2021 Annual Review

A reflection on 2021 and the master plan for 2022 (#99)

Jan 2

Howdy, and Happy New Year.

For the first time in my life, I sat down and did an outrageously tedious review of my past year.

I used this annual review template from Anthony Gustin and the result was pretty stunning: I had pages upon pages of notes on where my time has been going and where I’d like for it to go.

For both of our sanity, I won’t be sharing all of my notes. Instead, I polished up my key takeaways and condensed them into today’s email – which I believe is still the longest thing I’ve ever posted onto the internet and is definitely the most self-indulgent.

And as part of my plan to actually hit my goals in 2022, I’m announcing a somewhat ridiculous accountability challenge:

Over the next 3 months, if I do not publish a total of 12 Twitter threads (1/week) and 6 Stew’s Letters, I will give 10 readers $1,000 in cash each.

If you want to be one of these accountability buddies, hit reply and let me know. In three months, I’ll either confirm that I hit these goals or I’ll ask for your Venmo.

I wish I didn’t have to take such extreme measures, but laziness got the best of me in 2021 and I need a radical counter-force to pull me back.

Now, let’s get to it!

Stew’s 2021 Annual Review

2021 started off with a bang.

Foster was accepted into Y Combinator and we kicked off the year in their Winter 2021 Batch. My co-founder Dan and I busted ass for three months, learning from some of the most successful entrepreneurs on the planet. Shortly after starting YC, we raised around $3 million from some of Silicon Valley’s top VCs and angels.

My fiance Tricia and I moved to New York, excited to start a new life in a city overflowing with remarkable people and opportunities.

But around halfway through the year, something happened. I don’t know what exactly, but I felt myself slow down. I wasn’t writing and publishing as much as I had in the beginning of the year. I was still busting my ass working on Foster, but I wasn’t satisfied with the quality or impact of my work. I felt a general sense of malaise through most days that I couldn’t shake. Everything seemed twice as hard as it had just months earlier.

I assume that I probably experienced some mild depression. But even when I am fully “on,” I can struggle to act on my ambitions. One key reason is, hilariously, that I can usually enjoy myself in just about every situation. I find it easy to have fun. But that tendency to enjoy the moment often robs me of the urgency and motivation I need to actually improve my situation and to take action on my ambitions.

“Like water, many decent individuals will seek lower ground if left to their own inclinations.”
― Bill Walsh

For me, I need social accountability to deliver at the higher range of my capabilities. Going into 2022, I am actively seeking opportunities to create accountability and take more responsibility.

The post that follows is a review of the past year and a game plan for the next 12 months. I went through this extensive annual review exercise from Anthony Gustin and boiled down my main takeaways here.

In my full review, I audited and set intentions across a wide range of categories in my life, including my relationships, mental health, and family. But for the sake of concision and for some privacy needs (specifically with goals that involve other people), I’ve focused this post on my top priorities for the year – most of which are career-oriented.

With that, I hope you enjoy this shamelessly self-indulgent annual review.

2021 Milestones

I had a few major milestones and moments in 2021.

I turned 30. Of course nothing magically changes when you enter a new decade of life, but turning 30 felt meaningful. I find myself thinking more about the impact I want to have on the world, where and how I can step up and take responsibility in my life, and essentially how I can adult well while still having fun. It’s also fun to start seeing the fruits of certain skills and relationships I built throughout my 20’s starting to take hold.

Foster went through Y Combinator and raised a seed round. Taking our tiny startup through Y Combinator was an intense and fruitful experience. YC’s 3-month accelerator program is basically a socially-acceptable excuse to spend all your time working on and growing your startup. It gave my co-founder Dan and I an urgent window to figure out a number of core things about our business. Throughout YC, we also built relationships with people I had only ever dreamed of meeting. It was a huge source of momentum for us early in the year.

While in YC, we also raised a roughly $3 million seed round from some of Silicon Valley’s top VCs and angels. More than anything, this helped us elevate our vision for what Foster might become.

