What even is a “regular” job? Semantics aside, the heart of our question is about those moments when the stress of entrepreneurship is mounting – do you ever sit back and wonder what if you had just been working for someone else, what life would have been like without all the stress?

Tyler Taylor

I am happy that I own a business. However, I believe that to be a great business owner, you need experience outside of your business that you can apply to it. Often, we become fixated on seeking more money, constantly having creative ideas to share with the world, and desiring freedom from a strict “normal job” schedule. But being a business owner is quite the opposite. In my personal life, I’ve worked for top luxury brands such as Chanel, Loro Piana, and DVF, as well as small businesses. Being a part of these brands has allowed me to apply standard protocols, selling ceremony techniques, marketing strategies, and elevate my communication when conducting business with TAYLOR TYLER. Read more>>

Dara Walker

I am incredibly grateful for the decision I made to pursue my dream of being a business owner. Although there have been moments of doubt and uncertainty, especially during times of stress, when the thought of working for someone else seems more convenient and stable, I quickly realize that it is my passion and determination that drive me forward. Starting a business comes with its own set of challenges, especially in fulfilling all the roles required for a business to function. The uncertainties and the feeling of building something blindly can be overwhelming at times, making the thought of working for someone else temporarily comforting. However, this thought does not linger for long, as I am reminded of the fulfillment and the sense of purpose that comes with guiding myself and pursuing my own vision. The ability to make decisions and create something of my own is a dream I held since a young age, and I am committed to making it a reality. Read more>>

Andrea Levine

I am incredibly happy as a business owner. I’m the kind of person who needs to be in control and set my own rules. I had a “real job” as an intern when I was in college, and I absolutely hated it. I was constantly pushing boundaries, creating my own projects, and challenging my boss! As a musician, I’m used to a non-traditional schedule, so starting my own business was a natural transition. Occasionally, I do wonder what it would be like to have a traditional 9-to-5 job—especially after working non-stop for a month or facing a particularly stressful challenge. But the moment I picture myself commuting to an office every day, I feel immediately restricted. I love being the visionary, setting the rules, and having the freedom to make changes when something isn’t working. I realized that I’m not someone who can comfortably follow instructions that don’t resonate with me or that I feel aren’t the right path forward. Read more>>

Laurence Nozik

It was never actually my goal to “be my own boss”. I was laid off from my last agency Art Director position a few decades ago and started freelancing as a means to make an income, but also work with different agencies and studios. I was wary of the interview process after the last position, and hoped a fit would develop somewhere. Instead of interviewing and being hired to work at a place I didn’t know, I wanted to be hired somewhere I already had a rapport with the people and knew how they worked (and vice versa). Unfortunately, that full time position never materialized. The problem is, that mentality stuck with me the entire time and I never really grew my “business” in the right way. To me, it wasn’t a business to begin with. I was just looking for projects and clients and trying to piece together a salary every year, all while waiting for that good fit to work out. Thus, I’ve made many mistakes over the past few decades, but more from the things I wasn’t doing, than the things I was. Read more>>

Stacey Gish Wallenstein

I feel that all entrepreneurs have this feeling at some point. Especially those in emerging fields – like blogging and content creation – since people don’t understand what the job entails, how much work it is, and it’s not just getting “free stuff”. In essence it’s running a full scale digital marketing and advertising agency. Being in a creative field means you’re always on and always thinking. Working for yourself means that you’re always working and always thinking. If I stop I don’t get paid. There’s no bi-monthly paycheck regardless of my effort. It’s exhausting! I love the line I work 24/7 so I don’t have to work 9 to 5. However, after a decade of doing this, sometimes I fantasize about the other side. Of walking out at 5pm, closing my office door, going home, and being present in my life versus living amongst blurred lines. Read more>>

Ann Byle

I’ve been a freelance writer for 27 years, and during those years raised four children while my husband worked full-time as a teacher. I’ve loved this work for its variety, flexibility, and the fun of meeting new people, interviewing a variety of people, and writing their stories. I’ve worked from home all these years in a variety of home office spaces. Recently I visited a company I used to work for and so was talking to a number of friends there. As I walked through the building looking at the cubicles with no privacy, lack of personal space, no place to hide, and where everyone can see you all the time, I started to breathe deeply and twitch a little. I couldn’t even imagine how much I would hate being in an office setting after all these years. I realized that I had created a life that I love, working in my home office that I love, and doing a job I love. No more offices for me–ever. Read more>>

Mike C

As a business owner, there are definitely moments when I’m both excited and overwhelmed by the challenges and opportunities that come with it. There’s a unique sense of pride in building something from the ground up, and the freedom to make decisions and create my own path can be incredibly fulfilling. The flexibility, in particular, is something I cherish—whether it’s setting my own hours or choosing the direction of my company. That being said, there are days when I do wonder what it would be like to have a “regular” job—one where I could clock in, do my work, and then leave without worrying about everything else that comes with running a business. The constant responsibility, the pressure to perform, and the uncertainty of the future can feel exhausting at times. Having a clear boundary between work and personal life, something that often gets blurred as a business owner, can seem like a luxury. Read more>>

