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.

Mike Barnett

I am very happy to be a business owner! I have always had a job, since I turned 16. Along the way I had some good bosses and some really bad ones. I tried to learn as much as possible from each work experience. I owe a debt of gratitude to each of my former employers. I learned what works and what doesn’t. Read more>>

D. R. Sara

I’ve often contemplated this question, and it’s a reflection of the duality that comes with being a business owner. There have certainly been moments when I’ve questioned whether I’d be happier with a regular job, but each time, I’ve emerged with a deeper understanding of my entrepreneurial spirit. Read more>>

Patrick Salazar

I would say that being a business owner has it’s own pros and cons that come with it. Am I happier being a business owner? Yes. It’s allowed freedom for me and more time with the family. It’s definitely more rewarding being able to serve people directly than being an employee at a big name brand. At the same time it’s also exponentially more stressful. Read more>>

Stephanie Judd

I love this question. As someone who wants to live an intentional life, and not let inertia decide what happens to me, I ask this question to myself often. It becomes particularly relevant, of course, when we experience a setback in the business. Read more>>

Jenny Grether

Running a business is stressful. I know I’m not the only one who has skimmed LinkedIn or other job boards, updated your resume, and daydreamed of returning to a traditional 9-5 job. Read more>>

Helena Bowen

Am I happy? A thousand times, YES! When I worked in Corporate America (TM), I kept wondering, “Why are we doing this? Why are we doing it this way? Isn’t there a better way to do it?” As an entrepreneur, I love that I have control over how I spend my days, what I do, when, why, and how. I can prioritize the things that really matter to me, and decline the things that don’t suit me or my lifestyle. Read more>>

Jyla Rogers

I do believe I am happier as a business owner. Prior to working for myself full time, I worked as a pharmacy technician and a marketing intern at my University. I enjoyed each job I had but I knew I had to choose what would make me the most happiest in the end. Read more>>

Kathleen J. Shields

My Grandfather always said, “If you love what you do, it will never be work”, and he was right. When I was in school, I was under the assumption, thanks to my parents, that I could ONLY become a doctor, lawyer, engineer or secretary. There was no other job… and secretary was what you became if you didn’t go to college and become one of the other three options. Read more>>

Justina Salinas

The daydreaming of a “regular” job definitely comes up from time to time. Some seasons more than others. Lately, not so much which is really nice to reflect on. Read more>>

Lexi Rosario

I am extremely happy that I am a business owner and no longer have a regular job. My entire life I worked for other companies and people. I was a great employee and made life long friends at every position I ever had. In the back of my head, I always knew that being an employee wasn’t what I was meant to be doing for the rest of my life. I grew up in a family where I got to see both sides. Read more>>

Lily Dye

I can say without a doubt, I am so happy as a business owner. I’ve always prioritized freedom and that’s what my business offers me. Read more>>

Lauren Anderson AND Rachel Bridgwood

This answer has definitely changed during any given season. Sometimes it’s even day to day. Owning a business has been unbelievably rewarding and MOST days we find ourselves overwhelmingly grateful to have it. It can be wild to sit back and think about how far we’ve come and what this business has turned into compared to the tiny thing we started in our apartments towards the end of college. Read more>>

Katie Torres

I find great happiness as a business owner because it allows me to combine my passions for creativity and helping people into one fulfilling endeavor. Being a photographer provides me with the unique opportunity to exercise creative freedom and capture the beautiful moments in people’s lives. Read more>>

Holly Fitez

100% happier as a business owner. im a mom of 2 young daughters, i became a stay at home mom right before my eldest turned a year old and was pregnant with my youngest daughter. i absolutely loved working, i enjoyed my career as a scan coordinator for grocery stores but it was a very needy career. i was essentially on call all the time and finding the balance between being a mom and the best employee i could be, i couldn’t find. Read more>>

Lindsey Isaac

In my second year of running Fraîche Studio, I frequently face feelings of doubt, a sentiment I think many new business owners can relate to. There are moments of ambiguity, moments when what I do as a digital creative might not neatly fit into a box that people can immediately understand. Read more>>

Jordan Halem

As a business owner of 2 barber shops, I am constantly working. That means, even on my days off from cutting (Sundays and Mondays), I am still working. Whether it’s running payroll for the previous week, posting on Google or working on the SEO management of the websites, being a business owner is a 24-hour a day job. Read more>>

Michael Fragoulis

Becoming business owners of Adoniis Fiit was one of the smartest decisions Anthony & I have made. Being that we both have our own personal training businesses, we already had a slight sense of what people liked to wear when training in the gym. For this exact reason, as well as the fact that we both have a passion for apparel, we got together to create Adoniis Fiit and have not looked back since. Read more>>

Jessica Kircher

I am the happiest in my career than I’ve ever been or thought to be possible. The ups and downs of owning a business can be overwhelming at times, it’s about getting through the hard parts so that you can appreciate the good ones. Who knew working for yourself would be both defeating and exhilarating all at the same time. Read more>>

Rosalie Jade Tanzillo

A couple of years ago I made the decision to take a break from my jewelry business, which at this point had always been a side hustle, and accept a job designing full time for a fine jewelry line. The opportunity felt inconceivable – that I could get paid to simply design jewelry, without any formal training, and solely based on my creativity. I wouldn’t have to worry about any of the all consuming tasks required of having my own business and I would just get paid to create. Read more>>

Tom Kayonjo

I can confidently say I’m happy as a business owner. there is no need for me to wonder what it would be like to have a regular job cuz I did have a regular job. Me turning into a business owner was never something I considered when I left the University . As the usual script was for most of us back then,after University I got a 9 to 5 job but because of life is unexpected events, my contract of employment ended and I found myself unemployed. Read more>>