At one point, my brother and I were running around in nothing but our underwear. I was six, my brother was four, and the carpet in our new apartment was damp from a recent cleaning. We realized we could run and slide around like thieving baseball players from one side of the living room to the other. We did it again, and again, and again.

My mom saw we would not stop anytime soon and saved the rest of our clothing from being ruined. By the time we were done, our white underwear was the same color as the burgundy red carpet.

I’m 38 now and childhood memories like those are taking on dual perspectives. I can remember the fun we had and I can imagine the disappointment my dad would’ve felt signing the lease. He would’ve been a year older than I am now, and this third-floor apartment was the best he could afford as a dry cleaner. The bigger house in the better neighborhood would have to wait another 10 years.

If I could step into my memory and walk over to my 39-year-old father, I’d put my hands on his shoulders and say, “Dad, thank you. This place is great. I’m already having so much fun here.”

“Is it though? I should have provided so much more for you. I’m sorry this is all I can do.”

“Dad, why are you sorry?”

“I could have done so much more. I should’ve done so much more. I’m not a dumb person, you know. If my life was different, I would have done bigger things. But I’m sorry this is the best I could do. Don’t do what I did. Don’t make my mistakes. Do better. Dream bigger, Minnow.”

For as long as I can remember, that was the one consistent advice he’s given me: dream bigger. “You can do anything you want, so dream big. If you fall, I’ll always be here to catch you.”

I trusted he’d always be there and that has been a dam to the rapids of any anxiety or fear I had when I started my creative journey. But it wasn’t enough he’s be the last man standing for me.

What I needed was an example of what it looked like to dream big, but he always held himself as the example not to follow. When you’re a child, you learn from what people do, not what they say. You can’t think or act in the inverse, and my dad told me stories of his regrets, hoping I did the opposite.

The other night, my wife and I had dinner with my parents and he started telling us stories about his college years. I was surprised because he’s never talked about that time with us before.

He’s told me stories about his life before college, about how my grandfather’s business went bankrupt and they could only send my father to college. He told us stories about his life after college, about how he became a teacher and met my mom there, but never those in-between years.

He went to college during the late 1980s when South Korea was under the rule of a dictator. Korean citizens were being jailed and killed by the government. My dad attended Yonsei University, and he led demonstrations protesting against Park Chung-hee. He couldn’t believe his friends were being arrested and killed. He couldn’t sleep knowing other Koreans were being jailed and killed. He couldn’t understand how other people just lived their own lives, not caring about what was happening.

At one point, the government put him on a blacklist because of his activism. He never went to his college graduation for fear of being arrested. He instead escaped south back to his hometown and stayed there until a mentor of his arranged for him to become a teacher at a junior high school in Seoul.

It was there he met my mother, and married her in 1979. That year, Park Chung-hee was assassinated and Chun Doo-Hwan, who was worse than the first guy, took over as dictator. He couldn’t stand to be in Korea any longer, and that’s when he emigrated to the States.

I wish he told me these stories of activism when I was younger. I wish he told me about his big, beautiful, audacious dream of a just government that treated its citizens fairly. There was no one to catch him when he failed, and yet he gave his best years for that dream. Fifty years later, he couldn’t talk about it without crying.

My dad is turning 70 this year, but he’s young at heart, still wanting to learn and grow. We genuinely enjoy each other’s company. His humor is so corny it makes me cringe. He pranks my mom every April fool’s day (she’s as gullible as he is corny), and I think he’d slide around on a carpet in his underwear with me if I asked.

As I’m getting older, building a friendship with my dad has been a gift. He’s someone who did the best he could for me and our family. He’s spending his later years reflecting and understanding what he could have done better. Whatever example I wish he set for me when I was younger, he’s showing me today what it means to be young at heart, and continue to be curious and always learning.

I’ve always told people my personality is my mom’s and my face is my dad’s. But I’ve received his compassion, courage, and fire as much as his smile, his eyes, and the size of his head.

But the greatest blessing is how our values and beliefs resonate on the deepest levels of who we are. What he’s instilled in me growing up has now become my identity and a dream, a big, infinite dream inside of me.

As I slowly come to terms that there is, at most, 30 years we have left together I’m going to make it a point to share my big dreams with him: the dream to do courageous work and to support others who are doing the same to mend what is broken around us.

