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.
Shayla Burtin
I spent 15 years in the corporate world, feeling constantly stressed out, overworked, and underappreciated. It was during this time that I decided to take a leap of faith and venture out on my own as an entrepreneur. I reached a breaking point where I realized that if I was going to put in so much effort and dedication, it should be towards building my own company instead of working for someone else’s success. Read more>>
Jasmen Rogers
There is nothing like having the freedom over your time as a business owner. And with that heavy privilege comes the hustle to find and retain reliable clients, level up your skills, maintain your administrative tasks, develop consistency, and so much more. Read more>>
Marko Ramirez-Pursley
I LOVE being a business owner and I won’t ever work for anyone else if I can avoid it at all. I’ve definitely thought about how much less stressful my life would be if I could just clock out and leave work at work, especially when something unexpected challenge happens with my business. Read more>>
Josh Funk
For me, being happy running my own business meant finding balance. When you start a business, there is an initial happiness and excitement that comes with the ideas you had in your head coming to fruition, but that slowly starts to be replaced by stress. The stress of all the documentation, marketing, events, and gathering of needed resources and tools can start to overtake the happy feeling of being a new business owner. You start to worry about the longevity of the enterprise, if it really was a good idea in the beginning, or you start to change and adapt the original idea to something that you think might work better, or be more profitable, which decreases the happiness even further. In my own story, I started to realize I was buying less art, and more trinkets that were affordable and seem to sell the most at local events. Read more>>
Miranda Jayde (MJ) Anderson
The process of starting up, growing and maintaining a business has been challenging – a challenge I am definitely still in the midst of! I definitely did not know what I was getting myself into. I have certainly had the exact thought of “dang, it feels like it would be a lot simpler if I had someone else just telling me what to do”. One of the challenges of being a business owner is, simply put, responsibility. Something I’ve been faced with is that the main person holding me accountable is me, which requires a good deal of motivation. Read more>>
Destiney Lynn
I absolutely love what I do! I really enjoy being able to wake up everyday & work my own hours & make my own schedule. Especially this past year, being a new mom & small business owner. The thought of having to balance a regular 9-5 & motherhood scared me! It didn’t seem possible! I am thankful I was able to navigate motherhood as I built my business to what it is today! Shout out to all the hard working mothers! Read more>>
Marissa King
I honestly have never been happier in my career, but every so often I’ll get that feeling of being so overwhelmed and almost like I’m drowning in my responsibilities and wonder what it would be like to do something else…. And every single time I think there’s literally nothing else I could see myself doing. This is what I was born to do and I get so much joy out of making people feel good and looking good :) Read more>>
Dave Moore
I had a “regular job” in corporate leadership for 17 years. I did well for myself and my family, and at times I felt like I was even making an impact and doing something important. A part of the greater good. I also often felt like I didn’t fit in there, and that the effort I was putting forth was only to serve something that didn’t really provide reciprocal appreciation. I felt hollow at times, and given the direction the company was headed, it was clear that any future I had, and anything I had to offer, was largely going to go overlooked while I was being asked for more every day by the company. Work/life balance was almost non-existent. Read more>>
Miranda McIntire
I love owning my own business! There is no other way I would have been able to raise my kids right here with me every step of the way. They have been able to play, learn, and paint in my shop their whole lives. It has been very beneficial as a single mom. Most of my employees have been wonderful to help me with them if needed and I have been able to take off to be at their events, sick days or for appointments. There was a time before the wholesale line started that I thought I needed to be using my college degree to make better money and was looking at applying for an Extension Agent position. I was divorced, left with a lot of debt, no child support and two little girls to care for on my own. While applying, I realized how much I would have to be away from my kids at stock shows and other events. This would not be easy having to rely on family to keep the girls for such long time spans. So, I ended up sticking it out, working long hours to establish the wholesale line and thankfully things took off from there! Read more>>
Denise Thompson
I think being a business owner I have the freedom to make important decisions and have control over my work, which can contribute to my sense of fulfillment, satisfaction, Passion and my purpose, many business owners start their own ventures based on their passions and interests. For me Being able to work on something I love can lead me to a higher level of happiness, I also think having a Successful business can provide financial rewards that may exceed more than having a job. Read more>>
Jessica Kuehn
Yes, I’m definitely happier as a business owner. Not every day, necessarily, but overall I’m MUCH happier and more fulfilled than I was at any of my previous jobs. Sometimes I want to go back to a “regular” job where I’d get a steady paycheck, but I know it wouldn’t fulfill me nearly as much as what I do now. I do occasionally miss the stability and cycles of getting paid and knowing what’s expected of you from other jobs because there is so much pressure to be your own boss and in charge of your own business…but I’m done with other people telling me when to work and how much I’ll get paid. I started my business at the end of 2019, and I quit my old job and went full-time with my business in November 2022. I worked in retail at the time, and I did not want to spend another holiday season working countless hours with minimum appreciation at work. Working for myself full-time is so much more difficult with a lot more hard work than I expected, but because of that I’ve grown more in the past eight months than I have in a few years. So while every day is certainly not sunshine and rainbows, I’m so much happier, more content and more fulfilled with my life. I know my value (and my values!) and I don’t have to worry about other other people trying to compromise those to hit the bottom line for a major (or minor) corporation anymore. Read more>>
