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.

Michelle Brown

As a business owner, I have the privilege of having autonomy over what I produce, package and provide to my clients. This independence has cultivated a level of happiness that I have never experienced while working a regular. Every time a thought of working a regular job enters my mind I become overwhelmed with the feeling of anxiety and imprisonment. The knowledge of how I would lose my freedom over the way I administered services to my clients if I worked for another frighten me. I use this fear to fuel my desire to scale my business so I can continue to provide the quality of services my clients need and deserve. Read more>>

Elena Kazas

I am a happy business owner because I am pursuing something that I have a passion for. Being a college student, from time to time, the thought of having a “regular job” crosses my mind, especially when talking to my peers about internships and job offers that they get. Hearing about the companies they work for and all the things that their daily tasks seem great, especially for what they want to do. It also seems refreshing at times to leave everything at work between the hours of 9-5 and not essentially have your work cap on all day every day. But, with those things being said, I would still never want to work any of the normal jobs they have because they have nothing to do with what I’m PASSIONATE about. Yes, all the jobs/internships they have pertain to their related field of study in business, but just because I am a Marketing major doesn’t mean I want to take a Marketing job at any company. Read more>>

Asha & Cordarrius Pitts

Asha- As tough as this business can get, I can honestly say that I am happier as a business owner. I finally wholeheartedly enjoy what I do. I do believe that everyone is not meant to be an entrepreneur, but I can boldly say that being a business owner was meant for me. Read more>>

Antionett Beck-Doss

Absolutely I am happier being a business owner. In the beginning I did think about going back to my 9-5. It was very difficult wearing all the hats and being accessible to my clients. However I knew that wasn’t my plan or purpose working a 9-5. Being a business owner often provides a greater degree of autonomy and control over your work. You have the freedom to make decisions, set your own schedule, and shape the direction of your business. This level of independence can be rewarding i value my entrepreneurial spirit and the ability to create something on my own. Read more>>

Hannah King

Let me start by emphasizing that I am genuinely content and fulfilled as a business owner. The entrepreneurial journey has been immensely rewarding for me, filled with exciting challenges and significant personal growth. However, occasionally, I find myself wondering what it might be like to have a regular job, one with its own set of benefits. Read more>>

Collin Strachan

This has been a pretty consistent question for me over the past couple of years. The answer, simply, is yes. I am content with my decision to be a business owner, but it wouldn’t be fair to see that’s the reason I’m happy or unhappy at any given moment. Read more>>

Lane and Lani Bidlack

Both of us come from working above and beyond normal business hours in our typical 9-to-5 careers. Lani went from store manager to sales rep over the course of 15 or so years, and before Lane exited his service to the fitness industry, he had worked countless jobs trading his time for money. Since starting “life and hours on her own terms,” Lani has reflected about how poorly her old boss had treated her over the course of her career with him, as well thought back on the endless days of travel, the anxiety of meeting new people and hoping for new business, and the hours spent taking care of clients after her day was “supposed” to be through. For her, there was no going back! That determination has sprung her into snowballing her successful, franchised Party business- PartydreamsToledo, as well as her creativity, into the avalanche that it has become now. Read more>>

Mallory Cardillo

rowing up, I never saw myself happily working for someone else. I also never saw myself as a business-woman. When I realized that photographing weddings was my life’s purpose, I had to accept that in order to legitimize myself, I had to start a business and do it the right way. (As in, I had to pay taxes.) Now that I have been in business for 5 years, I cannot imagine doing anything else. Sure, there have been times where I have thought that working for someone else, receiving benefits such as health insurance, PTO, etc. would be nice. There has absolutely been times where I have had to take accountability for my mess ups, and have let people down. Read more>>

Katie Grimes

The last time I thought about going back to a 9-5 job was when my income dropped to less than $5,000/month and I had to ask my landlord if I could pay my rent in a month. I was embarrassed that not only did I have to ask, but I had to work a part-time job just to make sure I could pay my bills. I decided to show up at that part-time job (at a laundry mat) as if it was my business. I showed up early, I asked questions when I didn’t know the answers and always had a smile on my face. Even that time a friend walked in and was like “are you working here?” (in that tone of voice that she was as surprised as I was). Read more>>

Casey Benczo

As a business owner who has had regular jobs in the past, I’d say there are pros and cons to both paths. My experience as a business owner is unique, being that I’m in a heavily stigmatized industry (cannabis), where we’re very limited in our ability to get funding, advertise, post on social media without getting banned, etc. From day 1, I ran into obstacle after obstacle. From finding a physical space to contract issues with a previous partner, I’ve been tested to see if this is something I really wanted. Some days it was, and other days it was really hard to keep going. Everyone talks about having a dream and taking the steps to make that dream come true. Not many people will discuss what it’s like to make that dream a reality, only to realize that maybe it’s not what you want after all. Read more>>

Nicole Uthmann

I grew up in a family where my parents held regular weekday 9-5 jobs. Our weekends were reserved for family activities, took family vacations every summer, and holidays were carefully planned with extended family gatherings. However, when I married into a ranching family, I rapidly became aware of the stark differences. In agriculture, it’s not merely a job; it’s a way of life. The traditional concepts of weekends, holidays, and paid time off vanish. Animals require daily care, unexpected challenges become routine, and we feel like we are always one breakdown from financial ruin. Additionally, the weight of being self-employed, with both employees and family dependent on the financial success of the business, can lead to many sleepless nights. Read more>>