I’m reading this book by Susan Cain called Bittersweet and she starts with a story about the death of 22 people during the civil war in Sarajevo in 1992.

They were killed by a mortar shell as they were lined up in front of a bakery for bread. Vedran Smailović, a cellist who lived nearby, came out the next day dressed in his concert attire and played Albinoni’s Adagio in G Minor. He would play for 22 days straight in front of the bakery. The fighting was still going around him yet he continue to play.

My question is, why?

In the face of such horror and death, playing classical music feels like the least important thing to do. For you, the least important thing to do may be a drawing a picture, or designing a website, or building a company. For me it’s writing; doing this very thing you’re reading right now.

Cain calls what we are feeling: This pain of knowing this isn’t the way it’s supposed to be and the longing for things to be better, bittersweet.

Smailović also felt this, but why did he respond by playing music? Put another way, why should we keep showing up and doing our creative work?

Cain’s writes this feeling of bittersweet isn’t just a momentary feeling.

It’s also a quiet force, a way of being, a storied tradition–as dramatically overlooked as it is brimming with human potential. It’s an authentic and elevating response to the problem of being alive in a deeply flawed yet stubbornly beautiful world.

Most of all bittersweetness shows us how to respond to pain: acknowledging it, and attempting to turn it into art, the way the musicians do, or healing, or innovation, or anything else that nourishes the soul.”

…If we realize that all humans know—or will know—loss and suffering, we can turn toward each other.”

Yes, we need policy change. Yes, we need to protect the ones most vulnerable. But we also desperately need to help each other process and heal.

And so, I want to encourage you (and myself) to keep creating, to keep building, to keep doing the work you feel called to do.

Keep creating and sharing your art because that’s how we feel less alone, how we connect with each other, and how we feel a deeper sense of belonging.

This past week marks two years since the pandemic pulled my photography career from under me. Tens of thousands of dollars worth of client work vanished. My decade plus career of taking photos turned into filling out forms, and calling the Department of Labor hoping to qualify for unemployment benefits.

I found coaching four months later in July of 2020. I love coaching. I love the people I work with. And as photography has started to come back after it’s forced hiatus for two years, I wondered if I should just focus on coaching. Could I serve my clients better by letting go of photography and going all in with coaching?

I’m glad I didn’t give any final answers, because as I’ve started doing more portrait sessions, I’m seeing how well portraiture and coaching complement one another.

During a portrait session there’s a flow I enter into as I search for the moment when composition, good light, and energy come together. In that moment, that fraction of a second, I’m trying to capture the subject’s unique inner beauty—to make what’s unseen, seen. But without their participation and permission that moment will never present itself, no matter how hard I look. The space we’re in together has to be safe enough to let those hidden traits come through.

It’s the same thing with coaching. If portraiture is about bringing out someone’s photogenic potential, then coaching is about bringing out their creative potential. And each person’s creative potential is unique—whether it’s creating a consistent practice, shifting their mindset from scarcity to abundance, or coming to terms with feeling like an imposter. You need a safe space to wrestle through whatever’s getting in the way of unleashing these unseen forces to create life-changing results.

I recently had a portrait session with a coaching client who was launching her own business. We had worked together for a few months and decided to cap our time together with a shoot and a meal. We had gotten to know each other well as she transitioned into entrepreneurship. All of our calls were over Zoom, and this would be the first time we’d meet in person.

Being in front of the camera is an awkward experience if you don’t do it for a living. Most of the people I photograph find it awkward, and so I start each session by saying, “OK, so the first 10-15 minutes of this is going to feel awkward with this big lens pointed at you, but I promise it’ll get better.”

I probably said some version of that when my client and I met, but it wasn’t necessary. We jumped right into the shoot with no awkwardness or hesitation. The time we spent photographing was fun, effortless, and full of flow¹.

When I sent my client the photos a few days later she texted me, “I’m choking up looking at these photos. Whenever I feel down about myself I’m going to look at these photos to encourage myself. They are so beautiful I can’t believe that’s me!”

I don’t think her reaction was just because she received pretty photos of herself. It’s because the images captured both her photogenic and creative potential—those unseen forces that helped her own her identity as a founder and start a business centered around wellness and empowerment for women.

