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?

Sara Borgstede

Last year, my business saw tremendous growth. This was incredibly exciting but also overwhelming. I started the process of hiring additional help and dove into meeting my customer’s needs. I felt like every day was high-level, with onboarding, training, creating systems, and more. Read more>>

Bianca Flanagan

I AM happier as a business owner! Being a mom of two small kids, I wanted to work, but I didn’t want to spend too much time away from the home (and let’s be honest, daycare is essentially a second mortgage.) I wanted the opportunity to step out of the mom role, and jump into something that was my own. Read more>>

Julia Badji

Growing up, I was always an overachiever. I got my first job at 15, working at an ice cream shop, later becoming the manager. I also got my second job at 15 as a student assistant for a summer school program, later becoming the director. In high school, I held two jobs, while playing sports, was involved in various clubs and hobbies while simultaneously taking advanced courses. Read more>>

Zoraida Dobard

I’ll start off by saying that i’m an ex-educator. Business was not ever something i pictured myself doing, so when my husband and I started our two side-by-side businesses (his and hers), it was a very big change for me. In teaching you make an impact everyday and i didn’t think it would be possible through a business. Read more>>

Hillary Bloom

From an early age, my entrepreneurial spirit led me through various ventures. I started small, selling stationery door to door as a child and even delved into data entry work for my father’s side hustle. In college, I took it a step further, running a successful resume writing business. Read more>>

Brenten Tolbert

The last time I thought about what having a regular job would be like again, was right before the holidays while on a family hunting trip. Business had been a little slow and a couple of my fall weddings got canceled relatively last minute. Overall these are pretty normal challenges; client’s change plans and business has an ebb and flow life like the rest of life. Read more>>

Jenny Bolhofner

I learned early on in my life that I like to be in control, and have my hands in everything. Saying that out loud, I sound like I need a trip to a good therapist. But honestly, those traits serve me really well as a business owner. I am self motivated because I know I am solely responsible for the failures and wins of my business. Read more>>

G Bliz

I’ve had this thought many times, especially since I’ve never really had a 9-5. I got into music young and always had a passion for it. Later I found ways to add value to the music world and learned ways to monetize it. But what people with 9-5’s don’t always realize is the frequency (or lack thereof) of your “paycheck” when you’re a small business owner/sole prop. Read more>>

Albrianna Farnum

Both my partner, Nicholas Beni, and I work full-time as well use most of our free time to run our business. It definitely comes with its fair share of challenges and sacrifices. There are times where we’ve worked for over a month straight between both jobs and we can feel it starting to wear on us. Read more>>

TIFFINI SPRY

I am definitely happy as a business owner! There’s a big sense of pride in knowing that I’ve been able to create an avenue for myself and my family in a few short years that contributes to both our family income and my own personal growth. I’m working harder than I ever have (light chuckles) but I know undoubtedly that the efforts I’m putting in will pay off. Read more>>

Mariah Mitchell

Creating and running a business is a journey, it takes patience, consistency, and a willingness to fail. Ironically, the faster you fail at something, the faster you can learn from it and improve. Since I launched my website December 18th 2022, I have edited my logo and website design numerous times, changed my business card 3 times, and improved the quality of my packaging and products more times than I can count. Read more>>

Genesis Pineda

I used to have a regular 9-5 where I worked for a company in there Information Technology/Customer Support section. At the time I was only able to take clients on weekends while I started my business and set its foundation. After a year, I found myself miserable at the 9-5 and I would anxiously wait for the weekend to arrive so I could take clients. Read more>>

Yakima Chinn

Yes, I’m happy about being a business owner but it can be very challenging. Yes, I often think about getting a job because you never know how the money is coming in because you you can have a slow week and then you have a good week, You have to find many ways to get money coming in for your business, Read more>>

Conor Foley

If I am being honest, it depends on the day whether I’m happy or not as a business owner. The upside AND downside of being a business owner is that there is always something that can be done. The upside part is always having that next step, next goal, or next benchmark to achieve. Read more>>

Mikayla Radecki

Being a business owner is no small task. There are many responsibilities that come with it, as well as holding yourself accountable for your successes and failures. However, it is one of the best decisions I have made in my life, and I couldn’t be happier with my role as a small business owner. Read more>>

Danielle Lord, PhD

I am just starting my third year in business. I have spent my 30 year career in the corporate sector. So, I’ve had the regular job and I do not think that I could go back to corporate-life. In addition, I was also a graduate-level professor at a major university. Read more>>

Amber McCulloch

I am never going back to a regular job. In fact, the memories of working a regular job motivate me to work harder to build my business. Every once in a while – at 3 am when I’m hopped up on my 7th coffee and racing to finish a client’s writing project by the deadline, I’ll think back to my days as a marketing director. Read more>>

Samone Rankins

I have had the privilege to experience a lot of different job opportunities which includes being an assistant teacher, working at AMC movies, Six Flags, after school Site director, forever 21 etc. My most recent job and what most would call a career I was working full time for the City of LA. Read more>>

Cameron Ogden-Fung

The question of whether I am happier as a business owner or if I’d be better off in a regular job is one that surfaces occasionally, especially during moments of uncertainty or significant life changes. One such moment occurred recently.My partner and I were discussing plans to start a family. Read more>>

Briana Betts

I love this question! I am very much a happy business owner but recently have come to the realization of how hard it is to push through with one skill type. Every year I like to shift a little to gain a new skill that can be grouped within the platform of my business. Read more>>

Evan Leggoe

I am very content with the path I’ve chosen. My partner is also a small business owner so we discuss these topics a lot and there is an appeal to not having to make every decision regarding the business and getting to simply show up, do the work and go home. Read more>>

Hailey Jordan

I am the daughter of magic makers. The youngest of three, I grew up in Norfolk, Virginia before making a new home here in Baltimore for the last 10 years. From an early age, I saw first-hand what hard-work looked like. Read more>>

Isaac Session

I am happy as a business owner currently. I enjoy the freedom of taking off of work when I’m ready, more time with family if I choose to, I’m in control of my income, and I enjoy the fact that I can project how I want to grow my business. Read more>>

Nathan Schneider

Being a business owner has been one of the most exciting and rewarding experiences of my life. I remember the arbitrary question posed to me in school, “What do you want to be when you grow up?”. When I was a kid, I could never find the answer. Read more>>