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.

Emily Strong

Of course every job has its pros and cons, ups and downs, and that is as true for business ownership as any other profession, but I have learned that I can only be happy as a business owner. I had regular jobs for many years in a variety of fields and I was always deeply unhappy. Read more>>

Shelby Catlett

Ever since I was a kid, I dreamed of running my own business. I didn’t know what it would be back then, maybe a shop or a restaurant, but the desire to create something of my own was always there. Years later, while working in IT, I discovered photography and quickly fell in love with it. Read more>>

Lacey Darcy

I’m incredibly happy as a business owner! And guess what? I actually do have a regular full-time job! I do sometimes wonder what it would be like to focus solely on that. The last time I had that thought was right in the middle of wedding season, juggling client contracts, communications, social media, and coordination for The Wedding Officiants—all after a full week at work. Read more>>

Rachael Berthiaume

I am happier as a business owner, but I definitely think about going back to a regular job quite often. When I first started my business in 2021 as a social media assistant I had a part-time job on the side for an entire year as I grew my client base. Read more>>

Kelli Winkler

I’ve been self employed/business owner since 2009. In 2009, I started a cleaning and organizing business and at one point even had a wait list for clients. I absolutely loved my flexibility and control I had over my schedule and especially the clients I served. Read more>>

Jamar Jones

I’ve been running my business for 10 years—one decade. The question ‘Are you happy as a business owner? Do you sometimes wonder what it would be like to have a regular job?’ really hit me. That’s super interesting because happiness as a business owner is something we sacrifice the most when building something. Especially as a business owner, it’s your baby. Read more>>

Tomoko Wynn

To be honest, I cannot imagine having a 9-5 job five days a week. I think I last had a regular job working part-time as a mannequin at a clothing store for a short period of time about 25 years ago. I moved a lot because my husband worked for the military. Read more>>

Suzanne Connors

There are days when the thought of another job—or even selling the studio and starting something entirely different—crosses my mind. Running a studio has its ups and downs, and not every morning begins with the creative joy people imagine. I usually start at dawn, already deep into emails and marketing tasks before the sun is fully up. Read more>>

Bridgette Finley

I wouldn’t change my story, it has truly been a beautiful journey. My path has been a blend of both discipline and passion. I started music training with incredible teachers like Dr. Donald Beatti, who at the time was the head of the Beethoven Society, and had the privilege of learning under guest teachers such as Stephan Möller and Robert Roo. Read more>>

Keely Kapsoff

Yes, I love being a business owner, choosing the cliental that I prefer to work with and seeing the final product. I actually have a regular job as well as a Director of Sales and Marketing running a wedding venue in Lake Tahoe. Wedding Planning and venue operations are both a passion of mine. Read more>>

Erik Trinidad

I had intended to sell that story after all was said and done, but then another mysterious disease came about in February 2020—that one that spread all over the world—overshadowing any other medical-related news stories for years. Read more>>