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.

Robert Roth

Yes — I’m absolutely happy as a business owner. I knew it pretty early on, actually. I think I was around 16 during a school break, and I took this one-month summer job. It was at a company, connected to their bookkeeping team. It wasn’t really about what I had to do there, it was more about observing how the typical employee life worked. Read more>>

Fernanda Read

Oh, I am absolutely happy as a business owner, no question about it. I’ve always had a fiercely independent spirit. I don’t thrive in environments where I’m being told what to do, especially when I know there are better ways of doing things. I need space to lead, to create, to pivot, to push boundaries, and that kind of freedom just doesn’t exist in most “regular” jobs. Read more>>

Dr. Suzanne Kritz

This is such an amazing question. I graduated from physical therapy school in 2020 with my doctorate in physical therapy. I always knew that I wanted to have my own business one day. I started off working for other people as an employee so know what that is like. Business ownership is an incredibly turbulent experience with high highs and low lows. You need to get your name out there, get clients, maintain clients and do good work so they tell their friends and family about you. I am more of an introvert so getting out there for my business has been challenging. Sometimes I think to myself how much easier it is as an employee because you show up, do the work and leave. Read more>>

Alexandra Mohamadi

I don’t think I could ever go back to being an employee, or working within the constraints of the insurance system for that matter, but that’s a whole other conversation. Still, there are definitely moments when I think, just for a second, “Wouldn’t it be easier to be a barista again?” Back then, my biggest concern was whether someone’s cappuccino had enough foam. I still stressed unreasonably about mistakes like that, but in hindsight I should have reveled in the lack of responsibility I had for others’ wellbeing. Read more>>

Matthew Romero

For the most part, yes — I’m much happier as a business owner. I get to chase big ideas, solve problems with creative freedom, and build something that didn’t exist before. That’s exciting. But I’d be lying if I said I never thought about what it’d be like to clock in, clock out, and leave work at work. Read more>>

Jessica Milne

When asked the question “Are you happy as a business owner?”, my initial response is yes! I 100% love my job and what I do. But on a certain level I do wish I got to work a regular job sometimes. It would be nice to have a break every now and then, and also have some social interaction, since I mostly sell through online platforms (a few things that you only get when working a regular job). However, running my small business allows me to be a stay at home mom and raise my little boy. Read more>>

Joshua Sanchez

Being your own boss sounds amazing—and it is in a lot of ways. The freedom, the flexibility, the pride in building something that’s yours. But what people don’t always talk about is how heavy it can feel sometimes. You’re the only one responsible for whether it works or not. If you don’t show up for your business, no one else is going to. Read more>>

Brittney Adams

Yes, I would definitely say I’m happier as a business owner—but that doesn’t mean I don’t sometimes think about what life would be like with a regular 9-to-5. Entrepreneurship is deeply rewarding, and it allows me to be more present for my daughter, but it also comes with its own set of pressures, especially when you’re building something from the ground up and every decision starts and ends with you. Read more>>

Tiffany Joyce

Ohhh, I’ve absolutely had that thought before. Honestly, more than once. Being a business owner is wild—some days you feel like a boss-ass queen changing lives, and other days you’re crying into your coffee wondering if you should just go get a 9-5 with benefits and someone else making the big decisions. Read more>>