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.

Hannah Hays

I always think of this question! The what-ifs had I not taken my business full time. I always have had a passion for photography. When I was in high school, I was gifted a little green camera. I called it the grinch camera (LOL). Photography became an escape from reality. I immediately knew I loved it, but had no idea where to go with it. Then life happened and it got put on the back burner. Read more>>

Paige Neal

I can say with 100% certainty that I am happier as a business owner! I always knew that I wanted to have a creative career, and when I found photography it was an instant feeling of “this is right”. I love being able to have the freedom to make all of my own choices, to make my own schedule, and to be competitive only with myself. I appreciate the lasting friendships I have made with clients, and I enjoy watching families grow and change over the years. When I think about the negatives of owning my own business, there is really only one. It can be overwhelming to be a one person business. For example, here are the roles I play as a full time photographer: Read more>>

Johanna Voss

I couldn’t imagine working for anyone else! Being an entrepreneur is the hardest thing I’ve ever done in this lifetime and it’s definitely not for everyone. But I couldn’t imagine working for someone else. I’ve been working for myself since 2011, Before that I travelled the world for a year, lived abroad twice in Spain for a total of 18 months and did a lot of other travel and before that I worked on political campaigns for 8 years – No one has ever used the word traditional to describe me. Read more>>

Matt Haugen

I am very happy as a business owner but I have thought about what it would be like to have a regular job as well. My journey in entrepreneurship has required me to make a ton of sacrifices such as my physical and mental health, having a relationship, social life, having hobbies, and even more. If I had a regular job I could have a more stable and consistent life and not make so many sacrifices. The risk an entrepreneur takes is that in the end they will be successful and have changed their life forever, thus making all the sacrifice worth it. My goal in like if to create a story worth telling, so for me the sacrifice is worth it because I wouldn’t reach my goal if I had a regular job. Read more>>

Sarah Grondin

I think about this every day. Being a business owner is alot of hard work and you never really have a day off. There is always something that needs to be ordered or fixed or researched. There is always a client that calls or texts with questions on the weekends. There is always education and trainings that need to happen on your off hours. I love my job and my clients but I don’t have the normal perks of a regular job like paid time off, health benefits or 401k. Is it worth it? That’s a hard yes for me. I thrive on being my own boss and thinking outside the box. I love being responsible for my own ideas and my own failures. There is simply nothing better than only relying on yourself. Read more>>

Willet and Diane Feng

Yes and no. Compared to a regular job, the highs are higher and the lows much lower. Being the owner assumes more risk, while being an employee offers more stability. Owning a restaurant is a gamble, and it isn’t necessarily high-risk, high-reward. The risk is quite high, but the reward—monetarily—is medium at best. Passion fuels most business owners in the food industry, and you need a surplus of it to ride out the lows. Read more>>

Emmie Sellers

I am very happy as a business owner! I enjoy the flexibility it brings as well the control I have over what I feel is best for my business! There are times when I do think having a regular job would be nice, but that’s because I have a very hard time setting work hours for myself! In my busy seasons, I tend to work all through the day and into the night on my photography just to keep me from getting behind. I place these expectations on myself and just can’t seem to walk away from it by a certain time of day! With a regular job, Read more>>

Lemuel Mascarinas

There are a lot of benefits of being a business owner. However, together with these benefits comes a lot of responsibilities, expectations, sacrifices and stress. People from the outside looking in are amazed by the lifestyle and perks of having a successful business, but they are not privy to things that go behind the scenes and are not aware of the amount of burden we have to carry everyday. Entrepreneurs don’t work from 8 to 5 nor have weekends and holidays. Every day is a Monday and no matter what time of the day; it can be the middle of the night, we have to be there if the company needs us. Read more>>

Devon Salisbury

I am a mom of two school-aged kids. I have always been a creative type of all kinds, writing, photography, design, but am also very detailed minded, so I always thought I would have a regular 9-5 office job of some type. I have had that in the past, but after having kids I was able to stay home with them and use my creative side to build an Etsy business. It was so nice to use my brain, but also make my own hours and decisions and even build a very consistent customer base while staying home with my young kids. Now, my kids are both in elementary school and I have a lot more time in the day to devote to other creative avenues. Read more>>

Yen Ong

Being a business owner allows me to imagine our studio’s future and to take real steps forward without having to convince anyone with higher authority within the company. It is liberating. What becomes critical is the ability to create a composition of people with complimentary skills and knowledge who believe in the company’s purpose, are committed to the mission, and are excited to be part of that future, their future. Read more>>

Melvin Roberson

I think about this all the time. Honestly, probably every other week but I always end the thought thinking doing what I’m currently doing is best. At the last place I worked, they told the origin story of the business during onboarding and that particular business had started in 1971. When I began working there in 2010, I thought it was really cool that I was working in a place that had started that long ago and was continuing to thrive almost 50 years later. Now, that story wasn’t super detailed and definitely didn’t talk about any struggles that the owner had probably gone through but I’d like to think it took a lot of good and bad times that the owner had to persevere through in order to make it this long. Read more>>

