The highs and lows of the past year. My first attempt at an annual reflection.
January 7, 2024
I'm horrible at reflecting.
I often neglect to make room for it, because in many ways I’m one of those people who mutters, “Yeah that sounds cool but it feels like too much work.”
So maybe it's not a surprise that I’ve never written a long write-up about the past year.
But here goes.
What am I optimizing for?
Many of my career decisions stem from filtering for working on things I love, with people I love, from the places I love.
This has limited the prestige of my trajectory as a designer but exceeded it in many non-traditional ways. I never aimed to pursue roles in large FAANG companies, but instead looked for high-value opportunities to learn from others.
Sometimes that meant sticking it out at a startup because I felt loyal to my founding friends, creating products I wanted to see in the world, or moving cities to create new energy.
By most measures I’ve had a successful career anchoring myself to these values, but not one that has truly given me the independence I’ve sought.
Where that gets me into trouble is by programming my internal OS to make decisions on a whim, not thinking through my decisions fully, or by not sticking with things long enough.
My nightmare is dropping into a high-paying corporate ladder job in an office stuck in a location without access to nature and its energy. Thankfully more and more people can avoid this through remote work.
Something I’ve been optimizing for over 10 years.
Daughter #2: We welcomed our new daughter three weeks early in November. She came out screaming and fully installed with a hairpiece. Her big sister is thrilled to have a baby sister.
It feels like our family is set, and we can now focus on life after spending most of the past five years thinking about and trying to have kids.
And a huge thanks to my MIL for helping us through this initial period. I don't know how we could have done it without you.
Bro gets married: Seeing my brother get married this past summer was exciting to be a part of. For his bachelor’s trip, we went to Montana and spent some time snowmobiling with his friends.
Pregnancy: We have not had fun or easy pregnancies. After giving it the ol’ caveman go for almost a year, we went through three rounds of IUI, and one IVF round. It took us three years to see the face of our first daughter in 2021.
Like never wanting just one scoop of Jeni’s ice cream, we have always wanted more than one child. Both of us come from families with siblings.
Earlier this year, after a single embryo transfer from our frozen stash, we found ourselves in utter shock and pregnant with identical twins. We started to plan our lives around an unimaginable life.
Then suddenly—within three weeks—we lost both of them. Creating life can be challenging.
Friends: With the immediacy of a bullet, we had a close friendship with a married couple dissolve into a black hole after an intense amount of drama that spanned almost a year. We’re past the point of shock at how everything went down, but letting that relationship fold on its own was the best thing for our health and family.
More unfortunately, we have stored bottles of wine in their cellar that we'll likely never see again.
Cost of living: We live in a 3-bedroom home in LA (Echo Park), and the rent + utilities are not likely sustainable if we want to travel more as a family, get a dog, and live more flexible lives.
Our rent, utilities, daycare, and overall costs to live and work in LA are pushing against the edges of what we should be spending, and adjusting this might be the biggest lever for us to pull to increase happiness overall.
Dads health: My dad continues to have a number of health problems, and it seems he’s in and out of care constantly. On the bright side, my sister and her family moved to Minnesota to help care for my parents,
This year, it is all lowlights when it comes to health.
There's little to no good way to sugarcoat it. 2023 was completely average for me. I utterly sucked at keeping my body fat in check. I averaged 7,291 steps per day, and an average of 34 minutes of daily exercise.
But I have the willpower of a starving dog when we have snacks in the house.
My body fat % has slowly crept up all year. I'm at about 21% which is as high as it has been in the past six years. I've normally kept it around 18% (which is still not great).
State of Work
Freelance: After a record freelance year in 2022, I decided to pull back substantially on client services to focus on building Approachable Design.
My overall income was halved—but still equaled my full-time salary of 2021.
This gave me more free time to explore new ideas while leaning into new skills I’ve developed over the last couple of years, like SEO, podcasting, copywriting, marketing, and writing.
I doubt I’ll ever not freelance/consult, but I would like to minimize the load down to 4-6 select projects a year.
Approachable Design: This business is still not quite sustainable from a product standpoint, but it has opened new doors to work with clients I'm inspired by.
The type of work that walks through the doors of Approachable Design is much more interesting to me than from my past network which focused more on SaaS product design.
Product sales are not where I want them to be, but getting to work with creators like Paul Millerd, Lenny Rachitsky, Josh Spector, Khe Hy, and others have proven creatively fulfilling.
And I still believe the upside of this business can be 10x-15x.
Newsletter: I am still extremely grateful and bullish on building an email list. This list may evolve or change names, but it’s my way to reach you and share the things I’m building. I missed a few issues here and there but have a 90% publishing rate every week.
If there’s one improvement I’d like to make: It’s to send another weekly edition.
Hey, Good Game: Early last year, I pitched a friend an idea to build upon his already profitable web game. He pitched back an even bigger idea.
We corralled a couple of good friends and started a small brainy game studio called Hey, Good Game. We now have seven games, four of which we acquired. We have three full-time remote employees, and I’ll be devoting much more time to product and content over the next year.
The upside here matches my values and could have a significant impact on kids as a way to teach entrepreneurship through games.
