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.
Raquel Davidowitz

Becoming a business owner has been by far the most fulfilling move I have made in my life career-wise. I have had several 9-5 jobs where I didn’t feel valued for my individuality or skills. That all changed when I became a wedding photographer. Getting to work with couples in love is one of the most fulfilling parts about my job. I also have a toddler and I am grateful that I have the flexibility to adjust my work schedule and spend time with my family, which is the most important thing in my life. Read more>>
Carrie Cochran

2 of my first jobs were working directly for small business owners. One was at a UPS franchise where I ran around all day for just above minimum wage, and the next was at a retirement planning company where I worked as a secretary for a self-made millionaire. I remember being frustrated sometimes because of how much was expected from us, particularly at UPS. At the UPS store, if we had no customers or boxes to pack, we were expected to clean. The boss was constantly checking the cameras to make sure we weren’t standing still, and it drove me crazy. And at my secretarial job, there were often very busy days when I came into a task list over 60 items long, and the boss always had something new in the works. Read more>>
Meghan Najewicz

Sometimes I do think about what life was like, pre Covid, when I had a full time graphic design job. Life was a bit easier, and I had more stability. However, when the world shut down I really got a chance to be creative for me, which was a first. I spent all of college designing around our assignments, and then I got a full time job and designed around what they wanted. There was never a time where it was just me. Read more>>
Allison Carrillo

Being a business owner has always been a dream to achieve. I do find more happiness, and fullfillment in pursing my dreams of creativity. As an artist it isn’t always a smooth road but a learning experience. I don’t spend much time thinking about what it would be like to have a “regular” job. In the beginning, there will be times you will take free work to start getting your name out there while working a full/part time job to be able to pay bills at the same time, tons of assisting, imposter syndrome, difficult clients, and learning how to network. Building relationships with industry friends help you get the best advice, and mentors to learn from. Read more>>
Samantha Jade Alech

Being a business owner has its ups & downs but I wouldn’t have it any other way. Before I started by business, I worked a “nice cushy job” in the financial industry. Although I was very good it at, my methods weren’t very popular with the leadership because I led with my heart… always. Heart and finance just don’t mix… at least not yet (maybe one day). Ultimately, it came to a point where I couldn’t grow because my way just didn’t work for them. I wanted to continue to serve small business owners and support them along the path that we all know can get very bumpy sometimes. Read more>>
Isaiah King

The road has definitely not been the smoothest. On top of maneuvering the pandemic, starting a business from the bottom is one of the most time-consuming and difficult things to do. There were plenty of times where business was slow, things weren’t moving, and I was unsure about it all. As a creative based business there has been times where you wake up and think about how it may be easier to having a regular job. Read more>>
Beth Parkhill

I definitely think about that often. I love photography! Being in business by yourself is really tough. Especially as a creative person! My mind just doesn’t do the same things a business-minded person’s does. But being in business by yourself, you have to be all aspects of the business. On the days I spend hours answering emails/inquiries, planning social media content, and honestly, editing, I think about how much easier it would be to just back in a 9-5 working for someone else, with just one job to do. Read more>>
Alaina Booth

As a recent college grad, there’s a lot of pressure to put a name on what you’re doing after school. People want to hear a certain position, a company, a grad program. It’s not as accepted to say “I’m going to continue to freelance” after school. It took me a good bit of time to feel confident in letting people know that I won’t be getting a job. But the differences between my life and employed friends’ lives are pretty stark. And as young people entering the work world for the first time, there’s a lot of opportunity for comparison. Read more>>
Jill Patton

I love being a business owner! The fantasies of having other jobs are always fleeting because at the end of the day, I love what I do. I started Luna Tigre Candles as a side hustle at a time in my life when my career path was super unclear. I had graduated from college and worked in a law firm, at a Fortune 50 company and had also helped run another small business. Candlemaking was cathartic and allowed me to use some creativity beyond my jobs that were paying the bills. Read more>>
Charissa Lauren

I think every Entrepreneur has thoughts of the stability that a “regular job” brings, even more so once you start a family. The benefits of working corporate or for an employee always provide the sense of stability and benefits can sometimes be more difficult or more costly to achieve as an Entrepreneur. When I second guess my decision as a business owner, I always focus on the rewards that Entrepreneurship brings. Read more>>
Angel Moore

As a business owner I would have to say that that going into business for myself is truly self-rewarding. However, I don’t think I will truly be happy until Bol has reached the level that my husband and I have envisioned for our company. I am only guessing but I think everyone not just business owners in the formative parts of their dream struggle with am I on the right path or should I have done something else. Constant reaffirmation of your ambitions by yourself and others help those feelings subside so that you can remain focused. Read more>>
Jennifer Stein

In the 18 years I’ve been a business owner I cannot tell you the number of times I’ve wanted to sell the business or just give up and go work for someone else. Each time it’s happened there’s been one thing in common – burn out. The last time I felt this way was during the pandemic. We had lost more than half of our contracts and were looking at how we could keep the business going with very little money coming in and more money going out. Lucky for us, we’ve been a cash-operated business from the beginning so we had no debt and had money in the bank before everything shut down. Read more>>
Apryl Chanelle

I’m definitely happy as a business owner and have no plans on returning to a regular job! I love creating my own schedule, being my own boss, and having myself to answer to. Why would I ever want to give that up?! Read more>>
Patrick Bird

