When times are good it’s easy to feel like entrepreneurship is the only path for you, but what about the times when your hit with multiple crises at once? We wondered if all entrepreneurs have moments when they wonder whether they should have gone with (or stuck to) a more standard job where they worked for someone else. 

Sarah McRoberts

12 years ago I did rent a chair, and it was great for a time but than the owners were expecting me to work when they’re own employees would be working so they would have someone there with a managers license. But as a renter I’m only responsible for myself and my clients, so I can build my clientele. Read More>>

Paul Kiger

Whenever I tell someone I own a business they almost always say, “Wow! That is so nice you work for yourself and have all of the flexibility you want.”. My response always is, “It is so flexible, I get to choose which 22 hours of the day I want to work!”. Read More>>

Skye Warren

Yes, I am happier as a business owner—but that doesn’t mean it’s been easy. Last June (2025), I made one of the hardest decisions of my life: I went full time in my business. For five years, I was balancing being an Assistant Principal while also doing nails and running my salon. My days started at 6am and didn’t end until 10pm. Read More>>

Richard Van De Water

I definitely think about what it would be like to have a regular job, or at least be employed by a company to shoot, and usually that thought comes up less from a lack of passion and more from a longing for stability – to know what is coming or not wonder if the thing you are building will keep holding you up. Read More>>

Sanela Ebbeskov Jankovic

That is a very honest question, and I think most entrepreneurs would agree that the answer is not always simple. Yes, overall I am happier as a business owner. Building something from nothing and watching it grow into a real company is incredibly rewarding. Read More>>