to understand what matters to you because of your personal experiences (irreproducible!) vs. public popularity (surface-level as hell!!!)

When we are constantly bombarded with products in a never-ending cycle of 'want, need, changed X person’s life,” where ads, cinema, and art become blurred, it becomes hard to distinguish what we truly like from what we are actively being convinced to endorse.

Selective sharing & consuming

As Megan and I got to know each other better during our lovely coffee date, we began talking about her decision to delete her social media accounts. When I asked her about her reasoning, she said:

“I realized I would post pictures looking specifically for validation. And then I realized this is why I’m giving people power over me, and I don’t want to; I want to have that power in myself.”

So succinct and clear, yet often overlooked by most us.

How often are we sacrificing our power simply because it is a habit?

When we talked about authenticity in my relationships, she noted,

“Sometimes we get so excited in the heat of the moment, we just talk, but then sometimes you have just to think before you speak... is this something I genuinely want to share? Am I just sharing it because I want to feel connected?”

Maybe that’s why we feel so depleted after some conversations at networking events: instead of coming to listen, we sometimes just want to hear ourselves talk.

When things feel one-sided, we come with the intention of walking away as though we're “connected”, but we don’t actually connect. The LinkedIn requests sitting in your DMs don’t actually count for much.

It is a common, innate human need to want to connect. Especially after COVID, we have all felt a bit rusty in social settings.

Let’s be honest with ourselves, it can be weird.

But, it’s supposed to be weird!!! Because we are human!!!

While embracing this weirdness might feel vulnerable or uncomfortable at first, it’s a vital step toward genuine connection and self-confidence, and it’s worth the effort. Real life is not curated; it is experienced.

Stop expecting perfection. Like any skill, socializing, being charismatic, or working a room well takes time.

The foundation is always self-belief.

“Believe in yourself” is a cliche, but also probably the most important lesson to learn in adulthood. The posters stuck on your grade 3 classroom’s wall were right all along.

To get out of the stuck-ness, we need to reflect and unlearn our limiting beliefs, which Megan outlined as,

“People putting themselves in a box.”

Reflecting on her own personal experiences, she noted:

“I used to tell myself for the longest time, I’m not a morning person, but that’s a limiting belief... You could be anyone you want to be, truly, but you limit yourself by telling yourself that you can’t.”

The act of denying the ability to change is the most significant barrier to one’s self. What is often now framed as being “delulu” can be a trick to make yourself into your own biggest supporter.

We often assume that people are born a certain way. Some have faced situations that have shaken their confidence from a young age. Others have developed this strength and actively use it every day.

But remember, it is precisely that, a muscle. Use it, or lose it.

When you stop seeking external validation and develop internal conviction, you reclaim your power. You know what’s authentic to you. Your actual personal taste becomes clear.

Authenticity isn’t always about bringing your whole self to every situation. It’s about knowing what’s truly yours and being selective with it.

Those grade 3 posters told us to “be ourselves,” but they made it sound simpler than it is. Being yourself is an ongoing practice of self-discovery.

When you feel depleted or uncertain, return to what you know to be true, even if that means riding a bike because you liked it as a kid. Do the small things: the meditation, the journaling, the quiet moments that help you build a relationship with yourself.

Life is a series of self-discovery, happening again and again and again. Each time you find a way to return to yourself, you get a little clearer on what’s yours. That is power.

Thank you so much to Megan for taking a chance on a stranger and my project 52 Coffees! If you’re interested in getting involved, email me at bykstubbs@gmail.com :)

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This week, I sat down with someone who has shared many conversations through the highs, lows, and uncertainties of our own career journeys, navigating these “shoulds,” “cans,” and “wills” together since our time in university. Happy Tuesday, it’s time for you to meet my dear friend, Nate Thomas.

Doubting a lack of depth?

Is what I’m doing right?

Have I taken the wrong path?

What move will set me up the best?

Any ambitious young person is all too familiar with the self-criticism that can come with navigating life decisions. We constantly evaluate the choices we’ve made, the options we could have taken, and, often, our own harshest critic: our internal monologue.

Nate and I met at university, and he’s the type to always have insightful commentary—whether it’s about the state of the world, professional matters, self-development, or the new band he’s found. He’s an extremely perceptive guy, which we can also attribute to his curiosity.

Our conversation started with talking about breadth versus depth; the idea that in life and in professional settings, there’s interest in being a generalist, someone knowledgeable in various areas with a range of skills, hobbies, and interests, or on the contrary, a “subject matter expert” (SME), someone who has gone very deep into a specific area of expertise.

