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.

Angela Wong

I spent the first decade of my adult life as an employee, and while the steady paycheck and benefits were nice, it always felt like I was trading time for something that wasn’t really mine. There’s a certain comfort in that security—but over time, that comfort turned into a kind of restlessness and dissatisfaction. Read more>>

Matt Horwitz

Once I turned 19, I never thought about having a regular job again. In fact, I made a commitment to myself. Before I even had a business (let alone a business idea), I wrote down on a piece of paper, “I am an entrepreneur.” And I dedicated myself to the path of personal development and self-directed education. I became absolutely obsessed with learning and growing. I got my hands on anything I could. Reading books, attending seminars (while sleeping on couches to save money), downloading audio seminars (they were a big thing in the late 2000s), online courses, digesting insane amounts of video and podcast content, and surrounding myself with others who were on the path of growth and development. Read more>>

Stacey Swan

There are definitely moments where I start second-guessing myself and wonder if I should get a regular job. The feeling of knowing exactly how much I will make every month, and feeling that security. The feeling of walking into a job and having that confidence from other people recognizing the work you do. All of those thoughts come when things get quiet. When something unpredictable happens and money feels tight. During these times I would look at job postings just to see what is out there. It seems like every time I got to that point, it was a reality check. Do I really want to be held to somebody else’s schedule? Read more>>

Maurice Shingleton

I can say that I am happier as a business owner than working the standard 9-5. I do find myself at times, wondering what it would be like to only work for someone and not for myself. The last time I had this thought was fairly recently. My grandparents health was beginning to decline while I was attempting to juggle 2 jobs, my business AND college. I made a decision that could ultimately keep me from over working myself and to keep the level of respect at the 2 jobs i was working for, I chose to focus solely on my businesses to ensure I was there for my family and to grow my company. I have learned that when we overwork ourselves, we tend to miss things in life and it damages us overtime. Read more>>

Rachel Barnum

I love being a business owner! As a young adult, I held many different regular jobs but the schedule was too strict to grow a family. I graduated college in 2016 and worked for several years in different capacities as a journalist, social media manager and even got my real estate license. Over time I realized I wanted to be more independent and also create and manage my own schedule, clients and myself really. I am so blessed to do what I do and be able to make my “workplace” exciting each day, whether it be the office editing, scoping out a new photo location, or enjoying beautiful Michigan. Read more>>