We usually associate photos of ourselves with special occasions in our lives like birthdays, vacations or what I’ve spent a big chunk of my career doing: weddings. We don’t think of taking portraits to mark milestones of growth in our lives. Part of the reason is because we don’t give ourselves enough credit. We don’t think what we’ve done is special or worth celebrating, when compared to our expectations of ourselves or other other people’s accomplishments. We’re quick to move on to the next item on our list and try to make up for whatever we feel we’re lacking.

Both coaching and portraiture is a way to slow down and take notice of what’s happening in our lives. And while one is a space for us to gain clarity, talk through ideas, and have accountability, the other is a space to be seen, celebrated, and crystalized through a photo.

I’ve done a few more portrait sessions since then, and I’m going to offer portrait sessions to future clients. I’m excited to see where this goes. Just as composition, good light, and energy converge into a photogenic moment, my skills, passions, and the opportunities in front of me are converging into a moment I am uniquely ready to capture.

I feel like time has been moving differently these past few years. Rather than a river, time’s been flowing like an eddy, circling variants, masks, and social distancing. The joke that 2022 is actually be spelled “2020, too” feels all too true. But even with these unpredictable tides, reviewing and planning for the future feels necessary to build resilience and momentum.

If I had to say when this “year” started, it would be March 2020 when NYC shut down and along with it a year’s worth of work, plans, and dreams. Those first few months, I went from planning photoshoots to calling the Department of Labor hundreds of times a day for unemployment.

I had no idea what was in store for me. It’s been a winding journey to a rebirth of my identity, craft, and calling.

In the annual reviews I’ve been doing with clients, we’ve used the retrospective or a “retro” framework. I’ve personally been calling it, “Up, Down, and Onwards.”

It’s a simple, but hard to answer, framework where you answer three questions:

What’s worked (Up)?
What didn’t work (Down)?
How can we improve (Onwards)?

These are my answers to those questions.

Up (What Worked)

Coaching

Once the lockdown happened and the year’s worth of work disappeared, I had to think about what was next.

Ironically or serendipitously, I had started with my own business coach at the beginning of March to help me through the year and what I had to do. Around June, my coach suggested I also try coaching. It’s something I would have never thought of if it wasn’t for his suggestion, but it somehow made sense. In July 2020, I had my first session.

I recently counted up how many sessions I’ve done since then until December 2021, and it’s just shy of 750. What’s worked wasn’t the number of sessions, but how effortless it has been doing that many sessions. When starting something new, the hardest part is getting through the initial volume of work so you can get to the other side of experience, opinion, and vision.

The first 100 were just free calls for internet friends I met at a mastermind group in the summer of 2020. I was finding the edges of what coaching could look like for me.

As I started to get paying clients and going through sessions with them, I realized the most important work I do as a coach is creating a safe space for vulnerability, empathy, and discovery with my clients. I don’t start with an end in mind, it’s more about meeting them where they are and starting from there.

I love embracing the messiness of their creativity and humanity, and make their journey as free, productive and generative as possible. The result is a deep sense of alignment, clarity, and purpose.

Some clients need accountability, while others need a plan of action. Some clients want to be challenged, others want to talk things out. Some clients want me to strategize with them, others need a sounding board to talk through problems.

One client described it as, “After our sessions, I didn’t have homework to do, but I knew I had decisions to make.”

Seventh Week Sabbaticals

I took my first sabbatical in October 2018. The first four were about three days long, but since then I’ve given myself a full week of no obligations every seven weeks. I stopped taking them in March 2020, but resumed again in September and kept it steady since.

Sabbatical isn’t a vacation, as in taking time off from work to travel and relax. It’s a vacation from outside obligations. It’s more about self-directed work and reclaiming agency than it is about leisure. One of the most important projects to have come out of my sabbatical was this blog.

I’ve found resting well in this way is as much of a discipline as any other craft. I was terrible at it in the beginning. But as I’ve committed to it, I’ve built intrinsic motivation rather than follow extrinsic ones. It’s helped retrain my mind to work hard in service of other people, not to keep anxiety at bay.

Taking a Break from Upstream

I heard James Clear say in an interview that writing is like driving a car, and reading is like filling the gas tank. You can drive the car, but at some point you have to stop to fill the gas tank. I’d also add that thinking and chewing on ideas is also gas that fills your tank.

Around August of this year, I felt like I was writing for Upstream just to write something rather than because I had something to say. Giving myself permission to stop was a great decision for me. It’s given me time to refill my tank and rethink how to move forward with my writing. More on that in the next section.