When reflecting on his own experiences, with both professional and personal interests, Nate had the following reflection:

“I have a ton of variety… every interest I’ve ever really had, I like it for the variety… but then I also just… doubt it, like, oh, I haven’t really done one particular thing at a super deep level.”

There is a lot of cultural pressure to find “your thing.”

That special space where everything clicks, the birds are singing, and you wake up every day living, breathing, and obsessing over your passion.

Is this realistic? The jury is still out.

Still, especially for young professionals, that pressure persists, as being a “generalist” is often acceptable for the first few years of your career, but eventually you’re encouraged to specialize more and more, often aligning with the “up or out” culture common in prestigious jobs like management consulting firms. A book Nate mentioned, Range: Why Generalists Triumph in a Specialized World, by David Epstein, examines top performers and finds that early specialization is the exception, not the rule, for leaders in their field. Juggling many interests can actually make you more creative and foster your ability to see connections that more specialized peers can’t.

So, what happens if you get bored easily, enjoy exploring, and genuinely want to find depth in more than one domain?

Welllll, I’m glad you asked!

Breadth is data, not necessarily a distraction

When did exploration become a sign of uncertainty, instead of a way we can find joy?

Think back to when you were a child. You weren’t discouraged for trying out different stations in kindergarten day in and day out.

Our brains, more specifically, our dopamine, absolutely love novelty. According to an article by Alane K. Daugherty, Ph.D., on the Science of Novelty:

“A sense of novelty activates the dopamine system directly. As a result, it enhances mood, positive outlook, motivation, and goal setting. A positive sense of novelty has also been shown to increase creativity in dealing with stress, lower perceived stress, and anxiety, and lessen depression.”

So, why don’t we treat variety and our breadth of experiences with the same value we give depth or expertise?

The thing is, variety without active reflection can be viewed as simply a mixed bag of experiences. It is one thing to be curious about many things, but it is also important to determine what piques your interest and what does not.

At first glance, your scattered interests may appear random. You’re in a position where you can’t see the forest for the trees. Your brain is only looking at minor details and not taking the time to zoom out and evaluate the bigger picture, or what all of these interests together can collectively mean for you.

I asked Nate: “Is depth an indicator of passion?”

Which made us both pause.

To be interested in something, to find it fascinating, or to be passionate about it, do you need to dedicate all your time to it for a long period? What if your passions lie at the intersection of many different things?

Passion is not one-dimensional. It is not limited to expertise. It can reveal itself as a pattern across multiple environments, which, to explore, requires a broad range of experience.

Beyond the self-exploration case, there is practicality in gaining these signals in a breadth of experience.

1. You become more adaptable: A range of experiences allows you to drop into new contexts, giving you an opportunity to ground yourself in what is consistent across them. That pattern recognition is powerful. It can be the first step toward trusting yourself and your critical thinking.

2. You develop mental models, not just narrow playbooks: Complex problems, the more you encounter them, require you to rely on frameworks to kickstart your thinking. A skeleton gets you moving, but the willingness to break and rebuild that framework is crucial. As you engage with different contexts, you become less dependent on repeating the same playbook. You actively seek to challenge and disprove ideas to produce better outcomes. (Clear Thinking by Shane Parris includes an example of a framework that involves removing constraints to think beyond a problem.)

3. You become harder to displace: Narrow expertise is becoming commodified. Nate and I discussed the merging of roles (product managers moving from writing documentation to writing documentation and creating initial prototypes to gather feedback before presenting their suggestions to engineers). The ability to leverage your breadth of experience, your willingness to brainstorm and develop, and to understand human motivation are all essential skills, even with the uncertainties about how AI will influence the future of work.

So, what’s your throughline?

In my conversation with Nate, we spoke about his many interests: everything from self-development to badminton. His love for product management comes from the need for constant context switching. One moment, he is deep in security issues, the next, he is choosing a colour for a feature. The thing is, sometimes we need to give ourselves permission. So consider this a way to start: Passion doesn’t have to be about a specific subject (finance, art, athletics). It can be about an approach: how you think and learn, what you’re developing within yourself, and the patterns you notice.

However, this approach isn’t something that happens out of the blue. Nate emphasized the importance of building the scaffolding that gets you there. Through constant context switching, he has developed a repeatable method for learning and documenting insights for personal reference. This skill only grows over time. As you refine your approach to problems, it will likely reveal more about yourself, guiding what truly interests you each day: how to approach problems, the thinking you bring to your guests, customers, clients, co-founders… everyone!