Tricia and I moved to NYC. Once the pandemic turned my fiance Tricia’s job fully remote, it became clear that very little was keeping us in Seattle outside of a few close friends we were reluctant to leave. We have long wanted to live closer to our families on the east coast, but we knew we weren’t ready to live in a small town yet. So, almost by process of elimination, we chose New York City as our next city. It didn’t hurt that my co-founder Dan is also here, giving us a chance to work together IRL regularly.

I started surfing again. Surfing was my first love growing up, but college and my career have mostly taken me away from the ocean. But it turns out that New York has great waves. The subway will actually drop you right off in front of one of the better breaks. Being close to the ocean again allowed me the option to surf semi-regularly. It has been a source of profound joy and meaning and I intend to only deepen my practice moving forward. (I also got to surf in the middle of Texas at a man made wave pool this year… that was rad.)

I traveled to Maui to spend time with the Galapagos crew. A few years ago, I took a trip to the Galapagos Islands with Richard Dawkins. While it was cool to hang out with one of my intellectual heroes for a few days, but I ended up spending most of my time with a couple of other travelers who I immediately clicked with. Both are entrepreneurs – one is in his 70’s, the other in his 50’s. We joked that we are all the same person, but 20 years apart. Every year, we try to get together. This year, we went to Maui and spent a few days eating, drinking, snorkeling, and laughing until we cried. It was awesome.

I wrote some interesting tweets and Substack posts. Overall, I felt that I was able to write and publish a few interesting things that captured some hard-earned ideas (for a couple of examples, see here and here). I generally feel that the quality of my work is trending in a positive direction and I’m gaining confidence that I actually have novel things to say, even in well-trodden territory. My overall output, though, was far below what I would have liked.

I gained enormous clarity on the things I believe and value. Co-founding Foster and writing semi-consistently have both been sources of immense personal growth. The challenges that each of them have brought have helped me to develop character and clarify what I value. The feedback I get on my writing alone routinely bends and expands my mind. The end result is that I’m ending 2021 with an unusual amount of clarity on who I am as a person.

Goals for 2022

Purpose & Vision

I tend to take a pretty Darwinian view on life… I believe we are animals that evolved via natural selection and that the universe has not bestowed any particular “purpose” onto any of us, other than perhaps reproducing and not dying.

Instead, I think we’re free to create our own, more-meaningful reasons for being here. The purpose I’ve chosen for myself is two-fold:

To give my creative gifts to the world – through building things, writing things, and supporting things I believe in.
To be a provider – for my family and the people I’m closest with.

Moving forward, I intend to live in more alignment with this purpose. I want to unleash my creativity in ways that align with my desire to be a provider. I want to use my ever-growing (hopefully!) financial resources to give me the freedom to pursue or support projects that are more aligned with my truth.

For now, I’m focused entirely on making two projects succeed:

Foster. By far, the most likely opportunity I have to catapult my financial situation is to make Foster successful. Foster is also an amazing channel for my creativity. I feel very lucky to be working on it regardless of where it ends up.
Continuing to build an audience. I have more fun expressing my ideas when I know other people will engage with them. Also, an audience is an asset that will both help Foster succeed today and help any future projects succeed in the future. It’s a long-term investment and a multiplier on everything else I will do.

And while I have some relatively lofty ambitions for both of these projects, the reality is that I’ve been wasting so much time on things that are not aligned.

Things to improve

In no particular order, these are some distractions that I’d like to eliminate or vastly reduce in 2022:

Angel investing (though I love doing this & will be back soon enough).
Obsessively checking crypto prices.
Scrolling TikTok, Twitter, IG, and YouTube.
Hanging out in online communities that don’t support my goals.
Eating as a stress response (this is a huge distraction I was previously blind to).
Reading things that won’t actually help me (ex. thinkboi pieces speculating about the future in 20 years).
Reading a wide range of newsletters just because I want to support the writer. The best way I can support them is by building Foster.

I made a more detailed list of bad habits I plan to eliminate here (see the “Automate, Delegate, Eliminate” worksheet). I find it genuinely amazing that I get anything done given the sheer scope and magnitude of distractions I’ve invited into my life.

