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.

Sabika Naqvi

I’m incredibly happy I took the leap to start my own business. While it’s been challenging, it’s also been so rewarding. The biggest gain for me has been flexibility—having the time and energy to truly show up for my kids. In my previous career, long commutes and demanding schedules left me drained, and I often felt I wasn’t showing up for my family the way I wanted to be. There have been moments of doubt. I remember a tough week when orders were slow, inventory issues piled up, and my toddler was sick. For a brief moment, I wondered if I had made the right choice, leaving the stability of a regular job. But then I paused and reminded myself of why I started this journey. That same week, I was able to take an afternoon off to cuddle my little one while he recovered. No meetings to reschedule, no boss to report to—just the freedom to prioritize what mattered most in that moment. I also found that once the chaos settled, I had the mental space to dive back into my creative work, which is one of the aspects I love most about running my business. Read more>>

Brendan Mcdevitt

At 42, I’ve never had what most would call a ‘regular job.’ My journey has taken me through the tattoo industry, the auction business, and then back to tattoos. I could never see myself confined to a cubicle, staring at a computer screen all day. For me, the freedom and variety of these industries have always been more fulfilling than the idea of a typical 9-to-5. Read more>>

Erica Fant

Being a part of Farmhouse and working alongside my husband, Ben, is truly an ideal work environment. With the wide variety of clients we work with and the projects we take on, no two days are the same—and I love it that way! That said, I occasionally wonder what it would be like to have a standard 9-to-5. The idea of ‘clocking out’ at the end of the day or completely disconnecting with an OOO email sounds appealing in theory, but it’s just not for me. Read more>>

Nicole Gil

Being a small business owner comes with a unique set of challenges that often demand resilience, adaptability, and an unrelenting commitment to the work. Unlike traditional jobs where the end of the day signifies a stopping point, small business ownership comes with the reality that the work is never truly complete. There is always something more to do—whether it’s refining marketing strategies, managing staff, analyzing finances, or finding ways to grow and improve. The to-do list is endless, and the weight of responsibility can feel overwhelming. Read more>>

Tony Ezzell

I’m the happiest I’ve ever been as a business owner. It allows me to set my own schedule and manage my own rate of work. It also gives me the opportunity to provide a safe, supporting environment for other artists to create. I would never take a ‘regular job’ over it, as I have had other jobs in the past. I worked retail and food service as a teenager and then completed a 20 year career in the Army. I value the freedom of being my own boss too greatly to ever go back. Read more>>

Kathleen Diresta

Business owners need to be connected to all aspects of running a successful business. That takes a lot of focused energy and planning. In 1998, I started my jewelry business K. DiResta Design doing high-end craft shows and selling wholesale. Then I opened a retail space in the East Village in 1999. It closed when I moved to Long island. I continued selling my collection at shows until I opened K. DiResta Collective in 2012. Not only do I design and create, the shop is known for a custom jewelry design, heirloom design, and finding artisan gifts by many local artists (plus bills, marketing, posting, hiring, cleaning, etc). Don’t you feel burned out even just reading this? When I’ve taken on too much, or dealt with challenging customers, I search for a job with a salary or teaching position. But then, I make someone truly happy with jewelry that makes them cry or they say this means so much . Or someone walks in and says the store makes my soul happy. Or I take a trip to Thailand for two weeks after wonderful rewarding holiday season and I’m reminded I’m right where I’m supposed to be. Read more>>

Mila Jackson

Yes, I do think about it sometimes. As a small business owner, I have to take on many responsibilities and make decisions on my own without a safety net. From managing clients to handling marketing, scheduling, finances, and administrative tasks it can all feel very overwhelming at times. I remember one specific moment recently—it was late at night, and I was trying to complete editing for one client while also prepping for a major event shoot the next day. My kids had just gone to bed, and the house was finally quiet, but I felt completely drained. I caught myself wondering what it would be like to have a regular job with set hours, a predictable paycheck, and maybe even a team for support. Read more>>

Olena Pokalchuk

Am I happier as a business owner? Absolutely — most days, yes. But let me be real with you: there are moments when I think about what it’d be like to have a regular job again. You know, clock out at 5 pm and leave the worries at work. That thought isn’t about looking down on regular jobs at all — it’s just that entrepreneurship can sometimes feel like carrying an entire circus on your back. I’ve walked every path in the marketing world. I started with freelance SMM projects, had a few stints balancing office work and side gigs (a combo I wouldn’t recommend unless you love chaos), and wrapped up my corporate chapter at a massive IT company with 11,000 employees. I’ve seen what it’s like to have structure, steady paychecks, and team potlucks. Read more>>

Dayana Gonzalez

I am definitely happier as a business owner. Not only does it give me control over my time, but it also allows me to make a positive impact on others, especially the truck drivers I work with. However, owning a business comes with its challenges, and there are times when I wonder what it would be like to have a regular 9-to-5 job with fewer responsibilities. I remember one particular moment when I was juggling several issues at once: a shipment that wasn’t arriving on time and a client who needed immediate answers. I felt overwhelmed and thought, “Wouldn’t it be easier to have a regular job and leave these problems behind at the end of the day?” But then I reminded myself why I started this journey: I wanted to build something that would allow me to grow while helping others do the same.  Read more>>