Hilda Trigoso

Yes, I am a happy small business owner and certainly happier than when I had a regular job! My story is similar to many entrepreneurs out there that hold two or more jobs before deciding to fully commit to their own business. I had two full time jobs, a regular job and my balloon business, for a while when I finally decided that it was time to invest 100% of my time and effort to my own business. It was a tough decision considering the risk, insecurity and uncertainty of the new financial responsibilities and expectations. Read more>>

Safia Jafri

I am extremely fortunate and blessed to be in the profession that I am. To answer the question what would it be like to have a regular job. I’ve held several regular jobs in the past that were also fulfilling. After I had kids, I felt I needed to devote a little bit of time to them as well as being able to supplement my family‘s income. Education is something I’ve always had a passion for. I used to teach kids when I was in college and much later in the capacity as a teacher. I felt continuing my passion was more important to me than any other profession that I have previously been in. Read more>>

Garrett Turner

Being a business owner allows you to have a direct impact on your businesses success or failure and is quite an exhilarating feeling. Coming out of graduate school I was fortunate enough to accept a position with a Fortune 10 company. It was such a great opportunity to be surrounded with bright individuals and to be able to further grow professionally. After about a 7-year stint I decided it was time for me to make the transition full-time to my business and focus my energy and time there. Early on there were hurdles, like struggling to find a role in my business where I was able to add the most value. Read more>>

Brian Raitman

Being a business owner was probably my destiny. Growing up, I was always one of those people that had an extremely difficult time working for someone else. I quit my very first “real” job after three days. I was working at Baskin Robbins and had become friends with another kid that was hired the same day as me. I told my boss in the interview process that I could not and would not work on July 4th, as I had plans. Read more>>

Karsten & Belinda Ivey

We are very happy as business owners, but that doesn’t mean there aren’t any ups and downs when it comes to that emotion. When you own a business, all of the responsibility and pressure for the company being successful ultimately depends on the decisions you, your partner, or your team make. That can be very stressful at times. So much so that there are times we think it would be easier to just have a regular job. Read more>>

Brie Marie

I love being a business owner yes! I love having the flexibility to make my own schedule, but there have been some days especially when months are slow, when the stress of having your own business has been at a high, I’ve thought about closing this chapter and getting a job that has secured income. Covid and the unknowns the last couple years have brought to our industry has been hard, but I truly have the most supportive and loyal clients who have stuck by my side and continue to support this brand we’re building. I’m proud that I’ve continued to persevere and look forward to all the amazing things to come! Read more>>

Kirsty York

There are pros and cons to every job and that doesn’t change when you become your own boss. Being a business owner can be really hard and sometimes it can be easy to catch yourself daydreaming about having a “regular” job again. Being a business owner doesn’t mean just doing your job and then clocking out, you never clock out. There is endless work you have to do even after you leave the office. You are your own schedule maker, web developer, social media manager, and more. Especially in the tattoo industry, after leaving the shop I still have hours of drawing and email answering to do at home. Read more>>

Jorge Abarca

I feel extremely blessed to be able to be a business owner doing what I love the most! I am happier now than I have ever been in my career. A few months ago, I had the opportunity to accept a job offer for an Executive Chef position at a trendy restaurant. At the time the business was not doing great so I had to really consider going back into a professional kitchen. I knew I could do the job but I also knew that this meant having to go all in: long hours, long work weeks, more stress, more worries. I also knew that my family needed me. There was a lot to think about: Should I leave this venture as a business owner behind? Read more>>

Juzar “Jazz” Sulemanji

Yes, I am very happy as a business owner. At times it is very stressful since you don’t know when the next order is coming in. You still have bills to pay and still have employees to pay. When times get stressful, I think about selling and getting a full-time job. That thought goes away as fast as it came in. I love the flexibility owning a business provides. Read more>>

Natasha Nicholson

I LOVE being a business owner. It definitely isn’t easy and there are times I think of working a regular job when I get clients that stress me out or when I have slow days or weeks. However, I snap out of it very fast when I think about the flexibility of creating my own schedule, being able to be there for my kids, controlling how much money I make etc. I don’t believe there’s any job that will take care of and look out for me better than me. Read more>>

Dr. Julie Clockston

As a business owner, I am pleased. Most of the time. I would be remiss to say that as a business owner, everything is always grand. I would also be negligent in leading anyone to conclude that being an entrepreneur or solopreneur is synonymous with being a business owner. Many individuals believe or have flawed assumptions that being a business owner means you can do whatever you want to do. Read more>>

Sharon Birkman

With ownership comes huge amounts of privilege coupled with vast amounts of responsibility. On most days, I am intensely grateful that my parents founded our company more than 70 years ago with a brave new idea that continues to resonate and help people. My Industrial-Organizational Psychologist father was a pioneer in recognizing the impact of comprehending our social perceptions. And these days, our vision statement is “To harness the power of perception to improve and transform human relationships.” Read more>>