I quit the best job I've ever had
Day 3.
I gave notice five weeks ago, and I still can’t give a clean answer to the question that everyone asks.
Why would you leave that?
I had the title. I had the comp, which I won’t write down here, but it was the kind of number that quietly reorganizes your family’s life around it. I was good at the job. Nobody pushed me. There was no blowup, no betrayal, no story you could tell at a dinner party that would make the decision seem brave or obvious.
That’s the part that’s hard to sit with.
If something had gone wrong, leaving would feel like a reaction to a bad situation. Like I was objectively making the right call and one I could easily explain away to recruiters, family members, and former peers.
Instead, I left behind a role I was good at, a team I cherished, and enviable hours. And now, some mornings, that choice feels less like bravery and more like I’m trying to fix something that doesn’t need fixing.
The truest version I can give: I could see the next two years before they happened. And I just couldn’t do it anymore.
Same motion: run faster, chase bigger numbers, pour more of yourself into something that was someone else’s to keep.
And somewhere in the last year “I’m fine” turned into a thing I was saying instead of feeling that was true. I don’t have a more profound reason than that. I’m a little embarrassed it isn’t more profound. But I’m learning to accept that the desire to live authentically is a good enough reason, even if it’s not a banger LinkedIn headline.
The night before I decided to resign, I sat in the car in the driveway for longer than I want to admit, running the math one more time.
How many months of runway? What happens to that math if nothing works? Run the Monte Carlo analysis. Do the back-of-the-envelope math if everything falls apart.
Am I ruining my family's future? Will I lose out on a future of status and success?
Ultimately, I realized that regardless of the math or my account balance, it would never fully eliminate the anxiety of stepping off the train.
People keep telling me that I’ll figure it out, that I can always get another job, and that even if I fail, the experience will be marketable to a future employer.
And I want to believe it. Some days I do. Some days it sounds like the thing you tell yourself after you’ve already jumped, to make the jump feel less catastrophic.
I spent most of my career striving for growth, taking a company from something to something bigger. That’s the whole reason I think I can do this, and also the reason I know exactly how often “this is going to work” turns out to be wrong.
I’m going to write this down as it happens, before I know how it ends, because I don’t trust the version of this story I’d tell later if it works out. That version is always cleaner than the truth.
So this is the truth right now. I left, on purpose, for reasons I can only half-explain, and I’m not sure if this story will have a happy ending.
What today actually looked like
10:00 AM — Worked a cybersecurity booth at an event with a Fractional client. I wrote the post-event outreach for everyone who stopped by and asked about a free external attack-surface assessment, loaded it into an Apollo sequence, and set it to fire tomorrow at 10
12:00 PM — Lunch with my former Exec coach. Turned into a referral for a fractional opportunity with one of his former business partners.
2:00 PM — Accelerator discovery call. 25 minutes with Refinery Ventures’ X15 program.
4:00 PM - Co-created a workflow for Milkcrate with a $1m/year speaker. Could be a first paying customer, but the early work is pretty bad. More to do here.
The pipeline, in numbers
Sent a fractional CRO pitch to a founder at a Series A company. My actual line: “I don’t believe it’s justified to pay me $xxxk annually, but I can provide significant value to help you reach Series B in one day a week.”
Locked an intro call with the CRO at [Local Series B company] for Monday.
A partnership thread at [xxx] moved forward — NDA signed, two more intros lined up.
A new referral request landed for a Friday call; Sourced from lunch.
The idea I can’t stop circling
Buried in seven notes-to-self I fired off this morning was the one that matters: focus Milkcrate first on the work these businesses already pay outsiders to do and feel nothing about losing. Ad management, website building, content, lead gen. Attack the outsourced, unloved work first. That’s the wedge.
What you can steal from today
If you’re building too, name the objection before the buyer can.
My booth follow-up converts because it removes every reason to say no. The fractional pitch lands the same way: I put the $xxxk salary on the table myself, then took it off. You don’t need to pay me that yet; you need the system built.
Take the expensive thing off the table, and you get the meeting.
Signal of the day
Rawmilk.io is live. Custom domain confirmed. Blog block on the calendar. Topic list written this morning. The whole machine is built and pointed at the runway.
Which leaves exactly one variable: whether I show up and write the post every single day.
Starting now.
Foley
The line that stays with me is “I could see the next two years before they happened” — because that moment of clarity, when the future feels already lived rather than genuinely open, is something I hear again and again from senior professionals at the point they finally decide to redesign their working lives, and it is usually a far more honest reason for leaving than anything that would make a clean story at a dinner party.
This is going to be the most interesting chapter in the Ben Foley book and I'm here for it! Enjoy the ride, my friend.