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.

Nicole Davis

I sometimes wonder how my life would be different if I had started my creative career earlier. I have always been creative but growing up I didn’t see it as a career option. I chose to become a Special Education teacher instead. I taught for twenty-one years in public school systems. By middle age, I longed for something different, but felt stuck in the life I had built for myself. Read more>>

Violet Foulk

Back in my early twenties, after graduating with a music business degree, I lived in NYC and did publicity at a record label. Music was my whole life. I started bringing my film camera to shows just for fun, and I was enjoying taking photos of musicians onstage so much that when I ended up leaving that job, I pursed photography, although it was strictly live music for at least a year before I started taking photos of my family and friends. Read more>>

Jen McFarland

I registered as an LLC on February 28, 2022. One week later I gave my boss three months’ notice. I finished up my current projects and documented my work for the next person. And on June 6, I went to work in my guest bedroom for my first day at Marit Digital. If this all sounds well-organized, it was, and that’s because this idea of having my own business had been in my head for many, many years. Read more>>

Sonya Bertolino

I am a firm believer that timing is everything. Had I tried to start my business right out of college, I do not think it would have been the success that it is today despite knowing that I’ve always wanted to be a photographer. And had I waited any longer to start it I’m not sure I would have ever gotten around to it and would have let the opportunities slip by. Read more>>

Nina-Simone Jones

I started working for myself summer of 2017 and around this time I was just wrapping up my first semester in college. I would say after my first year that’s when I really decided that I wanted to start selling hair and selling wigs to clients but the thing is I didn’t know how to. While I was in school, whatever I learned I would just implement that into my business. Read more>>

Daye’Jah Coates

I started Daye’JahVu Aesthetics (Daye’JahVu Minks at the time) as a college freshman in November 2017. If I could go back in time, I would definitely start my business sooner. I spent a great deal of time putting in hard work for different jobs as a teen, and although I gained some great customer service skills, I can’t help but to think of the things I could’ve accomplished had I had the entrepreneur mindset that I do now. All in all, I’m grateful for the process! Read more>>

Ashley Shells.

I first started my business as a braider in middle school only then I didn’t have a business mindset to even look at it like a business. I graduated high school as a licensed cosmetologist and went into a full service salon at Salon LaRon. I then still didn’t understand the grind it required to grow my clientele and social media wasn’t a big thing back then so it would require footwork, going out there and marketing myself personally and of course patience but I had a kid and needed consistent income right away and went into banking leaving the salon for 12 years. Read more>>

Ugochi Onyewu

I started a podcast in 2018 celebrating women of color with connections to Igbo culture. The Igbo tribe is a tribe in South Eastern Nigeria. The following year I wrote a book, which I self-published at the beginning of 2020.
Then the pandemic hit, and with a full-time job, burnout became an issue. Read more>>

Rona Shirdan

Growing up in the 1970’s, the expectation was that you went to college, graduated, and then got a professional job with a good salary so you could raise a family. You continued working at the same job until you retired. Since the standard path was predetermined, those who deviated from the plan were considered “unsuccessful”. Like most, I chose the road to “success” and attended a prestigious college then continued my career journey. Read more>>

Rachel Exum.

I started my self-taught photography business about six years ago, and I definitely wish I had started sooner. It took me a very long time to figure out exactly what I wanted to do with my career, and it all started with taking pictures of sunsets. My escape from anxiety, stress, and depression was going to different areas at the time and watching the sunset. I only had a camera phone at the time but it didn’t matter to me, I just loved taking pictures. Read more>>

Stephanie, Stephanie Torres, Manning

We officially launched our business in the spring of 2020 and it could not have been a more perfect time. Rewind 20 years back. It was like love at first craft. One of us from the Midwest and the other from the East Coast, we were brought to the West Coast by our now husbands, both born and raised in Bellingham, Washington. Back in 2002, bonded by our names (Stephanie and Stephanie!) our creative adventures bloomed, beginning what would become a lifelong friendship. Read more>>

Mont Mccloud

So I have been making and putting out music since I was a junior in high school (2011). The main thing I wish I could change over the years is Consistency ! Over the years ill notice myself put out a bunch songs, or a consecutive visuals or even a mixtape or album. Then I find myself taking these long breaks could be months sometimes years before I put out content again. There has even been times where i caught a great buzz or a wave and still could not keep up. Read more>>

Azucena Teran

Sometimes I regret not becoming a makeup artist sooner, but when I reflect on my life I see that God had everything planned out for me. All things happen for a reason, and I am thankful it happened this way. In 2020, I bought my very first house at 22 years old. I earned my Bachelor’s Degree of Business Administration in May 2021 and received an amazing job offer right after. Read more>>

Treviana Walker

If I could go back in time I would have started my career as soon as I graduated in 2015. Following a year after graduation, I remained in town and worked as a sales leader in a retail store and tailored garments on the side. I would have started my LLC sooner because the sewing techniques and everything I learned about fashion was fresh in my mind. Year 2021 pushed me to pursue my dream and quit my full time job. Read more>>

Sarah Bentley

I have always loved singing, but in college I started to learn to play the guitar because I had a false belief that singing wasn’t enough. I thought I needed to play an instrument to be a musician. I also feared that classical training was superior to what I did, which was just singing from my heart. These biases really limited my growth as an artist. In my early 20s I was in a band (TreeRoot – roots, soul, folk) with some guys I worked with. Read more>>

Rachel Lynch

I wish I would have started sooner. I held myself back for many years because I didn’t think I had what it took or the skills needed to be on the microphone and do private events alone. I turned opportunities down for years because of self doubt. Who knows where I’d be now if I had started almost 8 years sooner. This business is about connections and relationships. For every “yes” there is a world of possibilities. Only god knows what changes I missed by not having the confidence to start sooner and stop saying no. Read more>>

Michelle Packer

My passion for making began beside my grandmother on our front porch. I was 7 or 8, and she was crocheting granny squares. Watching a little hook and a ball of yarn turn into colorful squares, and then blankets, just fascinated me. I taught myself to crochet from a book (my grandmother didn’t have the patience) and asked for knitting lessons for Christmas when I was 10. From then on I was never without a project. Read more>>

Chata Harris.

