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.

Shanaya Robinson

I can confidently say that I am genuinely happy as a business owner. Running my own venture brings me tremendous joy, and I truly wouldn’t trade the flexibility of my schedule for anything else. The freedom to set my own hours and pursue my passions is invaluable to me. Read more>>

Jessica Keller

I am extremely happy as a business owner. I love the flexibility it allows me to create my own schedule. I work A LOT but I love what I do. I have gotten to the point in my career of business ownership where I don’t feel guilty any more when I am not at the studio. I have made a promise to myself that moving into this next season I would prioritize my family more. I do sometimes think about what it would be like to have a regular 9-5 job where when I leave work I don’t think about it, but then that wouldn’t be me! I probably would hate it! Read more>>

Brittany Lane

Being a business owner is REALLY challenging. When you are the owner of an operation, you often feel the weight of that world on your shoulders. Many days I have thought about WHY I am a business owner and what even led me down the path in the first place. When I reflect on those things, I come back to my career as a collegiate athlete as a softball player where we had to work really hard not only to grow as athletes but to earn out spots on the field, maintain our grades and to be well rounded individuals who had integrity and authenticity to the brand we wore on our jerseys. I think much of my desire to become a business owner stems from those moments when was nearing the end of my career and realized that there are so many young girls out there that want to do what I do (play softball in college) but they don’t have consistent coaches or role models in their corner. Read more>>

Maggie Lewis

Yes, I’m genuinely very happy as a business owner. I spent over a decade working in both large and small companies, and I really value the experience I gained during that time—especially the skills I developed, the mentors who guided me, and the stability that helped lay the foundation for my career. That said, I reached a point where I wanted more control over my time and felt ready—both in terms of experience and mindset—to build something of my own. Starting my business was a mix of courage and a bit of naïveté, but it’s been incredibly rewarding. As an expecting mother, being my own boss—and having a business partner in a similar life stage—gives me the flexibility I deeply value. There are definitely trade-offs, like fewer safety nets, but for me, the autonomy and purpose make it more than worth it. Read more>>