I am happy as a business owner – it’s hard to imagine life a different way at this point. Many of my years were spent inside someone else’s machine – and that was miserable I’ve got too much to say and too many ideas to serve as a simple subordinate. Recently, I just remarked to my fiancé about how, “It feels like feast and famine is over… I used to be worried about the phone not ringing… Now I appreciate it.” Read more>>
Allanté Collier

What did Durk say? “And we ain’t goin’ back to being broke no more” I have the freedom I never imagined as a business owner with the weight of the world on my shoulders. I’ll be completely honest – sometimes I do think about what my life would be like with just a regular job. Weekly at that! Entrepreneurship is hard AF. If you want to eat, you have to hunt. If you want to rest, you have to earn it. If you want the glitz and glamour, you have to endure the ugly process to get there. It’s tough! Read more>>
Lana Moon

Being a business owner is definitely a Blessing and clearly a meaningful part of my existence and purpose. There are many misconceptions about being a business owner out there. People often think owning a business brings instant wealth and unlimited time off and I even had someone tell me that as a business owner they can buy a G-Wagon car and pay nothing for it and write it off annually. There are some great opportunities in terms of freedom; freedom to make decisions, freedom to be creative, and freedom to do what you love, but make no mistake it is work. Read more>>
Ratissia Johnson

I love being a business owner, its hard work but I love the freedom to move and make decisions as I please. I still work a part-time job but my employer is awesome, I never feel like I have to choose between my business and work because I work with other creatives and they understand the beginning stages of getting a business off the ground. Read more>>
Lauren McGurn

I got into the world of athleisure entrepreneurship because I was desperately craving creativity, autonomy, and excitement that my “regular job” wasn’t providing. For 4 years, I balanced building Sunderday with the frustrating existence of a high demand 9-5 which ended up being a strategic and rewarding move. Sunderday exercised my creativity, big thinking, and risk-taking side of my brain which helped drive innovation and growth in my day job. My day job kept me close to the happenings in the marketing and media world, Read more>>
Taylor Shira

The scariest thing about being a business owner is the uncertainty of consistent income. I have a three year old son to provide for, and I oftentimes wonder if I’m being an irresponsible parent by continuing to pursue my dream and maintain my self-employment. Is my small business enough to provide for us long term? Would I make more money working a regular office job? Is choosing the safe route more important than persevering and continuing to try to build my business? Read more>>
Sarah Balducci

We both love doing photography because it allows us to be creative & focus on that creativity aside from our “regular” jobs. Bo & I (Sarah) are not even “full-time” photographers……crazy right?! Bo is a physical therapist & I am finishing up my last year in pharmacy school so it kinda blows minds when we tell them photography is our “side gig.” We started photography during our undergraduate years as a small, simple business just trying to make a few bucks on the side & WOW has it grown! We do photography now because it does make us happy & we wouldn’t change that for the world. Read more>>
Justice Ali

I am happy as a business owner and feel like that is how it should be. The flexibility and freedom that comes with being able to be my own boss. I am able to create my own hours and make my own money. Having my own business affords me the ability to really enjoy what I do. Read more>>
Brian Robben

Yes, I’m extremely happy as a business owner. It’s a different kind of happy than the careless, free sensation. It’s a rewarding sense of happiness, which lasts longer and is a sustained feeling. In my business and real estate investing pursuits, the timeline from pursuing a deal to winning the opportunity, executing and exiting, can take years. During this period, every day is not sunshine and rainbows. It’s often the opposite. Though at the end, after a culmination of hard work, relationship building, and value creation, the experience and rewards pay a happiness dividend that can only come from accomplish hard and worthy problems. Read more>>
Emilly Lana Mayorga

I am happy as a business owner overall! Sometimes, I do think about what it would be like to just have a regular job. Meaning a 9 am – 5 pm job where I am in the office and the job starts and ends there. Only Monday – Friday. There are moments where I think there may be some peace that comes from this routine, from the stability, from the guarantee of a salary. I last had that thought when I again decided to be a freelance event planner. No salary, no retainer to depend on. It gets scary and causes some anxiety. Read more>>
Matt Sweetwood

I like to say, “as an entrepreneur – a business owner we work 80 hours a week so we don’t have to work 40. With that said, being your own boss, being in greater control of your destiny, and the personal thrill of success make business ownership worth the investment of time, money and soul. There are times when all the pressure is on you, and you are working late into the night, or you don’t get to sit in a bar on a Sunday watching football, you sometimes think to yourself about having that “regular” job and just living an “regular” life. However, the difference between being and entrepreneur and taking cocaine is that you can actually quit cocaine. So, wonder yes, but never will I go back. Read more>>
Maren Mullin

This is a question that I never get asked, so I leapt at the chance to pick it. Although I relish being a business owner, I think all the time about what else I would want to do. Or I dream about a job where I would clock out and leave the day’s worries behind. There are so many various career paths that I could have taken, and I enjoy dreaming about ways to incorporate them into what I currently do. A recent diversion has been floral; Read more>>
Christine Tanier

Marrying people is the best job in the world! In spite of an occasional ‘Bridezilla’, everyone is happy and excited. Stressed, yes, but it is part of my job to bring calm when I arrive half an hour before the ceremony. I will have been working with the Bride for weeks or months to get everything organized to help the day go smoothly so she can concentrate on getting ready. I have lots of little tips for her like “take deep breaths”, “hold the bouquet below your chest”, “take a tissue or hankie in case you cry” and “if you start to choke up when you are saying your vows – swallow. Read more>>