Experience is only wasted when you see it as a waste. When you view breadth as a weakness instead of something you can use to critically reflect upon, it can inform both your decision-making and your self-perception.

So, the invitation this week is: What’s your throughline? What appears regardless of the domain? What remains consistent across different contexts?

You can (and should) muster up the grit and focus to commit as much as possible to the experiences you participate in, but blind focus is just that... blind. We learn most about ourselves when we are actively engaged in the process.

The process might involve gaining deep expertise, but it can also mean fumbling around and discovering along the way.

Both are valuable pathways for professional and personal growth.

I hope you enjoyed this new version of “The Rule of 52” for 2026: 52 Coffees! A huge thank you to Nate for participating this week :)

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That’s what this 2026 series is all about: finding the beauty in the mundane, curiosity where we typically find normality, and re-engaging with the joy of conversation.

You build (or break) trust with yourself every day

If you’ve never met Eric Molnar, he does have a certain presence about him. Not only because he’s tall, or is willing to be the loudest one in the room (he once used tear-off pants and the YMCA dance to win a student election), but because he is willing to give a 100% to anything he is doing.

To the conversation he’s having with you.

To the project he’s doing a deep dive for.

Given his sub-3 marathon attempts, which push his physical capabilities to the limit of conscious awareness, it is difficult to gauge his level of grit. My first area of intrigue to explore is how he accesses that next-level gear some people never get to, I asked: “Do you have a secret sauce of like, how you access that, that grit, that diligence, that determination parts of yourself?”

Eric responded with:

Over the years of staying committed to yourself, you develop a kind of trust, like a partnership. Whatever I commit to, I won’t stop until I succeed. If you'd asked me a few years ago, I’d say I had commitment issues, not in personal relationships, but in goals. I wouldn’t want to commit to something unless I was completely convinced. I find it easier with physical goals because then I just ask myself, are you 100% committed? If yes, it becomes undeniable.

When I knew I would finish a marathon, I was more concerned about how much it was going to suck than about whether it would be completed.

The re-framing of eliminating the question of completion is interesting. When we set lofty goals, whether they be personal, professional, or physical, it is easy to start visualizing the off-ramps you are giving yourself. If something is difficult, you want to be able to land somewhere safe. Committing to something that feels daunting without any safety net puts you in a position of great disappointment if it is something you don’t achieve. However, if you are already thinking negatively about the outcome, you’ve already lost. The first step is visualizing yourself already at the finish line.

Eric’s physical goal has been to run a sub-three-hour marathon. Lofty? Absolutely. Difficult? Extremely. According to data from the 2010 Marathon Guide, only about 2.8% of male runners finished in under 3 hours. He outlined the following about his rationale for this goal:

The perfect example is the sub-three marathon. The reason I want that to be a goal of mine is that part of me will always believe that I can’t do it. You’re naturally going to have that part of you that is hesitant and doesn’t really believe you’ll ever do it.

Still, even now, part of me believes that if you asked me three years ago, that belief would be even louder, like a voice in my head, because I’ve now been able to prove that I can actually get pretty damn close to it.

But three years ago, I would have said, “Absolutely, there’s no way I could do a sub-three marathon. “ The whole reason I’ve committed to this goal is to prove to myself that some things I believe are impossible are actually totally achievable.

I think there is a myth around goal-setting and high achievers that some people believe those who accomplish these goals are more confident. However, genuine self-belief comes from doing things that you once thought were impossible. It is through these efforts that you learn how to quiet the voice in your head (that is always there), that it is simply a voice in your head. By actively pursuing things that feel incredibly challenging, you learn that the true power you have lies in your action and your ability to work in tandem with your own brain, rather than have it working against you. Each day, you work to build a testament to yourself that you should believe in yourself, or work against yourself.

Eric referred to David Goggin’s concept of “the cookie jar”. A common misconception is that people believe what is in the cookie jar, or what you pull out to remind yourself of your capabilities, consists only of your successes, the times you felt good about yourself. However, that jar also holds your life failures, alongside your accomplishments. These are the things you can use to prove to yourself who you are at your core, serving as a mirror when intrusive negative thoughts become overwhelming. It’s a way to quiet the inner voice.

Consistency in showing up and building the cookie jar is how you make your self-confidence. Outlined by Eric, he describes commitment to yourself as the same as how you may frame it in a romantic relationship:

I’ve come to the conclusion myself that, yes, I’m committed to the sub-3-hour marathon, I am super determined to get it done, but you can’t do that for everything. You can only have a limited number of those things, or else it’s like the idea of trust. Yeah, in the relationship you have with yourself, or else you’re going to be lying to yourself, yeah?

