14 May 2025

Leap from a cushy job to a startup founder

After 13 years as a designer climbing the corporate ladder, I'm walking away from my well-paid head of design role to bet everything on building my own thing. This is Day 1 of documenting what really happens when you trade security for the entrepreneurial unknown - no highlight reel, just the raw truth.

I just made what might be the biggest decision of my professional life.

After 13 years of designing digital products and climbing the corporate ladder, I recently walked away from my full-time, very cushy startup job which was paying $15k+ MRR.

Why? To build something of my own.

Learning from past "failures"

Now, I know what you're thinking – "Another designer thinking they can be an entrepreneur?" Fair point. I've tried this before. I've built side projects, created cool apps, even got some users in the past. But here's the thing: I never focused on actually making money from them. They were more like expensive hobbies that looked good in my portfolio.

But something's different this time. All those past experiences, all those "failed" side projects and working for more than a decade in the industry, have actually given me something invaluable: Confidence. I know I can build products people want to use. I know I can design experiences that solve real problems. What I didn't know before was how to turn that into sustainable income. I have a playbook to follow this time.

Why the timing feels right

I'm 33 years old (yes, I had to double-check that – getting old!), and I've been smart about saving up a proper runway. I've taken sabbaticals before (for 9 months), so the anxiety of not having a regular paycheck isn't keeping me up at night anymore. There's something liberating about knowing you have enough saved to take real risks.

My commitment to transparency

I am a big fan of building in public. So I'm going to document this entire journey. Every minor and major occasion for the next few weeks and months. I'll share what's really happening behind the scenes. The wins, the failures, the moments of doubt, and hopefully, some breakthrough moments too.

This isn't going to be another highlight reel of entrepreneurship. I want to show you what it actually looks like when a well-paid Head of Design leaves their comfortable job to bet everything on their own vision. The exciting part is to document the unfiltered experience of going from employee to entrepreneur.

What's next

So if you're curious about what happens when someone with a decent track record but zero business experience tries to build something meaningful – stick around. I'll share the good, the bad, and the ugly about this journey. I mostly post first on my socials (Instagram, Twitter, LinkedIn) and then update this blog as they're faster to push the content.

But I'll make sure to keep my notes updated on a bi-monthly basis.

See you on the other side.