Being a business owner isn’t easy. There are amazing highs, but the lows are often quite intense as well. Somedays it feels like the problems never stop – regardless of how much success you achieve. The problems just grow, evolve, morph. So we asked business owners if they sometimes wonder what it would be like to just have a regular job and have shared some of the highlights below.

Tiffany Drury

I feel like most of the time people look at business owners and think they have it so simple or easy because they can “make their own schedule” or “make the rules”. but in reality, being a business owner is the furthest thing from simple or easy and this is because you don’t just wear just one hat of a specific job tile, you wear ALL the hats. For me specifically these “hats” consist of being the Esthetician within the treatment room, the marketing team- so making sure to keep social media account active, scheduling appointments, making sure to do inventory and ordering when we are out or running low on things. Read more>>

Byron Hailey

Lately, I’ve been grappling with the idea of whether being a business owner is worth the constant uncertainty. The thought crosses my mind more often than I care to admit—especially during moments when I feel financially stretched. At the moment, my business is still in the early stages, and while I’m passionate about what I do, it hasn’t yet reached the level of financial stability that I need for the future I’m envisioning. I’ve been thinking about the kind of stability a full-time job could provide—consistent paychecks, health insurance, a 401K, and the ability to save up for long-term goals like buying a home. These things are hard to come by when your income is unpredictable, and right now, the uncertainty of my business sometimes feels like too much of a risk. Read more>>

Danny Sullivan

I am often accused of, “living the dream”; however, it can frequently be a nightmare.
As a business owner, I am often told, “You really should get someone to help you with that.” Unfortunately, the right help and good help is very difficult to find, and is often beyond my budget. So, it falls on me to do it, and make it work; which to my perpetual surprise, I have continued to muster for almost 3 decades of scrappy entrepreneurial survival. Read more>>

Gianni Marmo

I think very consistently during my slower periods what would it be like to have a job with a paycheck that I could predict. There are sometimes multi week spans where I panic and internalize what my career looks like and if I’m even good at it. Since I am now self-employed in two cities, I am fully responsible for the well-being of my business. Rent must get paid regardless of slowness. I go through this all the time, and I don’t know if it ever stops. Being a creative is hard! But I have these incredible bouts of an upswing in creativity, outcome, and business that reminds me how fortunate I am to do what I do. Read more>>

Josie Rappold

I’m genuinely very happy to be a business owner. Some days are more stressful than others without a doubt. On the harder days I ask myself, would life just be easier if I had a traditional 9-5 job. Like clockwork when I start to have my doubts about my business, or feel overwhelmed by being a owner/operator, opportunity comes ringing and I’m guided back to the reality that what I’m doing is truly the right path for me. When I worked a regular job I found myself to be really unhappy, stressed, and tired most of the time. I’m a hard worker, and incredibly driven and have learned some of the ropes of business start ups from mentors at previous jobs that I often reflect on or lean on in times that I feel uncertain about my path. Read more>>

Alex Nguyen

I think starting this year, I was beginning to find happiness as a business owner. At first, there’s this initial honeymoon phase of being able to start a business, but as I went along, it got tougher and tougher. What I mean by tougher is that I felt I wasn’t making a lot of progress in the direction we were going. At the same time, I realized that I needed to build my network more and I did not have the right resources and connections to go to the next stage. After I finished graduate school in business, it seemed like we kept doing the same thing over and over – production, popups, online sales, rinse and repeat. We didn’t enter into new stores, or pushed forward with grocery stores. Read more>>

Kate Petach

I never dreamed that I would be an entrepreneur growing up or even when I graduated college. I started my career in more “normal” 9-5 type jobs. So, I’ve had the benefit of getting to experience both. Even having been on both “sides” of working, I think it’s normal to fantasize about having a normal 9-5 job when you’re working late nights or you are getting demanding emails from clients at all hours. At the end of every wedding season, I take time to evaluate how things went for the previous wedding season, how we can improve, and whether what I am doing serves me, my family, and my clients best. Ultimately, the reflection leads me down the path of, “is this where I’m meant to be?” And, even when things are hard, this is what I feel like is best! Read more>>

