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Oct 23 • 6 min read

my story (2020 til today)


A few years ago, I turned down $170,000 a year.

After tax.

I said no to bet on a startup I co-founded and a side project with a handful of sales.

The startup died. The side project nearly did too.

Today that side project, UX Playbook, plus rectangles, has made over $700,000 and reached 100,000 designers (you're on of them!).

I told the whole story on this week’s livestream (we rescheduled How An AI-Native Designer Works).

I nearly didn’t give this talk. I kept asking myself who I am I to teach anyone this. Maximum imposter syndrome.

Then I realised that’s exactly why I should.

My numbers won’t get screenshotted on Twitter. But this is the reality of a solo's journey.

Here are the 8 lessons if you're just starting out:

1. Make it real v

In 2020, I quit my Head of Design job in Thailand. Then lockdown hit. No backup, no plan.

I rewrote up the guides and processes I’d built for my old teams, put them on Buy Me a Coffee, and sent the link to 5 design friends to test the checkout.

A week later, a stranger bought it. 9 sales in 3 months.

I’d written it for design managers like me. The people buying were juniors learning UX.

I’d never have known if I’d kept polishing it. Rounds and rounds of user testing and I might have launched too late, or never.

Have a hypothesis, build something quick, launch, then test.

2. Define your cushion

That $170K offer landed a few months in. I had about 2 years of savings, and that’s what made saying no possible.

I’m not a big risk-taker with money, so this was a massive step for me. Picking up consulting now and again meant I didn’t burn through those savings.

Before a call like that, I’d check:

  • 6 to 12 months of savings
  • Your expenses mapped, plus how they might grow
  • A realistic shot at landing a similar role again
  • The upsides and downsides, written down

This works for any career call, including this job vs that job. Define your risks.

3. Commit to the process

Someone posted a TikTok about UX Playbook. 200,000 views. I’d done zero marketing and still made $4,000+ that first year.

Maybe people like this thing, I thought. Probably time I told more people myself.

So I posted every day on LinkedIn and Twitter. Me, my laptop, and a shit ton of coffee.

I had no follower goal and didn’t sulk when a something flopped. I wanted the writing reps.

Most people get stuck in the “I suck” phase.

Commit to what you can control (your effort, your time, your skills) and push through it.

4. Validation = people paying you

  • Month 1: $400
  • Month 2: $2,300
  • Month 3: $4,200
  • Month 4: $6,000

I knew something was working because people paid.

Each post was an experiment: does this message resonate, does it build trust, does it convert?

Most of us aren’t building life-or-death products with 5 years of red tape.

Charge for the thing early. A sale is the only test I trust.

5. One believer is enough

Unemployed, creating content, fresh off turning down $170K. I’m pretty sure most of my friends and family would’ve thought I was dumb.

Miya told me to just do it and see what happens.

I’ve seen this before. The best manager I ever had made me do things I didn’t think I could. She set a bar, and I had to live up to it.

Going solo is lonely. Everyone gets told “this won’t work” or “this is a waste of time.”

One person in your corner is enough permission to trust your gut.

6. Stop, reflect, reframe

By July 2023, every other project had died. The startup, the Notion tools, the YouTube agency, Antler. All of it.

Miya and I went all in on UX Playbook. 4 months, 2 of us full-time, and we still couldn’t get past $5,000 a month. Meanwhile, people who started alongside us were doing $20K to $40K a month.

Then Miya said what we were both thinking...

I could’ve gone back to a design job, or even emailed the company whose offer I’d turned down.

We didn’t talk about quitting for 2 days. Then I asked her 2 questions:

  • If money wasn’t the immediate goal, would you still be working on this?
  • Do you have conviction this works on a longer time horizon?

Both yes. From then on, anything above break-even was a win. I get to decide what I work on, set my own schedule, and make things on the internet without losing money.

When you hit a low, ask yourself why you’re doing this, and what else you’d rather be doing.

7. The story you tell yourself matters

The very next month, November 2023, we hit $10,000.

December came in below average. Normally I’d spiral. This time it didn’t bother me.

In my head, $10K means I'm no longer a wantrapreneur.

The highs of doing your own thing are amazing. The lows feel like total failure (I have an existential crisis roughly once a quarter).

You can rewrite your story whenever you want. Pick one you can get behind.

8. It's a game of slow burns

  • 18 months to a $10K month
  • 23 months to $100K lifetime
  • 28 months to a $22K month (finally beating that $170K offer)
  • 32 months to a $42K month

Growth came in small tweaks, over years.

Famous designers get glamorised and social media trains us to want results now, so most of us give up before we’ve properly started. Without a head start, staying in the game is the ONLY strategy.

If we’d quit in October 2023, none of this exists. Including the thing you're reading.

​

If there’s only one thing I’d tell 2022 me, it would be:

“Have a beginner’s mindset.
Be willing to be naive and go head first.”

These days, before I start anything, I ask whether it’s viable and worth my time. Back then I just ship. I even launched 12 products in 12 months!

Most of what I know about running a business, I learned after the fact.

On the livestream, I get into the full story and the lessons in detail.

Watch it below ↓

​

A big thanks to our friends at Optimal for sponsoring this issue.

Imagine typing this into Figma:

“Look at my research for ‘enterprise dashboard’, read the participant feedback, and update the prototype. Put the new screens next to the original.”

That’s Optimal MCP, now connected to Figma’s Design Agent.

So your research goes straight into the canvas:

  • Ask the agent to review your study and flag the usability issues
  • Get suggested fixes based on what people actually said and did
  • Have the agent update your prototype, with new screens side-by-side
  • Keep iterating and feed it the next 10 participants and refine again

Test it. Fix it. Test it again. Here’s the setup guide.

Every designer on the team can design with the research in the room. Woohoo!

​

Our next livestream is How Designers Influence on October 28 (next week!).

Turn up, join the convo, ask questions, or just hang out.

Like always, we're on LinkedIn and YouTube.

Catch ya soon.

— Chris
​rectangles.fm​

🍔🍟 Add livestreams to your calendar Google, Apple, or Outlook​

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