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.

Mario González

Yes, I’m very happy. I always dreamed of having my own company and being “free” when it came to working and carrying out ideas. I think it is the best way to fulfill yourself as a person since it allows you to learn countless aspects about life on a daily basis and to be able to contribute and help many people thanks to your work. Read more>>

Nastia Vesna

As a business owner in the wedding photography industry, I find immense happiness in what I do. It provides me with a plethora of new emotions, skills, and sensations that would be difficult to experience in any other profession. Every obstacle or challenge I encounter becomes an opportunity for personal growth. I embrace the risks involved, as they are solely mine to bear. Read more>>

Talyn Rahman-Figueroa

Ugh, I’ve had “regular jobs” since I was 16 and I knew it was never for me. And regular for me, probably isn’t regular for everyone – I’m talking about working for the government, working alongside diplomats, being managed by someone else, and expected to come in at a certain time even if you had nothing to work on. Read more>>

Jessica Lea

I started my business over 15 years ago, as a part time side hustle. At the time I was working full time and really wanted to learn Photography and eventually have my own business. After a few months, it became clear that in order to succeed my business needed more of me, in it. Read more>>

Larke Brost-Kazmierski

As a leadership and systems consultant, I assess, design, and build capability for leaders of big initiatives and systems. And I actually like being on the inside, getting a firsthand look at how organizations tick. Plus, I genuinely delight in the long-term relationships I build with teams. But one thing that I’ve noticed, after 25 years in corporate positions, is how challenging it is to remain true to my values, aspirations, stories and decision-making. It’s a blessing and a curse to be a keenly sensing and empathic person in a systems role. I’m always examining and teasing out where I stop and the soup I’m swimming in begins. So part of what inspired me to put up my own shingle was to offer clients a detached perspective and inquiry into how they navigate their environment. Read more>>

Rachel & Tristan Thompson

Are you happier as a business owner? Do you sometimes think about what it would be like to just have a regular job? Tell us the story about the last time you had that thought, what was going on, really paint the picture for us so we can understand what you were going through and how you thought through this question and what (if any) conclusions or insights you came to. Read more>>

Jarrod Mason

I am no doubt happier as a business owner, but that’s not to say that this position doesn’t come with any challenges. When you’re building your own business, that means you are responsible for everything. That includes marketing yourself, finding customers, completing the work, managing employees/contractors, collecting payments, paying taxes, insurance, etc. The list of to-do’s never seems to get shorter as a business owner and it can be stressful. Read more>>

Jacqueline Taylor

I am happiest as a business owner; I have worked in corporate America for the past 37 years and now that I have “retired” I decided to lean into my passion which is helping minority businesses and people to grow. This is something that I did “on the side” while I worked but now that I have retired, I have the pleasure of doing this full-time. Is it sometimes challenging? Of course it is, but it is so rewarding! Read more>>

Desiree’ Nixon

Being a business owner is mentally challenging at times. There are some days when I want coworkers, a boss and a consistent income. The security of a “regular job” makes going down that route all the more tempting. Although I may have to spend some lonely, unstructured, penniless days, I wouldn’t trade what I have now for the world. Read more>>

Olivier Dressen

Reflecting on my entrepreneurial journey, I’ve always found a unique sense of fulfillment in it. There have been moments, though, when I’ve pondered the path of a regular job. One vivid instance comes to mind, encapsulating this contemplation. Read more>>

Lacey Prpić Hedtke

I’m definitely happier as a business owner than working for someone else! I worked in the non-profit sector for years before I made the leap to opening a business–I figured I could make that little money on my own and could always go back to a job that didn’t pay me enough and stressed me out–those will always be there! I started my business in 2017 and didn’t feel ready at all and then at some point just thought I’d never be ready, so opened and it’s just expanded from there. Read more>>