The Easiest Issue of the Year (That Somehow Took the Longest)

Entrepreneur Office Hours - Issue #312

Dec 23, 2025

fireworks at night — Photo by weston m on Unsplash

One of the underrated perks of writing a weekly newsletter like Entrepreneur Office Hours is that, once a year, you get to write an end-of-year retrospective. It’s the easiest issue of the year! No new ideas required. No fresh anecdotes. No clever framing devices. You just look back at everything you wrote, pick a few favorites, link to them, and call it a day. It’s the content equivalent of leftovers — and I mean that in the best possible way.

Or rather… that’s the theory…

In practice, this issue somehow always takes longer than a normal one, and I’m not entirely sure why. I’m guessing it’s because the moment I start looking back, I see more than just links — I see context. I remember what was happening when I wrote each piece. Which ones came from class conversations, which ones came from student emails, which ones were born out of frustration, excitement, curiosity, or exhaustion.

Suddenly, what was supposed to be a quick “greatest hits” becomes an exercise in reflection. And reflection, as it turns out, takes time.

So yes, I didn’t have to come up with a brand-new idea for this issue. But I did end up re-reading lots of what I wrote this year, thinking about what resonated, what didn’t, and how my own thinking about entrepreneurship has continued to evolve. Which feels… appropriate, actually. After all, that’s what this newsletter has always been for me. I realize, functionally, it’s a place to share advice for all of you, but, for me, it’s a running record of ideas tested in classrooms, office hours, conversations, and real entrepreneurial work. Looking back on it all at once is a reminder of how much can happen in a single year, even when you’re just showing up week after week and writing one email at a time.

Below, you’ll find a handful of my favorite articles from the past year. If you missed them the first time around, I hope you enjoy them now. And if you’ve been reading all along, consider this a chance to revisit the ones that stuck with me the most.

Heads up… this will be the final issue of Entrepreneur Office Hours for the year. And that means I need to end with a huge thank you. Thank you for reading, replying, sharing, disagreeing, and sticking around. I genuinely don’t take that lightly.

I hope you have a restful, joyful holiday season and a happy new year. And when we’re back in 2026, we’ll be rolling into it with some big, exciting updates for EOH that I can’t wait to share.

See you on the other side.

— Aaron

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