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.

Caitlin Eyk

I have a million reasons every day to be grateful that I am a business owner. There are a lot of perks that come with being your own boss but there is also a lot more riding on your shoulders. You have to wear all of the metaphorical hats and if a hat doesn’t fit right you have to delegate that role to someone else and pay them. Read more>>

Pamela Zeljak

When people ask me what’s the best part of owning my own business, I tell them it’s not having to go to meetings. And that’s mostly true. Not having to waste time in meetings that don’t pertain to my job or “could have been an email” has been a liberating experience. But there are drawbacks to not having meetings with contemporaries. I don’t get to bounce ideas off of them or get different points of view on solving complex problems. Read more>>

Tracy Kuch

As a new business owner coming directly from working for others, I find myself being happier on a regular basis. Daily, I am so thankful, even at this early stage in my business, for going out on a limb starting something that I never imagined doing. At this point, having a regular job and working for someone else has no space in my thoughts. I am realizing how amazing it has been to not feel the stresses from someone else’s business and direction. Read more>>

Nikki Anderson

I will be honest, it’s not always rainbows and butterflies but I wouldn’t go back to a “regular” job if it wasn’t absolutely necessary. The freedom of being able to make my own schedule, set my pricing, decide what orders I want to take on and more makes it worth it. Taking pride in what I make and seeing the joy in my customer’s faces is another selling point. You just don’t get that at most desk jobs. Read more>>

Ashawna Lane

In my experience as a business owner, I can say that it’s been quite the journey. I’m happy with the decision I made but it can be a very daunting task at times. I often think about what it would be like to go back to work. I’ve been able to enjoy the best of both worlds as a employee and an entrepreneur so I’m familiar with the pros and cons on both sides. Read more>>

Ebonee Danielle

Whew, this question right here is a doozy. I believe in transparency so here goes. My happiness as a business owner tends to depend on the day. I honestly wake up some days and say to myself, “what have you done?” Then there are days that I wake up and I say to myself, “I am running away from everything.” But then I have the days that overshadow those days. Those are the good days. Yes, I often think about going back to work where there is a steady flow of funds and regular hours and I can clock out. Read more>>

Kara Clark

When I started my own interior design business and began working for myself, it was in the middle of the pandemic, I had a brand new one year old and my marriage was only about 3 years in. Needless to say it was a pretty crazy time! Now that I am two years into running my own business, I can truly say that working for myself was the best move I ever made. I think almost daily as I pick my 3 year old up from school in the afternoon, how I simply would not be able to do that if I worked for another company.

Tracy Croushorn

This question comes at a very funny time… My husband and I were just talking about this very thing. Let me first start by saying that every day as an entrepreneur is a gift. Honestly, I wouldn’t trade it for anything. But it is NOT EASY! There are good days and bad days, but the bad days can get really bad. Sometimes the thought does cross my mind that it certainly would be easier just having a regular job and working regular hours. For me, that would not be fulfilling. Read more>>

Shikeece Rucker

I ask myself this quite often! Being a business owner has its ups and downs. I say that because one day everything can go so smooth and sales are coming in but then there are days where no sales are made or barely being made and you wonder to yourself are you doing enough! You have to promote constantly to get views and reach more people. Overall I do love being a business owner because you’re creating things that you and your supporters are interested in. Read more>>

Jenn Dickel

As an entrepreneur, there are many times I question myself about the direction to go, what to do, and how to get there. I believe I am happier overall as a business owner. I can definitely say that my everyday quality of life is better and more fulfilling. On days when it is rough, I remind myself that “divorce is not an option”. I relate owning this business to being married. Read more>>

D James

yes 100% happier. I have had a regular job and it is actually what pushed me into becoming a business owner. Ever since I left my job it has been a huge motivational factor to keep me working hard so that I never have to go back to working a regular job. Since starting my business I have thoughts of going back when times get rough. But my thinking is, If I have to do all of that for the job (Someone else) I can do those things for myself, and set my own hours. Read more>>

Rashae Glover

Overall, yes I’m happy as a business owner but there are some days where my emotions are on a roller coaster ride. A lot of days I’m mentally and physically exhausted and I have to put those emotions on hold in order to continue business. I think the toughest part of it all is pretending to not be human with bad days because you feel the pressure to present joy and excitement within each customer experience. My rule of thumb is to keep a sense of balance between work and life. Having the freedom to create income while bringing joy to my clients make the sacrifices worthwhile. Read more>>

Lorie Tonche

I am definitely happier as a business owner than I have ever been at a regular job! I absolutely love what I get to do for a living! It brings me so much joy and I also get to spread that joy with others, one event or delivery at a time. I mean, it doesn’t get better than that! I consider myself very blessed to have had some great jobs in the past. Those experiences have helped me appreciate my role as a business owner so much more. Read more>>

Savannah Stohler

I think every business owner thinks about what it would be like to have a regular job but I couldn’t be happier as a business owner. Last time I had this thought I had some financial problems and wondered if it would just be simpler to have a regular job. Then I realize how much I love photography, I love the art I create, how I can make my own schedule, work with clients across the nation, travel for work and meet new like-minded people all the time. Read more>>

Rachel Adelicia

There are days when I wonder if it would be easier to have a “real job”. This usually happens when I’m worried I making the wrong choices for something business related, or am a bit tired of wearing all the hats. Then, I realize that owning my own company lets me be as creative as I want, that the mistakes I make are mine to fix, and that I wouldn’t want it any other way! Read more>>

Seth Jones

All the time. I do enjoy what I do there is peace that I have when I am designing. sometimes I struggle with seeing the end goal, I focus on the moment a lot and what we don’t have rather than what we do. I’m entertaining the thoughts of quitting currently. It doesn’t go away, when the brand grows so does the doubt. Since I started Seasons there hasn’t been a day where I’ve wondered if I was doing the right thing. It’s a constant struggle, but it’s a good one. Read more>>

Hannah Kaminsky

I knew from an early age that I wasn’t cut out for a 9 – 5 office job. I’ve only worked as a baker and cook part time in various restaurants while getting started, which was ultimately holding me back from finding success in my own business. After sweating in the kitchen all day, I’d be too exhausted to do much other than watch movies, let alone feel creative when I got home. Read more>>

James Greene

I absolutely love being a business owner. There’s no other job like it. I tried the 9-5 lifestyle a few different times in my life, and it’s just not for me. My mind is built for strategy, and coming up as an athlete and Veteran, I have high expectations for one’s ability to execute whether it be a task for myself or others on the team. I am no worker bee. Read more>>