Almost every entrepreneur has had to decide whether to take the leap now or wait– perhaps they wanted to acquire more capital, experience or connections. Given how common this predicament is, we asked some successful business owners to reflect back on whether they wish they had started sooner or waited for a better time.

Allyson Blankenburg

I started my business in 2018 and I wish I had done it 10 years before, at minimum. I always knew I loved photography but never had the courage or the skill to start a business. Then I started having babies and it was just a hobby at that point. Read more>>

Rachel Ford

I wish I had started business sooner. But it makes a lot of sense why I’m starting now. When I got my LLC back in 2021 I originally wanted to run a healthy vending machine business. After the death of my father I really felt lost, and I truly lost control of my business.  Read more>>

Mally Becker

I wouldn’t wish away any part of my life. So, no, I don’t wish that I’d started writing sooner, even though I didn’t begin until I’d turned fifty. After The Turncoat’s Widow, my first mystery, came out, a podcaster complimented my writing. Read more>>

Author Khemistri J

That’s a great question and one that I’ve thought about often. If I could go back in time, I believe I would have started writing much sooner. I’ve always known that writing was my passion, but doubt, fear, and worrying too much about what others might think held me back. Read more>>

Alli Thomas

If I could go back in time, I think I would have started my business, Rooted Hair Shop, at the same time. I started Rooted Hair Shop after accumulating over 18 years of experience as a stylist and colorist in Raleigh. Read more>>

Sarah Schmidt

Three years after leaving my full-time job in pursuit of more freelance, I started paying my friend Ian to help me finish jobs I couldn’t handle on my own. From late 2018 to early 2019, we worked on at least 3 distinct jobs together and started to feel confident pitching on a handful of others. Read more>>

Meagan Forbes

If I could go back in time, I would 100% start my full time photography business WAY sooner. I started getting paid (veryyyy little) for my photography maybe 13 years ago, but always kept it as a side hustle. Read more>>

Becky Jo Harris

At one point I did wish that I had started my acting career sooner. When I was younger and found out Hollywood was a thing, I longed, with every part of me, to be a part of it. I would daydream of acting on a tv show and walking on the red carpet at award shows. Read more>>

Queen Ajima

I’ve thought about this question before over the years, and I can confidently say that I started my creative career right when I needed to. There was an opportunity I had when I was maybe 4 or 5yrs old, when my parents took me to my first photoshoot. Read more>>

Jon Fischer

My photography journey started out of a desire to be outdoors more. I grew up exploring the outdoors of East Texas where my parents had a lake home, fishing, boating, walking the woods around the home most weekends and summers. Read more>>

Nicole Pouchet

I graduated from college with an English major, drama minor, and film & video certificate. After graduation, I worked in several professional theatrical productions as lighting tech, stage management, props, house manager, anything I could do to get in the industry. Read more>>

Ella Pullicino

I was not a kid who grew up in music, well, not in the traditional way. My parents introduced me to the world of dance when I was very young. From the age of 5, I was spending hours at my dance studio, learning everything from ballet, to jazz, contemporary, and even hip-hop. Read more>>

Zhijun Song

If I could go back in time, I wouldn’t change the timing of when I started my creative career. The journey I took, beginning in college when I was an art school student, was crucial in shaping who I am today. Read more>>

NunAfterHours

I believe I started my music career right on time. I started a little late in the game, but I’m glad it unfolded that way because my mindset would’ve been way different if I had started earlier. Read more>>

Ronald Leonard II

If I had to be honest, now I can appreciate the time it took to get where I am and be comfortable & confident in my abilities. If this was some years ago, I bet my answer would be different. Read more>>

Annette Chaisson

I sometimes wonder what my career would look like now if I had started doing makeup earlier. I actually have a degree in Political Science and planned to go to law school. However, that went out the window as soon as I graduated and moved to L.A.  Read more>>

Mychael Zulauf

I honestly don’t know. I think my immediate, gut response is yes, of course i wish i had started making /publishing books sooner. My press, akinoga press, would have that many more books out in the world, and i would be that farther along in the development of my editing and design skills. Read more>>