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.

Leah Yard

This is such an important topic. The way entrepreneurship is shown online is very glamorous, and that couldn’t be further from reality! There are so many times I think about what it would be like to have a “regular job” again. When I started questioning my choice of starting a business it was in 2020. Everything felt impossible, and I started to assume I would have to close Leah Yard Designs. Read more>>

Sydney Boright

There’s no doubt in my mind that I was always meant to be a business owner. From an early age, I knew entrepreneurship was my calling, and I quickly discovered that the act of working brought me genuine happiness. I still remember at the age of four, asking my parents to buy me a waitress apron and order pad so I could take “orders” at restaurants. I wore that apron every time we went out to eat, always asking the staff if I could shadow them and take orders for them! At eight, I took my first entrepreneurial step, saving up all $21 I had to buy a cash register at a local thrift store. I spent countless days creating a “store” for my friends and family to play in, and to this day, they laugh and say I was destined to own a business. Read more>>

Emily Norris

In my career, I’ve worn many hats: school teacher, music teacher, office worker, and now business owner. At every stage, I’ve had moments of wondering, “Is the grass greener on the other side?” It’s natural to imagine how life might be different with a “regular” job, especially during challenging times. Read more>>

Ivan Zadikoff

Owning a business was something i sort of fell into. My parents built an engineering business that i was around my entire life. From 13 i was going into the field with my dad, wading in creeks having sharks swim through my legs all in order to do envrionmental testing for permiting for a project we were working on in the keys. Read more>>

Rikki Brew

I’m totally happier as a business owner. I’m currently a mom of a “spirited” 4-year-old boy. Most of my time is spent with him, and I shoot and work during my spare time. Having the flexibility to make my own schedule and work when I want has been a total game changer. I (mostly) love being his mom, but it’s so nice to have a job that I LOVE that offers flexibility, a creative outlet, and provides enough substantial supplemental income for our family. Sometimes, I wonder what it would be like to have a regular job, but I don’t think I would be as happy or flexible! So every time I think about that, I go back to the reasons why it’s so amazing to do what I do. I can be as present of a mom and wife as I’d like to be while still working, and that is a gift in itself. Read more>>