Skip to content

2021 Year End Review

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.

Minnow Park
Minnow Park
7 min read

Table of Contents

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)


A few weeks before the lockdown happened, I had started with my own business coach to help me become a better photographer and solopreneur. But a year's worth of work disappeared because of COVID, I didn't know how to think about what was next.

I don't know if I would've kept my head straight if it wasn't for the space he created for me each week. It was my coach who suggested I also think about coaching after we were working on whether I should offer strategy and branding for businesses and other creators and founders along with my photography.

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, and it’s just shy of 750.

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.

What’s worked wasn’t the number of sessions, but how effortless it has been doing that many sessions. I realized I was creating safe spaces and helping people be themselves the last 10 years of doing portrait photography. And while a portrait session's goal is to bring out the photogenic potential of someone, coaching sessions are about bringing out the entire potential of someone. Once that clicked, I realized I had trained to be a coach for a long time.

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.

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)


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. This review is the first piece for this new season.

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 and also seeing how I can blend coaching with my portrait work. It may come back full circle in 2020 where I do use strategy and marketing along with my portrait work. With a year and a half of coaching under my belt, I feel confident to offer that to creators and founders.

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.

Lessons from Building


Related Posts

Members Public

How Portraiture Complements Coaching

How I bring out someone's photogenic and creative potential.

Members Public

Lessons from a Year of Coaching

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

Members Public

Why We're Leaving Basecamp

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