Moving from Basecamp to Circle for Coaching Clients

With the racial reckoning that’s happened over the past two years, a material way it’s affected my business was having to move from using Basecamp for client management to Circle.

I wrote a letter to my clients back in May about why we are leaving. In short, Jason Fried and David Heinemeier Hansson, the co-founders of Basecamp made policy changes banning any political decisions in the company along with any conversation about past decisions. Here’s what I wrote in that piece:

Because Fried and Hansson have the privilege of not having political or societal issues affect their ability to do their best work. They can ban all commentary, move on from past decisions, not condemn white supremacy, and still do their best work because they aren’t directly affected by these issues.

But I do not share that same privilege. We do not share that same privilege. Women, people of color, and LGBTQ+ folks do not share that same privilege.

If we choose to show up as our whole selves, it immediately becomes interpersonal, political, and societal. Doing our best work means wrestling through issues of gender and race. Our full existence challenges the structures built to accommodate those who are most privileged and their well-being, as well as the myth that some people deserve to oppress and repress others.

After hearing this, I couldn’t stomach using Basecamp any longer. When I sent them the letter, rather than any backlash they welcomed the change, with some expecting me to change platforms in light of the news.

Since then, Circle has become a great fit for my coaching business. I’ve wanted to introduce a community component to my business, and Circle has made that easy to do and any future plans easy to implement.

Down (What Didn’t Work)

Health

I didn’t let myself go, but I also didn’t get healthier in 2021. By healthier I mean stronger, leaner, and having more energy. I had such a great rhythm coming into 2020, but I couldn’t modify or keep it going as much as I wanted during the year. I feel like I’ve gained weight the past few months, more so than the past two years, but I hope to change that in 2022.

The big cornerstone habit to keep doing is to cook at home rather than eat out.

Media Consumption

With all the issues around race and politics surrounding BLM, the election, vaccinations, etc., I was consuming far too much news and mainstream media ideas. I doused myself in the rhetoric I agreed with without realizing how anxiety and rage inducing it was. I went on a rant about social media and news,  but I still succumbed to its addiction.

I’ve unsubscribed from many newsletters, unfollowed accounts, canceled subscriptions to mainstream media news.

I’m planning to read more books, have nuanced conversations, and write rather than doom scroll.

Onwards (How Can We Improve?)

“Be a Lighthouse, not a Preacher”

I don’t remember where I heard this idea, but it’s been on my mind for a while now. As a coach, I’m very wary of becoming someone who doles out advice that he doesn’t follow, or help other people grow and succeed while I am stagnant and shallow.

In other words, I don’t ever want to be an “expert” behind a pulpit telling others what to do. I want to be a lighthouse, bearing the storm with nearby ships helping them get to safety. I can do that by continuing therapy, shipping my own creative work, and sharing what I am learning.

Learn More about web3

There’s too much I can say about this, so all I’ll say is I’ve taken the red pill. I believe in web3, not because of what it is now but for what it could be in 3, 5, 10 years. There’s so much noise, scams, and frankly privilege in the space now, but that was the case when cars, computers, and the Internet was invented. What web3 has started will forever change us as a civilization.

This past break I’ve really gotten deeper into the rabbit hole, and I don’t see myself looking up anytime soon.

Convergence and Simplicity

Looking into 2022, I’m realizing how much my varied experiences and skills from 12 years as a founder and creator are converging. They are converging around gathering, supporting, and helping other founders and creators fulfill their potential.

With that clarity comes a focus to the work I do. This newsletter has had many iterations, but this will be the place I share my story as authentically and vulnerably as I can. I’m calling Upstream my journey of unlearning, learning, and relearning. Those three disciplines capture how I have grown these past few years, and I hope in the years to come.

David and I are also doubling down on our podcast Greater Stories and expanding it to an online community. We want to bring fellow builders together and help them feel less alone. We’re working through a totally different format and focus for the podcast, as well as a newsletter, and Discord channel. Can’t wait to share it with you.

As for my business, I’m focusing this year on growing my coaching business. I want coaching to be the majority of my revenue so that I can do more personal projects for myself rather than clients.

It’s been a long, winding year. I’ve changed a lot. My work has changed, but I’m seeing the unbroken thread that has been running through all of these changes, not just the past two years, but ever since I decided to start on this path of creativity.

