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.

Quintin Collins

When I look back on my journey as a business owner, I can honestly say—yes, I’m happier now than I’ve ever been. But that happiness didn’t come without moments of doubt. The last time I thought about what it would be like to just have a regular job was during my first year in business. Read More>>

Ruchit Harneja

I won’t lie! There are moments when I glance back and wonder what it would be like to have a “regular” job again. But the truth is, I was capped out in my capacities in a traditional role. I’m not saying I wasn’t growing or learning while working for someone else. Every experience added value, shaped my skills, and expanded my perspective. Read More>>

Chanise Price

Yes, I am happy as a business owner. Owning my business has given me the platform and flexibility to truly connect with and support my local community — something I couldn’t do as easily in a traditional 9-to-5 job. Read More>>

Akinyemi Akinwumiju

I can honestly say I’m happy as a business owner. Leading Progressive Psychiatric Services has given me a sense of purpose that goes far beyond running a clinic—it’s about creating something that truly serves people. As a physician and mental-health professional, I’ve always believed in the power of compassionate, consistent care, and owning my practice allows me to put that belief into action every day. Read More>>

Alisha Moore

I am happier as a business owner because I enjoy much more freedom. I have occasionally thought about what it would be like to have a regular job, but whenever that thought crosses my mind, I feel grateful for my decision to become a business owner. The benefits and perks of owning my own business far outweigh the appeal of a typical nine-to-five job. Read More>>

Chris Davis

I’m currently in my fourth decade of freelancing as a professional commercial photographer. This should come as no surprise, but the freelance model is not for everyone. Some people need more structure and consistency, while others desire more freedom and control. Being a business owner is basically a full time job, but you set the hours. Want to hit the gym at 10:30am, no problem. Read More>>

Sally Nguyen

Yes, I’m definitely happier as a business owner but it comes with its moments of doubt and reflection. There are times, especially on the tougher days, when I think about what it would be like to have a “regular” job again. One where the paycheck is steady, the schedule predictable, and the responsibilities end at 5 p.m. Read More>>

Jessica Ortler

Am I happy as a business owner in my field and the healthcare industry? I will tell you what I tell everyone else- it depends on the day. Ask me today, I might tell you that it’s not worth it, but that answer could change in hours or sometimes minutes. The highs are very high and the lows are VERY low. Read More>>