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.

Lisamarie Thomas

Since stepping away from my job shortly after COVID began, I’ve developed a deep appreciation for the journey of building my own business, Lisamarie Thomas Publishing, into what I hope will become an empire. Today, I am not only an ordained minister but also the CEO and owner of multiple ventures, each dedicated to making a positive impact and fostering growth in various fields: Read more>>

Marcus Brown

I am a very happy business owner! I honestly don’t think about a “regular” job often. What is regular? haha. I’m a hard worker so anything I’ve ever done I gave my best. Being creative, it’s hard to sit still in a regular job, there’s so many things that can inspire a project, a song, a thought, and I don’t want to have to wait till the shift is over to explore that. Now respectfully, I’ll always jump into whatever is necessary to provide, but that’s why I give my business so much energy. Building relationships is key and I do that with intention with my clients and customers so they want to come back and bring someone else to experience what Deco has to offer. Read more>>

Erin Schmidt

Being a happy business owner is so much more than loving what you do. When I started my business, I was consumed by it. I loved what I got to do for a living and therefore ate, slept and breathed photography. It just didn’t feel like work, so I worked a lot. Then, there I was, making six figures working my dream job, but I really wasn’t able to do anything else. I had weddings every weekend and shoots throughout the week leaving very little time for my family and for myself. Though working a lot in the beginning was necessary to take my business to the level it was at, it was not sustainable over time Read more>>

Atalaya Hayes

I am happier as a business owner as opposed to having regular jobs. Being a business owner it’s hard being hit with expenses and being over worked and underpaid because you have to reinvest constantly until you reach a certain level in business. This is the phase where it looks like you have it all from outside looking in. To everyone so people who are in need may start to pressure you sold solve their problems. At certain stages in business you don’t get to keep much for yourself and still see the business grow. So it’s easy to feel overwhelmed. This phase in business will show you if you are cut out for entrepreneurship because you don’t know how long the phase will last. The benefits to having a job are most of your problems and all of the expenses, whether you make a mistake or not, fall on the employer. As a business owner everything is your problem to solve and everything is your fault. It isn’t for everyone. But the benefit that makes it for me is the opportunity for creativity and growth. I have the opportunity to build it up and get past the uncertainty phase. Read more>>

Sam Chapel

I love being a business owner! As someone who likes to be in control of their work and books, being my own boss helps ease my mind in many ways! I tend to run on the anxious side of the road and opening my own business actually made me feel less anxious once I was up and running. Everything being in my control was pretty amazing for my brain (for the most part!) Now don’t get me wrong, the process of opening up my business was nerve wracking for sure because you never know what’ll happen! Even though I’ve been loving working for myself, of course I think about what a regular job would be like- especially when it comes to time and honestly, benefits! Read more>>

Hannah Campbell

Sometimes, when I get really overwhelmed with small business ownership, or when I’ve made poor strategic decisions and am feeling the financial impact of those decisions on my business, I start to question if I’d be happier in a more stable “regular” job. Most recently, this happened this summer. I was vending at two different farmers markets for the summer and was performing poorly at one of the markets. When I commit to markets, I have to take on less custom work so that I have the time to bake for and vend at the markets. When I don’t make sales at the market, I’m out the money I could have made on those custom orders. As I watched my business account slowly dwindle this summer because of this bad strategic decision, I began looking at job listings. I saw bullet points on job postings like “must excel in a resource-lean environment” and had a full-blown panic attack. Read more>>

Sabina Bower

Honestly, I love what I do. I get to work with clients in multiple industries, and two projects are never identical. The work always feels exciting – even during long days. When I finish a project and a client comes back and tells me how they’re making more sales or have gotten more partnership opportunities because of our project together, it’s more rewarding than any 9-5. The only time I feel like having a regular job is in moments of panic: the “what if I never get another client again?” moments. But the opportunities keep coming and the business keeps growing. Read more>>

Eden McCloud

Yes, I am very happy as a business owner, but I do sometimes think about what having a 9-5 would be like. Nearing the end of the 2024 wedding season, it’s been very busy, especially with editing wedding galleries on the back end. I wonder sometimes what a more solid work schedule would be like. Wedding photography can be a bit of a seasonal job, with some months having lots of downtime, and some months having no days off. When I think about a “regular” job, I romanticize the ability to clock out, and to always have weekends off for family and friend time. Personally, as a creative person though, I do really enjoy a less mainstream work flow and the power to create my own schedule to a point. Read more>>

Sean Noche-Schultz

This question definitely resonated with me very well. I think about it every single day what it would be like to have a regular job. As much as I love being a business owner. I really do love it because I am doing something that I am passionate about. Which is photography and videography. I get to make new connections and meet new people on a weekly basis. Get to hear client stories and how they got brought up. I get to deliver services that my clients need. And I get to create memorable experiences for my clients. So many enjoyable experiences as a business owner. But I can tell you it is and can be stressful at certain times. Because everything is dependent on you. Everything depends on you to keep your business going. I have to do everything. I don’t really have a lot of help. So when I run into problems, it’s kind of up to me to figure it out. I am responsible for waking up in the morning and starting my day off. I’m have to do my marketing for myself. I have to put myself out there and self myself when there is times i don’t want to. But I really have no choice but to. I’m responsible for being in communication with my clients and giving them outstanding service. Etc. Everything is dependent on me to keep the business up and running. Read more>>