The Unexpected Challenge of "Success"

Entrepreneur Office Hours - Issue #270

I posted a video this week that’s getting lots of positive attention. It’s got hundreds of comments saying things like “Great teacher!” and “Best professor ever!” and “I wish I could go back to college just to take classes with you.” I’ve also gotten dozens of emails saying similar things, and even text messages from long forgotten acquaintances who stumbled across it and randomly reached out just to tell me how much they enjoyed the video’s message.

Despite all that praise, the one message that sticks in my head is an email from a mother — with my boss CC’d, interestingly enough — basically saying I’m the worst person ever, I’m stressing students out, and that my video might encourage some student somewhere to commit suicide.

When stacked next to all the positive feedback flooding in, it feels like an extreme reaction. It’s like opening ten gifts on your birthday, nine of them being exactly what you wanted… but the tenth is a box of rotting vegetables.

But, of course, which one do you think you’ll remember? The rotting vegetables, obviously.

That’s the tricky part of entrepreneurial success that nobody prepares you for. You’ll spend a decade trying to launch a world-changing product. And when you finally do, and when it starts getting used by millions of people, rather than being joyous about what you’ve accomplished, you’ll be obsessing over the angry tweets and scathing online reviews from the five who didn’t like it. In other words, no matter how much good you do in the world, negativity is inevitable. You can try to please everyone, but someone — somewhere — will still think you’re ruining the world.

That negativity creates a huge challenge for entrepreneurs because we pour so much of ourselves into our work. We are our companies, our products, our content. It’s not just a 9-to-5 job; it’s our identity. And when someone attacks the thing you’ve built, it feels personal, even if it isn’t meant to be.

Just know that when this happens to you — and it will happen if you achieve whatever entrepreneurial visions you’re dreaming of — here’s the upside: the very fact that you’re receiving negativity means you’re reaching people in a meaningful way.

Think about it… if only three people see your work, you might get three polite smiles. But if 3,000 or 300,000 people see it, you’ll find plenty who love it — along with a few who hate it. And as backward as it’ll feel, that hate is a sign you’ve grown beyond your safe bubble of friends and family. You’re playing on a larger field. That’s a great outcome, even though it won’t feel particularly great.

I’m sharing this strange paradox because entrepreneurs who aren’t prepared often get derailed by it. The inevitable negativity eats them up. It undercuts their passion and destroys their joy for achieving the dreams they set out to accomplish, and they can’t let that happen.

So how do you stop it? How do you keep the vicious emails, the nasty customer phone calls, or the scathing products reviews from overshadowing the value you’re creating?

It’s not easy. Humans are hardwired to fixate on bad things. But here are three quick suggestions for when you find yourself in such a strange situation:

1. Zoom Out: Remind yourself of the bigger picture. You’re touching a massive audience, and statistically, not everyone will vibe with what you do. Negativity doesn’t cancel the positive impact you’re having.

2. Respond Intentionally or Not at All: Don’t let negative feedback drag you into a defensive spiral. If it’s constructive, take what you can from it. If it’s purely hateful, recognize it for what it is — someone else’s issues, not yours. Perhaps directing rage at you provided a much needed cathartic moment. Sure, it didn’t feel good to be on the receiving end, but it was certainly a valuable outlet for a person who’s clearly struggling through something difficult.

3. Keep Doing Meaningful Work: At the end of the day, the best antidote to negativity is to keep creating value. If you let critics silence you, nobody wins. But if you persist, you continue reaching the people who genuinely benefit from your contributions.

So, yes, success will never feel exactly how you expect. It’ll come with flattering praise, but the stinging jabs are going to be much more memorable. However, if you’re serious about building something that matters in the world — whether it’s a business, a platform, or a message — remember that scale brings both applause and jeers. Stay focused on why you’re doing it, and take comfort in the fact that every negative comment represents a bigger stage than you had before. Above all, don’t let a handful of voices drown out the value you’re creating for so many others.

-Aaron

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This week’s new articles…

The Best Entrepreneurs NEVER Ask for Feedback

And it’s not because they think they’ve already got everything figured out and don’t need to hear other people’s opinions.

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Why Great Products Can Still Become Failed Startups

Even the best ideas aren’t so good when entrepreneurs forget to consider one important thing.

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Office Hours Q&A

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QUESTION:

Hello Professor Dinin,

I recently watched your YouTube video about students choosing to attend class despite the university closure. Your insights on navigating ambiguity and fostering decision-making skills are inspiring to me. I am eager to learn more about the strategies and best practices that can be employed to effectively guide individuals and teams to make decisions more efficiently and confidently.

I would greatly appreciate any resources, workshops, or reading materials you could recommend for deepening my understanding and enhancing my coaching skills in this area. I would also be very interested in learning more about any upcoming webinars or courses that might be beneficial.

Thank you for your time and assistance. I look forward to your recommendations and insights.

Warm regards,

Melissa

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Thanks for reaching out! I’m so glad you found that video insightful. Decision-making is one of those essential, lifelong skills that impacts everything from our daily routines to major career pivots, yet we often don’t learn it in a structured way. The good news is, there are plenty of approaches you can explore without needing complex frameworks.

When it comes to reading materials, two books I I’ve liked are:

• Thinking in Bets by Annie Duke: This book is fantastic for learning to make decisions under uncertainty. It frames decisions as educated bets, encouraging us to constantly update our thinking based on new information.

• Decisive by Chip and Dan Heath: A straightforward read with lots of practical tips on avoiding common decision-making pitfalls.

If you enjoy diving into the psychology behind choices, Blink by Malcolm Gladwell can also be eye-opening. It’s not a how-to manual, but it delves into the power of quick judgments and when they do — or don’t — serve us well.

One thing I find especially helpful is running short, scenario-based exercises or “what-if” sessions with individuals or teams. Essentially, you introduce a hypothetical challenge or real situation, give everyone a limited amount of time to devise a plan, and then have them explain their reasoning. It’s a low-pressure way to practice making decisions quickly and thoughtfully. Often, the group discussion afterward is where the real learning happens.

As for my classes/courses, thanks for asking. I’m actually planning on launching some online sessions and workshops in the not-too-distant future, which I’ll be announcing through my newsletter here and social media once things are a bit further along. Be sure you’re subscribed here to stay in the loop.

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