Top Goals in 2022

In one section of the full annual reflection exercise, I ranked ten different categories of my life in order of their priority. I also rated each on a scale from 1 to 10 on how healthy I felt they were.

These were my rankings and health score:

Work: 6
Finances: 7
Creativity: 6
Family: 7
Relationships: 5
Mental Health: 5
Travel: 8
Fun: 8
Physical Health: 7
Spirituality: 6

I fully lol'ed when I reviewed my list: work first, spirituality last… what the hell?! But I had to be honest with myself on which area I think, at this particular moment, is more likely to actually improve my life.

I set goals for all ten categories, but I’m just going to share my goals for the top three given that they’re the ones I spent the most time thinking about and will spend most of my year working on. Also, a few other goals are more sensitive and involve other people.

Work Goals

I spend most of my waking hours working. It is the bedrock of my future financial situation and thereby my ability to provide. It is a source of meaning and enjoyment when it is aligned with who I am. It’s a channel for my creativity. It’s also an amazing excuse to meet and build relationships with interesting people.

But my work ethic has slipped in the past few months. Maybe I was depressed or burned out. Maybe I’m fundamentally lazy. Whatever the cause, I’ve fallen into many bad habits (mostly, excessive phone usage and poor eating habits) that have drained attention away from work. I’ve also wasted time with other distractions, chasing hot things in crypto or with angel investing.

In 2022, I want to reorient myself back towards the projects I believe are most likely to improve my life. I split up my goals across three separate projects.

Foster Goals

Cultivate the most exceptional community of writers in the world. This is a qualitative goal that I’m still not sure how to measure, but in 12 months I think I’ll know if I’m on track or not.

Get Foster to next milestone. This will either be a growth, revenue, or fundraising milestone, or all three. I’ll be figuring out a tangible goal to measure here in the next month or so.

Twitter Goals

Write and publish one thread per week. Writing threads on Twitter is still one of the best ways to grow, but many threads quickly become self-aggrandizing grabs for attention. My intent would be to write things that are genuinely insightful or useful about things I feel that I actually understand. In other words, I want to do this without becoming an asshat.

Write and publish one tweet per day. Tiago Forte nailed it when he hilariously observed: “the secret to twitter growth seems to be tweeting.” It’s difficult to know what will resonate with people, so taking a lot of shots on goal matters. Also, I am lazy and will not produce consistently on Twitter without some sort of forcing function.

Rank in the top 30 of Readwise’s “Top Threads” list. While I ultimately can’t control this, I think one solid measure of my Tweet game is how many people save my work. This Twitter thread leaderboard from Readwise feels like a solid proxy for this. Current rank: 180.

Rank in the top 30 of Readwise’s “Top Tweets” list. Similar to the above, Readwise also has a leaderboard for how many times somebody’s individual tweets (not threads) are saved. Current rank: 468.

Stew’s Letter Goals

Publish two Stew’s Letters per month. Writing a newsletter consistently is hard. This is exactly why I need a regular publishing cadence to commit to. Otherwise, I find it too easy to procrastinate. Rather than resuming a weekly cadence, which I don’t yet feel capable of doing, I’m going to aim to publish two Stew’s Letters each month.

Announce an accountability challenge for my publishing goals. One of the clearest themes that arose reflecting on 2021 is that I find it far too easy to not do the hard things I want to do without the support and some healthy social pressure from other people. So, I’m going to do something radical and create a public accountability challenge tied to my publishing goals above. I’ll announce it in the email that this annual review goes out in.

Join or create a weekly accountability group for writing. If a little accountability is a good thing, then more accountability must be a great thing… right? To ratchet up the accountability even more, I intend on creating or joining a weekly writing group aimed purely at producing more. Thankfully, my day job at Foster should make this pretttyyyy easy to organize.

Finance Goals

Money is freedom when used wisely. It removes many unpleasant and undesirable constraints in life. It can be an off-ramp from the vicious competition to survive. Money is a lever for creating the change I want to see in the world. Money buffers stress – and stress often depletes life of joy.

