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.

Karen Canon

I absolutely love being an entrepreneur and having my own business. It’s funny because, growing up, I always dreamed of holding a leadership position in a multinational company. I pictured myself in a high-rise office, making important decisions, leading teams, and climbing the corporate ladder. That was the dream—until I became an entrepreneur. Read more>>

Jayda Gary

I started Rayne & Company during my sophomore year of college, and now, five years later, I’m a full-time nurse while still running my business on the side. While it’s not my full-time job yet, running a small business often feels like a 24/7 commitment — but it’s one that’s incredibly rewarding. The ability to be my own boss and make decisions for my business gives me a sense of freedom and fulfillment that’s hard to describe. Embroidery has always been therapeutic for me; it never feels like work because I genuinely love bringing my clients’ visions to life. While balancing nursing and my business can be challenging, the creative outlet and connection with my clients make it all worthwhile. Read more>>

Marc Guberti

I have always been happy as a business owner. Being a business owner offers more flexibility and control over your future. I know that I can increase my income by doing more prospecting, reaching out to clients for additional work, and tapping into new industries.

I first wrote blogs in middle school and never had a traditional 9-to-5 job. I recognize the advantage I built for myself by starting early and want to give my children a head start as well. The education system doesn’t invite people to pursue business ideas or career opportunities until high school at the earliest. Most people aren’t thinking about their careers and what they want to do with their lives until halfway through college or after graduating which is a shame. Read more>>

Mikelison Womack

I am happier as a business owner! My main reason for starting my fashion brand (Dumé) and my Non-profit (The Earth’s Tomorrow Foundation) is that I don’t like being told what to do. Not only this, but I found myself having to build my opportunities as my endeavors are very niche. I don’t think about having a regular because I decided to keep my 9 AM -5 PM while taking charge of my endeavors. Starting a business and maintaining one, especially as a start-up, can be expensive, and the start-up capital has to come from somewhere. As you know, money doesn’t just grow on trees. Money is a resource that makes things shake, and using my 9-5 to support my business financially helps it expand and grow. Read more>>

Monique Allen

I have been a business owner from the beginning, and yet I have always known that my inspiration and motivation come from being accountable to others and to a task or mission greater than me. This can be both an accelerator and a break when owning a business.

At 18, I took my first step into the landscape industry and never looked back. I had no idea that 40 years later, I would be deeply embedded in the industry as a business owner, employer, trailblazer, and thought leader. Over those 4 decades, I have had many opportunities to succeed and fail. There have been times when throwing in the towel seemed like the only sane option. And yet… I haven’t done it yet. Read more>>

Susana Lai

A question I often hear at events is, “Do you do this full-time?” When I share that I’m also a Speech-Language Pathologist, it’s met with surprise—after all, calligraphy and speech-language pathology don’t seem to be a natural pairing. While I don’t work full-time in the field of speech-language pathology, I can honestly say that, after establishing my business, the ebb and flow of entrepreneurship has made me realize I could never go back to the structure of a traditional 9-to-5 job. Read more>>

Robert Mickelsen

I would not trade my autonomy for anything. I could have chosen a field that was more lucrative, but it would not have brought me the joy or the understanding I have of myself that my art has. It has been said that the secret to happiness is to choose something you love doing and become really really good at it. Then you won’t “work” a day in your life. Read more>>

Susannah Barr

I became self-employed around 5 years ago as a professional player and coach, but in the last two years, we opened our first indoor pickleball facility. Our club has 18 indoor courts, a restaurant, a bar, and 10 pickleball coaches along with numerous other staff to help us be the best facility in the world. Within one year, we a have full membership with a waitlist to get in and are now opening two more facilities and franchising. Read more>>

Eileen Rose Miles

I think happiness in our work isn’t just about feeling good all the time. It’s about fulfillment, reward, and enjoyment. And yet, there are times when I don’t feel happy at all. Instead, I feel overwhelmed, exhausted, and stretched beyond my limits. In those moments, I catch myself thinking:

“Maybe if I had a regular job—one where I could just clock out at the end of the day—I wouldn’t feel this way.”

It’s a tempting thought, especially on the hardest days. The days when putting myself out there feels like too much, when things don’t go as planned, or when self-doubt creeps in and whispers: ‘Wouldn’t it be easier to slip into something more predictable?’ Read more>>