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.

Jeanne Micallef

Having recently celebrated 21 years as a business owner, I had a moment of realization — I’ve been my own boss longer than I have ever worked for someone else. That thought hit me like a quiet milestone, a reminder of the journey I chose. So yes, I love being a business owner. The flexibility, the creativity, the sense of ownership over my work — it’s something I never take for granted. But like any path worth taking, it’s not without its challenges. Read more>>

Michael Hulett

As a small business owner, I constantly fluctuate between the exhilaration of forging my own creative path and the sheer terror that everything could collapse at any moment. I genuinely believe that this push-and-pull dynamic is what keeps both me and the business moving forward. The fear of failure fuels my drive, keeping me motivated and hungry—without it, I wouldn’t accomplish nearly as much or take the necessary risks to succeed. Read more>>

Alexandra Booze

I started East Coast Contessa with a former business partner while living in Washington DC and working a demanding 9-6 (and sometimes much later) job. I was in desperate need of a creative outlet, and wanted to share my favorite local activities as well as my dining experiences throughout New York City and the DMV. Read more>>

Alexis Richards

As a small business owner you’re always challenged with the question “What else?” or “What would would you do if you weren’t doing this?” and as a YOUNG small business owner I’m constantly getting bombarded with the question of “What is your back up plan?” or “That’s all you want to do?”. With this constant skepticism you can’t help but think “Well…if I didn’t do this what would I do??” And I always rack my brain trying to answer this question because since I was in kindergarten I’ve always wanted to do my own thing. I was always the artist on Future Career Day while my friends and classmates were doctors and lawyers. Read more>>

Daisy Barbel

Nothing could’ve prepared me for being a business owner. I’ve had an interest in fashion since I was five years old, sketching dresses on any piece of paper I could find, watching runway shows with wide eyes, and making dresses for my toy dolls. I always knew I’d have my own brand one day. But I didn’t expect that dream to start becoming a reality so soon. Read more>>

Daniela Saioni

I am grateful every day for having accidentally ended up an online solopreneur when the events of 2020 essentially forced me to suddenly redesign my life at the age of 51. My main job for most of my adult life was working on film sets (which I still do from time to time, when there is a project or director I simply can’t resist working with, but it’s a seventy-plus-hour workweek so I always have to think long and hard before returning to that world). Read more>>

Justice Porter-Harris

Am I happy as a business owner is a question that runs through my mind often. I often reflect on the idea of what it would be like to just have a regular 9-5 job. Would it be easier to just go to work Monday through Friday and report to a higher authority rather than managing everything myself is a question I constantly ask myself. There are many struggles that come with owning a business. You are the boss, that means you make all the final decisions. It can be stressful when making those decisions. Whether your making the right or wrong choice for your business, comes with a lot of pressure. Read more>>

Illyne Ganley

By far the best decision that I ever made with regards to my work life was taking a risk, starting my own business, and becoming my own boss. Working for yourself requires a lot of self motivation, resilience, creativity, and the ability to pivot and collaborate, all qualities that I always felt pretty confident in so working for myself suits me. I’ve been very fortunate in that I’ve always had jobs that I’ve loved and have always worked with people who have inspired me, however there is nothing, in my opinion, quite like the feeling of being able to translate the vision and concept that’s in your mind into a reality for others to value and appreciate. Read more>>

Paul Nurnberg

Having been in my own business for 37 years it is hard to imagine having a “regular” job. Although I really don’t have to imagine too hard, as I had jobs in my field of photography for six years after graduation from collage. While there may be some advantages to working for someone else, such as paid vacation, and sometimes paid health insurance the freedom of owning a business outweighs the stress and uncertainty of being a business owner. My wife and I love to travel so not haveingh a set number of days a year I can travel is a wonderful feeling and lets me live a fantastic life. I have been thinking about it a lot recently as I am planning trips this to Costa Rica, Alaska ( for the 7th time in eight years), New Mexico, New England and NYC. And have recently been to The Everglades, Southern Florida, Alaska, and many long weekends away. Read more>>