Some friends challenged me to do a 2020 reflection / 2021 planning post, so here goes:

2020 Reflection

I loved this year. Highlights:

• My 1-yr old son is alive.
• My marriage is good.
• I feel that my family is putting deep roots down in Austin, TX. We’ve been here 5 years now, and some new friends are starting to feel like old friends.
• I was promoted to my ideal role at Dropbox (4 direct reports, but spend 80% of my time building).
• I spent 4+ months on paternity leave:
  • I got in really good athletic shape (6-min mile, backflip, 1k-pound-club).
  • I put more time into pooldash, which grew from 0 → 24 paid subscribers.
• I went deeper into js deployment infrastructure / CDNs / frameworks… plumbing-of-the-modern-internet type stuff.
• I wrote more
• I helped 2 friends get their first programming job

Lowlights:

• I put some time into a startup project that failed (afterpitch.com)
• I’m spinning my wheels at work — I’m stagnating a bit, and I still spend too much time confused by our internal frameworks, overwhelmed by the number of stakeholders on our projects, and patching mysterious legacy systems that my team is responsible for.
• I haven’t been able to self-learn physics like I thought. I never make time for it, and I have trouble focusing on academic papers.
• I’m getting complacent. My life is comfortable, and I’m not forced to step up & be a leader in many situations. However, my complacency has consequences (at least 2 of my friends would have happier lives if I had spoken up & expressed my opinion more firmly).
• I didn’t read many books

Observations:

• I’m a seasonal person — my interests will change month-to-month:
  • Learning the tech vs just shipping something
  • Learning physics vs reading fiction
  • Bulking up vs Getting lean
  • Dietary preferences (sugar, carbs, caffeine, etc…)
• I’m tired & busy. Having a kid means that my energy for anything else is now scarce, so my productivity is lower.
  • I need to take care of myself, and communicate a schedule to other people that want to help me.
  • I can’t just work whenever the motivation hits me.
• My relationship w/ social media has changed. I post silly, un-polished videos every weekend of me fixing something around the house, and it’s been a great way to connect with old friends.
  • I’m not trying to look great or entertain the masses — it’s just an approachable way to connect with my little community.

2021 Planning

I’ll break this up into 2 sections… “what I want” and “how I’ll get there.” I’m optimistic about next year.

What I want

1. I want to be a great father & husband; this is the most important thing to get right. I want to provide my kid(s) with:

• Lots of high-quality time from me
• A great community of friends / family / role-models besides myself

2. I want to build great products. I have long believed that I can build great products, but that my environment is holding me back. Specifically, I always sell my labor to the highest bidder, which means that I put up with a lot of wacky constraints. This is a really important distinction — I don’t build great products. Instead, I build the best products possible within those constraints, which actually means that I bend over backwards to make bad products with good excuses.

3. I want to be financially independent. Specifically, I want a passive income stream worth half of my current salary so that I don’t have to sell my labor full-time. This isn’t strictly necessary (I can be a great father & a great builder without achieving this goal), but it will enable me to spend more, higher-quality time with my family. It will also change how I decide what to work on (purpose > money); I’m leaning towards education, or open-source software.

4. I want to help more people flourish.

How I’ll get there

1. I’ll spend lots of time actively engaged with my family. I have a few specific dad-things I do regularly (bathtime every night, father-son date every Sunday, etc…). But, I don’t want to plan out a step-by-step schedule for being a great father — I just want to love my kid & encourage him to walk & talk this year.

2. I will build pooldash into a great product.

• No excuses
  • Minimize constraints, keep it simple
  • Build a great tool for a few people
    • No broad appeal (yet)
    • Ignore everyone outside of my target audience

3. I won’t get to financial independence this year, but I will make strides in that direction:

• I’m “earning & learning” at Dropbox, stockpiling cash
• I’m improving pooldash
  • I currently have 24 subscribers
  • I will have 500 subscribers by August 1, 2021 (20x growth)
  • I will have 2500 subscribers by August 1, 2022 (10x growth)
• I’m holding these investments:
  • Crypto
    • BTC
    • ETH
    • HNT
    • Lots of failures
  • Startup equity
    • Dropbox (the unvested portion of my employee stock grants)
    • rev.com (I exercised my employee stock options years ago)
    • Palantir (profit-share w/ early employee years ago)
    • Lots of failures
  • My house in Austin
• I’ll look for asymmetric investment opportunities (low risk, high upside)
• I’ll avoid distractions:
  • Credit-card points optimization
  • Small consulting engagements

4. I’ll get better at helping people (deeper & wider):

• I’ll grow my formal management skills at Dropbox.
  • I’m good at difficult conversations, but I dwell on them too long before & after.
• I’ll hire freelance junior devs to help with pooldash.com.
  • Experience is key when applying for full-time coding jobs, especially for non-traditional candidates.
  • This means building a product that can be worked on, productively, by junior devs.

Closing Thoughts

I’m absolutely thrilled to be alive right now. My family is blessed — our friends, careers, and assets are growing. Thanks to this growth, my life is shifting from defense to offense… I’m not just staying afloat, but also considering where I want to swim.

My first destination: 500 pooldash subscribers by August 1st, 2021.