Dr. Darren Burke on Entrepreneurship, Loneliness and a 25-Year Friendship
By Dr. Darren Burke, PhD | October 23, 2026
“How are you doing?”
I often answer that question with an update on my business.
What we’re launching. What’s going well. What we’re trying to figure out.
Recently, a conversation with a friend I’ve known for 25 years made me think about how often I do that. I can give someone a thorough answer without saying much about how I’m actually doing.
From professor and student to fellow entrepreneurs
We met during my first year as a professor. He was finishing his undergraduate degree and already running a business.
Our lives have changed considerably since then. We’ve built businesses, worked through challenges and taken on new responsibilities. Today, we’re both starting new ventures. Again.
There’s plenty to talk about: ideas, products, customers and everything involved in getting a business off the ground.
But recently, our conversation turned to how lonely entrepreneurship can be.
Even when your day is full of conversations. Even when you like the people you work with.
Why entrepreneurship can feel lonely
For me, part of that loneliness comes from the difference between discussing a business problem and explaining how it’s affecting me.
I can describe what happened. Walk through the options. Explain what I’m doing about it.
Saying it knocked my confidence is harder.
When a decision affects the people working alongside me, I’m also thinking about what they need to hear and understand. I want to be open about the challenge while giving them confidence in how we’ll work through it.
That’s a responsibility I take seriously. But it can leave some things unsaid.
A day filled with meetings and messages doesn’t necessarily include a conversation where I share those things.
I don’t think this feeling belongs only to founders. People in many roles may recognize the habit of explaining what they’re doing when someone asks how they’re feeling.
What a long friendship makes possible
That’s something I appreciate about a friendship that goes back this far.
We knew each other before most of our business stories had happened. Our conversations have continued through different ventures, difficult stretches and the decision to start again.
Neither of us needs to arrive with everything figured out.
We can discuss something that’s been difficult without needing to turn it into a lesson or a success story first. We can listen, offer a perspective and acknowledge that some decisions remain hard, however much experience we’ve accumulated.
Then we can get back to being excited about what we’re building.
That combination matters to me. There’s room for enthusiasm and uncertainty in the same conversation.
Still building, still learning
After years of teaching, mentoring and working with founders, I’m more appreciative of the people with whom I can have those conversations.
Experience gives me things to draw on. It also reminds me how much I still have to learn, and how helpful it is to talk with someone who knows me beyond my current venture.
I recently wrote about learning from my Gen-Z colleagues at Headstrong. This friendship is another reminder that learning continues long after the roles in which we first met.
Twenty-five years ago, I was the professor and he was the student.
Today, we’re two friends still figuring things out.
And the next time someone asks how I’m doing, I’d like to notice whether I’m answering their question or giving them a business update.
Do you ever catch yourself doing the same?
About Dr. Darren Burke
Dr. Darren Burke is an exercise physiologist, former professor, entrepreneur and co-founder of Headstrong. He writes about entrepreneurship, mentorship, relationships and the experience of building businesses. Explore his latest articles and reflections or get in touch.