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.

Stephen Mendoza

If I am being completely honest, I think about this question a lot. Overall, I am extremely happy being a business owner and being my own boss. I work when I want and am able to work with who I want as well. I’ve met so many amazing other business men and women along my journey as a photographer, but I would be lying if I said I didn’t think about having a regular 9-5 job. Read more>>

Emily Krings

There are many motivations for becoming a business owner. Some people want more money. Some people want the glamorous “CEO” title. All of that sounds cool to me, but what I’ve wanted from the start is freedom. I saw a meme circulating a couple of months ago that said “I quit my 9-5, and now I work 24/7,” and boy, did I feel that. Since I went straight from full-time student to full-time entrepreneur, I didn’t leave a 9-5, but I dodged one. Read more>>

Elizabeth Davidson

I am very happy as a business owner! Don’t get me wrong, there are days that I ponder going back to a regular 9-5 job especially when my days get overly stressful. However, I know deep down in my heart this is what I am called to be doing at this time of my life: exploring my limits, growing myself as well as my portfolio, maintaining and sustaining my responsibility, the list goes on. I’ve been in a regular job before. A regular job provides security, stability, and predictability most days. It is clearly the safest option. Read more>>

Pamela Davis

I am definitely happier as a business owner. Sometimes I think about what it would be like if I had a “regular” job. 9-5 desk job where I could leave the office and go home and not think about work again until the next day when I sat down at my desk. I would sleep more, I would be less stressed, but I would be WAY less fulfilled. I thrive on guest experience and standing out amongst the sea of caterers. I love providing a unique offering that will be talked about for years. I could never offer that at a “regular” job. I love the flexibility of running my own business. I get more time with my family and friends, and I can close up shop for weeks at a time in the off-season if I need to. Read more>>

Jenny Woudenberg

I am writing this in print to tell the universe and everyone who reads it that I will not return to a regular job! Even on days that I am feeling anxiety, fear, and uncertainty—I will keep moving forward because the lifestyle my business provides is totally worth it! As a freelance content marketer, I truly get to live out my dream life every single day. My schedule is my own, and so are the client partnerships I create. Read more>>

Alyssa Pittera

Every winter I contemplate going out to get a “regular job.” I think about how that would feel to have a consistent paycheck I could depend on when my slow season hits. These thoughts crept in around January this year, when I had some travel planned even though the bank account was dwindling, and business was real slow. Read more>>

Felipe Barajas

Sometimes I wonder what it would be like to have a regular job and regular routine just like everybody else. Growing up I didn’t necessarily experience that since I started my business when I was 13 years old. Building a platform, a form of income from that young of an age is extremely difficult but never impossible. Read more>>

Ariane Scholl

When the idea first bloomed in my head to start my own business I was sitting on the very crowded #9 Ashland bus in Chicago headed to my teaching job. There was a woman that was always on the same bus as me in the morning. As a young teacher in a school of primarily veteran teachers I often struggled with the dress code and what I should and should not wear to school to be seen as professional or serious. Looking back, I was far more concerned with this matter than I think any other person in the school but I believe the root of it was in wanting to do a good job — to be seen as a real teacher. Read more>>

Nikki Santigati

Starting my own business was the best decision for me. I have never been happier in my life and am so grateful for the enrichment both personally and professionally that owning my business has allowed me to experience. For over 20 years I had worked for someone else whether it was managing pet resorts & retail stores, to cashiering, or hospitality I knew that job setting was not my end goal. When I left my last industry I knew I was given an opportunity to bet on myself. But after a year of being in business learning, growing, succeeding, struggling, etc. it can be a lot. Read more>>

Nia Rowland

I am so grateful to be a small business owner! Though it is not Rainbows and Unicorns, I could not imagine doing anything else. I get to do what I am passionate about and honestly, How rad is that?! Being a small business owner takes hard work, dedication and discipline. I photograph milestones in people’s lives. Weddings, Engagements, Elopements, Families and Graduations! I am there for the happiest moments of peoples lives. Seriously, can my job be any more awesome?! Read more>>

Bryonna Williams

I think this question is extremely important because I feel society places a heavy emphasis on being an entrepreneur and business owner & somewhat downplaying those in the corporate world. Being a business owner is absolutely incredible, FOR ME. I 100% have thoughts all the time of how much easier it would be to know exactly what I’m getting paid every month, have a set start & end time, get paid vacation & sick days, & have free weekends. Being a business owner is one of the hardest challenges I’ve ever experienced in my life. Read more>>

