Not Everyone Should Be an Entrepreneur. Here’s Why a Good Mentor Will Tell You That

Entrepreneurship has become one of the most glamorized career paths of our time. Everyone wants to be a founder, chasing freedom, fortune and a sense of identity. Far too often, aspiring entrepreneurs hear the same recycled encouragement: Go for it. Bet on yourself. You’ll figure it out.

But after decades leading large organizations, turning around businesses and mentoring startup founders, I’ve come to believe something that may be unfashionable, but essential in my view:

Not everyone should be an entrepreneur.

If you’re serious about mentorship, you need to be willing to say that out loud and back it up with real standards.

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Encouragement is easy. Standards are not.

I spend a lot of time with founders and aspiring entrepreneurs. These are students, early-stage teams and ambitious professionals. What I’ve noticed is this: people want support, but they often resist structure.

There is an idealized idea of the maverick entrepreneur. The person who was too smart to be boxed in, whose genius is misunderstood by the establishment. However, entrepreneurship isn’t freedom. It’s full accountability. It means making decisions with limited information. It means showing up when no one’s watching. If you struggle with structure in a corporate environment, entrepreneurship doesn’t remove that pressure. It increases it.

The patterns that raise red flags

After advising dozens of founders, certain patterns have emerged that raise serious questions. These aren’t about someone’s character, but about their fit for entrepreneurship.

• Flaky commitments. Missed meetings, shifting deadlines, excuse-driven delays. Entrepreneurship doesn’t work without personal accountability.
• Chaos disguised as creativity. Great ideas mean little without systems, follow-through and the discipline to execute consistently.
• Chasing identity over responsibility. Loving the idea of being a founder isn’t the same as loving the work. Entrepreneurship requires hard choices and full ownership, even when it’s uncomfortable.

These behaviors don’t make someone a bad person, but they do matter.

Mentorship requires candor

Real mentorship means offering more than motivation. It means offering clarity, even when it’s uncomfortable.

Put simply, if there is any doubt, I would discourage somebody from founding a company. In a 2024 survey, 55% of founders said they suffered from insomnia, and 53% experienced burnout.

I’ve had direct conversations where I’ve said, “This might not be the right path for you.” Not because the person lacked intelligence or ambition, but because the habits required to succeed were not optional, and they weren’t yet present. Some of the points you may need to hit:

• “You tend to shut down in the face of honest feedback; entrepreneurship won’t be any easier on you.”
• “I’ve seen you struggle to follow through on basic commitments without oversight; there’s no safety net to catch you.”
• “If you keep delaying decisions, waiting for perfect data, the startup world will leave you behind.”

The people who benefit most from mentorship aren’t the ones who need constant encouragement. They’re the ones who are willing to raise their standards when someone points out a gap.

Why honesty helps

Letting someone drift into entrepreneurship without being clear about the demands isn’t support. It’s avoidance. According to Experian, roughly “4% of new businesses have ceased trading by the end of the first year of operations, more than a third (34%) by the end of the second, and half (50%) within just three years of opening.”

Unless they show you something special, I think it’s up to mentors to nudge kids away from the wood chipper.

I’ve seen talented people spend years chasing the title of “founder” when they could have thrived as operators or leaders inside strong companies. Entrepreneurship is one path. It is not the only one. And it is certainly not always the best one for everyone.

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A litmus test for aspiring founders

The irony is that the people who can hear “this might not be for you” without shutting down are often the ones who actually have a shot.

They listen. They reflect. They take responsibility rather than offense. After Michael Jordan was cut from his high school team, he didn’t hang up his sneakers and stick to baseball. He came back with a vengeance.

Before you launch a business, ask yourself:

• Do I do the work even when no one’s watching?
• Do I prepare without being prompted?
• Do I seek honest feedback, or am I just looking for validation?

Those behaviors will tell you more than any pitch deck ever could.

A simple question for would-be entrepreneurs

Before you start a company, ask yourself this:

Do I want the identity, or do I want the responsibility?

If you can’t handle someone telling you that this path might not be right for you, then you probably shouldn’t pursue it. And if a mentor cares enough to say it anyway, listen. That may be the most valuable advice you ever receive.