Common Mistakes First-Time Entrepreneurs Make

Dan Sullivan
4 min readAug 11, 2022

There are a handful of common mistakes first-time entrepreneurs make, and when you recognize them early, you can avoid painful and costly lessons down the road. These are the eight most common mistakes made by entrepreneurs.

Mistake #1: Thinking they are an entrepreneur.

Becoming an entrepreneur in the first place may have been a mistake.

Not everybody’s up to it, and sometimes people have an incorrect notion of what it means and what it takes to be an entrepreneur. Many entrepreneurial role models live a glamorous life, and it can be easy to get tempted by the lifestyle and get into entrepreneurship for the wrong reasons.

Right off the bat, the most common mistake first-time entrepreneurs make is thinking they’re naturally entrepreneurial when they aren’t. Unfortunately, if you make this assumption, you’ll miss out on the opportunities for the transformation required to become one.

Mistake #2: Not knowing what an entrepreneur does.

My favorite definition of an entrepreneur is from 19th-century French economist Jean-Baptiste Say. He said, “An entrepreneur is someone who takes resources from a lower level of productivity to a higher level of productivity.”

This shows that there are two factors involved — resources and productivity — but you need an agent to make things happen between the two. When entrepreneurs use resources differently, they produce value at a higher level.

Today, almost anything can be considered a resource, even an idea, product, or capability, and a common mistake made by entrepreneurs is not genuinely understanding this fact.

Mistake #3: Not delegating and seeing the business cycle.

Delegation is an excellent way to take resources from a lower level of productivity to a higher one. So often, though, first-time entrepreneurs have trouble delegating — not because they’ve actively chosen not to, but because they’re under such pressure just to pay the rent that they don’t have the time or energy to do it.

First-time entrepreneurs tend to be consumed by projects, much like being in love for the first time. A common mistake first-time entrepreneurs make is not realizing there’s a cycle to creating and delivering business so you consistently succeed.

I see the inability to delegate as the inability to see this cycle of existing and new business, which is probably where most entrepreneurial failures happen. They run out of cash because they don’t have time to create new opportunities while executing on existing business.

Mistake #4: Getting overcome by nerves and bad habits.

I can liken entrepreneurship to first dates or the first time onstage; there’s trepidation, a set of nerves that get triggered when you’re an entrepreneur. I don’t think any life experiences can prepare you for it.

Entrepreneurs can also pick up bad habits in how they treat their employees, which they excuse as “simply business.”

Mistake #5: They don’t ask the right questions.

There’s a cycle of finding out what people want, supplying what they want, and getting paid. This cycle is powered by asking the right questions. And, if you start this early, you’ll know how to present yourself and show up in a way that gets you further with your target market.

Mistake #6: They don’t understand their most important objectives.

As we age, we discover that what we thought would make us happy … doesn’t. There must be a more resounding achievement. There must be a purpose. The most successful entrepreneurs know there must be freedom. A juncture, usually between ages 30 and 50, can be a place to re-engineer your entrepreneurial streams so they align with that purpose. A common mistake among first-time entrepreneurs is not making their true purpose a key objective.

Mistake #7: They see the customer as an adversary.

Thinking of the customer as an adversary can get entrepreneurs out of their game. A common mistake first-time entrepreneurs make is thinking of customers as demanding and fear they are constantly judging and looking for ways to pay less. Successful entrepreneurs take their best customers and turn them into collaborative partners. That way, it’s not just about what they can be sold, but about looking at their problem and your solution from the same angle.

Mistake #8: Dividing personal and business.

In Strategic Coach, I ask my entrepreneur clients, “What needs to happen over the next three years for you to be happy with your success?”

Only one expert on the planet knows the answer to that question, and that’s the entrepreneur. In the entrepreneurial world, there’s no division between the entrepreneur’s personal life and their business. One’s definition of success is deeply personal, yet it can be made possible by entrepreneurial endeavors. At a corporation, this question would be met with strictly professional answers because an executive’s personal definition of success is separate from business success.

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I hope this article triggered some new ideas, projects, initiatives, and thinking for you and your business.

Thanks for reading,


These are the common mistakes made by entrepreneurs. To see more curated content by entrepreneurs for entrepreneurs to avoid the mistakes first-time entrepreneurs make, visit the Strategic Coach Resource Hub.

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Dan Sullivan

World’s foremost expert on entrepreneurship in action. Co-founder and President of The Strategic Coach Inc. Find out more: