Remember There's no Such Thing as Making Everyone Happy

Entrepreneur Office Hours - Issuer #294

Photo by Priscilla Du Preez 🇨🇦 on Unsplash

I just finished teaching a week-long, summer mini-class at Duke. It was a partial-credit course for graduate students pursuing a certificate in Innovation & Entrepreneurship, and there was exactly one requirement for passing: attendance. Show up to every session, you pass. Miss any of the class, you don’t.

That was it.

That single requirement was communicated repeatedly. It was stated clearly in the syllabus, announced multiple times before the course began, and emphasized again on the very first day. And yet — as happens every single year I've taught this class — some students inevitably missed a session and were surprised (even angry) when they didn't get credit.

Early on in my teaching career, I took those moments personally. I'd feel genuinely hurt that students could be upset with me after I felt like I’d so clearly laid out the rules. How could they be angry at me when I’d warned them so many times? Eventually, I moved into another stage where I started bending rules or adjusting requirements, mostly because it was emotionally easier to give in than to face someone’s anger or disappointment.

But recently, I've reached a new stage. I've finally learned to accept something every entrepreneur, creator, teacher — and frankly, every person — should eventually learn to accept: You simply can’t please everyone.

It's a tough lesson, especially for entrepreneurs. When you're starting out, it can feel like every potential customer, partner, investor, or user is mission-critical. Each criticism or angry email feels like a direct threat to your survival. You instinctively want to adapt, accommodate, and please every person who shows even mild dissatisfaction.

But trying to please everyone is a fast path toward pleasing no one. The moment you compromise your core values or fundamental business decisions just to prevent upsetting someone, you risk losing sight of why you're building what you're building in the first place.

This doesn’t mean you should disregard feedback or refuse to adapt. Great entrepreneurs listen, learn, and improve constantly. However, there's a difference between thoughtful adaptation and frantic, fear-driven people-pleasing.

As I've gotten older — and hopefully a bit wiser — I've learned that real success, the kind of success that lasts, comes from clarity and conviction. It comes from setting clear expectations and being willing to stand by them, even if some people end up unhappy. Because the alternative — trying to please everyone — leads to confusion, mediocrity, and ultimately failure.

So if you're an entrepreneur dealing with upset customers, frustrated partners, or critical feedback, know this: You're not alone, and you're not failing just because someone is unhappy. Instead, you're learning one of the most valuable lessons in entrepreneurship (and life): not everyone will love you, and that's OK.

In fact, if nobody ever gets a little mad at you, you're probably not making enough of an impact. Real entrepreneurship means clarity, decisiveness, and courage — even when it's uncomfortable.

Keep going. You're doing better than you think.

-Aaron

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This week’s new articles…

You’re Going to Ignore This Startup Advice, and Maybe That’s OK

Why the natural cycle of entrepreneurship includes ignoring the great advice you’ll get from more experienced founders.

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The Perfect Length for a Startup Pitch Deck

I quick lesson to help you understand what investors expects to see when you show them your slides.

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Office Hours Q&A

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QUESTION:

Hi Dr. Dinin,

I’m a senior in college, and I’ve been seriously considering starting something of my own instead of going the traditional job route. But one thing that keeps holding me back is health insurance.

I know that sounds boring compared to the excitement of startups, but it’s a real concern (especially for someone like me because I have some medical issues).

When you're just starting out and bootstrapping, how do people usually handle things like health insurance? And there’s probably some other “adulting” responsibilities that are similar I should also be concerned with. Like maybe a 401K or something? Anyway, are these things I should be worried about now, and how do you figure them out as you go?

Thanks for keeping it real in your content. It’s been hugely helpful as I try to make these big decisions. I love every video that comes up for me on Instagram!

—Jared

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Thanks for the thoughtful (and refreshingly practical) question. Also, thanks for the kind words — I’m really glad the videos are helping!

So, first of all, let’s just acknowledge something that doesn’t get said enough in startup land: this stuff matters. Like, really matters. Especially when you’ve got legitimate medical needs. So don’t let anyone shame you into thinking you’re “not cut out for entrepreneurship” just because you’re worried about things like health insurance or saving for retirement. That’s not weakness. That’s responsibility.

As for the reality of it… yeah. It’s a pain.

Most entrepreneurs either (1) stay on a parent’s plan if they’re young enough, (2) find a spouse with good benefits, or (3) grit their teeth and buy coverage through the healthcare marketplace. None of those are magic solutions, but if you’re bootstrapping, the marketplace route is usually your best bet. It’s not always cheap, but it’s manageable, and you might qualify for subsidies depending on your income.

As for other “adulting” stuff like 401Ks — it’s OK to let some of that wait. Not forever. But the pressure to have all that buttoned up right away can distract you from the actual work of building. In the early days, your biggest asset isn’t your retirement account. It’s your time, energy, and freedom to try things. That said, just because you’re not building a 401K yet doesn’t mean you’re failing. It just means you’re investing in a different kind of growth.

So here’s my actual advice:
You don’t have to choose between being a responsible adult or taking a leap. You just have to do both a little messily. That’s what every entrepreneur is doing, whether they admit it or not. You patch things together. You read boring IRS articles. You call customer service lines. You pay more for things than you want to. But you keep building.

And honestly? That’s kind of what entrepreneurship is.

Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.