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.

Sydney Hampton

I genuinely believe no one should seek a 9-5 as their final destination—at least not if they crave freedom, creativity, and unlimited financial potential. I know without a doubt that I would feel miserable and trapped in a regular job. I’ve been there before—working long hours, sometimes juggling more than one job, feeling like I was constantly giving my time and energy away with little to show for it. Read more>>

Jenn Cordell

Many times since I chose to pursue my freelance work, I have thought to myself, “What am I doing?” It’s a common thing to question your work when you also operate as the head of marketing, sales, accounting, and client relations. Imposter syndrome is indeed a plague to the creative mind. In each of those moments, I pretend I’m sitting at a static desk with a hardwired desktop and the omnipresent knowledge that I’m wildly uncomfortable. I ask myself, why do I consider that “real” work and the projects I’ve committed my heart and soul to “not real.” I chose to live ‘outside of the box,’ so to speak, which comes with benefits and challenges, though every perceived challenge is counterbalanced by the thought of limiting myself to a typical workday or life. Read more>>

Kirsten Valencia

There are moments when I wonder what it would be like to have a regular job, with a steady paycheck and a clear-cut schedule. The last time I really had that thought was during a particularly overwhelming week. I had just finished a market where I poured so much energy into creating new jewelry pieces, setting up my booth, and engaging with customers. At the same time, I was also preparing for a Reiki and sound healing event, managing bookings, and trying to keep up with my social media presence. I remember sitting in my car afterward, exhausted, and thinking, Wouldn’t it be easier to just clock in and out somewhere? To not have to carry every single responsibility on my shoulders? Read more>>

Claire Ransom

I never thought it was possible to be as happy as I am now as a business owner. Making the move from employee to business owner is probably the hardest, but best decision I’ve ever made. I know exactly what it’s like to have a ‘regular job’ because I did that for over a decade, and no matter what job I did, I always just felt disempowered to be able to create real and lasting change in whatever role I was in. Read more>>

Jordan Hewes

I think about this a lot actually. It usually creeps up when there is a big problem to be solved, or on days when it feels like nothing is going right. It usually presents itself in the form of a thought about how much easier would it be if I had someone to give this problem to or if there was someone else that had to make a certain decision or getting something done that is proving to be quite the challenge. I always thought that I started Craft because of my love for baking but being in business has helped me identify so many other things that I am passionate about – things like building a great team of people that are invested in this vision and love what they do every day. I have to remind myself about times that I did have a regular job and how decisions that were made by someone else didn’t feel like they were made with intention and purpose. Read more>>

Murielle Marie Ungricht

I never want or think about having a regular job, except when I’m taking big risks. I’m a risk-taker by nature and thrive on the challenges and rewards of being a business owner. However, there are times when the thought of having a regular job crosses my mind—and it feels like bliss to me. Read more>>

Kristin Ramirez

I think many business owners come from a “regular job,” or a “9-5.” My career after college was in healthcare administration— so I had the 9-5 and then some, because I was managing a 24/7 healthcare facility. When my priorities shifted after having my first child, I always felt like I wasn’t giving enough in either aspect of my life— If I was too committed at work, my personal life was suffering, and vice versa. There is a quote that has stuck with me for a long time: women are expected to work as if they don’t have kids and take care of kids as if they don’t have to work. So my path to starting my own business was truly driven by the fact that I wanted to be in charge of my schedule, protect my free time, and build the flexibility to be present for my family whenever needed. Read more>>

Lindsey Pleasant

As a business owner, I appreciate the flexibility that allows me to spend more time with my family, but I sometimes miss the structure of a traditional job. Working in hospitality and property management can be challenging because the work is continuous and often goes unrecognized. Balancing work and family life is something I think about often, and while I enjoy the independence of running my own business, I occasionally wonder what it would be like to have a regular job. Read more>>

Daisy Huang

Yes, I am incredibly happy as a business owner. From a young age, I envisioned myself as a strong, professional businesswoman, leading with creativity and purpose. I held onto that dream, imagining the moments when I would bring ideas to life, build something of my own, and make a lasting impact. And now, here I am—happier than ever, deeply grateful for the journey that has brought me here. Of course, running a business is no easy task. Ensuring smooth operations, maintaining creative direction, and growing a brand all come with their challenges and pressures. But I never take any of it for granted. Even when it gets difficult, I see it as an opportunity—to learn, to solve problems, and to create something meaningful. Read more>>

Lexi Nardini

The thoughts of imposter sydnrome, and stress of owning a business are things that im sure all young business owners have had to deal with! I do sometimes wonder what it would be like to be able to clock in, and clock out to a job! Owning a business does not have regular hours, I find myself thinking florals 24/7, making look-books for clients at all hours, and the occasional nightmare about an arbor falling over on a bride! Haha. I go to the studio all day, film my day, then come howm and edit a video about my day! When all of your success soley relies on your hard work, there is a lot of pressure. Read more>>

Luanne Prima

Yes I love having businesses. It’s a freedom like nothing else. I was a clinical esthetician for many many years and I had my own business Luanne Prima Clinical Skin Care going just to name the first. One day I’ll open a spiritual health spa in Hawaii. All about helping others feel better. Read more>>

Marcie Rial

Absolutely, I’m happier as a business owner.

I remember struggling in high school, feeling lost while everyone around me seemed to have their thing—the sport they excelled at, the subject they loved, the talent that came naturally. I didn’t feel passionate or particularly good at anything, and I wondered if I ever would. Then, I picked up a camera. And in that moment, everything clicked. I realized that God had been leading me to photography all along, and it felt like an answered prayer. Read more>>

Michaela Foreman

The shift from corporate suits to overalls and steel-toed boots was no small feat. Embarking on a new business venture while simultaneously mastering a whole new set of skills is a humbling experience like no other. It demands courage—the kind that pushes you beyond your comfort zone. There’s an exhilarating thrill in embracing the unknown, but it also requires a healthy dose of risk tolerance. You have to believe in yourself and trust that the universe will recognize your hard work and dedication. It’s a journey of growth, where every challenge becomes a stepping stone toward something greater. You have to approach it like an adventure. Read more>>

Jaclyn Proper

For years, I molded myself into the illusion of success—chasing the six-figure salary, the corporate title, the external validation that I was good at what I did. But I was also overriding who I really was, stretching myself thin to fit into a structure that was never built for me. I would overextend myself to prove my worth, burn out, take time off, start a creative or entrepreneurial endeavor, and then—without fail—convince myself to take the “safe” route and go back to corporate. Read more>>