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.

Tai Lewis

Sooo… let me be real for a second—like, really honest. I’ve been a full-time business owner for about three years now, and honestly, I still feel new in a lot of ways. There’s so much I’m still learning, and while that can be a little overwhelming, it’s also exciting. There’s so much room for growth—both in business and in who I am as a person. Read more>>

Melissa Dlugolecki

I think happiness is related based on how you’re, how you relate to your business, not onto the result.

I found my way into the industry by committing to the process, detaching from the outcome. I always had a story and a mission that I just wanted to help people. And I thought you either cared about business or you cared about people that led me to be six figures of debt. Read more>>

Evelin

Yes, I’m definitely happier as a business owner. Running my own coffee cart has been one of the most fulfilling experiences of my life. I love the freedom it gives me, the connections I make with customers, and the pride that comes from building something from the ground up.

It’s a lot of work—but it’s work I truly enjoy, and that makes all the difference. Sure, there are days when I wonder what it would be like to have a regular 9-to-5, especially when things feel uncertain or overwhelming. But then I remember why I started this in the first place: being outside, making great coffee, and chatting with people every day—it’s what I’m passionate about. Read more>>

Rheanna Bentley

I’ve been in the industry for many many years. I spent a large chunk of my career working in corporate chains. I was in management for a very long time with a very popular chain. I learned so much about our industry and about people in general…but I also began to learn what wasn’t working in that particular situation. I started to see that the focus was only on numbers. The bottom line. Not on the people! Our industry is centered around people and making them look good and feel good about themselves. So when I finally opened my eyes to what was going wrong, I decided it was my mission to do it right! I decided that I’d build my own brand, that focused on people and not just money. So far it’s going pretty good I’d say! Read more>>

Lizzie Pincoffs

Happiness is a choice, and I have learned to appreciate the freedom I have in life due to this path. I’m able to schedule work when it works for me. I can pick up my kids from school and rearrange things if they are sick. Owning a business gives me so much room and freedom. Freedom of expression in creativity because I don’t answer to a boss. The ability to pivot quickly when needed because I don’t have to send changes through a bunch of supervisors. Freedom to adjust the amount of clients I take on depending on outside pressure and other things happening in my life. Read more>>

Karin Cederskoog

I worked in video game development for over a decade, mostly as a designer & quest writer for large, AAA games & smaller, independent games.

With the video game industry in a state of turmoil (facing record layoffs in recent years), there’s more security in being a business owner. Instead of working at a single company, I can diversify my work (as I do for my investments). When my client pipeline ebbs and flows, I don’t automatically lose my primary source of income as I would as an employee. Read more>>

Shovon Ahmed

Absolutely—I’m genuinely happy as a business owner. For me, it’s not just about running a business; it’s about doing what I love. My journey started with a deep interest in personal branding and SEO. Over the years, that interest evolved into a passion, and now it’s the foundation of everything I do.

I’ve helped hundreds of businesses and individuals build strong digital identities, from creating Google Knowledge Panels to optimizing their online presence for search. That process of turning ideas into visibility—of helping someone go from unknown to discoverable—is something I enjoy deeply. It’s never felt like a job. It’s a craft. I enjoy the challenge, the strategy, and the creativity it involves. Read more>>

Kai Lanier

I’m genuinely happy being a business owner in both social media and photography—these are two passions that have opened doors I never imagined. But I’d be lying if I said it was always easy, especially when it comes to social media. There are definitely moments where I wish I could just quit and delete everything. What people need to understand is that with social media, hate is almost a badge of impact. If no one’s hating, you probably haven’t made enough noise. Ironically, the more hate you get, the more it confirms you’re reaching people. On the photography side, though, it’s nothing but love. If I could do a photo shoot every single day, I would—there’s just something incredibly fulfilling about capturing memories that mean the world to someone else. It’s an honor I don’t take lightly. Read more>>