The Pain of Choosing Vs The Pain of Staying
Brooke Castillo, a coach I follow, recently shared a podcast episode about taking six months off from her life. Admittedly, Brooke’s circumstances differ from most of ours: she owns a multimillion-dollar business, has a team to run it in her absence, her kids are grown, and she likely never has to work again if she doesn’t want to.
I, on the other hand, have managed to wrangle a month off work a few times (the chronicle of my last month off is here). I even tried to secure a six-month sabbatical last year, but it didn't work out. When I take a month off, it requires some planning, mainly moving 12 months’ worth of shifts into 11. It took Brooke three years to plan her six-month break. I haven’t taken any time off my entire life, but I have several things on autopilot (like lawn care, cleaners once a month, and bills on autopay). Despite that, a deep clean once a month isn’t going to cut it; there’s still a fair amount of tidying up to do. Groceries still need to be picked up. Laundry needs to be done. And those Amazon Prime deals aren’t going to buy themselves.
During her six-month hiatus, Brooke spent the first half decompressing and catching up on life admin: organizing closets, filing papers, and figuring out which cards paid which bills. But the second half? She asked herself, “If I were starting over, would I choose this again?”
That question hit me. Yes, we’re autonomous beings (hello, ethicist hat), but so much of our lives happen by default. A cascade of mostly small decisions, with a few big ones scattered in, made with the best info we had at the time. When do we stop to ask: Do I actually want the life I’ve built?
Would I choose my job in academic medicine again? Yes. It’s not perfect, no institution is, but the alternative of looking for another job feels way worse. I’m not deliriously happy in every area of my life (because, let’s be honest, there’s a lot we can’t control), but I’m content in many. And where I’m not? That deserves some attention.
We often avoid these questions for two reasons:
Things feel “fine” until they suddenly don’t.
We’re afraid of what honest answers might reveal.
But staying in a life you wouldn’t choose is its own kind of pain.
You don’t need six months. You just need a few quiet minutes, a pen, and a piece of paper (bonus points if it’s purple and not hospital-issued black). Writing forces you to slow down. Thinking can be slippery, but writing makes things visible. (If you hate writing by hand and that would be the thing you use to stop you from doing this exercise, then, by all means, type it into your notes app or favorite word processor.)
Start by asking yourself: Would I choose this again? Consider these domains:
1. Health and Well-being
Am I thriving physically and mentally?
Do I feel rested, nourished, and cared for?
2. Relationships and Connection
Are my relationships supportive and mutual?
Do I feel connected or isolated?
3. Work and Career
Is my work fulfilling, challenging, and aligned with my values?
Am I growing?
4. Purpose and Meaning
Does my life feel significant?
Am I contributing in a way that matters to me?
5. Money and Finances
Do I have enough?
Is my relationship with money healthy?
6. Time and Energy
Do I have agency over my schedule?
Is there room for spontaneity?
7. Play, Joy, and Creativity
Do I have fun?
When did I last laugh until my stomach hurt?
8. Spirituality and Inner Life
Am I grounded?
Do I feel connected to something bigger than myself?
You don’t have to tackle them all; pick one or two that feel especially loud right now. Will it be uncomfortable? Maybe.
But if you’re going to be in pain anyway, make sure you choose the pain that leads somewhere better.