Introducing the Squiggle

Each week in this email I'll have a short note about what's happening in my life, work, and/or entrepreneurial journey, along with a curated selection at the bottom of what's captured my attention, ears, tastebuds, or wallet this week.

The amazing feedback I got from my quarterly update has inspired me to write a more intimate missive for a much, much smaller crew. I've included you because I consider you one of my closest friends and mentors. But just as with my quarterly update, there's zero pressure to read or reply, and of course please feel free to unsubscribe if this is too much Alex in your inbox.

Each week in this email I'll have a short note about what's happening in my life, work, and/or entrepreneurial journey, along with a curated selection at the bottom of what's captured my attention, ears, tastebuds, or wallet this week. This week is a little longer than I'll normally aim to go, but the words were flowing and I decided to let them loose.

Déjà Vu

Something about the day after Halloween breaks my brain. Sugar hangover? Changing of the seasons? Maybe just the rumbling freight train of the holiday season barreling our way. In Austin, the air is crisp and unseasonably cold, but the sun is out. I’m layering up and for some reason I feel like I’m breathing nostalgia. There’s a feeling of déjà vu to everything, a Groundhog Day-vibe that I’ve been here before.

Welcome to the Squiggle, and thanks for reading.

I’m naming this little newsletter after the Process of Design Squiggle by Damien Newman. His illustration is meant to represent the design process, but I find that it applies to any new project, idea, or undertaking. You start with chaos. You seek, squirm, and struggle to find your direction—sometime doubling back, sometimes leaping forward—until eventually, someday, with persistence, you find your focus.

That Groundhog Day feeling? It’s me doubling back on my squiggle. Not to the beginning… but some days it feels close.

This time last year, I was beginning to think about starting a company. I gave myself a January deadline to decide: either explore my own ideas and start something of my own, or begin looking for jobs. Naïvely, I thought *deciding* to start was the hard part. I’ve got a million ideas, I thought, so the vision will manifest, I’ll hit the ground running, and boom, we’re changing the world.

Not so fast, little AP. I immediately hit a wall. My ikigai venn diagram of fun, impactful, viable business ideas (that I would be good at) felt more like four distinct circles on a page. I put on the pressure to come up with the Perfect Idea™️, because of course nothing generates great ideas like crushing, relentless, self-imposed anxiety, right? ;)

I bought a SXSW badge, convinced it might spark some brilliant idea in me after a session with Tim Ferriss, Incubus, or the AI guys. I talked to everyone I knew. I read books. I philosophized. I tried to narrow down my passion: was it travel? Was it giving people time and attention back in their day? Should I jump into the fray of the AI boom? Or should I open a coffee shop and wine bar?

I stressed about family and ambition, simultaneously. How do I show up and be present for my kids and my partner? But at the same time, how do I demonstrate to them that I’m making the world a better place and working hard on things that matter? What is my sweet spot between, as Sahil Bloom put it, these “two minds” in tension? In his words:

Understanding, navigating, and balancing the tension across these two minds is how I believe you ultimately "win" the game.

Put differently, the goal is not to sacrifice our career progression, fail to live up to our professional potential, and stop learning or growing in an effort to be constantly present with our kids.

The goal is to have the clarity to *choose*—to define your balance, to live by design, rather than by default. The goal is to ask the question, and to craft your own answer, not to blindly accept the "right" answer someone else wants to sell you.

I’m incredibly fortunate to have this ability to choose. But this choice can still be paralyzing. Truthfully, I’m still struggling with what my path is that can successfully hold these minds in equilibrium.

This last year has been a roller coaster. The beginning of the squiggle. Truly oscillating between focus, uncertainty, momentum, and analysis paralysis. But maybe there's a pinprick of light at the end of this particular tunnel—a promise of an ikigai with a little more overlap in my circles. I may feel my déjà vu, but this moment is not without its subtle differences and deep learnings.

Some takeaways:

  • I need it all. I’m not someone who can separate fun from purpose, or excitement from money. My work, ultimately, needs to have it all. When I find this I’ll be unstoppable. But if I’m missing one piece, I’m my own biggest obstacle.
  • My hobbies are not my purpose. Just picking something I like and trying to build an innovative business around it is not, it seems, going to be my path. They’re a signal, for sure, but my work needs to have deeper meaning and impact than just “this is something I love.”
  • Relax. I've released the pressure valve on needing to find the Perfect Idea™️ and found a little focus in the process. After all, as any musician, athlete, and artist will probably tell you: creativity and high performance come not from tension and rigidity, but from loosening your grip.
  • This is the hard part. Deciding to start is an important step, but ultimately kind of an obvious two-way door. Picking *the thing* to start on isn’t impossible to reverse, either—I fully expect to pivot, perhaps dramatically, from my starting point—but it requires a real commitment for it to have a chance. Picking the problem is the seed from which all other decisions are sown: who will I work with, how will I fund it, where and how will the work happen?
  • I’m not alone or unique in this journey. I’m fortunate to have an incredible community of brilliant, ambitious, accomplished people. And as it happens, plenty of them are in the same boat, or have been in the past. I’m grateful for the reminders that this is part of the journey—just the left end of the squiggle.

More to come. In the meantime, here’s what’s caught my attention this week.


🎧 I can’t get enough of FKJ’s Just Piano. And Bassti’s “pure imagination” is playing on repeat today.

📜 Neal Agarwal’s excellent Internet Artifacts digital museum is a blast to explore. (Side note: his “Where does the day go?” hits really hard.)

🤯 Blow your mind with the Ames Window.

🎨 I love these stunning palettes inspired by Dieter Rams. Present & Correct is also just a phenomenal curator of beautiful things—worth a browse.

🤔 I appreciated Mike Sowden sharing this xkcd about people learning things for the first time.

🎙 This episode of Search Engine with Ezra Klein, “Is there a sane way to use the internet?” is one of the best things I’ve heard in a while. (Also, Search Engine is just generally great.)

🗞️ “Confessions of a Middle-Class Founder”, unsurprisingly, hit very close to home.

🪦 RIP Robert Irwin. His work in Marfa, “Untitled (Dawn to Dusk),” is truly remarkable to walk through.

🎮 Dipping my toes back into gaming with Super Mario Bros. Wonder (an absolute blast) and the original Alan Wake (since the sequel just came out to rave reviews and, well, it’s spooky szn).

🍬 Taking advantage of the holiday to indulge in my favorite candy of all time, Caramel Apple Pops, alongside our newly discovered Rotten gummy worms.

Thanks, sincerely, for reading. It means the world to me. Thoughts, reactions, feedback? Please reply—I'd love to hear from you.

Until next week,

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