Being a business owner isn’t easy. There are amazing highs, but the lows are often quite intense as well. Somedays it feels like the problems never stop – regardless of how much success you achieve. The problems just grow, evolve, morph. So we asked business owners if they sometimes wonder what it would be like to just have a regular job and have shared some of the highlights below.

Sydney Cook

This is such a loaded question. I think people tend to have a lot of preconceived ideas about business owners because sometimes it looks like we have the freedom to work (or not work) whenever we want. Truthfully, before owning my own business I thought that as well. While that is true in a sense, there’s also never a time where I feel like I’m not working or on call. Every single family trip or vacation quickly becomes a work trip. I often reach for my laptop before even grabbing my keys as I walk out the door no matter where I am going. I’m up before everyone trying to get as much focused time out of the way, and up late at night wrapping things up before the next days wolves are at the door. Sometimes I do wonder what it would be like to have a regular job, I feel like I’d certainly be able to be more present with my daughter. But on the other hand, I am building something generational here and I know that putting in the work and dedication now is going to allow me the freedom and flexibility that I’ll want and need in the future. Read more>>

Lauren Hall

Owning CairbNb LLC brings both joy and challenge. The freedom to set my own schedule and grow my business is incredibly rewarding, but there are times when I wonder what it’d be like to have a regular job with clear boundaries. The last time I had this thought was after a hectic weekend managing last-minute bookings. I was exhausted, standing in one of the rentals, thinking how nice it might be to have a predictable 9 to 5. But after reflecting, I realized I wouldn’t trade the flexibility and sense of accomplishment from building my business. Even during stressful times, the rewards of entrepreneurship—control, purpose, and growth—outweigh the appeal of an easier, more predictable path. Read more>>

Taylor Cezanne

I’m extremely happy as a business owner and I would not choose to have a regular job again, but I’d be lying if I said I never think about what my life could be like if I clocked out at 5pm. There are days where things feel overwhelming, and my mind wonders what it would be like if I could show up, clock in, and clock out without all the added pressure of making decisions and thinking 5 steps ahead. I had one of these moments just a few days ago. I was in the middle of juggling multiple projects, planning content, managing my pipeline and brand deals, and wrapping up details on my new puppy guide. On top of that, I was behind schedule on a very important project. I remember sitting at my desk and just thinking “would I be happier having a job that I could clock out of and just forget all of this stress?”. Read more>>