Hi All!
You’re stuck. You’ve been working on something for months—maybe years—and it still doesn’t feel like it’s working. So you’re asking the question that paralyzes most people: should I keep going or quit? The problem is you’ve been given two conflicting pieces of advice your whole life. “Never give up.” And “Know when to walk away.” Both are true. Neither tells you which is which. This week’s newsletter is about building the wisdom to tell the difference, and then having the courage to act accordingly.
💬 Quote that stuck with me
“Winners quit all the time. They just quit the right stuff at the right time.” — Seth Godin
This quote cracked open something in me because it reframes failure entirely. We’re taught that quitting is weakness, that successful people push through anything. But that’s only half true. Successful people quit constantly. They quit projects that aren’t working, clients that drain them, strategies that don’t move the needle. What separates them from everyone else isn’t perseverance, it’s judgment. They know what to quit. And just as importantly, they know what to lean into.
The real cost isn’t quitting something that matters. The real cost is staying trapped in something that’s going nowhere while telling yourself you’re just “not trying hard enough.” Most people quit exactly backward: they abandon difficult pursuits that would have paid off with another six months of effort, and they stay in dead ends that will never produce results no matter how long they persist. If you can learn to tell the difference between a Dip worth pushing through and a Cul-de-Sac worth abandoning, you’ve learned something most people never figure out.
📚 Book of the week
The Dip by Seth Godin and Grit by Angela Duckworth
The Dip teaches you to recognize three curves: the valuable Dip (the hard middle where talent thins out competition), the Cul-de-Sac (flat progress going nowhere), and the Cliff (deceptively pleasant but catastrophic). Grit teaches you to develop the perseverance to push through real Dips and the four psychological assets that sustain long-term effort. Together they answer the question you’re asking right now. Godin shows you how to know if what you’re in is worth conquering. Duckworth shows you whether you have what it takes to conquer it.
→ Read my full book notes here.
💡 Book highlights I’m contemplating
From The Dip by Seth Godin
“Average is for losers.”
Sitting with this one because it’s harsh but true. The temptation when things get hard is to settle for “good enough.” To be pretty good at your job, pretty good at your side project, pretty good at relationships. But there’s a trap in that philosophy: in a world of abundance, “pretty good” is invisible. Pretty good doesn’t get you hired, promoted, or discovered. Pretty good doesn’t build an audience. You either push through the hard middle and become exceptional, or you quit and redirect that effort somewhere you can be exceptional. There’s almost no sustainable middle ground.
💭 A note from me
I quit something last month that I’d been working on for three years. I kept thinking if I just pushed a little longer, invested a bit more, the breakthrough would come. But somewhere in year two, I realized the problem: I wasn’t in a Dip, I was in a Cul-de-Sac. I was working hard but making zero measurable progress. The breakthrough wasn’t coming because there was no breakthrough to come to.
Quitting it felt like failure for about forty-eight hours. Then I freed up fifteen hours a week. In those fifteen hours, I doubled down on something else that actually had momentum. Within two months, that something else produced results I’d been chasing for years.
The counterintuitive thing I learned is that people who accomplish extraordinary things aren’t more persistent than everyone else. They’re just more strategic about persistence. They know what’s worth the slog. And they know when the slog is pointless. That’s a skill. You can develop it by asking three questions when you’re tempted to quit: (1) Am I panicking or thinking clearly? (2) Am I trying to influence one person or a market? (3) What measurable progress have I made in the last three months?
If you’re panicking, wait. If it’s a wall, find a different wall. If there’s no measurable progress, you already know what to do.
Much love,
Alex x