Here’s to 2022 not being 2020, too.

Thank you to Steven Ovadia for his feedback on this piece.

So what have I learned after a year of coaching? Well a lot, but if I had to sum it up, it’s two things: the act of coaching is about listening and empathy and the result of coaching is self-awareness. Here’s what I mean.

My job isn’t to have all the answers for my clients. The internet has all of them as Twitter threads, blog posts, or YouTube videos. But more than that, we already know what we have to do next. Actually doing it is the battle.

I’ve learned my role then is to create a space where we can process and talk about what’s blocking you, have a strategy to implement your ideas, and for me to keep you accountable. A new client recently ended our first call saying, “I just need someone to talk to about my next steps.” It’s not that they have no one to talk to, but to have time specifically for them to talk through their challenges and ideas is rare and valuable.

If there was one thing I had to unlearn, it was to not categorize my coaching as something specific like business, executive, leadership, career, life, etc. When I started I thought I’d be helping other creatives/freelancers like myself but my clients range from data scientists to writers, brand designers to software developers. People can’t be reduced to their work or industry. Self awareness is about the person’s whole self and how they move through the world.

So now when someone asks what kind of coaching I do, I say I coach creatives. “Creatives” is a word broad enough for them to come to their own conclusions or if they ask we can talk about what it means for them.

After a year and hundreds of sessions, I’m continually amazed at the brilliance and resilience of my clients. And when they tell me of a breakthrough or a win they had from our calls I get strangely quiet, looking off to the side, nodding with a big smile on my face. My usual boisterous and expressiveness becomes speechless.

I realized at that moment, what I feel isn’t happiness or pride in their accomplishments, but joy and gratitude; real, deep joy and humbling gratitude to be talking alongside them on this journey.

Something I’m trying hard to recover when working on projects is a sense of play.

It’s one that’s easy to lose because it doesn’t rank high in making a project feel worthwhile—productive, profitable, or prestigious, feels much more important. We’d certainly make time to work on those kinds of projects rather than playful ones. Starting something for fun to see where it goes feels like an indulgence at best, and usually a waste of time.

Recovering a sense of play is hard because it means trusting ourselves and our intuitions to locate what is fun and flow-inducing for us. Notice how productivity, profit, and prestige are determined by everything outside ourselves. Playfulness is determined by our interests and experience, no one else’s. There’s a self-care and self-centering element to play that we’ve been trained to think is self-ish.

Just spend some time with children to see what I mean. Since New York reopened, I’ve been reunited with friends and their children. Getting to play with them, you can see how they have no problem being completely engrossed in the smallest things—touching it, picking it up, dropping it with bright-eyed wonder. If something is fun, they want to do it again, and again, and again for no other reason than it’s fun to do. I like how Paul Graham describes it:

Remember that careless confidence you had as a kid when starting something new? That would be a powerful thing to recapture…

Kids bounce, or are herded, from one kind of work to the next, barely realizing what’s happening to them. Whereas we know more about different types of work and have more control over which we do. Ideally we can have the best of both worlds: to be deliberate in choosing to work on projects of our own, and carelessly confident in starting new ones.

There’s probably a long list of ideas and projects you haven’t been able to get off the ground because they don’t meet the standards set for them; a set of standards that meets everyone’s requirements except yours.

So, go start the thing you thought wasn’t worth doing. The one that feels “stupid,” “dumb,” or “I could never be that creative so why even try?”

Maybe it starts with a bit of dreaming because it’s been so long since you’ve asked what makes you feel alive. Start somewhere. It’ll be worthwhile.

I have another question for you today: How hard are you trying to earn your identity as a creator/creative/artist?

Because once we decide for ourselves that we start creating work that is generous, courageous, and intended to connect with others, most of us run straight into self doubt. We then burden ourselves with expectations, and create an unreachable standard and never-ending mountain of work so we can compensate for our fear of failure.

The counter to this is simple, almost too simple that it’s awkward: start with accepting who you are, where you are right now, and act accordingly.

Or as Brené Brown would say:

“We either walk into the stories of our lives and own it or we stand outside and hustle for our worthiness.”

What all this twisting and wrenching of ourselves boils down to is our worthiness. Am I worthy of being an artist? When I take stock of who I am, do I deserve to do what I feel called to do?

