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.

 

Sara Maida

Being a photographer, a solopreneur you wear many, many hats. From marketing, to stylist, to booking agent, to photographer, and occasional therapist and so many others, there are times it can be overwhelming. Honestly, I wouldn’t have it any other way. Having a “regular job” that you can leave at the door is appealing when I am laying in bed at 2am wondering if my client for the next day has found the right shoes, or up at 4am editing a session because I just LOVE how the light was shining and cannot wait to get my clients that sneak peek. But the benefits FAR outweigh any of the aspects that make being a creative a challenge. Read more>>

Amanda Moreno

I love being a business owner. It is definitely a challenge from just being a worker, then going into owning a business and figuring out everything that truly goes on behind the scenes. It was an adjustment, but in the best ways possible I was able to have full control over my schedule, my pricing and creative freedom on what I wanted to do. Sometimes I do miss being just a worker and only having to worry about work while I was there one thing about being a business owner is you are always on the clock but honestly, I would not trade it for anything. Time management is truly my saving grace learning this skill helped me out so much as well as being organized. I love what I do and I can’t see myself going back to just being a worker. Starting my business was the best decision I made for me and my future. Read more>>

Simon Yip

As a business owner, I can confidently say I’m happy with what I do—but my journey here hasn’t been conventional. I’ve been an autodidact since the age of 8, driven by an insatiable curiosity about how things work. Back then, I would take apart household appliances just to see what was inside and figure out how they worked. Admittedly, I ruined quite a few appliances in the process, but luckily, I was never caught—and my dad never scolded me for it. Curiosity was the spark that ignited my self-learning journey, and the sense of accomplishment kept me going. Over the years, I taught myself a wide range of skills, many of which weren’t directly relevant to my academic path but ultimately shaped my ability to run businesses today. Read more>>

Shavon Parker

Am I happier as a business owner? Absolutely. Being in business has allowed me to step fully into my purpose—not just as a nurse, but as a true advocate and leader in healthcare. I started my journey as a bedside nurse, but the challenges of that environment pushed me toward entrepreneurship. Hospitals often operate in a way that prioritizes policies over patient care. As someone who is deeply passionate about advocating for my patients and clients, I found myself constantly at odds with the “get them in, get them out” system. It left little room for the kind of care I wanted to provide, and I knew there had to be another way. Read more>>

Derek Tramont

The simple answer is yes. But the two are worlds apart in my view. The life of a business owner is more of a mindset and state of being than anything else. It requires all of your attention, all of the time. Regardless if you’re playing tennis (like I love to do), taking a walk or taking your loved one out to lunch. I promise you and all business owners know this, that you will be thinking about something you didn’t do or something you need to do, as soon as humanly possible. Whether it’s catching up on payroll before the bi-monthly cycle hits, sending out that invoice or touching up or proofing a new project before you send it out. It creates a constant in your life that you will love when you have a good month or you just made a positive change to a system you know needed to be revamped or your simply just content with the state of your business model and the good work your team has been providing to your clients. Read more>>

Brenda Blair

I’ve had many regular jobs in my life, and I’ve had jobs I thought I liked but were physically, mentally, and emotionally draining. When I set out to open up my own Pilates studio I knew it was going to be hard and that I would struggle at times but even though those things are true, I’m happier than I’ve ever been. As a part of my Pilates studio, community is really important to me, almost more important than the Pilates we teach. Yes, we teach Pilates and move bodies for a living but what we really sell here is community. On a pretty regular basis I question my choices as a business owner (i.e. did I pick the right location? Is my pricing right? Will my business allow me to thrive both personally and financially?) The last time these voices crept in, like literally the second they came to me, I received a text from a client. It was a long text, something that really should have been an email cuz it was so long. Read more>>

Angie Carr

I am very happy that I am a business owner. When you find your soul purpose , it brings great pleasure. I was a flight attendant for 10 years then went to school and was a nurse for 20 years. Because of my own story of healing naturally, that led me to my business today. My business is called Foodgoddess50.com. I represent several wellness businesses on my site that has helped me and thousands of others to become healthier. I am a health coach and I teach people on how to heal. God has led me on this purpose and I love what I do. I make my own hours, I travel and I educate what I have learned. I go live daily on social media and have helped lots of people. I do not miss past jobs because I am doing what I truly love to do. I love to inspire, motivate and encourage others to do the same. Do what makes you happy, instead of just doing a job just for money. Read more>>

Jennifer Arvanitis

Being a business owner definitely has its perks – being able to make your own schedule and be your own boss is definitely nice! However, that “schedule” usually tends to be 24/7 and being your own boss also means paying all the bills. For the first five years of having the storefront, I worked full time as a paralegal while my sister ran the store. Of course, having a steady paycheck and benefits (oh, the health insurance!!), my heart was always with the store and the ultimate goal was to be there full time, which I was eventually able to end up doing during Covid of all times! Read more>>

Sarae Smith

As a business owner, I could not be more fulfilled! I never dwell on what life would be like in a regular job because I know exactly what that’s like. To do my best work, I thrive in variety. Some days I need the energy of a bustling coffee shop. Other times, the quit solitude of my apartment is where I need to be. There are moments when I crave the camaraderie of a co-working space, or the inspiration of a new environment to spike creativity. Sometimes, a familiar bookstore is the perfect setting. No matter what, I wouldn’t trade the freedom to work from the place that lets me perform at my peak for anything. Read more>>

Cari Byers

I love what I do. As a retired performer I still get to be part of that world and work with performers, just in a different facet. It is not easy, and at times can be quite challenging, and maybe even stressful. But the good definitely outweighs the bad. I did have to learn about the business side of the industry, and how to navigate the challenges. I generally really get on well with my clients and enjoy bringing their ideas and success to their events. I have worked ” regular jobs” but is was definitely not as rewarding as what I do now. I enjoy being able to put performers to work, and helping clients to create their event concept. Read more>>

Kibri Everett

1. Are you happier as a business owner? Yes, I am happier as a business owner. This role allows me to leverage my deep passion for environmental justice and directly influence the outcomes of projects that have a meaningful impact on communities. The autonomy to make decisions, the flexibility to pursue projects that align with my values, and the ability to innovate in ways that can directly address the needs of historically marginalized communities provide a profound sense of fulfillment and purpose that I might not find in a conventional job setting. Read more>>