What Success Really Looks Like in Entrepreneurship
Entrepreneur Office Hours - Issue #262
Aaron’s Note: I’ll be taking next week off from publishing a new issue of Entrepreneur Office Hours during the holidays. But I’ll be back January 3rd, and we’ll plan to kick off 2025 with a bang. Or, at the very least, with a medium-sized pop.
Earlier today, one of my students was interviewing me for his podcast. Most of his guests are successful entrepreneurs and business people. Honestly, I might be the least impressive of them, but that’s besides the point.
The reason I’m mentioning this is experience is because I wanted to share how it ended. My students concludes his episodes by asking all his guests the same set of questions. The first was a question about what legacy I wanted to leave. The second was a question about what success looks like for me 20 years from now. And the third question was one thing I wanted to tell anyone listening.
I answered the first question by discussing how much I value the legacy of educating students. If I can die 30 years from now with, by that point, nearly a half century of educating students under my belt, I’ll have consider my life well-lived.
This led to an awkward exchange for the second question since the answer was obvious. Where will I be in 20 years? We both chuckled about how I’d already answered… if things go well, I like to think I’ll still be teaching entrepreneurship students.
Then we got to his third question, and I had a strange moment of imposter syndrome. After all, this kid’s podcast generally features wealthy and wildly successful entrepreneurs at the peaks of their respective careers. In contrast, there I was talking about how, 20 years from now, I’m going to still be teaching undergraduate entrepreneurship classes.
I began thinking about how his listeners were going to view my interview in comparison to the others on his show. Would they laugh? Would they look down on me for “just being a teacher”? Would they feel pity because I’m not living a life of opulent wealth and luxury?
I got to his third question — “What’s one thing you want to tell anyone listening?” — and, thanks to my self-consciousness, I decided I needed to redeem myself by giving an extra-insightful piece of advice or strategy about entrepreneurship that was going to demonstrate my “value” as an entrepreneurship educator. “I’m going to show them why I’m a great teacher,” I thought to myself.
However, a few sentences into my response, I realized I was saying something inauthentic. I was so busy trying to show I could “compete” on the same level as all those other “successful” entrepreneurs by sharing some sort of mind-blowing piece of startup wisdom that I was undercutting the thing that actually matters to me — being an honest, candid educator of entrepreneurs.
I interrupted my own response and asked if I could start over. My student nodded. I took a breath, refocused my thoughts, and began again.
If I’m being completely honest, I don’t remember exactly what I said, but here’s the gist:
“I’d like to tell anyone listening that you don’t have to chase what other people call success. Money, status, or flashy ventures might impress them, but none of that will matter if you don’t find fulfillment in what you’re doing. I’ve chosen to devote my life to teaching, not because it’s flashy or nearly as lucrative as I’d like it to be, but because working with students brings me genuine meaning. Day after day, I get to see them explore ideas, challenge themselves, and grow into capable, thoughtful leaders. That fills me with a sense of purpose I’d never find by chasing someone else’s idea of success.
“Your path won’t always feel amazing. Some days you’ll question your choices. You’ll wonder if you’re wasting time pursuing something that doesn’t sparkle quite as brightly in the world’s eyes. And that’s okay. Nothing worth doing is perfect, and no career path or lifestyle comes free of doubts. But if you’re dedicating yourself to something that resonates deeply with who you are — and if you can recognize that alignment as your personal success — then you’ve already won. That’s what I think about my career as an educator. And whatever you do, I hope that’s what you think about yours.”
I wanted to share this story because, with the holidays coming, and the new year soon after, I feel like my answer to his question is also some of the best advice I can end the year with for all of you.
Whatever you celebrate this holiday season, I hope you have a wonderful time with it, and I look forward to doing whatever I can to help you keep making progress toward your greatest successes in 2025… whatever those successes might look like.
-Aaron
Podcast: ThoughtWave Episode #8
What’s the Best Way to Sell My Product?
In this episode of ThoughtWave, Dr. Dinin and Chris Light tackle one of the most fundamental challenges for entrepreneurs: how to price, package, and sell your product effectively. They dive into frameworks for understanding value, setting price points, and identifying the ideal customer profile (ICP) to streamline the sales process. Through real-world anecdotes—from startups pricing their software at just the right threshold to lessons learned on focusing efforts on qualified leads—they reveal the importance of empathy, active listening, and confidence in selling.
The conversation unpacks critical strategies like the “so what” exercise for uncovering value, the role of psychology in pricing, and how the best salespeople prioritize asking questions over pitching features. Whether you’re a founder refining your sales process, a team leader optimizing revenue, or someone overcoming hesitancy to make the ask, this episode offers actionable insights to help you sell with purpose and integrity.
Listen now on: Apple | Spotify | Online
This week’s new articles…
Your Startup Needs Turn Signals (Yes, Really)
Your car has turn signals and they’re an important safety feature, but what if turn signals are for more than just safe driving?
What Every Entrepreneur Needs to Know About “Being Your Own Boss”
Entrepreneurs constantly say they want to “be my own boss,” but most don’t seem to understand what it actually means.
Office Hours Q&A
———————
QUESTION:
AARON’S NOTE — This question was submitted as a comment on one of the articles link this week, but it was a good question I wanted to answer it.
[Your article about turn signals] is an absolute masterclass in turning a mundane experience into actionable entrepreneurial wisdom. 🚗💡 The analogy between turn signals and startup communication is spot on. Clear signals create trust, prevent chaos, and keep everyone aligned — whether on the road or in business.
Also, "Signals, not surprises" is a mantra worth printing out and framing. 👏
Thanks for sharing such a thoughtful perspective! What’s your take on how entrepreneurs can strike the balance between signaling enough without overloading or confusing their audience?
-Alaa
----------
Great question! And, to continue the metaphor, I’d point out that striking the right balance is a lot like driving in traffic: you want to give other drivers (your audience) just enough information to know what’s going on, but not so much that they’re overwhelmed and stop paying attention.
In practical terms, that means being intentional about your timing and frequency. Don’t blast every update you have the moment it pops into your head; instead, think about what your audience actually needs to know at each stage of the journey. If you’re launching a product, give a heads-up when development starts, another update as you hit major milestones, and a final, clear announcement when you’re ready for them to take action. By spacing out these signals, each one carries more weight and is easier for your audience to absorb.
It also helps to keep your messaging focused and consistent. Rather than sending mixed signals across every possible channel, choose your platforms and stick to a coherent narrative. Each signal should build on the last, guiding your audience toward the next step rather than leaving them guessing.
In other words, don’t flick the turn signal constantly or leave it on forever. Flip it on at the right moment, ensure everyone understands your direction, and then move forward confidently. Your audience will thank you—and they’ll be more likely to follow where you’re leading.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer!