I’ve been thinking more about what I meant last week by, “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.” And part of it comes down to me wanting to help people find what brings them joy rather than what makes them happy. David Brooks put it this way:

“Happiness is good, it’s the expansion of self. You win a victory, you get a promotion, your team wins the Super Bowl, you’re happy. Joy is not the expansion of self, it’s the dissolving of self. It’s the moment when the skin barrier disappears between a mother and her child, it’s the moment when a naturalist feels just free in nature. It’s the moment where you’re so lost in your work or a cause, you have totally self-forgotten. And joy is a better thing to aim for than happiness.”

Happiness is easy to find, because it’s what right in front of our eyes. But joy is deeper. Much of the advice offered to us these days is to help us aim for happiness, not joy. But after what we’ve been through this past year, happiness is just not enough. Because even in all the suffering, death, and division, there was still joy.

Joy takes into account what’s unseen—what’s underneath our wants and goals, down to our beliefs. Beliefs determine our mindset, which determine our actions, to form our identity.

It’s like that scene in Inception where Fischer talks to his father, that dream within a dream, within a dream, that’s where our beliefs are. And when we go up each level and finally awake, we find ourselves a different person.

Different doesn’t mean you have to upend everything you do and change who you are. A practical example is when clients come with an either/or decision. They’ve thought something through and they need help deciding whether they should do this or that. The choices are right in front of them, but what if neither is correct?

Many times it’s a third choice, one completely from left field they would have never thought of on their own. That’s how the idea of coaching was introduced to me. I would’ve never thought of doing this if it wasn’t for Kenta, my coach.

That bit of insight, wherever it comes from is what I can do and what i’ve found to be the most helpful for my clients. How do I categorize that? I’m not sure. It’s taken this past year for me to understand the edges of my role as a coach.

It’s been my own winding and uncharted journey to find what makes me joyful. Or as Buechner calls, my deep gladness.

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?

I had an unexpected glimpse of normalcy the other day when I saw on Instagram my friend was at Madison Square Garden to see the Knicks at the playoffs. I don’t have an interest in basketball, but I was surprised to see an arena full of people, after almost a year of selfie printouts taped on the stands.

I asked my friend if he felt unsafe next to so many people who were not wearing masks. He said everyone there was vaccinated and had proof with the “Excelsior Pass”, which is New York’s vaccination passport—two new terms that will be with us for the foreseeable future.

I find myself thinking throughout the week what last year was like around that time. March through May were such scary times. New York City was whisper quiet, all eyes glued to the news and rising numbers as we became the epicenter of the pandemic. Memorial Day last year protests erupted as the world reckoned with racial injustice. And day to day I was still experiencing the whiplash of how quickly my year had changed: I was a photographer with no one or nothing to photograph.

I also think back to two years ago and how I was feeling about my life, myself, and my work. The start of this newsletter in March was the inciting incident that started a journey of change I am only now starting to piece together. Everything about me and my life was put on the table, open to change, and what’s resulted is something I would have never imagined.

I’ll share with you once my brain catches up to this new reality. Till then, I hope you’re vaccinated, healthy, and finding little moments of normalcy in your days.

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.

Speaking about leaning into what we’re feeling and not pushing it aside, these questions offered by Catherine Andrews are a great place to start.

• Am I attempting to mind-read somebody else’s intentions in this situation?
• How could I give myself what I’m hoping this other person will give me?
• Is this thought arising from shame or fear? What is a thought I can have from self-compassion or hope instead?
• Can I name three things I need right now?
• Can I name three things I could let go of right now?
• Can I figure out a way to make this 5% easier on myself?
• What answer feels easiest to me?
• What if what felt right to me, was right?
• Who may be benefiting from how I am thinking or feeling right now?
• Is there a way I am benefiting or protecting myself from continuing to believe or act this way?
• Where is this situation reflecting some hurt inside of me, and how can I tend to that hurt?
• Where am I feeling this in my body? What wisdom does that sensation have to tell me?
• If nobody was watching or judging me, what decision would I make?
• What would 5-years-down-the-road-me tell me to do?
• What would it look like to trust?
• Would this decision make my life bigger or smaller?
• Is it true? (hat tip to the great Byron Katie)
• Do I want to keep thinking this thing? Why or why not?

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.

A goal I have with my clients is to help them get to a place where they can say:

”Nothing I accept about myself can be used against me to diminish me.” — Audre Lorde

Because usually the person diminishing us isn’t others, but ourselves. If we can own our story, we go from being driven by our ego to being pulled by a calling. It’s a simple but profound transformation that affects every part of our creative journey.

I’ve found the path to getting there is nuanced and unique to each person. Much of it has to do with unlearning rather than learning anything new or profound.

We have to unlearn the framing we put around our lives in; unlearn the reasons for doing what we are doing.

Shame accuses us, with, “Who do you think you are?” But our soul wonders, “What is life expecting of me, and how can I answer its call?”

Creating a space for that still, small voice to be heard and nurtured is how we own our story. In that space, shame suffocates and our soul breathes anew.