Brandt Bishop

I am, without a doubt, happier as a business owner. The sense of purpose and control I feel in shaping my own path has been incredibly fulfilling. These days, I rarely wonder what it would be like to have a regular job. My energy and focus are so deeply invested in driving my business forward that the thought barely crosses my mind. The challenges of entrepreneurship, though demanding, keep me motivated in a way no traditional job ever did. The last time I seriously considered the alternative was back in 2022, when I was working at a winery and distillery. I mostly remember learning the wine blending process, while also exploring distillation, cider making, sanitation and even picking up some minor forklift skills along the way. While I valued the experience and gained a lot of knowledge, there was always a nagging feeling that I had more to offer. I wanted to create something of my own rather than contribute to someone else’s vision. Stepping away from the food world for a brief time ultimately reignited my passion for it, reminding me that cooking not only served others but also fulfilled me in a way no other work could. Read more>>

Veronika Richardson

I have owned several businesses throughout my working life, and I have also spent some time working in the corporate world. While a steady paycheck and benefits are alluring, the pride and satisfaction of owning my own businesses is incomparable. Corporate life taught me a lot about what I would and would not put up with. It taught me lessons I’m grateful for; the courage to unyieldingly advocate for others, the power of resiliency, and to not put up with other peoples’ BS. But the most important lesson I’ve learned is that the only opinion that really matters, is the one I have about myself. I’m the one who is fully responsible for making myself proud. Read more>>

Clifford Baker

As the owner of Clifford’s Junk Removal, my journey has been a unique blend of entrepreneurship and military service. Starting this business while serving in the Air Force was a challenge, but it was also incredibly rewarding. My time in the Air Force taught me discipline, resilience, and the importance of a strong work ethic, all of which have been invaluable in running my own business. Transitioning to the Air Force Reserves allowed me to continue serving my country while also dedicating more time to growing my business. There have been times when I wondered what it might be like to have a regular job, with more predictable hours and perhaps less stress. However, the satisfaction of building something from the ground up, the freedom to make my own decisions, and the ability to impact my community through my business make the challenges worthwhile. Read more>>

Jesse La Flair

I think about this question often because being an artist isn’t just what I do—it’s who I am. It’s been over fifteen years since I worked a nine-to-five job, and my life has been a constant dance between risk and reward, creation and uncertainty. As a father of two, I’d be lying if I said I never wondered what it would be like to have a steady paycheck or a more predictable path. Those thoughts usually come late at night, in the quiet moments, like when I was sitting in my studio rehearsing an upcoming scene while the kids were finally asleep. Then bam, the oh so familiar uncertainty of this creative life crept in. What if I didn’t have to think about whether the next acting role or creative project would come through? What if I could just choose the safer, steadier path? Read more>>

Alyssa Fitchie

What a timely question! About once a year, usually in the dead of winter when production is slow and jobs are meager, I find myself wrestling with the question “would it be easier to have a regular job?”. And then I frantically apply to open roles and look into fields that I have experience in, but would really rather not jump back into knowing that in the long run they won’t be satisfying and I’d be dreaming about freelance again. The teeter-totter of life! And then calls start coming in. Someone finds your work and wants to hire you for a role. Production starts again and you’re just want the client is looking for. The pendulum swings in your direction and somehow you’re onto your tenth year in the industry. Read more>>

Sexy Coyote

Creative work is real work. Creative jobs are real jobs. But they come with the added bonus of not being thought of as such by a lot of people who consume the fruits of creative labor nonetheless. Working as a performer, for instance, demands far more than the perfomance itself – which on its own requires expertise an overwhelming number of skills and carries magnificent personal risk. It also requires a critical and business-savvy approach to all negotiations to ensure fair treatment and compensation in an environment of sufficiently intense competition and notorious potential for all kinds of abuse. It requires too a gift for budgeting, accounting, design, marketing, technological prowess, networking personability (on and off stage), and often even manual strength and dexterity to be able to transport your own equipment to and from performance venues. All this through your own means, of course. Read more>>

Fox Michaels

Am I happy? Not really, no! But. I think at this point, I am what I am, an artist and creative. It sort of feels like I don’t have a choice but to be. I’ve truly tried doing other things. I’m really not good at other things that aren’t artistic or creative. I don’t want to seem overly aggrieved about it, we’ve seen enough tortured artist types. I have free will, to an extent. There is a lot to enjoy about pursuing the arts! Knowing this about myself, there’s also a comfort in thinking “It couldn’t be any other way”. Read more>>

Sam Tchortov

Honestly, music is my job, always has been and always will be. I’ll keep that mindset no matter what anyone tells me, but if I was doing anything else as my job I’d probably be miserable. Read more>>

Daniel Katzman

Happy is very broad. I’d say in general I am happy that I decided to choose the path of an artist. I think it’s knowing that I could’ve taken an easier and more direct path but choosing the artist path that makes me happy. It’s a constant struggle as an artist trying to “make it”. There are many days where I am at my job to pay the bills, living paycheck to paycheck (which is awful) and I just hate my life so much. However, when I think about why I’m there, it helps push me further. It’s a steppingstone to get to where I am meant to be. To stay afloat right now. However, that gets clouded. I feel like I may be saying my entire life that I’m working toward something. But if I never get there, does that make it a waste? Having a regular job would make things easier for me financially for sure, but in the end, I’d be so unhappy. I’d look at who I was meant to be and wave to them in the window and never see them again. I think it’s so sad that so many people turn the route of what’s easy, what is financially stable, because of societal pressure and fear. Read more>>