The Systems That Constrict Us (Whether We Like Them or Not)
Entrepreneur Office Hours - Issue #308
I know this newsletter is supposed to be about entrepreneurship, but I heard a story this week I have to share. It’s too good not to. And, sure, I’ll try to tie it back to entrepreneurship if I can. But, either way, enjoy this story purely because it’s ridiculous…
It’s a story from, of all people, my mom. She’s at that age where she seems to be traveling every other week. Her most recent trip was a cruise that left from Canada, floated down the East Coast, and eventually dropped her off in Fort Lauderdale.
Nothing unusual… until she disembarked.
Apparently another passenger grabbed the wrong suitcase at the port on the way out. Not just any suitcase — my mom’s suitcase. And he didn’t realize it until he’d already flown all the way back home to Canada.
To his credit, once the cruise company tracked him down, the gentleman who took her suitcase was mortified. He marched straight to FedEx and shipped the suitcase back to her immediately.
Sweet, right? Heartwarming, even?
Yeah… no.
That was two weeks ago, and my mom still doesn’t have her suitcase. Why? Because it’s stuck in customs!
Yes, customs. As in: the U.S. government is holding my mom’s suitcase hostage because… wait for it… they want her to pay import duties on her own dirty underwear.
And no, I’m not joking. She literally cannot get her own belongings back unless she pays a tariff on items she already owned, already wore, and almost certainly needs to wash.
The whole situation is absurd. I feel terrible for her, but, when she told me the story this afternoon, I also couldn’t stop laughing because it’s just too ridiculous.
You’re all welcome to join me in my laughter. However, as promised, I also want to tie the story back to entrepreneurship. After all, the entire situation reminds me of something that’s deeply and painfully relevant to building companies:
Systems don’t care about your story. They care about their rules.
In the case of my mom’s luggage, the cruise company knows it was an honest mistake. The guy who mailed the suitcase knows it was an honest mistake. My mom definitely knows it was an honest mistake. But to the bureaucratic system evaluating the package, none of that matters. There’s a process. There’s a workflow. There’s a checkbox. And that’s the only reality the system sees.
Entrepreneurship works the same way.
You can have the best intentions. You can know your product is valuable. You can be certain your customers should want what you’re building. But the world doesn’t respond to your intentions. The world responds to its own incentives, workflows, and constraints.
Customers don’t buy just because you worked hard. Investors don’t write checks because you’re passionate. Partners don’t sign deals because you’re a good person.
If you want something to move — whether that’s a business or a suitcase — you have to design for the system you’re operating in, not the story in your head. And you have to accept reality as it is, not as you wish it were.
My mom, by the way, still doesn’t know whether she’ll pay the tariff or let the suitcase go. (I’m personally hoping she fights this on principle — the thought of a customs officer forced to process a tariff for used socks is objectively hilarious.)
But for the rest of us?
I’m actually sharing my mom’s story because It’s a good reminder that the world is full of systems we don’t control. Our job as entrepreneurs isn’t necessarily to fix all those systems. Our main job as entrepreneurs is to understand them well enough to navigate them anyway.
-Aaron
This week’s new articles…
Your Big Startup Idea Doesn’t Matter (Until You Do This)
The best entrepreneurs know the difference between the stuff that sounds impressive and the stuff that actually is impressive.
The One Lesson About Startups No Business School Can Teach You
You’ll learn a lot in business school about building and running companies, but there’s one thing that’ll never happen.
Office Hours Q&A
QUESTION:
I’ve been following your stuff for a while now, and one thing that really resonates with me is how much you emphasize actually doing the work, not just talking about it. And I also noticed that was a theme of some of the other people you work with who were giving advice. So here’s my situation…
I’ve had an idea for a product for over a year. I’ve talked to a few friends about it, written out some notes, and have my domain name. But I haven’t launched anything yet because I’m nervous it’s not ready. My question is: how do you know when to stop planning and just go?
You make it sound so simple, but it never really feels that way.
-Arvan
You’re not wrong. I do write a lot about doing the work. And I stand by it. But I also get why it feels frustrating to read, because — let’s be honest — it’s easy to sit here and say, “Just launch.” It’s easy to write it in a newsletter. It’s even easy to believe it in theory.
But doing it in real life? That’s the hard part.
And that’s what makes entrepreneurship so difficult.
Entrepreneurial concepts aren’t particularly hard…
Solve a problem. Launch a thing. Listen to users. Improve. Repeat.
None of it is some big secret. Instead, the hard part is the reality of actually doing the work. Honestly, “doing the work” is what keeps most people stuck in planning mode.
So if you’re wondering whether it’s time to launch, or when to launch, unfortunately I don’t have a perfect answer for you. I can’t promise it’ll go well. I can’t promise it won’t flop.
The only thing I can promise you is that clarity doesn’t come from more notes or another brainstorm session. It comes from momentum. And momentum only starts when you begin.
So maybe that’s the only real advice I can give: Don’t wait until you feel confident. Just pick a day, and begin.
The work is hard. That’s why it matters.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.