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.

Erica Catherine Fulp

Being an artist and owning your own business is never without bumps in the road. You have the distinct challenge of not only making every decision for your business but also making sure you feel grounded in your choices for your creative work. After all, that is the heart and soul of your business. I ran my business part time alongside other jobs for a few years when I first started. It was a nice way to develop my business without the major pressure of having to have it succeed. Read more>>

Shanika Issac

The short answer is YES. Despite the financial stress, general difficulty of running your own business, and long hours, I am happier as a business owner. Before the pandemic, I worked as a Sous Chef for Marriott Hotels. It was a great experience, but what I saw lacking in the workforce was a work-life balance. As a small business owner I have more time to spend with my family. I work fewer than 40 hours a week and can take at least four weeks of vacation. I flourish alongside my business, take pride in my work, and the company’s success is immensely satisfying. Read more>>

Savannah Toal

I do think I am happier as a business owner, but there’s definitely moments where that’s not the case. I actually had that thought the other day about what if I just had my old job. I think the thought came up because I am going through some changes and making some big decisions. It’s sometimes lonely owning a business especially when it’s just you or a small team. You have to make the big decisions and that’s daunting sometimes. When I get into new things or projects/situations, I doubt myself. Read more>>

Handmade Cabinets LLC

This is the first time in our lives that we are business owners, so we have already been into the “9-5” world, plus we also went through the hospitality schedule which is more nights and weekends. All of them have advantages and disadvantages. The 9-5 jobs free you during the nights and weekends, so you could have more social activities if your families and friends also have that similar schedule, but the disadvantages are that you need to request a day off if you need to go to the doctor or run some errands that can only be done during weekdays. Read more>>

Chalcia Nicholas

Am i happier as a business owner? Absolutely! I love it here lol. & i do sometimes think about what it would be like to have a regular job & it’s a no for me. Been there, tried that, didn’t like it. 0/10! I am my happiest when I’m doing exactly what i want to do, on my time and on my terms. Making my own hours, setting my own schedule and being my own boss has also done wonders for my mental health. Doing what i enjoy for a living, successfully is as gratifying as it sounds. Read more>>

Temi Coker

As a business owner I am for sure happier but it’s sometimes seasonal. When you own your business you’re in charge of paying your business taxes, insurance etc. When you work full time the taxes are taken out so it doesn’t “hurt” as much cause your paycheck is after taxes. As a business owner I save about 30% of every payment into a tax category so i’m prepare for tax season. The number vary based on your location, how much your business is bringing in etc. Read more>>

Maegan Jackson

I absolutely love being a business owner and “being my own boss”. I love the freedom and flexibility it allows me and all the wonderful opportunities and doors it has opened. However , I would be lying if I said it never crossed my mind to go back to having a “regular” job. No one prepares you or warns you of what owning a business is really like, although it’ has a lot of perks to it I feel it is over glorified in todays world. They don’t warn you of really no days off , no paid vacations , sick time , someone offsetting the cost of health insurance and other insurance , 401 k and other benefits you can get from an employer. Read more>>

Anna H.

Honestly, anything I aspire to do takes consistency, time, patience, and simply believing in myself. I am beyond happy as a business owner, but often people do not realize that sometimes you have to sacrifice your time for your business to grow, and it’s not always an overnight success. I am learning to embrace the challenges and milestones of being a business owner. It’s rewarding and draining, but it’s molding me to become more polished as a business owner. Read more>>

Hannah Korte

The short answer, yes! I am extremely happy doing what I do, but I do wonder if having a regular job might be easier. I often get overwhelmed as a business owner, and I often think it would just be easier to work for someone else so I can clock out at 5pm and not think about anything until the next day. However, any other time I have had a “regular job” all I can think about is how much I would rather have my camera in my hand, photographing life’s milestone and being in the studio. For me, there is no other feeling like it. Read more>>

Desiree Hawkins

This is actually a great question. Recently, I can say I’ve had my doubts. I have questioned if this is really for me and if I’m just chasing this impossible dream. I let the thought linger in my mind for about a week. I even talked to my boyfriend about it. One thing that stuck with me and kept me going was, how hard I worked to get here. Having your own business isn’t easy. Especially me being the only one in my family that is a beauty entrepreneur. If this is truly something that was not for me, everything else would have worked out the way it should have. Read more>>

Ella Andre’

That is a heavy question. There are times when I wanted to give up completely. Being an entrepreneur is hard and it keeps you up at night, Just this past weekend I was having second thoughts of whether all the sacrifices were worth it. There are times when business is so slow that the money made is just to buy more supplies for your inventory, I handle every aspect of my business, so I know how much is spent and how much is made every month. Read more>>

Patience Brunson

Becoming my own boss was the best decision I ever made, I have had doubts at times on whether or not I should follow what my parents think.. and also what society typically considers is the successful path (go to college, get a good job, work until your 65) but the universe always had a way of simply showing this is not my route. I was in school for surgical technologies, and everyday I went into the hospital for clinicals I realized more and more how much a lot of people may not be necessarily happy with their chosen career path .. seeing frowned faces .. annoyed gestures .. tensity, was not my thing. Read more>>

Zenobia Taylor-Weiss

Running the business that I started has by far been my most rewarding job experience to date. I’ve found that I really thrive in creating my own goals and keeping myself accountable. I love dreaming about new directions in which to take the business. I do occasionally wonder what would happen if for some reason my business didn’t exist anymore and I had to get a “regular job”. I’m sure I could handle it, since I have before, but it would definitely be an adjustment for me! Read more>>

