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.

Derek Mastay

Owning a business is like painting on a vast canvas where each stroke reflects my dreams and aspirations. As a business owner, I’m not confined by the rigid frameworks of a traditional job. I’m free to explore and create, forging my path with the colors of my passions and ambitions. Read more>>

Paul Napier

I am very happy being a business owner my previous job was a truck driver. after 13 years of driving/working 70 to 80 a week I began to get very frustrated and tired of not enjoying life, my family, or just plain resting. I forgot what it was like to have holidays off but if I did have that day off such as Christmas I’m getting off Christmas day which means I’m to tired to enjoy the day or I can’t stay up past 8.p.m Christmas night because I have to get up between the hours of 12 a.m. and 3 a.m. Read more>>

Linda Brumbach

The answer is YES. I never thought or dreamed of being a business owner in my college years as a music major at Indiana School of Music. Coming to New York in 1985 and having the opportunity to work along side of so many artists experimenting in all genres was a lighting bolt and inspiration so I wandered into as many different spaces as possible – exploring that landscape for about 15 years before deciding to start my own company with my long time producing partner Alisa Regas in 1998. Read more>>

Mahyumi Recker

I actually had a regular job for a long time, from my 20s to my 30s, and I loved it. I held several positions, from big corporations to startups. I met so many great people who have become my lifetime friends, and I learned many skills that are now helping me run the business I currently operate—skills I could never have learned in school. Read more>>

Jake Levy

As a restaurant owner the only thing I really think about related to another profession are weekends. We have been operating Desperados a really long while and the weekends are a time when it’s all hands on deck. I wonder what it would be like to clock out on Friday at 5 and not return till Monday. Read more>>

Yelimar Rodriguez

Calling myself a business owner feels weird cause I feel I’m not, but the answer is yes, I’m much happier now than when I was working retail. Not that retail was a horrible job, but it always felt like I was stuck. If you’ve ever worked retail, you know what I mean – it pays the bills, but it feels like you’re going nowhere. Read more>>

Carolina Conejo

Being a business owner is rewarding but also challenging. I run my own personal training business and I need to have a balance of both being a trainer and business owner. I recently had a baby so I did have the thought of going back to a regular paying job. Why you may ask? Well first things first maternity leave. Read more>>

Savanna Toporek

Everyday I am grateful that two years ago I decided to take the leap to start my upcycled brand. I am truly a creative at heart, and after a few short years working different corporate jobs, I felt incredibly unfulfilled and exhausted. I’ve always been super passionate about following your heart and living your life doing what truly brings you joy. Read more>>

Justice Strong

Yes, I am definitely happier as a business owner. I’ve always envisioned a life where I have complete control over my own destiny. The freedom to travel when I want, work on projects that excite me, and set my own schedule without asking for permission is invaluable. For me, being a business owner is synonymous with freedom. Read more>>

Noor Hussein

Being a business owner is not an easy thing to do on a daily basis. It comes with its own unique aspects, and at the same time dealing with all the lows the business experiences itself. It requires every day growth and choosing the right team for higher success. As a business owner, it’s very important to put yourself out there and take the risk. Read more>>

Brie Nicholson

Am I happy as a business owner? Absolutely!! I believe I was made for this. I tried the regular jobs and they never last for me. Well they last a few years but all in all not really for me long term. Yes there is times where the business is slow and I have to work somewhere to make money. Yes there is times that I want to give up and figure out a way to make a steady income. But I promise you on those days where I think about giving up, I have a client call me to do an event lol. Read more>>

Rachel Gazes

As someone who has had “regular jobs” in the past, I can honestly say that I am happy to be a business owner. However, that does not mean that having the freedom to create my hours and build my success does not come with it’s trials and tribulations. Read more>>

Frannie Williams

I think about it often. What if I took a different route? Would it be easier? Would I be able to do or have more? I think about milestones that I have yet to reach, because I am literally playing the long game. I see people around me getting to financial milestones sooner and I get discouraged. I wonder at times did I make it more difficult for myself? Read more>>

Maddi Brown

I absolutely love being a business owner! I do think sometimes it would be easier to have a regular 9 to 5 job. I think about how my schedule could be set and all I have to do is show up to work and do my work and go home and that’s the end of it. I think About how when I have slower months, it would be so much nicer if I didn’t have to worry about if I’m gonna make enough money that month or what can I do to drive more business? Read more>>

Chante’ Williams-Stone

As a business owner I find great fulfillment in my work, especially when it’s driven by a personal mission or purpose, such as my father’s battle with ALS and my mother’s battle with Cancer. Balancing the challenges and rewards of running a business can be quite different from having a regular job. As a business owner I often enjoy the freedom to make my own decisions and the satisfaction of building something meaningful. Read more>>

Katie Blondin

Being a wedding photographer and running my own business is very rewarding. I love the creative freedom and getting to be part of couples’ special days. Sometimes the responsibilities can be a lot, and I do wonder what it would be like to have a regular 9-to-5 job. The last time this crossed my mind was during a really busy wedding season. Read more>>