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.

Erick Donoghue

I concluded a long time ago that I would never have a “real job” or a “normal job.” I’ve tried a handful of times to leave things I was passionate about for the security of a steady paycheck. It never worked out, I was miserable every time. I’m a weed-in-the-wind, go-with-flow type of person and value quality of life over money every day. Read more>>

TDP Israel

Am I happy as a business owner? Before I answer the question allow me to first say that business is full of ups and downs, never the less the vision is what keeps a business owner going, in stormy times it is the vision that keeps it going it the vision that i am in love with so despite of the challenges i face my eyes are set on the future. to answer the question yes i am so happy to be a business owner. Read more>>

Leah VanHoose

I have worked for myself since 2001. I have been many things but working for myself has always been top on my priority list. I started out as a massage therapist opening up my own studio and transitioning into a Crossfit affiliate owner and after 10 years I sold the gym and moved to Florida. Here I have had a photography business for 9 years and a realtor for the past 4 years. Read more>>

Monica Reyes

Never been happier being my own boss! I truly love what I do, and I will hustle for it everyday then being at a regular 9-5 job where I am miserable. Yea, it’s hard owning a business and having a regular is comfortable. There is nothing wrong with regular jobs. But if you have passion, creativity for something you truly love, I believe you should be a business owner. Here’s a quote- “If you don’t build your dream someone else will hire you to help build theirs.” ― Tony Gaskins  Read more>>

Emilee Maxwell

Yes! I am much happier owning my own business and planning my time to be more efficient. It’s empowering to take on more responsibility and I am so much more invested in the success of TwentySix since it is my own. I’ve really tried to take on higher quality projects rather than quantity of projects, which has allowed us to be much more selective with the clients we choose to work with. This has been such a game changer over the past few years and has strengthened our service offerring. Read more>>

Harshika Amin

I ask myself this question at least once a week. The answer has been different each time. It’s an important point of evaluation on how far I have come and where I need to get to. It is also important to me that I not only love my work but also that I am happy doing it. I can say I am happy most of the time, and it is truly a gift to be able to follow my dreams. Read more>>

Rachel Johnson

Being an entrepreneur is probably one of the wiiiillllllldest decisions that I’ve ever made! (LoL) Oftentimes I feel that people only see the “glitz and glam” of it but never the sacrifice. They see that I work for myself, I set my own hours, I can work from home or away on an island, and from the outside looking in it looks fun. But if I’m honest entrepreneurship can truly be ghetto. It’s some days that the invoices are going out and being paid consistently and then there are other days when the invoices and payments received dry up. Read more>>

Rachel Vasquez

Who really believes that owning your own business would be so much work. Social media has brainwashed us to believe life as a business own is just looking good, making money and traveling . Well let me tell you from experience I have worked every 9-5 you can think of and I work more now than I have ever worked before. I am so happy to be a business owner but is there times that get overwhelming? YES times I think about giving up the responsibility? Read more>>

Kati Brayton

Going full time with photography was the best career move I’ve ever made. My photography journey began as a hobby right after I graduated high school, and as I began to enroll in photography college courses (originally just for elective credit) I fell in love with the craft and the creative outlet. I began taking free and (barely) paid sessions for friends, classmates and family, and quickly realized that it could turn into something more for me. Read more>>

Shab Azma

I am very happy as a business owner. I never set out to be an entrepreneur! My father always said I was a leader at a young age but when I started working I had never thought about having my own business. I had worked at a big studio and a big management company after that and it wasn’t until the company was starting to downsize where I realized that I had better start thinking about a plan B and decided to take a chance on myself, knowing I had one potential client who had sought my expertise when I was still an employee at my job. Read more>>

Merrill Rainey

The question of just giving up the freelancers life and taking a regular full time job pops into my mind more often than you would think! Being the sole proprietor of a business, I am constantly working; it is a 24/7 job. I am on the clock all the time… working on current projects, thinking of new projects, refining projects and skills, marketing my work, managing everyday office tasks, being my own HR and finance department…it’s all me! In the ten years that I’ve been on my own, I have only taken one true vacation where I didn’t bring any work with me. Read more>>