If I could go back in time I definitely would have started my creative career sooner. When I 1st started out in the beauty industry I was very scared to be creative. I didn’t want to be looked at as weird. But soon I realized embracing my individuality in the beauty industry was so Freeing beautiful and inspiring to myself and others. I feel that whenever you start doesn’t matter essentially we all kick ourselves for not doing things. Read more>>

Granny Wowzers

Since I learned how to write , I have been writing stories and poems . I never thought I could actually make money from it . So it was always a hobby not an income . Same with music I always loved and daydreamed about being a radio personality. Even use to make my own music playlist and mix tapes . Back when it was still on cassettes . Then learning to burn CD’S, was a whole game changer . Funny that in my late 40’s , I would be known for both writing and radio . What a huge difference from hobbies and daydreams . Read more>>

Stephen Cameron

I wish I had started sooner. Around seven years ago I was working in a printer parts factory, felt I had very little purpose, and had few encouraging voices around me. I felt stifled in my creativity and wanted something new, so I took a risk. I watched some videos, got some flowers, and tested my hand at floral design. Designing clicked. Something about arranging florals resonated with me. I sought out every florist I could find asking if they would take an apprentice, and after a lot of knocking a door opened. Read more>>

Jaquan Carvin / CarvinsWay

I wish I would had started sooner , I had this same vision since high school EARLY ON before it was so many influencers . But at the time I just ain’t have the right people around me. Also I had videos going viral back in 2013 before going viral was a thing but at the time I really ain’t like the attention every where I went people knew who I was so I kinda backed off and let the fame die off “ which was one of the worse decision of my life” Read more>>

Matt Cooper.

Despite being a musician since age 10, when I got my first guitar, and having taken a few video editing classes in high school, I wasn’t in a career that had anything to do with either until I was 31 years old. It was January 2021, at the height of the pandemic, and I was spending 50+ hours a week operating a forklift at a warehouse job that had little to no upward mobility. Read more>>

Piper Punches.

My creative career started in the summer of 2013, although I’d been writing since childhood. I’d always had creative aspirations and dreamed of becoming a published novelist. Yet, as cliche as the story is, I’d always put it off for one reason or another: I had little kids. My writing needed to be better. I didn’t have a publisher interested in the story. Read more>>

Shannon Meinking

When I think about the past, I regret how long it took me to pursue my passion for artwork. When I became a stay-at-home mom I lost my identity. It took a complete change of my routine for me to realize I can make time to create for myself. Prior to this, I found myself making excuses, and my love for creativity was never prioritized. I let society convince me that artwork wouldn’t create the cash flow that was needed to sustain a comfortable life and because of that, Read more>>

Rahmar Duffy

Wow, without a doubt I wish I would’ve began waaay earlier. Funny enough whenever I see those, “What would you tell your younger self?” post’s my answer is always the same- “Start DJ’ing now!” My official journey as a DJ started around 2016 however, I think was I was always- sometimes unknowingly working towards being involved in music. Read more>>

Julie McLellan.

I lack patience, I admit it. My younger self had even way less patience than I do now. I tried to start my art career many times and had a few successes, but did not really stick with it long enough to gain any momentum. I loved being in the classroom with 20 plus energetic children learning, discovering, creating and making a mess, and then doing it all over again 6-7 times a day for over 20 years. They fed my energy and I fed theirs. Read more>>

Christine Riutzel

I come from a strange background. I grew up in an Evangelical Fundamentalist cult. (Think Duggar family) which wasn’t the kind of environment to encourage creativity. From a young age I thought my only purpose was to get married young and have as many kids as possible to further the Kingdom of God. There was never talk of a potential for me to have a career in the arts, or a career at all. Read more>>

Victoria Jackson

I have always been an artist but becoming a tattoo artist was never part of the original plan. I began my professional artist journey at the University of North Texas, I received my Bachelors of Fine Art in Studio Art with a concentration in Drawing and Painting. My goal was to become proficient in portraits and realism. During that time I began getting tattooed to cover visible self-harm scars I wanted to stop receiving negative attention for. I shortly after began my tattoo apprenticeship under Rich Session in 2011 while still in college. Read more>>

Hannah Serapiglia.

I’ve always been a creative soul. As a child, I was constantly drawing, writing, singing, and creating things. Like many of us, as I grew up and prepared for the adult world, I was guided towards “traditional” career paths. I was constantly told by people in my life that the arts make great hobbies, but terrible careers. I did try to swim against the current in my college years, where I studied music and songwriting; but by the time I reached graduation, Read more>>

Patricia Regier

Part of me wishes I had started earlier for various reasons, but I believe that every experience I have had has led me to this point. I started my business 5 & 1/2 years ago, which was the perfect time. However, this journey requires a lot of believing that what is around the corner, even though I can’t always see it, will be amazing. Read more>>

Jada Samone’

If I could turn back the clock, I certainly would have started my career in TV/Film & Modeling when I was a child between the ages of 8 and 10. I began my TV, Movie and Modeling career in January 2022. I was at a place in my life where I decided to just up and go where the opportunities reside. I was in a place where I worked full time and frankly that’s not for me and that’s not who I’m meant to be. Read more>>