The past couple of weeks I’ve made a big deal about a big shift. I told you Entrepreneur Office Hours was about to evolve, and I was excited to bring in new voices from my Duke colleagues.
And then… life happened.
Classes required extra prep. A surprising number of students needed recommendations. I had a keynote to plan that I should have finished a month ago. And so on.
Simply put, other projects demanded attention. And, somewhere in there, the whole “let’s reinvent the newsletter” project slid down the list. So here we are, Issue #302, looking pretty much like the 301 issues before it.
I could beat myself up for it. A younger version of me probably would have. But honestly? It’s just the reality of entrepreneurship. Building anything — whether it’s a startup, a class, or even a newsletter — means juggling an endless stream of shifting priorities. Just when you think you’ve cleared space for the big, exciting new initiative, a dozen other things rush in demanding attention.
This used to frustrate me. I wanted progress to feel linear — like checking boxes on a to-do list. Instead, entrepreneurship is more like playing Whac-a-Mole. You hit one thing, and three more pop up. You make a plan, and reality laughs. And if you can’t find peace in that chaos, you’ll drive yourself mad.
The point isn’t that you never make progress. You do. But the progress happens in fits and starts, often when you least expect it, and rarely in the order you planned. The real skill isn’t rigid execution — it’s adaptability. It’s forgiving yourself when the plan changes. And it’s trusting that the work you’re doing today, even if it isn’t the work you expected to do, is still moving you forward.
So yes, the transition for Entrepreneur Office Hours is still coming. It just didn’t happen this week. And that’s okay. Because the truth is, in startups and in life, things almost never happen on the exact timeline you set. The trick is to keep going anyway.
- Aaron
This week’s new articles…
The Addiction No Entrepreneur Talks About
When founders obsess about the wrong thing, they also forget to do the work that actually matters.
Founders Can’t Sell for the Same Reason Middle Schoolers Can’t Flirt
What if the same fear that makes asking someone out on a date is ruining your startup, too?
Office Hours Q&A
QUESTION:
Hi Dr. Dinin,
I’ve been following your work for a while, and it’s been really eye-opening. I especially appreciate how you talk about entrepreneurship beyond just the flashy headlines and funding rounds.
I wanted to ask something I haven’t seen addressed much. I recently had to shut down a small project I was working on. It wasn’t huge, but I’d put a lot of myself into it. I thought I was ready to move on, but now I’m stuck. Not in a “I want to keep doing that thing” way, but more like… I don’t know what to do next. Every new idea I think of feels either too similar or not exciting enough.
Is this a normal part of the process? How do you find the next idea after something you cared about doesn’t work out?
Thanks again for everything you share — it’s helped me more than you know.
- Maya
What you’re feeling is normal. Painfully, maddeningly normal. Shutting something down is rarely just about the work. It’s about the identity that came with the work. And once that identity’s gone, it makes total sense you’d feel a little untethered.
I’ve gone through it myself more times than I’d like to admit. One project ends, and instead of feeling relieved — like I’ve finally freed up my time — I feel aimless. Worse, every idea I come up with in that state feels like it’s trying too hard. Or not hard enough. Or too much like what I just left. Or nothing like it, which makes me question whether I care at all. That’s not a lack of ideas. That’s grief.
What’s I’ve ultimately learned is you don’t find the next idea by forcing it to look like “the one.” You find the next idea by moving. Not launching a company. Not building a deck. Just moving.
Start writing again. Start tinkering again. Start talking to people again. Start following your curiosity, even if it doesn’t seem “useful.” Eventually, something will stick. But you won’t get there by sitting still and waiting for lightning in a bottle.
Keep moving. Something new always shows up.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.