Ariel Bonkoski

I am extremely happy as a business owner. Prior to and during the first couple years of business, I was still managing a retail store full time. I worked for a great company! But that’s not where my passions were. Starting my business was my way to make my life more fulfilling and make my passions into my career. I am SO glad I made the leap into starting my business. I am also glad that I stayed at my retail management job while I started my business even though it was extremely difficult. I was working 70 hours a week some weeks, but it allowed me to save a lot of money to further my business. Read more>>

Sara Rutten

As a business owner we always have the days where we wonder or desire the “ease” of a regular job. Then I remember that I used to have that “regular corporate job” and I lost myself in the grind of that world. On cold winter days when everyone else (or it feels like everyone else in the world) is warm and safe in their house not worrying about animals being cold, frozen water, needing feed, needing new bedding; those are the days I wish I had a “normal” job. Read more>>

Chelsea Husum

Being an entrepreneur definitely is not for the faint of heart, let’s be honest. You literally have everything on the line: your home, everything you personally own. It can be pretty crazy to think about. But for me, I absolutely adore this company that I’ve built and am so grateful that I am my own boss and I own my time. There is no way I could ever go back to working a “regular” job or working for someone else. As a business owner, you’re pretty much constantly working in one way or another, but you also can create the flexibility you need at times. Read more>>

Stephenie Boys

I love being a business owner! It allows me to set my own schedule and be present for my kids activities as well! I do sometimes think about having a ‘regular job’, but quickly remember my distaste for answering to a boss, going in when I don’t feel like it, and the rigid schedule etc, whereas now I can work as many or as few hours as the demand calls for and take as many breaks for as long as I’d like! Read more>>

Brian Kearney

I think about this all the time! I’m continuously asking myself, “Is it worth it”? Half the year I’m on one side of this fence and the other half of the year, I’m on the other side. Back and forth all the time. Currently, I am leaning toward being happy as a business owner, but I know January and February will come around and I’ll be on Indeed… Again! Recently, I took the reins back and let go of my entire staff. I only had one high school student left on payroll, but I decided to let her go. I’m the only one here now, like it was when I first opened in 2018. Read more>>

Neaisha Seawright

Yes, I am so much more happier. I love the freedom that comes with being able to make my own schedule. I’ll admit days I miss having a “regular” job but it’s always short lived. I usually feel that way on my slow weeks, it can be hard navigating through those times of uncertainty. Whenever I have those moments I just write out the pros and cons of working for myself versus someone else and honestly it’s just never that serious. Ha! Read more>>

Juan Esguerra

Entrepreneurship versus a 9-to-5—an eternal dilemma! Picture this: I’m at my desk, juggling a gazillion tasks, and suddenly, the thought hits me—what if I just packed it all in, traded this chaos for a cushy job, and clocked out at 5? Wouldn’t that be the dream? Running my own business is like riding a rollercoaster with no seatbelts. There are moments of sheer thrill, but yes, there are also times when I contemplate the serene simplicity of a regular job. Just the thought of closing my laptop and vanishing from the digital world, even if just for a weekend, sounds like a dream. Read more>>

Caroline Arendt

All the time, especially when it comes to bookkeeping. Ha! But really, I’m an oldest child and a rule follower. I never saw myself being self-employed because going to college and getting on a career path with an established company was all we were ever taught in school. Grow up, go to the career fair and get a job, rinse and repeat. Self employment was a big no-no. I’m glad I’ve had experience working in both situations, for agencies and for myself. Read more>>

Angelina Dobbins

I am definitively happier as a business owner. I have and still do wonder what it would be like if I were to go down a different career path or work a “normal job.” When I’ve been discouraged, or business wasn’t doing as well as I’d hoped, I wondered if I made a mistake. But the moment I try to actually picture myself doing something else, I can’t. I am passionate about skincare and helping people with their individual skin journey. I know being an esthetician and business owner is my purpose, and I will continue to follow it! Read more>>

Maureen Zappala

I spent almost 14 years as an engineer with NASA, conducting jet engine research, and I LOVED it. My childhood dream was to be an engineer, and it was my focus all throughout my school years, all the way through college. I loved the gritty test facility environment, the smell of aircraft engine fuels, and the technology we were developing. I loved the teamwork, the camaraderie, and the feeling we were on the edge of fascinating groundbreaking developments. Read more>>

Drew Tilton

Honestly, I feel draw of a “regular” job all the time. I think it is more the imagined ease of such work that tantalizes me. I imagine myself swimming in endless healthcare—with no co-pays and a deductible as low as that old Lil Jon song. I dream of a pay check that you know is coming—and it is the same amount no matter what! Imagine that! Life would be easy, breezy, beautiful (and the readers say in unison: “Cover Girl”). Read more>>

Lindsey McClafferty

I could not imagine doing anything else than I am doing right now! Being a business owner is for sure stressful, I wont lie but there is also no greater reward than being a business owner. My company is made to empower women and when I get to see that come to life there is literally nothing better. On the outside it’s just lashes, all she does is sell lashes what is the big deal? But on the inside I see how my lashes instantly transform a women’s confidence within seconds. On the other note being a business owner brings so much freedom, I no longer have to ask to go to one of my children’s school events or a vacation I can just go and freedom is amazing. I encourage anyone thinking of starting a business to just go for it, there is no better time than the present time to chase life. Read more>>

Leah Patrick

I have been working as a coach since 2013. I didn’t start out immediately as my own boss. I worked for one of the major gyms for seven years before I started my own business. My time there was really wonderful as I was able to grow my skills as a trainer, learn about the industry, and how to effectively manage my clientele. I also met tons of wonderful people and created life long friendships. My time there was really wonderful in many ways but, like every job, there were pros and cons. The tough part was they always wanted more. I was always pushing myself to hit hours or sales targets designed by the corporation so I could be considered a top coach. Read more>>