That said, I’ve continued to spend excessively on things that bring me little joy (ex. takeout). I also do not do any sort of monthly review of my finances. I also foolishly dragged my feet on finding a tax advisor, which has likely cost me… painful amounts. I have generally taken the gas off of the financial pedal the past few months and it feels like it’s time to course-correct.

Also, I have also wasted a huge amount of time on things like angel investing (mostly, reviewing AngelList and Gaingels deal memos) which, to date, have not outperformed the S&P 500 (I’m extremely conservative about mark-ups) and is not something I intend to become world-class at this exact moment. I can imagine this eventually changing, though.

Here are my goals:

Retain a tax & financial advisor. This is self-explanatory, but I need to engage a tax / financial advisor who can help me out with more complicated money questions. Otherwise, I will continue to incorrectly Google things and regularly squander money. In the world of money, ignorance is not bliss – it’s expensive.

Double my net worth by Dec. 31st, 2022. This is a somewhat ludicrous stretch goal that I hope will push me into fundamentally new ways of thinking about how I earn.

Do not make a single angel investment in 2022. I do best with simple rules, so I’m going to make this one radically simple. I do not intend to stroke a check into any startups in 2022. I hope this will free up attention and energy to focus on the projects most likely to improve my life. Ironically, this often creates more exposure to interesting deals as being a successful founder immediately plugs you into a network of exceptional entrepreneurs you may want to back one day.

Charge money for something that will force me to do more of the things I want to do. In line with creating more accountability in my life, I want to charge money for something that will force me to do a thing I want to do more of this year. I’m not exactly sure where this one will lead, but it might be something like writing a short guide on something I know a lot about, pre-selling copies of it, then using that obligation to actually write the thing (and publicly share tidbits along the way, helping to support my publishing goals).

Creativity Goals

I believe that my creativity is possibly my most unique and valuable skill. I cringe a little bit writing that as “creativity” is a hopelessly broad word, but whatever. I know what I mean by it. If I were to stifle my creativity, I believe I would be robbing the world from enjoying my unique gifts. I would also be robbing myself of the immense pleasure I get expressing my creativity. If I do not prioritize my gifts, I run the risk of commodifying myself.

I started off this year strong, publishing newsletters, tweets, and interviews on a regular cadence. But, like in the “work” category, I entered a slump. I published far fewer tweets, threads, and newsletters than I intended to. Some combination of sloth, self-doubt, and perfectionism took me off-course here. When I did channel my creativity, though, I did it in the right places (Foster, Twitter, and Stew’s Letter).

My publishing goals will carry most of the weight here, but I’m adding two additional “housekeeping” goals that I hope will keep my mind firing.

Journal for 10 minutes at least 4 times per week. More than any other single exercise, writing a stream-of-consciousness journal entry in the morning is the most effective way to clear out my mental cobwebs. Many of my best ideas often appear during these sessions, in between blocks of rambling, confusing text. It’s a no-brainer to deepen this practice going into 2022.

Tweet one opinion, observation, or question each week that makes me uncomfortable. As I’ve amassed a bit more of a following on Twitter and in the newsletter, I’ve noticed fear creeping into my writing. I imagine an army of thousands of nit-pickers combing through every word I publish, finding all that’s terribly wrong about my worldview. For example, I remain skeptical of a lot of the “web3” zeitgeist but I fear being ostracised for expressing that skepticism. So I’m going to just bite the bullet and Tweet more things like this.

2022 Theme: Growth

If 2021 was riddled with feelings of stagnation, I intend for 2022 to be a year of growth.

Many of my 2022 goals focus on developing consistency, which I hope will force me to grow into the type of person who reliably shows up. I hope that inviting more accountability in my life will similarly help me grow into a person who reliably meets their commitments. And I hope that the overall volume of work I produce will grow more objective measures around my audience size and the health of Foster.

Ultimately, I’m pretty pumped about the year ahead.

Time to get to work.

Other Stew’s Letter Things:

Fire TikTok: This is so goddamn stupid. I love it.
Bonus TikTok: This is a video of a horse walking into a house. That’s funny, but the laughter of the kid in the video is sheer delight.

Happy New Year,
Stew