Coaching/Consulting: I explored coaching this past year with several people. It’s something I love, but it’s difficult not to tie the work to the design work itself. I’m not sure I can escape this, but I’ll keep looking for more opportunities here to work with design teams of one, or with creators who need a design eye on their brand.
Fresh Prompts: Drawing has been a core focus of mine for the past few years, and so I wanted to build a site that felt like a long-term content play.
In the past year, I’ve written and worked with a content writer to publish 40 blog posts, drive 6,600 monthly visitors, and start to build an email list.
The only problem I’ve run into is how to best monetize a site like this. Still experimenting but proud of what we built in the past year.
Misc Side Projects: I illustrated 2.5 books this past year. (The 1/2 might be dead in the water). I also ran collaborative cohorts called Figma Thinkers, and Drawing for Writers.
These projects spun me in different directions, but I’m glad I did them. Overall, it gave me a sense of where I might want to spend my time, even if they weren’t financially lucrative.
I made close to 16k with these different projects, but they all felt very disconnected. I’m at a point where anything I build should ladder up to an existing offer.
No Live Approachable Design Workshops: After running seven cohorts of Approachable Design, I felt lost and disconnected about the viability of that part of the business, and the overhead it required to scale.
I’m not sure what the answer is here, but it’s likely going to be a hybrid or a self-paced version to replace the live workshop.
Sponsorships: This is an area I have not done well in seeking out. I do believe in advertising as a way to monetize, but I have not sought out the right partners.
Paid Advertising: I’d like to start increasing my advertising spend for my courses, but I’ve yet to run a single campaign. I’ve held myself back due to trying to perfect my landing page, but I think there’s more opportunity here.
Internet Friends: The past few years have redefined who I spend time with. This past year I’ve gotten to hang with a bunch of friends I’ve met online. Too many to name, but a shout-out to Khe Hy, Cam Houser, David Sherry, Will Mannon, and Lawerence Yeo. More of this, please.
Tulum: We love to rent, but I’m sure we’ll buy a (non-investment) home at some point to plant our flag.
However, there are much more affordable options to own abroad than there are here in the US. We also want to spend more time traveling for longer periods as a family, so we found a small place in Central America to stay/rent in Tulum, Mexico. We put a deposit down on a new construction 2b/2b condo which should be ready by June.
To contrast this, maybe we’ll need to move somewhere colder than LA?
Travel: Travel was limited this year, especially in a year filled with IVF shot routines. But I made two trips up to San Francisco and two trips to Minneapolis.
This amount of travel is like a July for me in a past life.
Bike Build: It feels like I've been building my old steel bike for years now. I am going to be asking for some help here as it's taken a back seat to the goals of hauling my daughter around town in a bike trailer.
Ideas, goals, and plans for 2024
To set some intentions for next year, and to proactively reflect on the upcoming year, here are some questions I’m thinking about.
Where will I devote my focus?
Simply, I’d love to focus on my family, Hey Good Game, and Approachable Design. Anything that I decide to work on should be connected to these projects.
I’ve been approached about what writing a book could look like, but I don’t think I have it in me yet. Maybe 2025.
These two projects satisfy my need to build something ambitious and give me the flexibility to be a present parent.
What was surprising and delivered an enduring lesson? (Paul Millerd via Matt Ziegler)
Like Paul, I find myself loving being a dad. It was scary at first, knowing you’re not perfect and just trying your best. But I love spending time with them and I can’t wait to explore more of the world with them.
Another surprise was how much happier I was this year making less money, but working on so many more interesting things with the right people. Money is still stressful and I’m not near a place where it’s not something I don’t think about, but it sure beats working a full-time job focused on building only for other people.
How am I blocking myself?
Not being direct with people. I find myself wanting to be helpful, but it comes at a cost. I have likely given up leverage (in both money/time) by not being more direct and honest with people.
Another correlated piece is not making enough time for myself to write and reflect. I’m constantly pushing on something outcome-oriented, but I have gotten away from devoting more time to reflection pieces like this.
What am I missing?
I miss hosting events and brunches at our place. I’ve somehow let being a family of 3-4 now become more of an excuse not to do this, but that’s a script I need to let go of. I’ve been reluctant to spend money on hiring a babysitter (We have hired one maybe 5x in 2.5 years?) but that should change.
What routines have I failed at maintaining?
Finances: We used to be a family devoted to YNAB and keeping a good eye on our budget. It’s easy to do with fixed incomes. But as we have added two kids, and removed one job, it gets trickier.
I downloaded Copilot (Part of my design vault) and hooked up the account pipes with much less day-to-day maintenance. But I’ve been missing this glimpse into our finances over the past couple of years.
I also have been operating under a sole-proprietorship for the past five years, mixing my business and personal finances, making taxes a headache. I just created Approachable Design LLC using Northwest Registered Agent (Thanks Nick!), set up bank accounts at Mercury, and opened a business credit card at Chase. I’m also testing out Kickfor my automated bookkeeping. I’m not screwing around.
Health: 21% body fat is far off where I want to be, and I know what I need to do from a diet perspective. I plan to hit and steady myself around 16% this next year.
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