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?

Montana Martinez

Yes, I am a happier business owner. I do not wish I had a normal job. I had a ‘typical job’ for five years out of college and I like being completely in charge of my own schedule despite the uncertainty in when I will be paid. However doing real estate does come with it’s frustrations. It is a ton of work to be successful, and there have been several times where I have wondered if I had made the right decision for my life and decided moving back to Hawaii and going back to my old job specifically in the first six months because I had zero income with more work than I have previously done. You make thousands or hundreds of calls, get a bunch of nos and finally get someone to say “maybe” to selling or buying a home. Every time I felt like this, I told myself I was too far in to quit and worked harder. Read more>>

Rodney Bowman

If I could do this all over again, I would started my journey of being a business owner much sooner. I have no regrets because I have a good career in banking but the excitement that I feel being my own boss is something special. The experience that I’ve gain working in Corporate America working with a team to achieve a common goal has definitely helped me start my own journey. I know what it is to always put the customer first. Read more>>

Jerry Ware

Being a business owner is a mix of highs and lows, but I’ve found the experience incredibly fulfilling. Running Skylight Music Records and working in the sync world—where music gets placed in TV shows, movies, and ads—keeps me on my toes every day. It’s not easy, but the opportunities to help artists get their music out there, while also navigating the business side of things, is so rewarding. Read more>>

Rebecca Martinez

Yes I am definitely much happier as a business owner compared to when I was working for someone else, 9-5. I never think about what it would be like to have a regular job ever again. I cannot imagine having to report to someone else, get told what to do and where to be, and to be putting my time into making someone else richer. Being an entrepreneur and business owner is a dream come true and I will do everything in my power to live a life of freedom and financial freedom until I die. Read more>>

Sara Sanchez

I often have to check in with myself and ask “am I happy being a business owner and would I like to go back to a 9-5 job?”. The answer always is, no. I would not like to go back. I love being a business owner. It’s not weakness to go from business owner to having a regular scheduled job, but as life is constantly changing we need to know what is going to fit our needs both financially and mentally. This past year has been difficult for many people, both wealthy and not. We often look at the financially well off as being unfazed by a changing economy when it comes to providing for their families and still getting to take that vacation. But thats not always the case. As an investor myself, finding a healthy balance between economy, meeting the needs of my businesses and growing family, this year has been financially challenging. No matter how many hours spent working, nothing seemed to be changing and I would ask myself, would a steady 9-5 be a safer option. Read more>>

Johannah Labissiere

Being a business owner has its own challenges, but I’m much happier as a solopreneur. Oftentimes, when people think of being a business owner they think of all the glamourous parts, such as being your own boss, setting your own hours, financial freedom, traveling, and all the other things portrayed on social media. But they often don’t think about the long hours of work that no one sees, the delayed gratification, the countless risks, the rollercoaster of emotions, the trial and error, and the possible financial instability that comes with business ownership, especially in the beginning stages. There have definitely been times when I considered going back to a regular job because of the stresses of business ownership. One of the main reasons I’ve contemplated going back was due to the financial instability that I faced at the beginning, if you’re an entrepreneur then you know that financial rollercoaster that we all experience. As a business owner, you have high- highs and very low lows. One season your business can be doing amazing and the next season you could barely be bringing in revenue or breaking even. That’s why it’s important to manage your finances well as a business owner. Read more>>

Mary Tindall

Yes, I’m much happier as a business owner than I was an employee. My business has given me full autonomy over my work and life, which is a rare privilege. I can make a living for my family, homeschool my four kids, and work on impactful projects with smart clients and colleagues, all at the same time. Sometimes I can’t believe my luck! That said, I sometimes entertain the idea of returning to a W-2 role. Being your own boss can feel lonely sometimes, and it would be energizing to be part of a team with a strong mission and supportive culture. Right now, I don’t feel the urgency to make any changes. After seven years, owning a business has become part of my identity. I’m content with my current season… but I’ve learned to never say never!  Read more>>

Stacy Gunderson

Being a business owner, especially one running an animal sanctuary like Animal Tracks, is a unique journey filled with immense challenges and rewards. Every day, I carry the weight of these animals’ lives, ensuring they have the resources, care, and environment they need to heal and thrive. But sometimes, yes, I do wonder what it would be like to have a regular job, with set hours and a clearer boundary between work and personal life. The last time I had one of those “what if” thoughts was after a particularly exhausting day. It was one of those scorching California afternoons, about 108* and we were experiencing equipment issues with the sanctuary’s cooling misting systems. My day had started at 5am and would not end until well after the guests had left, animal needs had been met and I fixed the broken system no matter how late that was as tomorrow was going to be another brutally hot day. Read more>>