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.

Chris Henderson

You know I do wish I would have started my business sooner. I started in June of 2020 during covid, and I mean with covid and everything it was a little odd to start something. Read more>>

Clover Haugerud

Although I’m happy with how things turned out, and I’m not one to “wish” for different outcomes or get caught up in past thinking. I do believe that something most people could benefit from is JUST STARTING even when they don’t feel ready. Read more>>

Brian & Alisha Echol

Definitely sooner. We had always known that we would be business owners. Both my spouse and I had completely different careers prior to starting our catering service. Read more>>

Nicolette Cochran

I started my business last summer, June 2023. Up until that point, I had been working at agencies for most of my career, and I was feeling totally stuck. Read more>>

Susana Sordo

I wish I had started my business sooner because the most important thing about it is that I discovered my passion. My business wasn’t planned or wished, I had the fortune of starting it without an effort. Read more>>

Charita Snow

If I could go back in time, I honestly wouldn’t change a thing. Everything in life has its own timing and mine just so happened to have started right before Covid. Read more>>

Mathamatics Patterson

Starting a business earlier in life is something I wish could have happened. Back when blogging was a thing I wrote for a magazine named 21-7. Our slogan was “for the artist who need three hours of sleep”. Read more>>

Valerie Vedral

I started The Vulgar Vegan in 2021 after many years of dreaming about opening my own vegan restaurant or cafe. Several years before business was born, I actually had baked cupcakes for a wedding. Read more>>

Kenny Bailey

Being impatient in business can be an asset but also can lead to a harder road to travel. In hindsight, my impatience to open a business as soon as possible made my road a steep climb. Read more>>

Tiffany Vaught

I started my business when I was 26, so I don’t wish I’d started it sooner…I wish I had started running it like a business sooner. Working on my business instead of in it. Read more>>

Jessica Ullyott

I think I started my business at just the perfect time. I had been a teacher from 2010-2020 but decided to take time off to be a full-time mom. During an exercise class in 2022 with some other other moms, I was asked what was the most challenging thing I ever accomplished. Read more>>

Millie Finch

My husband, charlie and I started our business in 2018. It began as a small homestead business. We were planning to sell fresh eggs, veg, fruit. We addition we were brewing kombucha and roasting coffee. Read more>>

KEYONDRA & KIMBERLY LOCKETT

We believe we started our business at just the right time. Keyondra and I aren’t new to business. We previously owned an eyewear brand that we had to dissolve because we didn’t know how to market and get customers and our website developer no longer had time to devote to making changes to the site. Read more>>

Michael Palmer

I would’ve started younger. It would’ve allowed me more opportunities and gain more stage experience with other well rounded musicians and to be able to reach out to the younger musicians and be able to mentor them. Read more>>

Rin Varga

This is an intriguing question for someone like me who’s always known she wanted to be an artist from childhood, but has had several different “starting” points that make me wonder when I’ve truly begun. Read more>>

Ashley Perkins

Reflecting on my journey, I find myself not wishing I could have done things differently, but being curious on where I could be now. I was an art major in college, however, upon graduation I found myself veering into the hospitality industry, working on cruise ships and in hotels for several years. Read more>>

Bram Jongebloet

I do sometimes wish that I had started my process sooner. I always believed it was impossible for me to learn, but as they say, if you never try, you never know. Read more>>

Charlotte Canion

My journey started when I was young, but it took over 60 years to realize what my real purpose was going to be. I have always been a free spirit and thought my mission was to be a mother and raise my children. Read more>>

Lila Rose

I have sometimes considered it, but I firmly believe everything happens for a reason and when it’s meant to happen. The confidence I have in my work today is different from what I had before; it does take time to gain confidence in your artistic voice. Read more>>

Robin Hohweiler

I would like to have started my creative career much earlier. Although I kept my hand in writing throughout the better part of my adult “regular job” life, it was usually confined to writing analytic reports, some scientific reports, correspondence, newspaper writing, and the occasional (very occasional) short story. Read more>>

Lynn Heinz

I think there’s two answers to that question for me. I was interested in the arts as far back as I can remember. I studied art all through high school and community college. Read more>>

Malcolm Minor

To be honest, I wish I had the right people behind me to have started my creative career sooner. I started acting at 8 years old. I had the opportunity twice to try and move forward in this business. Read more>>

Angel Ramon

Sometimes I do wish I started my creative career sooner. With what I know now, I could’ve learned ten years ago. I was working a decent job with good hours. Read more>>

Ida Rezaee

I regret not starting sooner, but I do not fault my past self for any perceived lack of judgment. I understand that we make decisions based on what we believe is best at the time. Read more>>

Henri Pearson

I recently released my first ever single “Stormy Weather” aged 28, I have been performing since I was 5 but never had an opportunity like this. Read more>>

Shanna J

I definitely wish I had started my creative journey much sooner. I can only imagine where I might be at this point in my career if I kept consistent and truly put my best foot forward from a younger age. Read more>>

Glory Harris

I wish I had started my creative career sooner! I’ve always loved photography however, I wasn’t in the right environment/networks to nurture my passion for it. Read more>>

Jocelyn Krodman

Looking back, as unhappy and lost as I felt at the time, I feel very thankful to have worked jobs in the service industry and a traditional 9-5 office job before veering off onto a path of self-employment. Read more>>

Colin Dale

This is a tough one. Lately, I’ve almost wished that I had started later, because as a young person it’s difficult to get people in the film industry to take you seriously. Read more>>

Logan Cole

I absolutely wish that I started content creating earlier! It is so fun and really allows me to explore myself in more creative ways! It truly shows you how multifaceted you can be. Read more>>

Warren Hart

Despite having started drawing at the age of 5 and acquiring graphic design skills 24 years ago, it wasn’t until 15 years ago that I truly invested in myself and began selling my art. Read more>>

Emily Webb

As a young child I showed a talent & love of all things creative. I would make up stories to tell friends… I would always be creating something….I adored art class… & was so curious about all things creative. Read more>>

Flex J

Honestly, I feel like I’m right on time. Who’s to say too soon or too late when the music is timeless? If I really told y’all when I wrote Next Stop Hollywood, yall would be sick. Read more>>

Ashley Baker

My initial answer to this question was yes. But after I thought about if for a few minutes, I’ve changed my answer. No, I do not wish I’d started my creative journey sooner. Read more>>

Sofia Damianovich

I started my creative career at 28! Looking back I wouldnt have started it sooner, there was still so much to learn from the different work enviroments at my current job. Read more>>

Clark Lawlor

That’s a good question. My situation is a bit unique, having started over as a composer in my 40s. I had basically given up on my dream of being a composer through my late 20s and 30s, but you never know where life will lead you, and now here I am again. Read more>>