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.

Jessica Franz

The thing is: I’m so happy as a business owner, I would never get a regular job – and I never really have. But that is just me. As a very independent spirit and valuing my own space over anything, it would be hard for me to operate any other way. It makes me happy to oversee what I’m doing, when and how. Read more>>

Tatiana Jones-Waldon

Being a business owner gave me the freedom to spend more time with my children which made me happy. During the peak of the pandemic I was able to stay home, perfect my craft and raise my children. In the summer of 2022, I went back to working a regular full time job while still working my businesses after work and on the weekends. Read more>>

Brittany Patterson

I am happy as a business owner, I love the freedom of it all and I get to stay home with my kids, however I do think about going back to a regular job… ALL THE TIME! I am a stay at home mom of two and my boyfriend supports us, and as a business owner there is no guarantee of sales, leads etc. Read more>>

Truman Griffin

I believe I am happier as a business owner, but at times I have thought about what it would be like to have a regular job. I started my personal training business Truman Griffin Fitness 4 years ago. I’m an actor, so for most of my career I’ve had multiple side jobs so I could have a flexible schedule to audition. Read more>>

Jef Caine

I worked a regular in-house job for many years and was always curious about freelancing. I was fearful of being overwhelmed with all the business of finding clients, invoices, health insurance, taxes. Fast forward a few years later all those fears have come true. Read more>>

Christina Hong

I am the happiest as a business owner, I had regular jobs to get here. The best job is working for yourself. If you are confident in who you are and confident in a vision, you should be your own boss. I knew I wanted to share my culture with the world, that was my purpose. I could only do that by being in the role to make those decisions Read more>>

Jessica Ajeman

Don’t get me wrong, being a business owner has it’s perks for sure, but it definitely comes with it’s own set of challenges. It is hard trying to wear all of the hats, making sure everything gets done, take risks, deal with setbacks- just to name a few. People sometimes ask ,”why did you leave your 9-5 to work 24/7?” Read more>>

Riva Johnson

The foundational stage of business has been a process of overcoming for me! The stress of being a solo entrepreneur during the foundational stage makes me constantly question “Is it all worth it?” Read more>>

Sau-Sha Hill

When I first started pursuing my dream of becoming a content writer, I was excited but uncertain. I had always enjoyed writing, but I wasn’t sure if I had what it took to make it as a professional. Then, as I began to build my portfolio and search for clients, I faced many rejections and setbacks. It was discouraging, and I wondered if I should give up and get a regular job. Read more>>

Tau Tau Menghan

Yes,being a business owner is the best choice to balance my my ‘JOb ‘ and ‘Dream’.I don’t need to think about what it would like to just have a regular job, because I tried it when I started as a Timber sales’.Maybe not everyone is lucky like me to finally find a way to balance the dilemma between between the ‘dream job’ and the ‘money business’. Read more>>

Ruth Smith

I think its natural for any business owner to have this thought on a regular basis. There is a lot of stress that comes with owning your own business, When I have a lot of projects going on at the same time, it can feel overwhelming and I long for quieter times. When things are on the slower end of the spectrum, I feel like I should be doing more. And yea, healthcare benefits are alluring sometimes too haha. Read more>>