Yes, 100% yes. Not because of what you’ve done or will succeed to do, but because who you are and where you are right now is exactly where you need to be. If you start there, the work you do will be supported by a foundation of peace and acceptance that will probably make the work better.

When I started Upstream, each week I routinely wrote these really serious stuffy 1500-word essays. Part of that was the excitement of me owning my story as a writer but most of it was me going, “Look at how hard I worked on this! Does that make me worth saying I’m a writer?”

Years later my posts are shorter, more casual, and probably cringeworthy to Minnow who started this in 2019. What’s changed? I think it’s that awkward self work of owning who I am and where I am that’s been the most helpful.

That self work has led me to think of my dad and his 70-hour dry cleaning career. He’d say he worked that hard so that I can become a businessman with an MBA, but what I’m doing now is completely different from all his expectations. I am my father’s son, and I’ve had to face the fact I am different from him in fundamental ways, and that’s ok.

It really is ok.

What are the expectations that you have of yourself this week? Said another way, how high are the expectations you’ve stacked for yourself?

Every few months I feel as if I learn a different sides of my role as a coach. I realize it when there is a theme to how we tackle challenges in different sessions. The theme recently has been reframing our current expectations to have them be more sustainable, generative, and generous to ourselves.

This resulted in one person taking two months off publishing their newsletter. Another didn’t force themselves to launch their course, but took time to rest and learn more about the people they are serving. Another client released herself from the pressure of having to redesign their website, because the marketing they were already doing was working as they were booked months ahead with clients. And last week, another client came to the realization they didn’t want to turn their art into a freelancing business just yet, but rather grow as an artist and build their expertise.

Personally for me, this means reframing the expectations I have as a writer. Practically, it’s thinking of Upstream as more of a blog than a newsletter. The semantics of newsletter vs a blog matter to me because a newsletter carries with it so many expectations, while a blog is much more sustainable, generative, and generous to myself. I’ll be posting once a week, maybe more, and each one won’t be burdened with having to be this epic essay of ideas. They will be lighter, more personal, and hopefully more enjoyable to read.

The expectations I’ve had to let go in making this decision was my ego telling me I needed to have this newsletter to be the backbone of my business so that I can have subscribers and launches and revenue. Those things aren’t bad goals, it’s just not for me and what I have been actually building this past year. The letting go or changing of expectations seems like irresponsible advice from a coach and also for my own business. But really, I think it’s us detoxing from a steady dose of toxic productivity.

Doing things that are sustainable, generative, and generous to ourselves starts with learning how to be playful again. When we’re so burdened with expectations, we can’t be present with ourselves, others, or the work in front of us.

So if I was to reframe the question above, I’d ask: What are some ways you can incorporate times of presence and playfulness within your week?

Below is a letter I wrote to my coaching clients this past week about why we wont’ be using Basecamp anymore for our communications in between sessions. Since the start of my coaching, I’ve been using Basecamp, and so this is a major but neccessary move.

In our coaching sessions, we’ve talked about what it means for us to show up as our whole selves to do our most courageous, generous, and meaningful work. I am so grateful for the space we’ve created together, It’s one I do not take for granted. We’ve been using Basecamp to build on our conversations after our calls, but after recent events at the company I don’t think it’s the right place for us to continue our work. Here’s why.

In the past few weeks, Basecamp has internally imploded. It started with a blog post by Jason Fried, Basecamp’s CEO, announcing six policy changes, three of which are very concerning to me:

• No more societal and political discussions on the company Basecamp account.
  • No more committees.
  • No more lingering or dwelling on past decisions.

As reported by Casey Newton here and here, these policy changes happened when a list made in 2009 called “The Best Names Ever” resurfaced. It was a list of funny-sounding customer names.

Fried and his business partner, David Heinemeier Hansson, had known about the list for years but had done nothing about it. When the DE&I (Diversity, Equity, and Inclusion) committee and employees brought up why the list was offensive and dehumanizing, the conversations got heated. After a particularly harsh back-and-forth Hansson had with an employee, he was reported to HR.

Two weeks later — on Monday, April 26th — Fried posted the policy changes on his blog before communicating them to his team. Some employees first heard about them through his blog. Friday of that week, Basecamp held a company-wide meeting that resulted in a third of their employees, including some senior-level employees, resigning.

