Sometimes the Best Way to Fly Is With a Little Push
Entrepreneur Office Hours - Issue #260
One of my students this semester keeps stopping by my office hours wanting advice about content strategy for his social media accounts. But there’s a big problem: he isn’t posting anything!
Instead, he just wants to talk about what he should do or could do or might do.
At office hours this week, I couldn’t take it anymore… I finally cracked.
“Go post something,” I told him. “Get a few weeks of content up, and then I’d be happy to sit down and analyze the results with you so we can learn from real data.”
He tried to ask another question, but I wouldn’t let him. “Nope, go post.”
“But, Dr. Dinin…”
“Nope. Go post!” I said again, and kicked him out of my office.
A few hours later I happened to pass by him in the university’s cafeteria. “I’m editing some videos right now,” he said. “Can you take a look and tell me what you think?”
“Have you posted anything?” I asked.
“Not yet,” he said. “But I will once I’ve got some edits that I’m happy with.”
“No,” I told him. “Post a video.” Then I walked away.
It might sound like I was being mean. But I promise, I wasn’t. Instead, I was doing exactly what he and so many other young entrepreneurs need.
He didn’t need more thoughts, theories, or hypotheticals; he needed momentum. He needed to understand that the best feedback isn’t from some mentor tapping his chin and pondering possibilities. It comes from the real-world reactions of real people actually seeing what he was creating. If you really want to know if your idea is any good, share it with the world and find out!
To be clear, this isn’t just about social media strategy — it’s about the entrepreneurial mindset. You can’t learn by endlessly planning or asking for advice. You learn by doing. You learn by seeing how users respond, then adjusting accordingly. Without real-world data, you’re just guessing.
If it felt like I was being mean, I get it. But I wasn’t. I was delivering what every young entrepreneur needs: a push out of the nest and into the unpredictable, messy world of actually trying things. It’s scary, sure. But that’s how you learn to fly.
And for any entrepreneurs out there reading this and struggling to take flight, consider this message you’re push out of the nest, too. In fact, I’ll go so far as to tell you to stop what you’re doing right now and focus on getting your idea into the world. Reading this newsletter isn’t nearly as important as you launching and learning.
-Aaron
Podcast: ThoughtWave Episode #6
How to Know If I Should Pivot My Business
In this episode of ThoughtWave, Dr. Dinin and Chris dissect the art and science of business pivots, exploring how these strategic shifts can shape the trajectory of a business. They discuss offensive pivots, like Apple or Meta’s forward-looking adaptations, which seize emerging opportunities and set businesses apart. Defensive pivots, designed to counter threats and maintain market relevance, are highlighted through examples such as Meta introducing Reels to compete with TikTok. The hosts also warn against squirrel pivots, the misguided chase of trends that often derail strategic focus.
Drawing from real-world examples, the conversation emphasizes the importance of aligning pivots with clear goals and values. They stress how seasoned experience, thoughtful decision-making, and strategic investments in expertise can save time, mitigate risks, and accelerate growth. Whether you’re an entrepreneur evaluating a potential shift or striving to avoid shiny-object syndrome, this episode offers actionable insights on how to pivot with purpose.
Listen now on: Apple | Spotify | Online
This week’s new articles…
The Best Startup Opportunities Aren’t as “Revolutionary” as People Think
Every entrepreneur wants to “change the world,” but, if you’d stop trying to build something “revolutionary,” you might actually help make it a better place.
The Day a Championship Basketball Coach Taught Me How to Be a Better Entrepreneur
Founders love learning from other founders, but the best entrepreneurial wisdom doesn’t always come from entrepreneurs.
Aaron’s note: Instead of a Q&A this week, I’m sharing the article I published Thanksgiving week that you probably missed since there wasn’t a newsletter. Enjoy!
Are You Humble Enough to Know Your Greatest Entrepreneurial Asset?
The most successful entrepreneurs all have one thing in common, and it’s related to something they don’t even know.