Carol Gavhane

I think about what it’d be like to have a regular job all the time! I recently chaperoned my child on a field trip and my first thoughts were “I am so lucky to be here sharing this time with my kid right now” while also thinking “There is so much I need to get done today.” While I do work a lot these days (after the kids have long gone to bed), there is really nothing like owning every aspect of the business. Read more>>

Tiara Robinson

I’m very happy as a business owner but I would be lying if I said it doesn’t become overwhelming and stressful. There’s time where I really want to give up and say let me just do the corporate for life but there’s just something inside of me that keeps on going. I actually have a corporate job at the moment and it’s helping me learn valuable skills such as time management, following up, being organized and just being proactive. I’m taking these skills and applying them to my business. So yeah having a corporate job isn’t ideal, however I’m changing my mindset and figuring out how this job can work for me and my business. Read more>>

Nick Bowie

I would have to say yeah I am happier, but it’s like a I’m happier I tried rather than just said “nah don’t think I can cut it” and never tried at all type situation. I’ve always had a 9 to 5 even when I was just doing music. Like Idk what Dame Dash was talking about, trying to make a living off of something you love to do while being your own boss is not cheap. So unless you really willing to get out there and lose 92 bricks having a “ Regular Job” is more than necessary. Read more>>

Wendy Myers

I am so happy being a business owner. I really can’t imagine doing anything else. I love that I am in control of my business and can make decisions that I feel are necessary for growth or change. Being able to make changes and having the flexibility to move in different direction or explore new avenues for my business is really exciting. Being able to try new products lines, explore social avenues or expand online has been a key driver in growing my business. Read more>>

Tino Flowers

I am happy as a business owner. Although there will always be ups and downs, I enjoy what I do because I am free to do it. I know that as an adult I need to work in order to provide for myself. I can work for myself or work for someone but I definitely need to work. I sometimes think about having a regular job when the business gets stressful. I remember a time when I needed a business loan but the banks were saying they wouldn’t do it unless I had a job. I got a full time job to get the loan but it made me miss out on time growing the business. Read more>>

Sam (Shena) Smith

Becoming a business owner was one of the scariest but necessary decisions I’ve made. Choosing to forgo a consistent stream of income to “follow a dream” was a foreign concept. There were absolutely moments of fear, doubt and loneliness, however, allowing myself the space to fail (fast) and learn faster helped me rediscover confidence in this new space. Read more>>

sydnie pettingill

I am very happy being self employed. I can be more flexible with hours (to an extent) , I can choose which jobs I take and which ones I don’t. I choose how much I get paid and best of all, I get to work from home most days! The downsides are that I don’t always have a consistent paycheck or consistent hours. Working on a wedding day calls for long hours, travel (sometimes for 2-6 hours round trip), Read more>>

Tasha Thurmond Carlie Beran

The simple answer is — YES! We love being business owners and have been truly blessed to have our dreams become a reality. We would be lying if we didn’t think about having a regular job, when things become stressful. Owning a business comes with major responsibility. Particularly during the onset of Covid-19 in the US, it definitely would of been easier to simply be an employee. As an employee neither of us would of had to carry the weight of making sure each person in our company was okay financially, and most importantly had a job to come back to. Read more>>

Christian Baylis

I believe I am way happier running a non-profit. I worked in churches and regular jobs, which never seemed to fulfill me the way doing my own thing has. I mean that running a non-profit is my calling and what I know I was created to do. Read more>>

Ruthie Skillman

I’m definitely happier as a business owner. That’s not to say it’s easy. I didn’t realize I’d be working more hours, but every business owner knows that it’s hard NOT to work when you’re running a business. We don’t get to clock in, leave work at work, and clock out. I have to know everything about the business–the accounting, the advertising/marketing, the art itself, client relations, etc. It’s all on me. Sometimes I do think it would be great to work for someone else, so I could just show up, do my job and go home. But having a business is truly like being on a roller coaster. Read more>>

Meghan Brodie

I am definitely happier as a business owner than I was when I had a “real” job. Prior to starting my organizing business, I was an elementary school teacher for six years in Atlanta, Charlottesville, VA and finally Richmond, VA. While I was a passionate teacher and thought I would be a lifer, my personal life changed and caused me to reevaluate my career. My pregnancy with our first child put me on bed rest for four months, partially in the hospital. Read more>>

Beryl Hudson

I am extremely happy as a business owner. This is something that I have wanted to do my whole life. I am the definition of a true entrepeneur, in that I started several businesses before I found the place where I actually needed to be. I have worked for other business owners and always had the feeling that this was not the avenue for me. I am a true entrepeneur.. I worked for several years in the social security industry, and all the time I was working I knew that as soon as I learned enough to go out on my own I would do so. Read more>>

Matthew Belcher

I love being a business owner! I feel that entrepreneurship takes a certain type of person. If someone goes into business ownership and is not fully committed, majority of the time, that business will not survive. You must be fully committed and willing to fight your way out of the struggles and hard times that come along with entrepreneurship. The best way I like to use as an example would be jumping off a cliff and building a plane on the way down. If you have in the back of your mind that you will simply go get a job when the times get tough, you’ve already failed. Getting a job is the easy way out. Read more>>

Bria Stifter

There are so many perks to being your own boss and running your own business. I love that I have control over my own schedule, and how I build my brand that sets me apart from the rest, but there are also a lot of struggles, and learning curves to starting your own business. I always knew I wanted to take the private chef career route out of culinary school, but I have never imagined that I would be where I am today. I developing this dream in Minnesota in 2015 with a friend of my that I met while working at a restaurant through culinary school. Read more>>