There are really thoughtful pieces on dynamics of power, broken management, and a searing open letter from a former employee that give insight to working at a place like Basecamp. I can’t speak to any of that. I’ve never worked in tech, and I haven’t had a boss for the last 12 years. But as a creative entrepreneur, I’ve relied on Basecamp’s products to run my business, and I’ve learned a lot from Fried and Hansson.

For example, I’ve probably talked to you about my seventh week sabbaticals: I work six weeks and take every seventh week to do work that interests me without any outside obligations. I first learned about this kind of working cycle from Basecamp (their whole company operates this way). I’ve also embraced remote work and built my business around being location independent, something Basecamp has been a proponent of for years.

But Basecamp has changed. It has gone through as Fried says, “a full version change” and I can no longer support them, and regret giving them so much credit.

Here’s a quote from their latest book, It Doesn’t Have to be Crazy at Work:

“The worst thing you can do is pretend that interpersonal feelings don’t matter. That work should “just be about work.” That’s just ignorant. Humans are humans whether they’re at work or at home.”

They were able to proffer such bold ideas like these because they never had any real skin in the game. Fried even wrote an article for Inc. about how Basecamp needs to be more diverse. They may have gotten backlash, but it was all to bolster their reputation and influence as thought leaders. Fried and Hansson “practiced” what they preached as long as it didn’t disrupt their status quo, a status quo steeped in white privilege. And since the changes were made, they have since doubled down on shaping the company in their image. At the end of the day, this is about two men using their power to avoid painful change and to not be held accountable.

Because Fried and Hansson have the privilege of not having political or societal issues affect their ability to do their best work. They can ban all commentary, move on from past decisions, not condemn white supremacy, and still do their best work because they aren’t directly affected by these issues.

But I do not share that same privilege. __We__ do not share that same privilege. Women, people of color, and LGBTQ+ folks do not share that same privilege.

If we choose to show up as our whole selves, it immediately becomes interpersonal, political, and societal. Doing our best work means wrestling through issues of gender and race. Our full existence challenges the structures built to accommodate those who are most privileged and their well-being, as well as the myth that some people deserve to oppress and repress others.

Fried and Hansson want to focus their business solely on meritocracy and profit. This is antithetical to the work we are doing together. We talk about how courage, vulnerability, and generosity are foundational to what we do. The conversations we have together reflect that, and I can’t imagine anyone telling us we can’t have them or that we shouldn’t discuss past decisions and instead just move forward.

Basecamp’s products are well made and have served us well, but I can’t keep using them, knowing where the company’s founders have placed their values. This isn’t about “canceling” Basecamp, because losing my business won’t matter much to them. And there are many other options out there. They aren’t the only ones doing what they are doing. For me it’s about upholding that trust with you and being true to what we are building together.

We will never be able to live 100% true to our moral values. It’s impossible for us to live with complete privacy, eat only organic, sustainable foods, or to be carbon neutral. There will be contradictions within ourselves and the world around us we must live with, compromises we must make. But there are some things within our realm of choice and actions we can take.

For me, this is one of them.

Thank you for hearing me out. I wanted to be transparent and share my heart with you. I know I’m risking overreaction and sounding too emotional, but I think I’m preaching to the choir.

Thank you to Paul Jun, Justin Bridges, Lyle McKeany, Ryan Williams, Joel Christiansen, Steven Ovadia, Casey R, Nick Drage, Amber Williams, Max Pete, and Kenta Naoi for their feedback and help on this.

When trying show up everyday to do courageous work, every part of our lives matter. Different spheres of our lives either give or drain us of energy, and I’ve too often let myself run dry.

Ending toxic relationships, sleeping 7-8 hours a night, eating nutritious foods, spending below our means, or setting time aside for restorative rest is not just healthy living, but intentionally designing our lives to be the best environment for us show up and do the hard work before us.

In other words, I’m helping future Minnow do his best work.

For me, that’s been about focusing on my breath. My therapist and I have been talking about me learning to accept all the ranges of emotion I have, not just the happy feel good ones. In our last session she said, “When you feel all the emotions, you live a more vibrant life, but you have to tend to them. If you don’t tend to your emotions, you will be reactive.”

So now, whenever I feel an emotion I would’ve rather not dealt with, I’m working on identifying what I’m feeling, locating where in my body it is, and breathing into it rather than reacting or suppressing.

The goal is to express what I’m feeling or needing without being defensive, emotional, or passive aggressive.

You’re welcome future Minnow.