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.

Jose Rodriguez

I started my business about 12 years ago, when I was in my mid 20s. At that point in my life, I had been working in various jobs for several years and was feeling unfulfilled and a bit out my own loop. Read more>>

Joshua Crump

J Crump Productions officially started in 2021. However, I started taking pictures back in 2018 while I was a senior at Georgia Southern University. At the time, I just wanted to be a photographer, and I didn’t have the vision for what my company is now. Read more>>

Celene Estrada

I started with the idea of learning about beauty related services in 2021, back in 2015 I thought of enrolling in school to learn how to do makeup. But I couldn’t do it because I was working full time ad an insurance agent and I had my son Aaron of 5 years old who was very excited about sports, wr have a lot of activities with him, my husband decided to start his own business in 2016 so I was supporting my family for a while it just didn’t seem like a good idea. Read more>>

Latreasha Givens

I’ve been in the beauty industry as a hairstylist, for over 30 years. 7years ago, I stepped out on faith and decided to turn to a Salon suite. 2 years ago I signed my 1st commercial lease and found the perfect building. Read more>>

Tiffany Castagno

This is such an interesting question. At times I wish I started it sooner because I’m grateful for the path I’m on and how I’ve been able to scale up, Mentor others, empower Leaders, teams, and organizations, and support the type of impact I’ve always wanted to make outside of the bandwidth I’d ever have within a traditional organization. Read more>>

Joshua Thompson

It was 2020, the pandemic was in full swing. I was sent home from a job for 6 months. With nothing to do but sit back and think. I was fortunate to still continue receiving full pay while at home. Read more>>

Rebekah Starin

If I could go back in time I do wish in a sense I started earlier, but not in the ways you may expect. In college I went for an Advertising/Public Relations degree and in doing so had a photography class to take. Read more>>

Filippo Nenna

If you are thinking about starting your business, then you’ll be interested in this… I was wrong about a lot of things, and it set my business back about 5 years. I assumed my peers and managers at my corporate job would not like it if I had a side-hustle. Read more>>

Nekeshia Hayes

Things tend to unfold according to plan, whether it’s by fate, destiny, or simply just the events we put into play. Many years ago, I won’t say how long, I started down the path of launching my own business. Read more>>

Caleigh Churchey

Looking into my business now, I would say I started at the perfect timing. Previously, I worked at a daycare and photography was just a hobby. I was rather shy before working at this job. Read more>>

Charlene Walters

If I could go back in time, I mostly wish that I had started my business earlier. I am such a big believer in entrepreneurship and setting your own career goals and trajectory. Read more>>

Darrien Curry

I wish I wouldve started a little later than I did. When I first came with this idea I mainly had good surface level ideas. When it was time to actually start up there were so many small detailed things that i had to learn along the way. So i took a couple losses just to learn. Read more>>

Jamie Lynn

In the ethereal tapestry of time, I sense that the timing of my business initiation was divinely orchestrated. Commencing my psychic venture in my late teen years, guided by ancestral whispers, has shaped a unique path. Read more>>

Rachel Kay

Looking back at my career, a pivotal moment was the opening of my 10 chair salon in Renton Washington in 2019. After 12 years of hustling behind the chair, I felt like I had reached the pinnacle of my career. Read more>>

Alex Strahan

So I started my business after my son was born in 2022. At the time I had my son, I was working at a childrens hospital as a therapist and had plans to go back. Read more>>

Ashley Childers

Really good question! I’d say if I could do it all over again i’d start sooner. I have been a photographer for 15+ years and I only pursued it as a career once covid hit. Read more>>

Clinton Nors

Sooner. The earlier you start the more time you have to hone in on your craft and it gives you room to pivot. Read more>>

Noelle Rhodes

I started my journey to becoming a stand-up comedian “later” in life. Most comedians start in their 20’s but I decided to forgo the obligatory mid-life crisis and jump into something I always wanted to do but never had the courage. Read more>>

Barbados Black

Honestly I don’t think there is a wrong time to start your creative career. If you start sooner you get more time to create but that time doesn’t guarantee success anymore than starting later does. Read more>>