Matt Walsh

the simple answer is YES, I am very happy as a business owner, however, it’s not without its challenges, both normal and extraordinary. Normal challenges include getting your idea off the ground and making sure it’s a viable business model. Extraordinary challenges would include everything that is going on today including COVID, rising interest rates, inflation and the possibility of a recession. So, despite these extraordinary challenges, I still prefer owning my own business and it’s during these time where the rubber really hits road as far as being an entrepreneur. Read more>>

India Kior

Yes! I am happier as a business owner for a fact! I actually was very curious about how it would be to work a job, so I went and applied to multiple jobs hoping for an opportunity. Sometimes I’ll get so locked in with my work that I wouldn’t realize that i’ve been cooped up in the house for 3 consecutive days with no sunlight. I thought it would be better for my mental health if I got a job and would be able to have a reason to leave the house everyday being that I run an online based business . I also thought i’ll be able to find balance in my daily routine If I worked a job and ran a business at the same time. Well, I thought wrong! Read more>>

Lisa Steinkamp.

I’ve always wanted the freedom to create something on my own. I spent a long career in marketing before finally deciding to take the leap and start my own business, but I thought about it for many years before that. I worked for some pretty great brands and liked what I did, but spent probably the last 5 years of that marketing career thinking about what kind of business I was going to start someday. I guess it was sort of a creative itch. Read more>>

DeAsha Redding

When I look at it, yes now I am a happy business owner. Before I was not so happy because I was afraid of the unknown. I do think about getting a job, OFTEN! Sometimes I get on Indeed and apply for jobs when I am upset in my business. However, I know this is where I need to be. Read more>>

Chelsea Berman

While being a business owner is the most important thing in my life that I have achieved, it’s also the most stressful! When I started this business it was out of necessity and honestly, boredom during the pandemic! Being sidelined at home from my full-time pastry position I was itching for something to do! So I launched my first menu online and sold to friends and neighbors. While owning a business was always in the plans for me eventually, I never expected it so soon! I had to grow my idea of the business along the way with me, to make it work for me and what I want to do in my life. Read more>>

Aroon Duncanson

I grew up in a household where both of my parents were business owners, and I always knew I would one day work for myself. I am so incredibly grateful for the business I have built for myself, and having the ability to create my own schedule, make my own rules and build my ideal work life. But that is not to say that owning my own business does not come with a plethora of challenges and demands that a regular job would not. As a business owner, I am CONSTANTLY working, even on a holiday, Christmas, New Years, family vacations, no matter the day, I am available and busy. That can be tough, but for me it is totally worth it. Read more>>

Jennifer Shun

I started my first company three years out of undergrad. After the traditional path of college, interning, and new hire, I quickly realized the slow, seemingly stiffing pace of the corporate ladder was too tedious for my energy. Within a few short years, what started as a side-gig, turned into a full-time commitment — an entrepreneur was born! Over the last twenty-six years, have I looked back? To be completely honest, of course! Read more>>

Brittany Bartholomew

Am I happier as a business owner? It’s not really a question I considered until this moment. Of course, I’ve had thoughts about going back to having a regular job many times over, but I can’t remember the last time I sat with myself to think about if I am in fact happier. The reason for that is because, a majority of the time I am happy even when things are tough or I’m feeling stressed. Read more>>

Trey Winfrey

I am very happy as a business owner. I no longer think about what it would be like to have a regular job at all. From having my first job a teenager, to going to the Airforce right out of high school, I knew that having a regular job wasn’t for me. I always felt that I had more to offer than I was allowed to do, and I always did more than I got credit for. I felt much more valuable, than I would be recognized for. I always loved working with food and in the kitchen, but I didn’t exactly love cooking someone else’s recipes. When customers would complement me on how good the food was, I couldn’t really accept it, because I felt that it wasn’t me. Read more>>

Daminique Washington

As a business owner I have had my moments of ups and downs. I would say in my happiest moments it wasn’t the profit or the exposure, it was always the feedback and genuine appreciation from customers enjoying my products. From the tagged post of what my customers made for breakfast, lunch and dinner would light a fire in me. There’s been numerous times where I’ve learned how to create a new dish with my products from my customers sharing their own recipes. That alone made more than grateful, happy, and excited that I did not give up on my business dream. Read more>>

Karen Navarro

Im happier now, I used to be hostess on a restaurant in Miami, South Beach area, for more than 5 years and every shift I was on, this idea of becoming a bussiness owner was taking over my thoughts, I learnt a lot of custumer service and my top notch experience in fine dinings allowed me to push myself harder when i comes to work however, I dont want to go back on a regular job at all, i feel i can do a lot of more things and money creating and expresing myself through my clothing bussiness, God gave the chance to be on a regular job in case my plans go down, Read more>>