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.

Chris Amendola

Honestly? I think about it all the time. And the answer — like most things in business — depends on the day.

There are moments when I imagine the stability of a steady paycheck, clocking out at 5, and leaving the stress at work. But then I remember what this journey has meant to me. Being a business owner isn’t easy. It’s a constant mental, physical, and emotional grind. The highs are incredibly high, but the lows can be crushing. And more often than not, it’s the latter that we’re quietly carrying. Read More>>

Jessica Um

Of course I have thought about what it would be like to have a regular job–more than I would like to admit! Any time I have a difficult client, or I forget to make an order, or I’ve been at work for 10 hours standing on my feet all day, or have to miss an event because I was working a Saturday, I think about how nice it would be to work a regular job. However, when I am in my space and get to chat with my amazing guests all day long, or my client squeals with joy because they love their hair so much, or I take a trip with my husband and don’t have to worry about anything, or I get to take time off to take care of my family, I remember how much I love being a business owner. Read More>>

Allyson Garcia

Happiness as a business owner looks different in every season – and right now, I’m in a really complex one.

I recently moved from California to Utah, and even though I’ve been a full-time photographer for years and am still fully booked back in California, it truly feels like I’m starting over. I spend a lot of time traveling back and forth—shooting weddings, sessions, and serving the clients who have grown with me and trusted me for so long. California is still a huge part of my business. Read More>>

Natalie Stephenson

I started my photography business in 2004, slowly and intentionally. At the time, my main job—the one I cared most about—was being a mom to my two boys. Photography had been a passion since I got my first camera at nine, and I loved the creative side of it deeply. But the business side? That did not come naturally. I often felt like I was winging it—underqualified, overwhelmed, and just trying to keep up. Read More>>

Danielle Fleming

My husband and I both run the business along with our amazing employees.

Most days, yes — I really am. Owning our own business has pushed us, challenged us, and made us grow in ways I never expected. It’s not always easy, and it’s definitely not always glamorous, but there’s something deeply satisfying about knowing the work I do directly impacts my customers and my community. Read More>>

Cookie Davis

Yes, I am happy as an artists! I worked for years in the radio/broadcasting industry as an executive. In that business it is literally all about time, 60 second commercials, news breaks and spinning records. This was back when radio was “personality” radio. After over twenty years as a vice president and traveling over several states to different broadcast sites, I walked away at the age of 58. Read More>>

Nolan Brown

I can thankfully say I AM happy (and fulfilled) as a performing artist / creative. I’ll begin by acknowledging my immense gratitude to be where I am, and the wonderful family, friends, and mentors that have helped me along. Without sulking or seeming ungrateful, I do think it’s interesting to open up about some of the challenges of “living the dream.” Read More>>