Darrin Archer

I got into acting and filmmaking rather late in life. I was 43 when my wife read a script I had written years before. In fact, I had a box full of movie scripts I wrote while working in law enforcement. Read more>>

Aaron Varnell

To answer this question, let’s start with a somewhat simplified history of my career path. While I was going to college for engineering in Houston, I bartended and worked for a few catering companies on the side. Read more>>

Christine Alice

I learned my first chord on the acoustic guitar when I was 27 years old. A little old for music industry standards. I also was a little old to be living with roommates for society standards, but I usually have this inner voice telling me that I’m behind in almost all my avenues of life. Read more>>

Fernando Fula

I started my journey as an artist later in life. At first, I wondered if I should have started earlier. I was worried about not making enough money as an artist, so I chose a technical job as a designer because I didn’t believe in myself. Read more>>

Amar Bhuee

I wish I started my creative career earlier, but I’ve gained invaluable experiences and connected with incredible individuals along the journey. For over 15 years, I’ve been immersed in the world of art, balancing it with various day jobs to make ends meet. Read more>>

Davie Rickenbacker

Reflecting on the journey, I often find myself yearning for an earlier initiation into my creative career. The realization that every moment holds the potential for growth and expression prompts a sense of missed opportunities. Read more>>

Kristin Ellison

From my first art class in nursery school, I knew that I loved taking materials and making something from them that became uniquely my own. Doing visual art has always been my favorite way to spend time. Read more>>

Tyler McDonald

I always think to the first time I told my mom I wanted to make music. I was standing next to my mother at one of my brothers baseball games. The rustle of the leaves, the crowd talking, and a far away car alarm all came together in my head and I started jamming in my own mind. Read more>>

Steven Pacheco

Absolutely! When you’re working in a creative field, which in this case is writing and podcasting, it can be a really scary thing to take those first steps. Fears that you’re not good enough, fears of criticism, fears of failing. Read more>>

Kiara Swanigan

I wish that I would have started creating much sooner because the freedom it has given me to produce things that help others feels like such an accomplishment, that I can’t believe I lived without before Read more>>

Brenda Garcia Jaramillo

I have been enamored by the glamour of runway makeup and also a spiritual practitioner since I was a young girl. But while thirteen year old me through honestly even most of my 20’s has been very headstrong and determined to accomplish whatever I set my mind to…when it came to my creative and magickal expression, I always felt this intense imposter syndrome. Read more>>

Daisy Orellana

When i turned 25 was when i really decided to commit to becoming a tattoo artist. The learning process has taken a long time and i’m learning every day and i love and enjoy it so much but initially i had a lot of doubts about it because of how much i wish i started my path earlier in life. Read more>>

Taylor Munsell

I absolutely do. There’s a saying about the best time to plant a tree being twenty years ago, and the second best time is now. Of course I wish I had spent more time dedicated to writing when I was younger. Read more>>

Jess Buttermore

There’s no short answer to this question, but it’s a great one and I’m excited to share how the evolution of my life played such a significant role in the evolution of my career. Because before I was a mother, a gardener, a folk herbalist, even before I was a wife, I was a photographer. Read more>>

Timothy Hooper

Back around 2000, I quit my job and decided to be an artist full-time. I was young enough then that I wasn’t thinking about health insurance or retirement. As long as I had a roof over my head, food to eat and art supplies, I felt as if I was a success. Read more>>

Kevin Stock

I totally get where you’re coming from! Looking back, I do sometimes wish I had kicked off my creative painting journey a bit earlier. There’s this entire world of expression and fulfillment that I feel like I missed out on. Read more>>

Ariane O’Day

I went to college to get an art degree. I originally wanted to be an art teacher, but I ended up becoming an elementary teacher and left art to be a hobby. I taught for nine years before leaving education to bartend full time. Read more>>

Jazimane “Jazzy” Maryland

As a business owner now that i think about it, I started my business exactly when God wanted me to start it. Not too late & Not too early, i launched my business July 2020 yes it was during covid but, it was a time where i could fully focus! Read more>>