Jessica

Yes, I am undeniably happier as a business owner. There’s a profound sense of ownership and fulfillment that comes from building something from the ground up. However, that doesn’t mean it’s always sunshine and rainbows.
Yes, I absolutely have those moments where the thought of a ‘regular job’ creeps in. The last time it happened vividly was about three weeks ago. I’d been battling with some frustrating algorithm changes that were impacting my content reach. Then, I received a barrage of, let’s just say, ‘less than constructive’ comments on a video I’d poured my heart into. Finally, several project realignments had me battling with changes to our calendar and itineraries that we had spent days constructing. Read more>>

Hollie Hauptly

Being a business owner isn’t for the faint of heart, but I absolutely love it! I love the freedom and flexibility to create and build a business that works for me and the life I want to live. I love having the ability to schedule mine and my family’s life as I see fit. Sure, there have been hard days and times where I question everything and want to quit, but I always stick with it and we always figure things out. I always go back to my why. Why do I do this? Why is the work I do so important? What impact do I want to have on the world? As a business owner, it’s important to be anchored by these beliefs that will keep me going when the times get tough. Read more>>

Lillian Oler

Absolutely, I’m happier as a business owner. But let’s be real—happiness doesn’t mean it’s always easy. Running a business is like having a front-row seat on the world’s wildest roller coaster. The highs are exhilarating, but the lows? They’ll make you question everything. Read more>>

Rebekah Weiss

I have this thought several times a week. I work part-time as an attorney. I own Basic Biscuits, kindness and coffee a café, and I am also an elected city council member. Not to mention I have two teenage sons. Hardly a day goes by or I don’t wonder if life would be easier if I just had one full-time job One place to go every day with one set of tasks. Plus, even though I have a lot of flexibility with my myriad jobs, there’s almost never an actual day off. For example, I’m currently in Puerto Rico on “spring break” but I’ve sent payroll, made a schedule for the biscuit shop, and have been fielding texts and phone calls from legal clients and various cafe employees about call offs, etc.. Read more>>

Taylor Huggins

Being a small business owner is something I truly love, but it’s also one of the hardest things I’ve ever done. I get to create things that bring people joy, and that’s incredibly fulfilling—but at the same time, I’m constantly reminded that I’m selling products people don’t need. I’m not offering a necessity; I’m offering something that makes life a little brighter. And in tough times, that can feel like an uphill battle. Read more>>

Natalie Werness

Being happy as a business owner can be a bit of a roller coaster ride – the lows are lower and the highs are higher! The thrill of experiencing success, having ecstatic clients, moving through challenges and providing for your family while making your own schedule – is incredible. On the other hand, the pressure to perform, the lack of boundaries between your business and personal life, the fear that arises when things are slow, needing to learn how to wear every single hat of an entrepreneur WELL – can be all consuming when all of the responsibility is on your shoulders. Read more>>

Mariana

Gosh, I’ve come to realize that being a business owner is less about just owning a business and more about being ready for constant change and deep spiritual growth. There are seasons—especially when I’m going through growing pains in business or my personal life—where I catch myself reflecting on the days when I had a regular job. Oddly enough, those moments always ground me. Because back then, I used to *pray* and *visualize* for the life I live now. A life filled with abundance, growth, flexibility, and surrounded by a community and friends who share those values. Read more>>

Jessica Hudgins

I absolutely love being a business owner. Although I do contemplate regularly what it would be like to have a “normal job” with good hours, retirement and a steady income, I love my freedom. I am a single mom with 2 children full-time. I need to be able to work as much as possible but also be able to be here for my kids for all of their activities, school, social lives and family time. Also I am the walking definition of neuro”spicy” so part of that is that I absolutely love the crazy day to day that I have where no hour is the same. Every client who comes in is dealing with different issues whether it’s with their skin to their personal life. Read more>>