A New Day. A Familiar Format
Entrepreneur Office Hours - Issue #289
For nearly five years I’ve published this newsletter — Entrepreneur Office Hours — on Friday mornings. However, as I mentioned in last Friday’s issue, I’ve launched my new Learning to Fail newsletter (Yay!!!! subscribe here), and that’s also publishing on Fridays.
Since I’m worried about the practicality of writing two newsletters for the same day, I’m moving Entrepreneur Office Hours to Tuesday mornings.
And that’s it… that’s all the news. No grand proclamations. No big announcements. I just wanted you to know why you’re seeing this issue in your inbox today instead of Friday. Otherwise… the rest is exactly what you’ve always enjoyed.
Thanks for reading!
-Aaron
P.S. Also, to compensate for the schedule shift, you’ll notice I’m sharing three articles in this issue instead of the normal two.
This week’s new articles…
Is This the Reason You’re Startup Is Struggling to Make Sales?
A successful sales process requires going beyond what you’re seeing and hearing from customers.
This One Question Will Tell You If Your Startup Is Going to Fail
The potential of a startup idea is easier to judge than most entrepreneurs think, but it does require asking a simple question that’s surprisingly difficult to answer.
Founders Love Talking About Hustle; They Should Be Talking About Something More Important
Sometimes entrepreneurs need a little reminder about what actually matters in the startup world (and beyond!)
Office Hours Q&A
QUESTION:
Hey Aaron,
Here’s a bit of a weird question for you. I’ve been bootstrapping a business for the last two years, and it’s actually doing well. Like, profit-in-the-bank, thinking-about-hiring kind of well.
And now I’m stuck. As strange as this is, for so long, all my energy went into surviving, and I actually don’t know how to manage success, I’m scared to mess it up. I’m scared to stop pushing. I’m scared to burn out by keeping the same startup pace when maybe I don’t have to.
Do you have any advice on when or how hustle mode ends? Or does it ever actually end?
Thanks,
Izzy
You’re right… that is a weird question. But only because most people never make it far enough to have the problem. So first — congrats! You’ve made it out of survival mode. That’s a rare and remarkable thing.
Second, you’re not crazy for feeling confused. I realize success seems like it should come with automatic clarity, but the truth is, success just creates a new kind of ambiguity. Sure, you’re not worried about dying anymore, but you are worried about screwing up what you’ve built and wasting the life you’ve earned.
I suppose the best way to answer your question is to just tell you hustle mode doesn’t “end” so much as it evolves. Early on, you’re sprinting just to stay alive, but once the business stabilizes, sprinting becomes inefficient since you’ll start tripping over your own feet. What used to be the thing keeping you alive starts becoming the thing holding you back, and now you’ve got to find a new balance… equally productive but maybe a little more nuanced.
But don’t worry — the urgency never fully disappears. You’ll always have the quiet fear of messing everything up. And in small doses, it’s probably healthy since it means you care.
The real key is learning how to replace reactivity with strategy. Replace “go-go-go” with “what are we actually trying to build here, and what kind of life do I want while I’m building it?”
Because the goal was never just to survive.
You survived. Congrats?
Now what?
You keep going. Welcome to the next phase of entrepreneurship. You’ll quickly realize it doesn’t look wildly different than the first.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.