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.

Hillary Boutin

I’m definitely happier as a business owner, but I’d be lying if I said I never wondered what it might be like to have a regular job. The last time that thought crossed my mind was during a particularly crazy week. I had back-to-back shoots, client deadlines piling up, and emails I could barely keep up with. On top of that, my kids had school events, and it felt like everything was happening all at once. Read More>>

Jasmine King

Honestly, entrepreneurship is not for the weak. You have to be okay with failure, months of making little to no money, times when business is extremely slow, and moments when all your clients have ended their contracts. Right now, I am battling with myself, questioning whether I should continue to ride this out or return to the corporate world. Read More>>

Kassandra Companioni

Yes. Yes. Yes! I feel as a business owner I couldn’t be happier. Making my own schedule, having the advantage to rebrand my business whenever I feel fit or having the flexibility to take clients whenever I want. I sometimes wonder what my life would be having a regular job and it really makes me appreciate and love being a business owner even more because having to rely on having to report to someone whenever I need to take time off or whenever I need a mental health day, it would complicate so many of the things I have going on in my life personally. Read More>>

Micah Woldenga

Yes, I’m a very happy business owner, and I’ve had that mindset since I was a kid. I’ve always known I wanted to be in charge of my own path, and I don’t see that ever changing. That said, there are moments when I think about how much simpler life might be with a regular job. Read More>>

Laura Heckman

Absolutely, I’m happier as a business owner. There’s a freedom that comes with running your own business that’s hard to put into words. The ability to create something from the ground up, to set your own goals, and to work in alignment with your passions is deeply fulfilling. Read More>>

Kelly Peterson Frazier

The short answer is yes because I’m someone that is both good at coming up with my own structure, plus thriving in change. I think it’s the perfect combination of freedom and diverse hard work. What I mean is that it takes a ton of different skills, especially when you’re starting out, to be a successful business owner in the creative world: the photography skill in this case, finances, logistics, organization, marketing, sales, copy writing, client rapport, networking, graphic design, you name it. Read More>>

Seline Solberg

Am I happier as a business owner? The answer is yes—but it’s a layered, thoughtful kind of yes. Owning a business brings a deep sense of purpose and fulfillment that’s hard to replicate in a traditional job. But, like any meaningful journey, it comes with moments of doubt. Read More>>

Alissa Whitaker And Yvette Maniak

“we are incredibly happy as a business owners. There’s a sense of fulfillment in building something from the ground up and watching it grow. That said, being business owners is not without its challenges. There are moments when the weight of responsibility feels overwhelming, and in those moments, we do sometimes think about what it would be like to have a regular job—something with clear boundaries, a predictable paycheck, and less emotional investment. Read More>>

Jack Bride

My art business has scaled both up and down, and up again, over twenty years. I had to learn the business end of things after learning how to paint, first. I went to school for fine art, and never took any formal business classes. I learned as I went, which was a rough ride. However, if I’d played things safe and went for a regular job, I can only imagine how much, and how often, I’d long to be an artist. Read More>>

Kayetlynn Johnson

I love being a small business owner, I get to create real personal connections with my clients and that is truly a blessing. But I would be lying if I said that I haven’t reminisced on what life was like when I worked an hourly job. When you are a business owner, work never ends. It’s the weekend? Got to work. It’s a holiday? Got to work. It’s my birthday? Got to work. When I was younger I never understood when business owners would call their businesses their “babies.” Now I completely understand, I have birthed the idea of my business and nurture it everyday to make sure it is successful. Read More>>

Meet Chris Tyrrell

Owning a business has been both the best and worst thing I’ve ever done—it just depends on the day. I never set out to start my own business, but I saw an opportunity, took it, and have been learning ever since. For me, fulfillment comes from within, so whether I’m a business owner or an employee, my contentment and joy aren’t tied solely to my role or circumstances. Read More>>