The uncertainty of entrepreneurship causes many entrepreneurs to put off starting their business. For others, losing a job or other economic hardships push them starting their businesses earlier than expected. In our conversations with thousands of entrepreneurs we’ve seen so much variety in when, how and why people started their business and so we wanted to share a wide variety of views and reflections on the question of whether these folks wished they had started sooner or waited longer before starting their businesses.

Tabitha Larke

Looking back, I honestly believe I started exactly when I was supposed to…even if, at the time, it didn’t feel like ideal timing. When I officially launched The Glam Suite Beauty Co. in 2016, I was a single mother, recently terminated from a job at MAC Cosmetics after being pushed into a management role I didn’t truly want. I had bills, a baby, and a choice: either fold or bet on myself. I chose the latter … and that leap of faith changed my life. Read more>>

Katheline Jean-Pierre

I wish I had started my business sooner. Back in 2018, my manager at Google Anders Mortensen during one of our career conversations told me what he saw as a strong career path for me. While I was obsessing about getting promoted every 2 years at Google to get to the top, he saw the power of the leadership program I had started in 2015 that had caught up like wildfire. Read more>>

Rebeckah Blossman

I’ve spent a lot of time pondering this question. Since starting my business, I’ve become a much happier and healthier person, and I often wonder if I could have reached this point earlier in my career. Ultimately, I believe every step I took was essential to the personal and professional growth needed to get to where I am today. Read more>>

Khristee Rich

Interesting question. I had never thought about this before. It really wouldn’t have been possible for me to start my business earlier. I was sick with a debilitating chronic illness for fifteen years. My illness was all consuming. It was even hard for me to work. But eventually I got a full-time job working at a contemporary art museum in Connecticut. Read more>>