 Jabin & Natalie Olds

Is owning our own business the right thing to do? It’s something we lie awake at night asking ourselves repeatedly! We could be in a much stronger financial position, personally, if we worked regular jobs. Currently we are only able to pay ourselves about 50% of what we made before we started our bakery. The recent inflation has put even MORE strain on that and what we are able to do to build any kind of security for the future. Read more>>

April Swierenga

I absolutely love owning my own business! Sure it comes with its own set of challenges but to be able to set my own schedule and to allow myself time to take care of others as well as myself has been such an amazing journey! Read more>>

Regina Alhassan

I am happy as a business owner. That has been a journey for sure! I’ve had to redefine and create my own version of happiness. And, then get comfortable living it on my own terms. Coming from a working class family, leaving a good job to start my own consulting firm was not the norm. Getting there meant I had to dismantle versions of myself and confront many of the value systems around me. Read more>>

Jack Tolzmann

I would say that I’m significantly happier as a business owner. There is much more responsibility, and in a sense I’m always working. Whether it be sorting out next week’s comics and orders, or the countless small tasks that never end such as cleaning, organizing, and helping customers. Read more>>

Heather Rymer

I definitely feel happiness being a business owner! I love the freedom and flexibility it gives me to create my own schedule. I love that it allows me to tap into my creative side when planning out the events and working with so many incredible people! Read more>>

Kelsey Pettus

As a business owner, I find great happiness in being able to work for myself and help support my family. It brings me immense pride to have built something from scratch and witness its growth over the past three years. I am excited about the future and the possibilities it holds. While I acknowledge the benefits of having a regular job, such as set hours, I am constantly driven to improve our systems and brainstorm new creative products. Read more>>

Thi Dang

Working as a business owner requires a lot more effort and entails greater responsibilities compared to simply working alone in one room. However, despite the challenges, I wouldn’t trade it for anything because having a regular job can feel limiting and confined to a single location. As a business owner, I have the freedom to unleash my creativity. The role of a business owner is incredibly multifaceted and intricate. Read more>>

Katy Bonello

When I decided to become an entrepreneur and start my own remodeling company, it was because I learned by my mid twenties that a “regular job” was not for me. I had several of those right out of college, and they were not fulfilling. I’d even say I struggled with bouts of depression and anxiety that came from the monotony of a nine to five office environment, and that’s what inspired me to try my hand at starting a business of my own. Ultimately, I decided it was better to try and fail than not try at all. Read more>>

Justine Olsen

This question is often viewed differently to me based on how my business is going in the moment. I am the kind of person who has really always had some kind of a desire to create something artistic and make a living out of it. I mean, who wouldn’t? I have 3 kids at home and worked nights at our family’s bar for over 17 years. My long-term goal was to go from managing and bartending to running the bar after my father retired. The stress and late nights got the best of me, and I realized this may not be my forever thing. Time to re evaluate. Read more>>

Tyler Thomas

I’m much happier as a business owner and freelancer. I love to curate my own style of work and the way I want to get things done. I also enjoy being able to make my own schedule. It’s just like if I need time off of work, I don’t need to request it off, I just need to accept that I won’t be getting as much done, which has its ups and downs. Read more>>

Tyler Thomas

I’m much happier as a business owner and freelancer. I love to curate my own style of work and the way I want to get things done. I also enjoy being able to make my own schedule. It’s just like if I need time off of work, I don’t need to request it off, I just need to accept that I won’t be getting as much done, which has its ups and downs. Read more>>

Jose Garzon

Being a business owner has Its ups and downs. I’ve been independent since I was very young. The stress, the long hours, the constant hustle to make it through another month. It’s all very intense but in the end is 10 times more rewarding than getting a check every Friday. Ps: I also never had a “regular job” or a 9-5 so to me there’s no difference. Getting a regular job has never been a thought in my head. Read more>>

Ryan Hudson

If any entrepreneur tells you that they never considered going back to work for someone, they’re lying. It’s easy, show up, punch a time clock, do some task that has already been laid out in front of you, complete task, punch out, go home (and leave work at work). But I had always found that mind numbing. I’ve even had some really exciting jobs before music like repairing electronic devices for a major audio brand, Read more>>