If you lie to yourself enough, just like in any relationship, if you lie to them enough times, the trust will be lost, and then it’s really hard to rebuild that trust.

What does full commitment look like?

You may be thinking to yourself, “How can I find the thing I want to commit 100% to?” “Where do I start to build a cookie jar?”

Ultimately, the first place is reflection. We all have hard things we have overcome in our lives, and that can be the foundation of your cookie jar. The next thing is small efforts you can take to show up for yourself.

Did you say you were going to be a morning person? Show up by not snoozing and following through. You’ll begin the day with a win.

Did you want to host that event with friends? Put it in the calendar. It’ll force you to follow through. Put the ideas into action. The execution will build your cookie jar — and your confidence.

Eric reiterated over our coffee that energy is limited. Giving 100% to a goal means being strategic or selective about what you commit to fully and what you hold back on. Like many times at the start of the year, we want to do everything, everywhere, all at once. We feel compelled to reinvent ourselves over and over.

So, we must ask ourselves, is this being fueled by ego, or does this push to do something new align with the person I want to be? Who are you really doing this for?

Give 100% to uncover your true path

When Eric and I first met, he gave me a tagged version of his favourite book, which is also the cover art for my piece:

The Alchemist by Paulo Coelho is Eric’s favourite book and one he has recommended to countless people, many of whom have shared that it has changed their lives.

The concept that has resonated so profoundly with Eric, to the point he has it tattooed on his right bicep, is maktub (مكتوب), literally meaning “it is written”. In The Alchemist, maktub is a phrase repeated by many characters throughout the book to convey that something is “meant to be”. When I asked Eric about his personal interpretation of the phrase, he outlined:

The book The Alchemist discusses how life is written for you. You need to follow your heart; your personal legend is waiting for you.

So, my perspective is that maktub means following your heart. If you’re not, if you’re attracted by ego, money, or anything else that’s not authentically you, then you’re not on that path.

You’re not on the path that is written for you. You’re onto a different one.

Now, the idea that you must learn how to challenge yourself to build up your self-confidence, your personal relationship with yourself, your internal “cookie jar”, can be viewed as quite different from maktub, which often encourages you to have faith in your journey. But Eric and I, after some more reflection, found that they are actually quite similar. Eric noted:

My perspective is that overlapping these ideas means that, as long as you’re giving your 100% in everything you do and in how you present yourself as a person, each day you are on that true path.

If you reach a point where you’re not giving your 100%, like if you hold resentment for a project you’re working on, a job you’re in, or a relationship you have, you’re not truly engaged. These are signs that, hey, you’re probably not giving your best, right? For example, you’re on a really lousy project at work. You don’t want to be there. You’re unlikely to be your authentic self: keen, motivated, and fully committed, even if you’re giving 100% of your effort. That’s an indicator that this might not be the right path for you.

It’s a sign that you need to figure out how to give your best. So the overall message is: instead of blindly following your heart, you should find a way to align your efforts accordingly.

His explanation: that the true path will be easier to give your 100% to, reminded me of another comment that was made about faith by Kerry Washington. She said that you pray to catch the bus, but then you run as fast as you can to catch the bus.

Watch the full video below:

It feels comfortable to overshoot the expectations that fate has for our lives. It takes the accountability off your shoulders. However, we must remember that if we didn’t run as fast as we could to catch the bus — to achieve our dreams, to make what we have longed for happen — then that could be our path.

Rejection is only redirection when you know, deep down inside, that you gave it 100%.

A last thought

I hope you enjoyed this new version of “The Rule of 52” for 2026: 52 Coffees! A huge thank you to Eric for being the first one!

If you or someone you know would like to sit down at some point over the next 51 weeks for a coffee to share some stories, reflections, or life lessons, or even something as casual as a hot take, please send me a message on Substack or email me directly at bykstubbs@gmail.com :)

Also, if there is something you are committing to, once a week, for an entire year, I want to hear from you! I recently launched my Substack chat, so we can support each other as we strive to abide by The Rule of 52 in 2026. A big shoutout goes to Elizabeth for her ambitions to start a Substack and to Lorraine for her hopes to live with more intention. I’ll also be posting more high-level takeaways on my Instagram @bykstubbs if you want to follow along there, too!

Looking forward to what’s ahead in 2026!!! Chat soon :)

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