Gabby Torres
Before starting my business, I had never dreamt of being a business owner or even a photographer. It wasn’t even an idea in my head, so having a successful business and working full time as a photographer definitely feels surreal to me. My family and I came here from Brazil when I was still in elementary school for better opportunities. I was told I needed to go to college and get a good job, so that’s what I dreamt of. I fantasized about working at an office and wearing business attire and most importantly making my mom proud. I ended up going to college in the city (Boston), which was something else I dreamt about and graduating with a public relations degree. I soon started working at a marketing company and it seemed that everything I was fantasizing about came true. The only thing is I absolutely dreaded going to work. I’ve worked my whole life in restaurants and I’ve always been able to keep a job, so working hard has never been an issue. The problem was that I didn’t love what I was doing and I was honestly sick of working for someone else. So I quit. Read more>>
Kaylyn Rogers
I am definitely happier as a business owner. I would not change my career path. I have always had a passion to help others. Previously I worked in property management. I excelled in my position however I tended to grow bored easily. I reached the top job title, and pay. I weighed the beinifits of my job against being a business owner and I decided it was more important to me to spend my time building a business than just being a good employee. Read more>>
Jimmy Gomes
Being a business owner has truly brought a newfound happiness into my life. The journey of entrepreneurship, with all its ups and downs, has filled me with a sense of fulfillment and freedom that I never experienced before. Read more>>
Amanda Barrett
I’ve had both and can confidently say that YES, I am truly happier as a business owner. There are some great benefits to having a corporate career, and I grew up thinking I’d always climb that ladder, but I am so grateful for the opportunity to step away from that, and build something that is for my family. I’m happy to have the freedom to build it how I want, and not have to worry about the corporate structure. On the flipside, I’m truly grateful for the career I had, and I do think it’s led me to be a better business owner. I am a toddler mom, and I’m hyper-aware of how fast time is flying by, so for our family – having my business is 100% the right move for us. There are times I briefly wonder if I should go back, but I’m very quickly reminded of the freedom that allows me to focus so much on my baby while she’s still “a baby.” Read more>>
Jason Cellars
I have found that happiness as a business owner comes down to balance. There are many days when I wish I could clock out at the end of the day and spend an entire weekend not thinking about the office. Especially with so many people working flexible hours from home, However, I know that, for me, I would soon envy the business owner and entrepreneur more and want to be back on that side. I love the visionary thinking that I am able to do as a business owner and I love that my success is directly related to what I do. Read more>>
Taylor Gorman
I think being self employed can definitely be a double-edged sword, for me anyways. I have been my own boss since 2016, and sometimes I feel like I’m the worst boss I’ve ever had. Read more>>
Shunta Grant
I am happier as a business owner not simply because I am a business owner but because of what being the owner of my time has done for me and my life. I set my work hours, I am able to plan my days and decide what will fill it. Yes there are team meetings, client work, work to do, but all of that is planned and accounted for after the things that matter more than work–space for me to rest, think, write, and take care of the requirements in this season of life. Read more>>
Allie Kuppenbender
I love the flexibility of being my own boss and I genuinely love the work of farming and the creative outlet of floral design. But I’m also often working ridiculously long hours and running myself ragged to stay on top of the seemingly never ending work load during the growing season. It also doesn’t help that we live where I farm so its hard to turn the “work” side of my brain off when I’m supposed to be relaxing at home. And on the flip side, things grind to a halt on the farm in the Minnesota winters so it’s definitely a balancing act making sure you’ve made enough money to get through the winters when there isn’t a lot of cash flow. I’m constantly thinking about sustainability in terms of agricultural practices, but I’ve also began to broaden that definition of sustainability to include the question “is this a sustainable work load for one person mentally and physically?” I’ve definitely made changes over the years–turning down weddings that I don’t feel excited about, hiring people to help with field work and harvesting, focusing on big ticket wholesale clients vs one-off retail sales. All that being said, I genuinely do not think I could have a regular 9-5 office job. I like being outside too much and I do enjoy the cyclical nature of farming; the lull in the winter is what makes me so excited for spring every year! (Also maybe this was a cynical time to answer this question–all farmers get major burn out come July!) Read more>>
Alyssa Hunter
Running a business is incredibly tough and a 25/8 job. I also work by myself so when I’m having a bad day, my whole business is having a bad day. Right now I’m not outsourcing anything so I’m the owner, photographer, editor, social media manager, IT support, etc. It makes it hard to balance my work life and social life. That’s probably the toughest for me. If I’m not actively working, I’m not making money. It makes it harder to have office hours and put my computer away so that I’m present for my own life. Read more>>
