Read This Book to Help You Quit, Breakup, or Move on
staying feels safer, but leaving feels right
Most people quit too late. I did too. I stay too long in things that don’t feel good. At least, that’s the pattern I hope never to repeat.
Sometimes it’s not outright painful—just uninspiring, stagnant, lackluster. A slow fade.
I stayed in a straight relationship for seven years because I didn’t want to face my gay feelings. Oops.
I once stayed in a job I was completely bored with because I felt like I wasn’t good enough for anything else. Ouch.
I lived in NYC for a decade, unhappy, but had no idea where else to go, so I stayed.
(Happy ending to this one: Once I came out, I found happiness in myself first—then in the city. I was thankful to be young, gay, and free in NYC.)
In the summer of 2023, when I was completely depleted, I read a book that helped me step out of my emotions and see things clearly.
The Book Helped Me Quit
📖 Quit: The Power of Knowing When to Walk Away by Annie Duke
Annie Duke is a poker champion. She knows when to hold ‘em and when to fold ‘em. But this book isn’t just about poker—it’s about life. It helped me see quitting not as failure, but as strategy.
One passage hit me hard (paraphasing):
Imagine it’s a year from now and you stayed in the job you’re currently in—what’s the probability you’re going to be unhappy at the end of the year?
Now, imagine it’s a year from now and you left. What’s the probability you’re going to be unhappy then?
Put numbers to it. Then look. Numbers helped me ground all the emotions.
That question alone cuts through the noise of self-doubt and fear.
Then there was this:
If you quit on time, you will feel you quit early.
By the time something is unbearable, you’ve already stayed too long.
💃🏾 “I want to make sure I am dancing, not shuffling.” – Dave Chappelle
The Moment I Knew It Was Time to Quit
The moment I felt the most pride wasn’t in building my company—it was in walking away from it.
I stepped down as CEO of the company I founded. I had achieved everything I set out to do, but I was in so deep that I couldn’t feel it. I was detached. Numb.
That summer, I went on a retreat with other founders. A beautiful resort in Utah’s Canyonlands, surrounded by people who understood the weight of running a company. We shared what we were struggling with.
I summed mine up in one line –
Plan of attack for peace.
People laughed, maybe uncomfortably. Many came up to me and said they related to the sentiment, too.
After the retreat, one of my investors phoned me and asked, Are you okay?
That was the moment I caved. Everything spilled out.
I hadn’t said the words out loud before, but as soon as I did, I knew: I had to leave.
A few weeks later, I stepped away. It was terrifying. But immediately, I felt lighter.
Lessons from quitting too late
🚨 Your gut knows before your brain does.
By the time you’re constantly wondering Should I go?—you already know.
🚨 The ‘perfect time’ doesn’t exist.
Quitting always feels premature. But staying too long is worse.
🚨 Fear of ‘starting over’ is a lie.
You’re not starting from scratch—you’re bringing everything you’ve learned.
🚨 Someone outside of you will probably see it first.
It took my investor checking in for me to finally admit I wasn’t okay. Sometimes, other people see our burnout before we do.
🚨 You don’t need permission to leave.
Leaving is an act of self-trust.
TL;DR – when to walk away
✅ If you’re constantly asking, you already know.
✅ Quitting on time feels too early.
✅ You’re not starting over—you’re moving forward.
✅ The cost of staying too long is resentment, exhaustion, and missing out on what’s next.
What’s something you quit that changed your life for the better?
Or—what’s holding you back from making the move you know you need to make?
I’d love to hear your experiences. Cheers to quitting. 🎉
So real! Dealing with lots of this in many areas of life. Quit my business, quit friendships, relationships and more. I always hold on longer than necesarry but that might be part of it...grieving while its in our hands out of fear we might regret the decision.
Quitting is something I'm coming to terms with and welcoming into my life as a moment of possibility as opposed to a moment of failure. Cheers to quitting, indeed! :)