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.

Anna Nguyen

Am I happier as a business owner? Absolutely. But do I sometimes think about what it would be like to have a regular job? More often than people probably expect.

The last time I seriously had that thought was during one of our biggest production weeks last year. We were ramping up for a major launch at Central Market while keeping up with Mitsuwa, pop-ups, and Revolving Kitchen. Orders were piling up, staff was stretched thin, suppliers were running late, and I was running on fumes. Read more>>

Heather Peterson

I love being a free-lance artist and entrepreneur. It is definitely not for everyone. It requires a lot of trust. Trust in the quality of the product you bring to the world, or your community around you.

I am happy I chose this path, because it allows me freedom to create flexible boundaries and hours, expand or contract my clientele based on what else is going on in my family life, and share what I love with clients in ways that work for me without overextending or draining myself. Read more>>

Schakara Arrazola-tiscareno

I am happiest working for myself, pursuing my own dreams and passions. Being a business owner is not easy—it demands grit, dedication, and resilience. You can’t simply “milk the clock”; every day is a fresh opportunity to invest in yourself and your craft.

The lack of traditional hours can make balancing life and work challenging at times, but it also offers the flexibility and openness I need as both a wife and a mom. I’ve always believed the traditional workforce isn’t designed to fully support working mothers, which meant I had to get creative when I had my son. Read more>>

Kristel To

I love being a business owner! It’s a lot of hard work, but meeting my customers and hearing how much they love my teembun (teembun is the cantonese word for desserts) makes it all worth it. I graduated college in the peak of the pandemic (May 2020). It was a really uncertain time for everybody and it was definitely not easy to find a job. But, I followed the path that I was always taught to follow. I found a corporate job and have been working in various HR/Recruiting roles for the past 4-5 years. If anybody has ever been in a corporate environment, you know how some can be. Some workplaces are filled with amazing talent and people that empower you to grow while other places treat you like a machine rather than a human. I’ve seen it all. Despite all that, I am still working at my corporate job to this day. From 8am-4pm, I work my corporate job. Read more>>

Sonali Morris

In short, yes! But, it’s definitely mixed emotions.

There are times where I love the freedom, creativity and autonomy that comes with it. But, there are days when the weight of responsibility feels overwhelming. It sometimes makes you wonder about what life would be like with the security of a “regular” job.

The last time I had that thought was years ago — as we were shutting the business down for covid. It was a crazy, challenging time. It would have been so nice to have someone looking after me and my family — telling us what was happening, how our work would be changing and how we would all get through this. Instead, we were looking after two businesses and more than 120 employees. We were the ones that had to provide the reassurance and stability so many people needed at the time. Read more>>

Ray Hattori

My answer for the question must be yes! I always feel my life as a business owner is fulfilling even though a problem after another pops up out of nowhere every minute every second. More than a decade ago when I was a President of the U.S. operation at my previous company, they asked me to come back to Japan as regular personnel change. Then I decided to leave in order to pursue my dream. The company provided me with much more-than-average pay and a great package of benefits. When I joined them after graduation, my goal was to become the main guy in their U.S. operation. I was lucky enough to become the one after 18 years of service. I met a lot of great work associates, friends and bosses whom I still get in touch with. My parents were kind of disappointed with my decision at the time. Read more>>

Alexia Wilborn

I am happiest as a business owner. I’ve had regular jobs and often used to romanticize them when I was single, but my goal was always to have the ability to stay home once I started having children. I usually work alone, which is my least favorite thing. My husband helps me after work, but we currently have one-year-old and are expecting twins later this summer, so I have been praying for a shop assistant or two. I expanded the shop’s inventory last fall and want to continue growing. I hope that God will provide at least one suitable assistant before the babies are born. I’d love for my work life to be less of a one-woman show and more of a team effort. Rather than people with a regular job, I often envy those who have family members or friends who are willing to help them run their small businesses. Read more>>

Quanella Jordan

I love being a nanny and the entrepreneurial journey I’ve been on for the past 10 years. It’s hard to believe I’ve been in this field for 25 years, and I recently added birth and postpartum doula services to my repertoire in 2020. The freedom that comes with being a business owner is incredibly fulfilling.

However, there are moments when I reflect on what it would be like to have a regular job. Just the other day, after a long day of caring for a toddler, I sat in my living room, enjoying a rare moment of quiet. The sun was setting, casting a warm glow through the window, and I took a sip of tea, considering my day. It was busy juggling different clients and dealing with last-minute schedule changes. Read more>>

Celina Mendoza

Yes, I am happy and proud to be a business owner. It’s not all rainbows and butterflies—while I’m my own boss, it can be incredibly challenging at times. There’s a funny saying that goes, “I traded my 40-hour week for a 100-hour week,” and it’s true! The hours can be endless, working from morning to evening, around the clock. But even with all the hard work, there’s still so much joy in it. The best part is that I’m able to be present for my family, which is something I cherish. Read more>>