If you're thinking about quitting your job to build something on your own, please read this first. This is the advice I wish I had yelled in my face a year ago:
Build it at night. Build it on the weekends. But, keep your job.
I say that as someone who did the opposite.
One day, I decided I was out, gave my 2 weeks, stayed 3 weeks to help the transition and then landed in the abyss of unemployment. No salary. No healthcare. Just time.
Where This Comes From
At the end of August 2025, I walked away from a well-paying job. I knew I wanted to build something for myself, and I was completely burnt out from the work I was doing. So, I sat in that moment and I told myself, I think it's time to go and I left.
As August approaches, I've now gone roughly 12 months without a salary.
It has been quite the rude awakening.
What You Actually Keep
When you keep your job, you keep two things.
One is obvious: the money.
The other is the one nobody talks about, but is honestly more important: your healthcare.
Two things I've been without, or barely holding onto, since the day I left.
I've been living off contract work here and there, and it's really never been enough. I've cut my expenses down to basically zero. I moved back in with family. I gave up a really nice apartment in South America. And, with inflation it's still never enough.
Then there's the part that's been genuinely dark — living or trying to live off crypto.
Since I left, crypto has gone down seemingly monthly. And, this wasn't play money. This was crypto I never planned on selling, that I never wanted to touch. This was my retirement plan.
I say was, because I've had to sell it down, month over month, just to keep going.
The Most Honest Thing I've Shared Here
If you’re following this newsletter weekly, you know that I should launch CHUMP soon. And, if I am being honest I have doubts.
I'm not scared of the launch. I'm scared of doing it alone.
Building by myself has taught me that it's lonely. There are days I wish I could just sit down across from someone and say, hey, what do you think about this? Does this make sense? And have them tell me, no, it doesn't and thank them for helping me think it through or challenge me on it.
Because, I'm tired of iterating with AI. At the end of the day, it mostly tells you what you want to hear. Even when you ask it not to, it still finds a way to make you feel good inside. Something that shouldn’t always go hand in hand with bootstrapping a tech start up for the first time on a shoestring budget.
Now, this isn't a call for someone to come build CHUMP with me. It's just a real share of where I am right now.
The closer I get to launch, the louder one question gets: do I actually want to do this on my own?
I've learned this year that I get my energy from other people. They say introverts lose energy around others and extroverts gain it — and I'm the second kind. So, the thing I've now spent months building, I'm not even sure I want to launch alone. Which is a strange place to be standing 36 hours out from a potential public launch, but here we are.
What Building CHUMP Has Given Me
Building CHUMP has taught me: I want to work with other people, and it’s given me skills and confidence around AI that I flat-out did not have six months ago.
Every time I sit down and build — CHUMP, or the things I've built for other people — I feel like I’m learning at lightspeed. I can confidently sit here today and say that I feel comfortable now with finding a solution to almost any problem given enough time and vision. And, that's a valuable toolset in today's world. A world that’s ever more rewarding the builders and doers.
I feel confident in my ability to build. To find the answer. I know I have a unique skill set regardless of what happens with CHUMP.
Where I Am Today
As I write this, I'm in the part of the arc rappers always talk about — the stretch where nobody would sign them, nobody saw what the potential could be.
Once I overcome my current fear of going alone into the entrepreneurial wilderness, I’ll launch CHUMP and no matter what happens, and as a good friend reminded me last night, “you probably should launch it, because you’ll learn A LOT”.
Financial Oxygen Mask
I’m also going to dive back into podcasting and support some Founders and startups to launch their own shows. I love podcasting and think it's an extremely valuable skill that I have to be able to work with a Founder or startup and take them from no show to publishing shows weekly with clips across their socials. If you know of anyone looking to launch their own show but not sure how to, have them reach out.
Podcasting is the current plan to get some money moving and put back on my financial oxygen mask, while I build CHUMP and some other projects.
The Reality Of Being Unemployed
We live in a world that looks down on the word unemployed. It doesn't know where to file you.
The wild part is the person that potentially judges you might have a job they hate or one that’s driving them into depression or straining their marriage, but society will say they're the one doing it right. Meanwhile the person who stepped away because they were burnt out gets the side-eye at the dinner party. I know, I’ve gotten many side eyes.
Leaving the comfort of a salary is not the safe bet. It's not the move society rewards or thinks is cool, but it's the bet I made.
I asked to go into the abyss. I asked to give up the salary, the healthcare, and the ability to comfortably live on my own in my late 30s. I asked for this.
En Fin
This is the behind-the-scenes of my life right now.
It’s not comfortable. It’s not what I thought it would be. But, it’s what I asked for.
If you're out there doing the same thing — left, got let go, trying to build while corporate America looks easier and safer by the day — you're not alone. I've talked to a lot of people living this exact reality.
And, to anyone standing where I stood a year ago: don't quit your job to build.
Do it on the nights and the weekends. You'll save yourself a whole lot of new challenges.
But, build. Now is the best time ever to build something, so start today at night when you have even 30 minutes.
As always — nothing replaces action.
Thanks for reading, and see you next Tuesday.