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.

Ashley Corral

I started my business about 3 years ago, when I was newly licensed. At that time, I had been working at massage franchise for a few months and was feeling like it just wasn’t for me. Read more>>

Raven Steward

In 2016, I worked for my sister running her company. I was responsible for all tasks such as processing her orders, handling customer service emails, inventory, and more. During this time, I was employed at a hospital. Read more>>

Shaq Palmer

I’ve been in business as a Wardrobe Stylist since 2019 I wish I would’ve started my business later with the knowledge I know now. Read more>>

Bill Ross

So that’s a great question. I think the biggest factors impacting my decision to start a business later rather than sooner are my fear of failure and being comfortable with where I was—even though I was not happy. Read more>>

Marissa Gove

If I could go back in-time I would have started my business as soon as the idea had come to me in 2019. I ended up starting my business in August of 2022. Read more>>

Alexandra Papavramidi

I wish I had started my online Pilates business back in 2016 when I left my Pilates studio in France to move to Quebec for my husband’s career. Read more>>

Ronda Walker

I started my business in 2021 I’ve been a nurse for approximately 30 years Being a restaurant owner/ cook is a new career I was 48 going though a divorce and a major health crisis Read more>>

Lela Hinds

I started looking for a location for a Wedding and Event Venue in July 2019. I knew that I wanted a central location with outdoor space for weddings and garden photos. Read more>>

Logan Saxon

If I could go back in time and start my career sooner rather than later, I would have still started it when I did. See, like many of us during the pandemic, I lost my job and really needed something to keep me busy and starting my crochet business did just that for me. Read more>>

Allison Bigaouette

If I could go back, I don’t think I would have started my business earlier. I was 22 when I came to a point of realizing I wanted to pursue photography, before that, I was pursuing nursing school. Read more>>

Alfredo Landazuri

I entered the restaurant industry at the age of 16, and now, at 41, I’ve finally opened a small food trailer catering business back in 2022. Read more>>

Alowe McCants

Oh, diving into the business world was like stepping into a double dutch game at just the right moment. Before launching into being a book-publishing guru, life was already a whirlwind of roles—minister, mom, wife, and motivational speaker, gym manager all wrapped up with a bow of Birmingham charm. Read more>>

Jen Heard

For years, as my young daughter was in school, I told myself I would start my dream business when she graduated college. I didn’t believe I could do it all, She gratuated from Michigan State on a Saturday. Read more>>

Roshan Spottsville

I’ve wondered where I would be if I had started pursuing photography earlier. I remember several instances growing up where I would tell people I wanted to be a photographer and I was always told something along the lines of “That’s a hobby, not a career!” Read more>>