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.

Terri Becker

Being a business owner is hard. Anyone who tells you it isn’t, is lying. There is no rule book. There are things that come up that you could have never anticipated or thought of. Like how to be a successful new business during a global pandemic. There were times when I struggled because of the realities of being the sole owner of a boutique design and remodeling firm. All that it entails. It’s a LOT. Would it have been easier to take the easy out and go and work for a firm or back to corporate? Absolutely. Read more>>

Emma Kaufman

I love this question. I think it’s REALLY common for entrepreneurs and business owners to have that moment where they think: can I really pave my own way? The world often makes us feel that “paving our own way” means that we have to choose between having a regular 9-5 or writing off the corporate world completely to forge our own path. I’m here to show you that there’s an expanded realm of possibilities for you! What if it isn’t about choosing your own business OR your corporate career? What if your path is rooted in following what gives you the most joy, regardless of the environment? Read more>>

Suni Gargaro

I don’t just sometimes wonder would it would be like to have a regular job – after retiring my first business (a retail boutique with an ecommerce component) I actually *did* go back to work full-time for a period of about 1 year, prior to becoming pregnant with my son. At that point, I took a break from work and business to have my baby and start a family (which is whole other story!) Read more>>

Eric

Being a business owner can really be hectic, but I wouldn’t change it for anything. There’s ups and downs being a business owner. Having to make sure everything is going the right way, solving all the problems, dealing with clients and wanting the best for all your barbers. You really have all the pressure on your shoulders, but I love it. Knowing you can change people lives, put them in position to be at their best and earn the most money is really an accomplishment for me. I love to inspire and influence people, so I try my best to do just that. Read more>>

Forever Nika

Becoming an entrepreneur was the greatest decision I’ve ever made. To be able to use my God given talent on my terms is a huge blessing. Being your own boss has its perks, but it comes with huge sacrifices and much more responsibility. Sometimes I wish I had the “luxury” of clocking in and out- leaving work behind when I walk out the door, but working a regular job has never worked for me in the past. My vision of how things should be usually clashes with how things are, thus leading me to resign or be released lol. Read more>>

Pam Brown

Yes, during the past two years, as I have tried to bounce back from client loss due to Covid, going back to a full-time job has weighed heavily on my mind. Trying to win new client pitches or even freelance gigs has been more challenging than prior to the Pandemic. Times have changed, a lot. I never had any intentions of being a solo-creative or a design studio owner for that matter. My plan was to continue being a Senior Designer and level up to a Design Director at an agency/studio. Read more>>

Molly Racette

When I first started my herbal business, it wasn’t because I thought I would actually succeed at running a business. I started a business because I am creative and I felt like I needed to give it an honest try. The problem was, I never really expected it to succeed. Of course, because I didn’t believe in myself, it didn’t necessarily succeed…at first. I kept Herbellion alive in those beginning years, but just barely. I didn’t have a plan, I didn’t have a strategy, I just started and kept going. Read more>>

Cara Callaway

There were times in the beginning, after I had quit my day job that I wished someone would still just had me a paycheck once a week and tell me what to do. That was 23 years ago and now I couldn’t be happier as a business owner. In the beginning when I was just starting there were times of financial uncertainty and wondering if my student list and the business would grow, and there’s more to being a sole business owner than just being your own boss. Read more>>

Laura Bright

I’m definitely happy being a business owner. It is a terrifying job but just rewarding enough to keep you coming back for more. Once upon a time, I had a regular job. I was an elementary school teacher for almost 15 years. I absolutely love it in the beginning. However, as time progressed and teaching evolved, I found that the changes in education played more to my weaknesses than my strengths. So I knew a change was in order. Read more>>

Bettina Benizri

This is an interesting topic that’s a lot more diverse than many can imagine. It’s not as simple as a yes or no question and it’s something that is hard to describe if you’re not a business owner but i’ll try to do my very best starting from the beginning. The generation I was born into had a little bit of a different ideology behind the modern day “career choice.” We had a small pool of “successful” career paths to pick from and we all felt a little push into a direction that would not necessarily fit our ideal life choice but most of us followed those paths anyway thinking it would lead to immediate riches. Read more>>