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.

Janaya Black

After working in corporate America for over 30 years, I am definitely happier being a business owner. While working a 9-5 afforded me the opportunity to learn many important skills and provided a way for me to provide for my family, I have found so much more fulfillment in working for myself doing what I love. In 2004, I began balancing being a filmmaker with working in the mortgage industry. With filmmaking being my hobby and passion, I had to use weekends and vacation time to pursue that endeavor. As my passion for filmmaking grew, I began to see my regular job as a safety net, and while I wanted to make films full-time, I was afraid to walk away from my guaranteed paycheck. After a while, I told myself that after my youngest child graduated I would go in to film full-time, but the year my daughter was graduating Covid hit. After that, I fell back into the comfort of my 9-5 due to the uncertainty of the market at that time. Read more>>

Mirlina Jean Mary

Being a business owner is definitely a rollercoaster, and there have been times when I’ve asked myself what it would be like to have a regular job. It’s in those moments when things are tough—maybe when cash flow is tight, or I’ve made yet another mistake that set me back—that the thought of just having a steady paycheck feels like a relief. You know, waking up, doing your job, and going home without worrying about the countless hats I have to wear as an entrepreneur. The year 2024 taught me a lot of lessons, both in business and from the people around me. To me, it was the hardest year I’ve had to face so far. I did a lot of self-examination, and it took every ounce of strength not to quit. But through it all, God blessed me with a wonderful family and prayer warrior friends who have fought with me and for me. Their support, love, and prayers have been my anchors, reminding me that I’m not alone in this journey. It’s those moments of faith and community that push me to keep going, no matter how tough things get. Read more>>

Lizz

I’m very happy owning and running my own business. It gives me a sense of freedom I’ve always desired. Tattooing is what I’ve wanted to do since I was 6 years old. If you’ve read previous interviews of mine I go a little in depth with what sparked that for me. In today’s world, being a tattooer isn’t what it used to be. I’ve found myself ebbing and flowing with the changes in the industry and outside of it. My work goes everywhere with me. Being a business owner is a lot of responsibility—taxes, bookkeeping, managing client interactions, making sure people feel safe and heard, paperwork, emails, DMs on Instagram, content creating—the list goes on and it doesn’t start and stop only when I’m in the studio. Tattooing is an inside, outside and internal job. Read more>>

Lorena Romero

Starting my own company meant I could be flexible and creative in my work. It allows me to develop unique services that truly fit the needs of each client. I wanted to offer more than just a typical image consultation; I wanted to create a personal experience, where people felt heard, understood, and empowered. Being independent allowed me to craft my own approach, focusing on what mattered most: the individual. This flexibility also allowed me to build personal relationships with my clients. As a business owner, I can take the time to truly connect with each person, guiding them step by step through the process of discovering their personal style and learning how to wear colors that made them feel their absolute best. I listen to their needs, understand their struggles, and customize my services to meet them where they are in their journey. Read more>>

Syd Fuller

I’ll definitely say that I’m happier as a business owner! But there are moments where I find myself longing for the guidance and structure of a traditional job! The last time I seriously thought about taking a 9-5 gig they ultimately offered me the position. It was a full-time role and checked several boxes but I took a pause to reflect on my trajectory and thought about how every year in photography has shown growth and each challenge has taught me something new. I really feel that taking the 9-5 would have meant putting all of my progress on hold, possibly for years. Since then I’ve maintained the confidence that having my own business offers a chance for a future that is more aligned with my longterm goals and aspirations. Read more>>

Brittney Cee

I am, without a doubt, much happier as a business owner than I ever was working for someone else. But let me be clear: no career is perfect. Entrepreneurship often gets glamorized as ‘living the dream.’. The reality? It’s round-the-clock work. I respond to inquiries during late hours or while on a vacation, because I don’t want a lead to run cold. The highs are exhilarating, but the lows can be crushing, especially when bookings slow down or a stressful client situation occurs. And, of course, there’s no such thing as paid time off or guaranteed stability. Read more>>

Lucy Schoenfeld

It’s most certainly never boring as a business owner in the freelance creative space. I’m so grateful and lucky to do what I do, with clients who trust me and value what I bring to the table. Nevertheless, when it comes to working in a creative capacity, the spectrum of good days to bad days occurs just like in any other job. Do I think I would be as happy doing something else? Absolutely not (and trust me, I’ve tried). Much like acting or any other passion pursuit, there have been times when working high-flexibility part-time jobs fueled my ability to take on projects—and those were the times I most often went to sleep wishing I could make photography work all the time. Read more>>

Catie Menke

I am very happy as a business owner! I am grateful that I had the resources and opportunities to start my own business. It was scary to let go of a corporate job with a dependable paycheck. However, I feel so fulfilled in my current creative work, and I’m proud that I took the risk. I also think I had perfect timing in starting my business because I spent time preparing to leave my corporate role. I gradually added clients and proved I could make money on my own as an artist. I think there’s always a “what if,” but honestly I wouldn’t change it at all. Read more>>

Pascale

I am, for the most part, really happy as a business owner. After 12 years of working for myself, I’ve found so much joy in the freedom, creativity, and meaning that comes with it. But I’d be lying if I said I never have moments where I wonder what it would be like to have a regular job again. Sometimes I catch myself wishing for the things I imagine come more easily with a traditional job—someone to tell me what to do, a colleague to chat with over coffee, a clear line between work and home, and, of course, the stability of a steady paycheck. I admit thinking at times: “Wouldn’t it be nice to just show up, do the work, and not carry all this responsibility on my shoulders?”  Read more>>

Sharee Campbell

Saying I’m a happy business owner would be an understatement. For eight years, I worked a steady 9-to-5 job. It was great in many ways—normal business hours allowed me to spend time with my family—but my true passion lay elsewhere. I’ve always had a deep love for animals, and I wanted to share that love with others, especially families like mine. Growing up, I didn’t have the chance to have pets because our time was consumed by sports and after-school activities. Thankfully, I have an incredibly supportive husband. Back in September, he encouraged me to take a leap of faith when I was offered a position with S&S Services in Lynchburg, VA. That decision changed everything. Not only do I now have a job I genuinely enjoy, but I also have the flexibility to grow my own business: Jeffry’s Funny Farm. Through our mobile petting zoos, we bring animals to families for special occasions, creating unforgettable experiences. Read more>>

Victoria Laessig

The Challenges of Being a Business Owner Sometimes I wonder what it’d be like to have a 9-5 job. Do I catch myself daydreaming about a weekly paycheck? YES! It would definitely beat having no-shows and cancellations at the salon. Being a business owner, you need to face these challenges. I work roughly 20 hours a week in the salon—100% optional. I love having the choice of picking my own hours and days. This is a career choice that is incredibly important to me. I believe in having a work-life balance. I wouldn’t have much of an option if I had a “9-5 job”! Slow Months and Building a Career Read more>>