Paradox of “better”

Lessons learned as a PM and writer

The first big mistake I made as a writer and a PM was the exact same: believing more is better.

Words are free… right? I saw every word as an opportunity to hook people. I’ve since learned that every word carries an opportunity cost. They take time to process, and if they don’t bring value, they will be abandoned. Similarly, every feature imposes a learning cost on your customer.

Writing is a game of how simply can you write to express a lot. Building products is a game of how simply can you build to solve what matters. In both cases, your biggest competitor is likely to be bloat.

Don’t write for length. Write for resonance. Don’t build to ship. Build for impact.

Stephen King once said: "When you write a first draft, you write it for yourself. When you rewrite it, you write it for everyone else.” Take this to heart when you write for others, whether it’s a scoping doc, OKR deck, or even microcopy.

Writing is a mirror of your thinking. If your thoughts are foggy, so will the words on the page. As you re(write/think), the mirror clears up for you and others.

To get to better, you need more

Yet the only way to start your journey towards better is to do more. You can’t get there unless you write and ship consistently.

When you start, most of what you make will be bad. You won’t know it. Slowly, you begin to recognize the flaws in your production, but you’re unsure how to make it better. This is where the going gets hard. Your taste will exceed your grasp, and that’s very frustrating.

If you can push through this trough of disillusionment, you’ll get to the slope of enlightenment.

Popular advice from successful writers and product leaders: Focus on quality! More wood behind fewer arrows! Be 80/20!

What does quality mean? Which arrows matter? What is that elusive 20%?

Until you’ve produced a lot of quantity, it’s hard to get to quality. You need to pay the price of admission: unglamorous work that challenges your commitment.

What’s more, you need to rebuild your intuition for each new context. I’ve seen plenty of people with fancy titles get hired and quickly flame out. They bear the confidence of past success, and come in wanting to “apply their playbook”. But there is no one-size-fits-all playbook, especially in building products.

The secret to reinvention is to embrace being a beginner again.

The cheat code

Extraordinary and sustained results only emerge from compounding. The non-negotiable to compounding is consistency.

I used to think the cheat code is willpower. If you’ve got fire in your belly, you will outlast everyone else. But that’s not true. Willpower is finite.

Genuine interest makes consistency sustainable. The best test for genuine interest? Whether the activity gives you energy. Linking genuine interest with long-term goals makes consistency guaranteed. With both, you don’t need to burn willpower.

I thought I was interested in learning Python and Swift. But I stopped after 1-2 courses. Once the materials got hard, I somehow “ran out of time” in my schedule. In hindsight, they were never tied to my long-term goals, so it was easy to leave at the first exit ramp.

I’m consistent with writing because it energizes me, and it’s a key part of the flywheel to my long-term goal: making a living on the internet. I hope to be consistent with building products because I enjoy making things, and it’s a highly-leveraged activity towards my long-term goal.

Both gave me energy before they were ever publicly rewarding.

Play a differentiated game

My “long-term goal” has taken on many shapes, from police officer to surgeon and head of product. Changing goals can be scary especially if you’ve invested a lot of time and energy into constructing your identity.

If you use the greedy algorithm, you will always make the locally optimal choice at each step. You will keep ascending (in your bank balance or status in society), but you may find yourself the king of a mountain you don’t want to be on.

I used to climb metaphorical mountains in hopes that the world could finally see me. Then I realized the world doesn’t care. The point of climbing is to embrace the challenge, behold the view, and see more of the world. Seeing more things has helped me hone in on my non-negotiables, and what I care about most.

Venturing back down the mountain into an unknown valley is not locally optimal. Fortunately, I have time on my side, and can afford to shed old goals for new goals.

Another major fear is erasing all progress, and starting back at square one. When I left consulting and analytics for product, I thought I would be a complete noob. In some ways, I was. But I was also surprised by the overlap between the consulting / analytics toolbox and the product toolbox.

You get to take everything you learned in the past, and apply it to a whole new domain.
The more uncommon the transition, the harder it will be, but the silver lining is a unique perspective that will help you connect dots invisible to others.


When I look back on what I’ve written and built this year, I feel embarrassed about the quality, but proud of the journey. I take it as a sign of growth.

Here’s a throwback to a post from May:

I’ve been telling myself to start a blog for over 6 months. Four months ago, I started writing privately in search of my “voice”. Two months ago, I started telling people about my plan to increase my accountability. Two weeks ago, I claimed my handle on Substack.

I still haven’t shared any of my posts publicly as of this writing. It’s hard to face the music not knowing what it will sound like. But wherever this goes, I do know that the feeling of creating something from a blinking cursor is the kind of thrill that Paul Graham wrote about.

Glad I started, proud I continued, and grateful for 3620 more reasons to keep going. Happy new year, everyone!

Favorite books of the year

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