What’s Stopping Me? Three Questions I Couldn’t Stop Answering
I’ve listened to the same 32-minute podcast episode five times this week.
That’s not something I do. I move on to the next thing, the next book, the next idea. But this one — Jay Shetty’s On Purpose episode called “How to Let Go & Start Over” — kept pulling me back. It ends with three questions, and I couldn’t just listen to them. I had to sit down and actually answer them.
So that’s what this post is. Not a summary of the episode. My answers to the three questions it left me with.
What am I holding on to because it feels familiar?
The idea that I have to have a traditional 9-5 job.
No one has ever said this to me directly, but I’ve felt it. When my husband made the decision to go part-time thirteen years ago, we dealt with a quiet current of judgment neither of us asked for — the sense that choosing time together over money needed defending. I’ve felt echoes of that same judgment more recently, in the way people talk about anyone who isn’t grinding toward a paycheck, as if not working is something that requires an explanation, or an excuse.
I’ve heard people my age talk about working until they physically can’t anymore, like stopping is something to resist rather than something to welcome. I understand that instinct less than I used to — I’ve always said I’d never be bored in retirement, that there are so many things I’d do if I never had to work a traditional job again. And now here I am, in that exact position, still struggling to actually let go of the idea that I’m supposed to want something else.
Here’s what I noticed writing this down: none of the evidence I gathered for “I need a traditional job” actually belongs to me. It’s my husband’s choice being second-guessed thirteen years ago. It’s the way people talk about work and worth in general. Not one piece of it is something I actually believe when I ask myself directly. The idea feels familiar because it’s the one other people keep handing back to me — not because it’s true.
What identity am I afraid to release because I don’t know what I’ll become without it?
I don’t need to keep calling myself a teacher, or a development manager. Those chapters are complete. What’s actually hard is not having a one-word answer anymore. If I meet someone new, what do I say? It’s tempting to reach for, “I lost my job as a teacher, and then I lost my job as a development manager” — starting with the loss, both times, instead of anything else.
But here’s the thing I had to correct myself on while I sat with this question: those job titles were never doing the heavy lifting of who I actually am. Not for twenty years as a teacher, not for three more at the shelter. A title was always just society’s shorthand — a neat little bow it likes to tie around a person so it doesn’t have to ask any follow-up questions.
I recently came across a line from Adam Grant, shared in James Clear’s newsletter: when you meet someone new, don’t ask what they do — it limits the conversation to their job. Ask what they love to do instead. That’s exactly the gap I’ve been feeling. It’s not that I lost my answer. It’s that most people only know how to ask the smaller question.
I actually already answered the bigger one, months ago, without realizing that’s what I was doing. I built a twenty-slide PechaKucha about myself, recorded every bit of narration, and gave it a single throughline: that’s how we roll. Not my job title. Just — the sum of me, in twenty slides. Turns out I already had the fuller answer ready. I just hadn’t caught up to the fact that I no longer need the shorthand.
What is the next honest step I can take toward the next chapter?
Explore. Try everything.
Volunteer. Join a board. Spend time with the people who fill my cup instead of the ones who drain it. Go on artist dates. Take a class. Write the children’s book that’s been circling in my head. Write more for the Oodlearium. Figure out what Wanda does next. Learn more about plants, just because I want to. Get my arthritis under control so I can get back to running. Start a local Chatterbox Creatives chapter. Finish the collaborative altered book. Finish my Dad Project.
Some of that is maintenance — the artist dates, the classes, the people who fill me up. Some of it is just following through on things already in motion. Some of it is a genuinely open question I get to explore for the first time in my adult life without a job pulling me in a different direction. And some of it — the arthritis, the running — isn’t really exploration at all. It’s just taking care of the person who has to carry the rest of this list.
None of it fits in a single sentence. I’m okay with that now.
If any of this found you at the right moment, the episode that started it is Jay Shetty’s How to Let Go & Start Over (4 Shifts That Will Change Your Life) on the On Purpose podcast. It’s 32 minutes. The three questions come at the very end — but I’d bet you won’t get through it without starting to answer them before you get there.
What’s stopping you?
