Entrepreneurs Entering the Corporate World: How to Tackle the Elephants

Kyla Duffy
2 min readAug 8, 2023

Entrepreneurship is hard. It requires a great deal of hard and soft skills. Titanium resolve. Dogged tenacity. Unwavering faith.

At first glance, it makes sense to create a resume that screams, “Hey! I’m an entrepreneur!”

Think of all the good things you get from an entrepreneur!

· They can wear many hats

· They can build a strategy and execute on it

· They are innovative and forward-thinking

· They have experience building teams

· They’re motivated and solutions-focused

· They’re not afraid to take risks and fail

But there are a few big red flags that come to mind for employers when they hear “founder,” “owner,” or “entrepreneur.”

1. Is this person a lone wolf, or can they work well with others?

2. How does this person function within a team?

3. Is this person difficult to get along with?

4. Can this person execute, or are they only able to create ideas?

5. Can this person assimilate into our culture?

When I say “big,” I mean these flags are quilt-sized!

Entrepreneurs have a reputation for being a pain in the ass and not the best team players.

If you’re an entrepreneur transitioning into the workforce, you must understand what you’ll be facing during the hiring and interview process so you can address employers’ concerns.

It’s best not to get run over by elephants.

You can get on top of the elephant in the room by proactively addressing it rather than letting the employer bring it up. In this way, you can control the narrative.

When writing your resume and crafting your interview questions, demonstrate your ability to collaborate, assimilate, and execute, and you’ll be ahead of the game.

It’s a good idea to also share examples of when you were at the losing end of a conflict and got on board with someone else’s idea.



Kyla Duffy

Energized by “A-ha!” moments, I’m a career coach and resume writer who helps people move toward happiness & fulfillment. Get help at https://kyladuffy.com.