This week, one of my former students was back on campus. She’s been out of school for a few years now, working on her own startup, and during our brief conversation she said something that made me chuckle:
“Half the things you taught me in college didn’t make sense until after I graduated.”
At first, I didn’t know whether to feel proud or insulted. But then she explained: “It wasn’t you. It was me. I just had to actually live it before it clicked.”
And she’s right. Unfortunately, that’s exactly how wisdom works.
I can vividly remember the same thing happening to me. People — mentors, colleagues, family members — told me things that, at the time, seemed irrelevant, exaggerated, or just plain wrong. I nodded politely, maybe even wrote it down somewhere, but I didn’t really believe it. Years later, I’d find myself in a situation where their words came rushing back, suddenly undeniable. The problem wasn’t their explanation; the problem was that I hadn’t lived enough to understand.
That’s the frustrating paradox of teaching, mentoring, and entrepreneurship. Heck it’s true about most things. Driving. Eating. Parenting. Simply put, wisdom can be handed to you, but it rarely sticks until you’ve earned it. You can’t fully absorb it through lectures or blog posts or clever stories. Some lessons only reveal themselves in the doing. And, unfortunately, many of the most valuable lessons don’t just require doing — they require failing first.
Of course, nobody wants to hear that failure is a prerequisite for learning. We want clean, easy paths, and we want shortcuts. But that’s not how growth works. The things that shape us most — both in startups and in life — tend to be the things that knock us down and force us to get back up.
That’s not failure. That’s how learning works.
-Aaron
This week’s new articles…
The Only Way to Create Loyal Customers
Startups don’t just need customers. They need *loyal* customers. And getting loyalty has a real cost.
The Feeling Every Founder Mistakes for Failure
When you’re building a startup, success will rarely feel like you expect, and that’s going to make it hard to stay motivated.
Office Hours Q&A
QUESTION:
Hi Aaron,
I’m trying to figure out how to hire my very first freelancer. It’s nothing huge — just a designer to help with a couple of assets for my landing page — but I’ve never hired anyone before, and I’m nervous about doing it wrong.
Do you have any advice for first-time entrepreneurs who are just starting to delegate small pieces of work?
Thanks for all your content — it’s the only entrepreneurship advice that actually makes me laugh while I’m learning.
- Caleb
You’re referencing that magical moment when a founder hires someone for the very first time.
Sure, it doesn’t feel like a big deal — just a freelancer for a few design assets, right? But it is a big deal. It’s a rite of passage and the moment your company expands beyond your own two hands. That’s huge!
For starters, be very clear on what “success” looks like for this task. Most people mess up their first hires because they’re vague. “Make me something nice” is not a brief. “I need a 1200x628px homepage banner that feels premium, matches the rest of the site, and includes this call-to-action” is a brief.
Honestly, a good comp is AI prompting. You’ve surely noticed the more explicit your are in AI prompting, the better the outputs. The same is true in hiring.
Why does this matter? Because the clearer you are, the more likely you’ll actually get what you want (and the less likely you’ll blame the freelancer when you don’t).
Next, remember that hiring someone isn’t like hitting a button and getting a finished product. It’s a conversation and, more importantly, a collaboration. Even with great freelancers, you’ll probably need to give feedback. That doesn’t mean they’re bad at their jobs. It means they’re not in your head — and that’s a good thing. You want to work with people who bring their own perspective.
Oh, and don’t ghost your freelancers if something feels off. I know it’s tempting. But communication is a skill, and this is a great moment to practice.
The last thing I’ll mention is that you’re not hiring someone to do all your work for you so you can relax. You’re hiring someone to do work for you that they can (hopefully) do better so you can do — great ready for it — do more work!
I see all the time founders imagining a world where hiring is what finally lets them kick their heels up and take a break. Wrong! Hiring doesn’t stop you from having to do work. It gives you the ability to do more.
Oh… and it also creates more. Yay! Congrats. You're officially a boss.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.