Amanda Bauch

My husband nodded his head as I spiraled yet again. “Maybe I should go back to work full-time. Maybe I shouldn’t have been so dismissive of that job offer this summer. Maybe . . .” my voice trailed off as I fantasized about having a job where I showed up, put in my time, came home, and no longer had to think about work. No phone calls, texts, or emails at all hours of the day. It was time for what I’ve coined “My Annual Freakout.” Book publishing essentially comes to a screeching halt during the winter months, something I know only too well after twenty-plus years in the industry. Even so, this dry spell never ceases to catapult me into panic mode—especially my bank account balance dwindles to nothing. When I decided to leave my full-time corporate publishing job three years ago, my husband and I agreed we’d take it one year at a time. I had a monthly income threshold I needed to meet, to ensure we had the funds for what my income provided for the family. In spite of my endless hustle, I often fell short of this goal, leaving me guilty and stressed. And feeling like a failure. Read more>>

Shiran & Noy

First off, we’re the happiest business owners. We started out working together in the sales space and always spoke about how we’re going to change the event industry. 9-5 never worked for us; we’re way too outgoing for one on one’s and knew we’d thrive in front of crowds. When we started TMUNA NYC LLC, we knew it was going to be a hit. We’re finally doing what we love, day in & day out. We’re at events, sharing in people’s celebrations – and very often (knowing us) we’re bringing the vibe to the party. We always knew we love working with people, and we always thought about how we’re going to bring our personal touch and style to both our business and clients’ events. Now that we’ve been doing this for over 2 years, we know we’re finally in our comfort zone. Read more>>

Caitlin Willardson

I have gone back and forth on different perspectives with this same question SO many times! I have thought about how nice it would be to just show up at a job, work normal hours, and get to turn the clock off after hours. On the other hand I often think how lucky am I that I get to set a schedule based around my needs, treat my clients how I wish they could be elsewhere, and run my business in a way that aligns with my values. The times where the wishing becomes too powerful can often be difficult and disorienting. The times where it hits me most is in the height of growth. It ALWAYS is during the growing pains. Once I started realizing this it has made it easier to overcome even though it doesn’t solve the problem. Read more>>

Kelly Mcdaniel

I do not have to wonder what it would be like to have a “regular job”. I was working as a Litigation Specialist for an insurance company (out of my home before it was commonplace) and was handling injury cases that were heartbreaking. I was a walking checkbook, paying the injured or heirs who suffered injuries and catastrophic losses and it was beyond soul crushing for me. I was moonlighting as a photographer (as a creative outlet and for my mental health) for two plus years when I went full time in 2016 and I will be forever grateful that I summoned up the courage to go out on my own.  Read more>>

Anya Farmer

I remember one morning this September when I had a tough week — deadlines were missed, money was tight, and everything just felt harder than usual. After getting my kids off to school, I sat down with a cup of coffee, and for a second, I thought: “wouldn’t it be easier if I just had a regular job?” I imagined it — a 9-to-5, a steady paycheck, someone else making the hard decisions. For a moment, the idea of following someone else’s plan seemed like such a relief. Being the sole provider for my three kids can feel overwhelming, and the weight of that responsibility hits hard some days. The idea of safety, of something predictable, made me think twice. Wouldn’t a regular job make life less stressful? Read more>>

Nikki Garrison

This is such a thoughtful question. I’m very happy and grateful as a business owner. I must say I could never do it alone though. My husband, Chris, and I make a great team. He’s good at everything I’m not and vice versa. He’s great at managing all the tasks I hate, like taxes, operations, contracts, systems, equipment…all the stuff that I forget is necessary to run a business successfully. I prefer to focus on getting to know people – our customers, vendors, partners, etc. or getting locked into working on a particular project for longer than I should, and especially continuing education to make me better at my job. These are just a few of the things I love about being a business owner. Read more>>

Lorenzo Leyva

I am happy as a business owner but it can be overwhelming at times. I suffer from burn out pretty consistently, and a lot of the time I feel overworked and underpaid. It’s hard to be accountable to yourself when you’re doing it alone, my success is largely dependant on me and the discipline I have to continue my business while trying to grow and improve. It’s a delicate and difficult balance. Sometimes I feel like I’m doing too much, then it feels like I’m doing too little. I’m constantly battling myself. But then I think what would it be like if I had a regular job? I think about this all the time. It happens every time things get really tough. Or something falls through, or there’s not as many jobs this month as I would hope, or a project doesn’t quite come out how I wanted…And I think it would be easier. I think it would be a lighter workload. I think it would be better pay, probably, maybe worse depending on my role… I think it will have benefits, pension, paid vacation days… but it also would be boring, it’d be frustrating, I’d get less respect, have less creative freedom, less say, I’d start to feel slow, stagnant, soulless. I wouldn’t have my heart or head in it. Read more>>

Jennifer Bigler

A few years ago, I found myself at a crossroads in my career. It was right after COVID, and like so many others, I felt the pressure to pivot. The uncertainty of running my own business became overwhelming, and I started to question if I was on the right path. I needed stability, structure, and maybe even a bit of predictability. So, I decided to take a break and accepted a job with the local school district. At first, I enjoyed it. The social interaction of being around coworkers and the consistency of a 9-5 schedule was refreshing after so many years of working from home. But that feeling didn’t last long. By the end of the first week, I found myself restless. The work was monotonous, and I realized how much I missed the creativity, problem-solving, and sense of purpose that came with running my own business. Read more>>