What we talk about when we talk about leaving the 9 to 5
What 3 humans taught me about leaving, longing, and the limits of AI advice.
Did you know you can keep your ambition intact even if you’re going through burnout?
And that the problem with career advice is that it’s usually about work?
And that if you’re feeling disconnected from your day job... you are most definitely not alone?
These are just a few of the things I learned from three generous interviews with people who want to leave their 9 to 5 (and who enjoy playing around with AI).
Today I want to share some of the wisdom they passed on to me, and give you a peek into the next step in shaping a prototype for a small business.
Before we dive in: a reminder to stay curious
The first is about the incredible feeling of asking open questions and having people be open and vulnerable in return.
It reminded me that we all share the same doubts, the same fears, and the same quiet "what ifs."
It also reminded me to stay curious. To keep listening.
For a moment, I forgot I was doing these interviews to validate a business idea. And I was just learning how us, humans, think life, work, time, meaning.. and everything in between.
And a shoutout to friends that believe in our ideas
A thank-you to my friend A., who reminded me not to let go of The Letters Club.
He told me he believes there are people who would find immense joy in receiving a letter: in opening it, reading it, and feeling seen.
He said he would’ve loved to gift that to his mother, if he’d had the chance when she was alive.
I don’t know if I replied properly at the time, but this is me saying thank you: for believing in the “crazy” ideas, for encouraging me not to give up, and especially for sharing a memory of your mother.
Although I didn’t meet her, I bet I know a little bit of her through the man you are.
Let’s deep dive: Mapping the Problem
I mapped what I learned from the interviews onto a whiteboard. This was a conscious decision to stay systematic, and avoid jumping straight into a solution.
I wanted to sit with the problems. Let them brew a bit.
I started by breaking down what I could sense (either explicitly said or subtly implied) about how they see the world: their fears, ways of thinking and wishes for the future.
To be honest, I recognize myself in a lot of it.
Then, I zoomed in on the specific problems they’re currently facing while in this in-between state of wanting to leave a job, but not quite being able to.
And finally, I went a level deeper: what disappointed them when they sought help (through coaching, courses, or even career tools)
I did ask a question about using AI — but since that’s already leaning toward the solution space, I decided not to summarize those learnings just yet.
Here’s why:
Each of these problems could have its own solution. Or maybe… one solution could touch them all.
But AI is just a means. So is a landing page. So is a conversation.
So I won’t dwell on it yet.
Interview Snapshot
Q1: “Tell me about the last time you seriously thought about leaving your job.”
“I think about it every day. Meaning, the last time it was today. I am renting out my life time in order to get paid… something I cannot get back.”
“I started to feel like a mercenary, trading my time (and quite literally my life) for something I didn’t really believe in.”
“The rat race is real. And when I realized there’s no way I can win this race each day, it was time to reevaluate how I see work.”
Q2: “What have you tried so far to move away from your 9-to-5? What got in the way?”
“First you need to search within yourself… there is a journey until you get these things figured out.”
“I was in resource-gathering mode… but I think it’s easy to get stuck there while life passes us by.”
“What’s gotten in the way is lifestyle. That shit is boozy as f.”
Q3: “Have you ever paid for any kind of help around your career? How did it go?”
“Later I realized I didn’t need coaching. I had already made the decision.”
“Career advice, really, is essentially life advice.”
“I’m ready to try again — but only if I get a better fit.”
Q4: “Have you used ChatGPT (or similar) for career-related help? Did it help?”
“It amplifies my potential. I realized how much I can do as a one-man show.”
“I find the results subpar… I use it mainly for direction, then rewrite everything.”
“I expected a roadmap… it came back with generic advice. I think I don’t know how to ask the right way.”
There’s so much more wisdom in these conversations. They’re gems!
And if you’ve read this far, I want to invite you into the process too.
Is there something I’m missing?
Did something here spark a thought I should explore?
Or maybe… I didn’t interview you, but you’re also thinking about leaving your 9 to 5. I would love to add your story to the mix.
Let me know.