Audra McElyea

I do feel like I’m doing what I’m meant to do right now, so therefore I am beyond happy and content. For years, I felt like I didn’t belong career-wise in the corporate buying world I was in, and I could never quite put my finger on why that was because I definitely didn’t hate it. But now that I’m an author, everything seems to make sense in terms of why certain things didn’t work out or weren’t a great fit for me, Read more>>

Missy Adiego

This question hits so close to home. Since my business is just over one year old, I’ve had the chance to try my hand at other careers, some I loved more than others. For me design was a passion that turned into a career. There are positives and negatives of your own business but the positives far out way the negatives. Starting out is a struggle as with any  business, building from the ground up takes hard work and hustle. Read more>>

Toni Hardy

Being an entrepreneur/business owner I often experience a range of emotions from exhilarating on most days to serious anxiety on others. I’ll explain that response a little more in depth because most paint this glamorous picture of entrepreneurship, but if I can be completely honest and transparent this journey is not for the faint of heart. There are days where I do feel discouraged and truly want to quit, but then I remember my “why.” Read more>>

John Brady

I am much happier being a business owner than I ever was as an employee. My wife and I started DevlinLee Designs when we were 25. We both had full-time jobs, I was a paramedic so my schedule offered me about 4 days off a week. I spent those four days building furniture. In our first year, we only offered three products built to order. Read more>>

Tiff Marie

Yes, I am happy as a business owner. I take pride in knowing I am making decisions for myself that will move my brand and my career as a music artist in the right direction. I have worked a regular job for a good portion of my life, and even though I was paid for my time and my skillset. I used it to make someone rich or stay rich. Read more>>

Andrea Luke

Becoming a business owner has been one of the most rewarding goals I’ve completed in my life but I think every business owner, at some point thinks about going back to a regular job, especially on the really tough days. As a business owner you do not get to physically leave your office at 5pm each weekday and mentally or emotionally check out until the next day. Read more>>

Gerry Romanelli

I love being the owner of a small business. I transitioned from the corporate world to business and franchise ownership and wish I had done it sooner. When I started in corporate out of college it provided job security and great benefits as I was starting a family. If I showed up, worked hard and stayed out of trouble I had job security. In fact, many people spent their entire career at one company. Read more>>

Krista Kunkel

I haven’t always been a business owner. I’ve had multiple jobs and multiple bosses. I’ve had strict clock in times and clock out times. I realized that I was putting so much work in for these companies but the companies didn’t really appreciate it. I never got raises or position advancements. I worked at a company for years and never got a raise and had to take on second seasonal jobs to pay bills and still stayed at the company because I loved it and was a loyal worker. Read more>>

Johnny Przybylek

I think most business owners would agree that your emotions are like a roller coaster when it comes to owning your own business. Some days you are so happy that you work for yourself, that you are finally doing what you love to do. Other days you contemplate if its worth it. Are you going to be successful? should I quit all of this hard work and take a nice salary job and have the comfort and predictability of a weekly salary. Read more>>

Kasey Luft

I have this thought every day! If I’m not second guessing myself daily, am I even doing it right?! I’m joking… but there is some truth to that. I believe all entrepreneurs face some sort of existential question on a daily basis. It’s the ability to continue pushing through when the going get’s tough. As an employee you don’t have to worry so much about the things an owner does. An employee can take time off on holidays, vacation, sick days, mental health days. Read more>>

Mel Carroll

I am asked often if I am happy being my own boss / if I miss having a “regular job” and my answer is “yes and no, respectively” – please allow me to elaborate. The “not-so regular jobs” that I have been so very fortunate to have had gave me the valuable knowledge and experience I needed to launch Total Asylem Marketing & PR in 2008. Read more>>

Sophie Nelson-Crouse

Yes, I am ecstatic about being a business owner. I don’t see myself working a regular job after being self-employed for the last few years. It’s mostly because I enjoy the flexibility of having more free time to enjoy my hobbies. The last time I worked a regular job was before I took an educational leave. Upon finishing my law studies abroad I came back to Canada and delve right into entrepreneurial mode. Read more>>

Helen Hồng Nguyen

Since my parents fled the Vietnam War as refugees, the responsibility of building generational wealth falls on me. While a regular 9-5 job offers stability, it doesn’t provide the financial freedom I aspire to create for my family. Witnessing my mother’s ownership of a nail salon during my upbringing instilled an entrepreneurial mindset in me from a young age. Read more>>