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.

Janae Burris

I never intended to own my own business. I’m an actor and stand up comedian and I’d like to be staffed on a television show. I’d love to call Issa Rae or Lena Waithe my boss. I’d happily clock in to write quips for Jimmy Kimmel. One route to becoming a television writer is to get really good at stand up comedy and the art of writing jokes. As a stand up comic I am my own boss. I decide which jobs I say yes to and I determine my own salary. Read more>>

Whitney Mayhew

Being a Small Business owner is one of the hardest things you can do. Especially in this economy. I’m not going to lie, I ask myself quite often why I choose to be open when I could pack it all up, work fewer hours, and bring in more money working a nine to five. I wouldn’t have to deal with the spam phone calls. I wouldn’t have to deal with people trying to spoof my social media accounts to try and steal money from my customers. I wouldn’t have to stay up to date with Meta’s newest algorithm so that my posts are actually seen. Read more>>

Daniel and Jade Torres

First response is yes! We are grateful to be business owners. Why? I think my answer is based on past experiences and ability. In order to bring forth context I have to paint a picture first. Growing up, college was strongly encouraged and seemed like the only option to succeed. Fast forward to sophomore year in college picking a major was crucial and caused stress to make the right decision. In order to help make this decision, we interned, interviewed and asked all professionals about the possibilities of picking a certain career. Read more>>

Coco Roberts

I thoroughly enjoy being a business owner, because it gives me the freedom to do other things, like volunteer. I have the freedom to schedule clients the way that I would like so that it fits other areas of my life. I will admit that sometimes when business is slow, I think about getting a regular job lol. But then I remember that I can not just take off and go on a four day weekend whenever I want or take a mental health day without explaining to someone why I need it. Read more>>

Ashley Heleringer

Prior to founding Heleringer Events, I worked in the corporate world for over a decade. I have a degree in Management Information Systems, so I pursued a career in the IT and digital marketing fields. After moving up the ladder through various roles of increasing breadth and experience, I just wasn’t feeling fulfilled and felt that I was meant for something greater. During this time, I had been producing events on the side, however I was considering it more of a hobby and something that fulfilled me creatively, than a viable full-time career option. Read more>>

Ariel Celeste Pirela

I am much happier as a business owner! I appreciate the opportunity to build and solidify a legacy each day. There was a point in my career when I had to think critically about my path and purpose. My personal mission in life, now, is to seek perfection in creating something that will carry my name forward long after I’m gone. This epiphany happened about 7 years ago. I speculated then that what I would leave behind would be in the form of a book or a novel. Read more>>

Breyona Sturghill

Embarking on the journey of being a business owner is like stepping onto a rollercoaster of highs, lows, and unexpected loops but receiving a greater return at the end. It’s not merely a trend, yet some think so, but its; it’s a profound choice that puts your resilience, determination, and vision to the test. A business owner isn’t just someone who starts a venture; it’s an individual who understands the soul-stirring potential their business holds. It’s about enduring the late nights, weathering the storms, and making decisions that often feel like tightrope walks. Which can also be one of the hardest and best decisions in your life. Read more>>

Taylor Swenning

I love owning my own business. I never could imagine having a regular job. To me, life is about experiences and learning as much as you can in the short time we’re here. In college at Texas A&M, I studied Construction Science. My parents were always home builders and that’s all I ever knew. I wanted to follow in their footsteps by owning my own home building company. College was actually the place I learned, I most definitely never wanted to work for anyone else, but myself. Read more>>

Troy Browder

I’m completely thrilled to be a business owner. I couldn’t imagine working for someone at this point, some 10 years after I went out on my own, but that said you always have moments where you think of going back. That constant paycheck every 2 weeks. Health insurance, 401k, etc. all kind of taken care of in the background… it’s certainly “easier” in many ways to work for someone. Summers can be quiet in the video world and there are times after enjoying the inevitable downtime you can get bored and scared about the next gig. Will it come? Read more>>

Miranda Rights

I think about this all the time! I wake up every day feeling extremely lucky to be able to do what I do. I make an effort to sit in gratitude and let me customers and audience know how much I appreciate them every chance I get. The pandemic was very scary (for all small businesses, I think), and I have to constantly keep up with social media trends in order to reach my audience. There have been times where I envied my traditionally-employed friends and family for their paid time off, benefits, and general safety net. Read more>>

Katy DeZellar

I think about this often, honestly, and it constantly comes up in conversations with my fellow freelancers. It’s a tough question, because there are plusses and minuses to both kinds of jobs. I personally love being a business owner! I honestly don’t think I could go back to a regular job. I hated it and never felt I could be myself or do my best work. Switching to freelance was tough, but worth it. I really appreciate the flexibility and freedom it gives me. If I have something I’d like to do with family, or I have an appointment, I feel sick, or I just don’t feel like sitting at a desk that day, I can move things around to fit my needs. Read more>>

Shaleen Hauck

I remember reading a quote before I opened my first commercial business that said something along the lines of “I would rather work a 16 hour for myself, then work an 8 hour day for someone else”. I think I was scrolling away on a sleepless night waiting for our lease agreement to go through. I remember thinking to myself – “No way is that going to be me – I am going to have a staff that make money for me while I am busy living the good life”. Read more>>

Tamarya Cobb

First, I’m going to start by saying yes, I am happier as a business owner. It took me some time to get to this point so let me explain. Going into business I’ve always had the idea that it’ll be peaches and cream. Well….that didn’t age well. I was 15 years old when I started so of course I didn’t know all the key points of running a business. I was so focused on the glitz and glam when in all actuality that’s just a taste of business. Read more>>