Danielle Baselice-King
Honestly, I’ll never regret my experience and hardwork that was put into creating my small business and learning this craft and art. You see these posts that say something along the lines of “I didn’t want to work a 9-5 job, so now I work 24/7!” It’s absolutely true. It takes absolute commitment and passion. Trying to manage consistency as a mom of very young children, a business owner and a wife isn’t a piece of cake. Trying to get your name and brand out there doesn’t come easy. But when you get even just ONE customer who shares their story of how much your products have helped them.. it really flips a switch sometimes in the best possible way. It’s the best feeling in this line of work, and I’ll never wish differently. I’ve realized if I’m not doing what I love as a career, I’ll always be missing something. Read more>>
Allison Yang
I am truly grateful that I chose to become a business owner. However, I am also aware that what people see as the end result is only 10% of the entire workload of an owner. Why do I say this? I believe that every person who chooses to be an owner carefully envisions their business before starting. Setting goals and ensuring action is taken is a part of the work that others cannot see, but it requires a significant amount of time and energy. What people see is the outcome, but what the executor sees is the entire picture. In my experience, good owners care about the details, and time management. Read more>>
Macee Binns
Before answering this question, I went back and read an old blog post that I wrote in 2016, while I was working a “regular job” at a film school in Los Angeles. Despite the fact that I physically needed this desk job in order to buy boxed Kraft Mac and Cheese and survive, I was apparently willing to risk my livelihood just to share with the world some creative ways I came up with to kill time at work and prevent me from stabbing myself with a ballpoint pen out of sheer boredom. Read more>>
Kirk Hutchinson
Being a business owner comes with a lot of emotions. It’s a constant roller coaster of big wins and anxious lows. I occasionally think about what it would be like to go back to working for someone else. It doesn’t happen often that I have that thought, but the anxiety of knowing everyone and every part of the business relies on you can really make you feel overwhelmed and want to toss all your hard work away sometimes. Read more>>
Lorenzo Jackson II
I’m extremely happy as a business owner. You cannot put a price tag on the freedom it allows me to have. I took the entrepreneur route directly out of college. So I’ve been freelance for almost 20 years now. Though there was a time in 2014/15 where business wasn’t going so great. I got tired of penny pinching and not knowing who my next client might be or more importantly, when would the next check come. I was behind on bills and I just felt am immense pressure to relieve myself of the burden. So I put my resume on Indeed and was contacted shortly thereafter by a company in Indiana. They were looking for a photographer/videographer/designer. I told them I could do the first two jobs, the third I could manage, but it was not my strongest attribute. They assured me that graphic design would be a very small part of my job. So I took the job and 90% of the work they had me doing was graphic design. I only stayed two weeks. That short stint as an employee reminded my of why I wanted to go the independent route in the first place, even it if meant continuing to struggle. It turns out, that may have been the final test in my resolve because three months later my phone began ringing non stop. And it hasn’t stopped since. Read more>>
Jing Feng
I think about this very frequently, and in many ways the tension between being a business owner and being employed by someone else (whether it’s in a creative field or not) holds a significant presence in my everyday life. Operating, and being able to be creative within a business, has brought a great deal of joy, meaning, and fulfillment to my life. Harlot Hands started in the beginning of my junior year as a fine art major in college. At the time I was filled with fear and uncertainty about my future, and wasn’t sure about the avenue best suited for me in the creative industry. I never imagined that I would start a business, and I had little to no idea of how to navigate it. I feel so grateful that it has come this far, and it has brought so much to my life: familiarity and confidence about what I want to make, communities to be a part of, opportunities to challenge myself and learn (both creatively and logistically), a way to turn what I love into what I do for a living, self-growth, agency, and much more. It was a miracle to me, this thing that allowed me to express myself and engage myself with my interests, ideas, and sensibilities in art and fashion. And to think, people being interested in and allowing me to continue to share the things I make, that changed my life in so many ways! But there are also great lengths of difficulty and conflict in terms of stability, mobility, and freedom. It’s a strange phenomenon, the emergence of creative social media-spurred businesses. The commercial nature clashes heavily with the creative aspect, and it can be isolating and all consuming. Configuring an appropriate framework of a sustainable business model, healthy work/life separation, models of algorithmic marketing, building and nurturing networks, administrative procedures—these are just some of the growing list of things we’ve just needed to learn as we go. Basically— learning a specific business-language of your own to fit into the industry of things. Read more>>
Lola Adewuya
Up until a few months ago, I have always run my branding business alongside another full-time role. First it was college. After I graduated, I continued to run my business while starting a full time job in tech. In January of this year, I was laid off from my corporate job and decided to take it as an opportunity to pursue entrepreneurship full-time. 6 months in, I can confidently say that I am happier as a business owner. Running a business comes with many ups and downs and challenges. It isn’t always a blast, but I knew that this path was right for me when those challenges still felt rewarding and motivating. Read more>>