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.

Al Vargas

As a creative and business owner, you inevitably go through seasons of self-doubt. Sometimes it’s imposter syndrome — that sneaky voice that tells you you’re not good enough or that you don’t really belong here. Other times, it’s the comparison game — watching others seemingly thrive while you feel stuck, overwhelmed, or like you’re falling behind. Read more>>

Unlock Collective

Yes, we are truly happy as business owners! After leaving jobs where we felt constrained and unable to make impactful decisions, starting our own business has been incredibly fulfilling. Being able to help passionate entrepreneurs while building something meaningful on our own terms has made all the difference. What really drives our satisfaction is seeing the direct impact of our work and being able to support small businesses in creating sustainable, human-centered practices. Breaking free to pursue our own vision was one of the best decisions we’ve made, and we haven’t looked back since. Read more>>

Joelle Cipriotti

I am most definitely happy as a business owner, I have two businesses Cip of Joelle and BriJoLNE Assisting and Handling Services. I am able to work on my own schedule and can balance the two different jobs really well. If I find I am low on creative energy, getting out of the studio for a weekend and attending a confirmation dog show helps me refresh my energy and look at my paintings in a different perspective when I come back. Often I do think about having a steady income from a regular job, but then that interrupts the free time I do have control of to work on my paintings. I have had a regular job, I bartended for a winter, but I felt like I had no energy to paint after work, and not doing what my soul absolutely craved to do just brought about drained energy. Read more>>

Tiana Sheppard

The short answer is yes, I’m happy as a business owner, however, it comes with many unexpected challenges. As a part time lash artist with a full time job, it becomes overwhelming balancing the two. It’s been dificult for me to feel movitivated to put effort into my business, and when that happens, it shows. It shows through my booking, my engagement, sales, everything. I’ve had to learn the hard way that despite the many things I have going on in my personal life, I still have to MAKE time to show up for myself and my business. The biggest lesson I’ve learned is to always remember my why, which is: I’m building this business so that I can provide the lifestyle I dream of for myself and my family. Read more>>

Alex Lindsey

As a business owner approaching 5 years of whiskey production, I frequently discuss with my partner whether this is truly worthwhile. The inherent risk, insecurity, stress, and responsibilities all become a weight at some point, and they can be extremely heavy at times. I also wonder if we have the skills and abilities to remain competitive while organically growing our brand; can we actually accomplish our goals? Some days you just wake up and go back to work because that’s all you know how to do to survive. Needless to say, there is always doubt. Read more>>

Dr. Morissa Schwartz

I’m definitely happier as a business owner, although I’ll admit there are moments when a traditional job feels tempting—steady paychecks, clear schedules, and maybe even the occasional leisurely coffee break.

Recently, I found myself seriously considering what life might be like with that kind of structure: predictable income, benefits, and maybe even weekends without email. But the more I imagined it, the more I realized what I’d lose: the freedom and flexibility that entrepreneurship allows. Read more>>