What's in today's newsletter?
- Are you ready to be a founder?
- Better design feedback
- Slider for your age
- Retro voice record for meetings
- Healing the city through art
Back in 2020, I found design Twitter.
Watched designers building in public. Post Stripe notification screenshots. Pull $10K based on a few tweets.
Slowly, then all at once... I got sold.
Founder.
Say it at a dinner. Watch people turn their heads. Suddenly you're interesting. You're doing something important. Instant status. It's a vibe.
I wanted the vibe.
Honestly, I wanted it before I had a real business.
Then I quickly learn what the actual job is:
- Selling before you feel ready
- Making calls on bad information
- Owning outcomes you can't control
- Doing it all again tomorrow, with nobody clapping
No promotion. No feedback. No "good job, buddy".
The title "founder" wasn't what I thought it was. The problems never stopped. People, product, cash. Rinse and repeat.
There's barely a moment where it settles.
My journey looked like:
Month 1: exciting
Month 6: uncertain
Month 17: I nearly quit
Month 18: I hit $10K that month
Nobody actually cares if you didn’t come out the gate swinging.
At a job, stress runs on a timer. 5pm hits, you leave. You’re done for the day. When you're the founder, you’re never done.
I'm not saying don't do it.
I turned down a few roles to bet on myself. I'd do it again (YOLO!) I did it because I had to build UX Playbook. Same for rectangles.
Not because "founder" looked good in a bio.
Strip the title. Remove the audience.
The only test that matters:
If you'd still choose the work with nobody watching, go build.
Hesitate, even a little, and maybe you're chasing the story.
Maybe you're asking...
Which career path is right for me?
Everything is a trade-off.
Being a founder (what you gain vs what it costs)
The founder upside is real:
- Genuine autonomy over what you build
- Disproportionate reward if things work
- Makes people at parties lean in when you answer "what do you do"
What it costs is felt deep in your soul:
- Income gets unpredictable
- Work bleeds into everything
- You carry the emotional weight of outcomes, not just for yourself, but often for others too. Every decision matters, and there's nobody above you to escalate to.
Being an employee (the path people underestimate)
The alternative path (working as an employee) is often treated as the “safe” or less ambitious option.
That framing is lazy.
- Predictable income means you can actually plan your life
- You build deep expertise instead of spreading yourself thin across every operational gap
- Your feedback loops are clearer — you know what progress looks like
- Your mistakes don't usually threaten this months rent money
You're not steering the ship, upside is more linear, and the role doesn't carry the same narrative weight as “founder”.
But over time, what this path actually builds tends to matter more than it gets credit for.
How to know if being a founder is actually right me?
Good question.
You're probably suited for the founder path if you:
- Can operate without structure or external validation for long stretches
- Are comfortable being bad at things; sales, especially, for longer than feels reasonable
- Don't need immediate financial stability to feel like things are working
- Will take full responsibility for outcomes, good or bad, without needing someone to share the blame
- Care more about building the thing than being known for building it
You're probably chasing the wrong thing if you:
- Associate "founder" with short-term freedom
- Feel more drawn to the title than the actual daily work
- Avoid conflict, selling, or high-stakes ambiguity
- Need regular feedback to stay motivated
- Would hesitate if nobody knew what you were working on
Both paths are hard.
Corporate ladder? Hard.
Building from scratch? Hard.
Watching your work make someone else rich? Hard.
Choose your hard.
Just be honest about why.
Which hard are you choosing right now?
Hit reply if you're still unsure which path to pick.
