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.

Deuce B

I’ve been recording music since my freshman year in high school and built a pretty decent fanbase at a young age. However, I didn’t decide to invest in myself and take music seriously as a career until just a few years ago. I think taking it seriously earlier and taking advantage of the fanbase I built would’ve put me in a better place career wise, but at the same time, I’ve learned a lot creatively and would rather be successful with my current sound than with the sound I had back then. Read more>>

Kaitlin Amanatullah

If you were to ask me this a year or two ago, my answer may have been dramatically different, but I wouldn’t change a single thing about the timing of my business! I started back in 2018 after working in the industry for a couple of years. I’m incredibly grateful to have started when I did, because it means I got a solid year and a half to familiarize myself with entrepreneurship before Covid hit and the chaos ensued! Read more>>

Kimberly Kirt

I feel that I started my business at the exact right time. I had a few years in the “corporate world” to learn that it absolutely was not for me, but also HOW an agencies and creative teams work. I was lucky enough to work for a renowned Dallas Marketing Agency as well as an international software company, so I learned a lot along the way! Read more>>

Cristina Soto

Not only do I wish I started my business sooner but I wish I gave it my all from the beginning. Part of not doing so was fear of not making it and looking silly but another part of it was still having an 8-5 for 5 years while running a photography business. I opened up my social media pages and started my website in 2017. I was a medical assistant from then until I quit this year in January 2022. If I would’ve cared less what other people thought and had the guts to really put myself out there more, I would’ve been been a fulfilling life a lot sooner. Read more>>

Whitney Marshall

I did not start my Photography business until Fall of 2019. My husband and I moved to Colorado Springs, CO from a small town in western Kentucky in the summer of 2019. I always had an interest and love for Photography, but due to my focus at the time being on my academics and graduating, I never actually took the time to pursue Photography and try to make a career out of it. I spent a total of 6 years working hard to obtain my Master’s Degree in Speech-Language Pathology (SLP). It wasn’t until the Fall of 2019, after the Summer when my husband and I moved to Colorado, that I connected with another Photographer in Colorado through social media. Read more>>

Desilin Drayton

If I could go back in time I wouldn’t change nothing honestly. I believe I started my business at the right time in my life. Yes I do think we’ll what if I had started earlier on would I be farther then where I am now? I would be lying if I did say I don’t ask myself those types of questions. But I believe everything happens for a reason. I started at the right time because who knows what I would have went through if I started to early. Mentally I wasn’t at the right place to even carry a business let alone be a business owner. Read more>>

Monique Williams

As a creator, my artistic activities have run the gamut from publishing to painting and producing events. Somewhere in the mix was my enduring passion for fashion which included a penchant for purchasing pieces – lots and lots of vintage and secondhand goodies. In 2019, I parted ways with yet another group of creatives who did not understand me or my vision and were stuck trying to implement ideas I’d had a decade before. I needed new energy, a new focus, and, most importantly, a new team of forward-thinking artists. Read more>>

Melody Wilson

Sometimes I think back and wonder how life would have been if I started pursuing life as a creative sooner but then someone told me that now is my season and I am in the right place at the right time- for me! I have had multiple jobs, too many to count, that was either bearable with horrible bosses or great people around me but a horrible job. I didn’t know if I could make a living as a creative and thought, wow, this is truly the definition of a starving artist. The moment that I finally said enough is enough, Read more>>

Kristen Newsome

I would probably say I wish I had started a business sooner than I did. I waited to become an empty nester before focusing on my dream of becoming an entrepreneur and pursuing my vision of creating a mentoring program for young women. I am currently looking at expanding that entrepreneurial vision to include curriculum development, books, professional development courses and executive coaching for educators, nonprofits and youth-based organizations that serve BIPOC students. Read more>>

Roshale Thompson

with the mentality of graduate from college, obtain a great paying job, and work my way up. However, that’s easier said than done. I spent countless years in college earning both my bachelor’s and master’s degrees and studying as a doctoral student. What I found out is no matter how much education I obtained, I would never be good enough or valued by an employer. Every day, I was faced with many challenges and stumbling blocks regardless of how hard I worked in my career. By nature, I’m an ambitious go-getter and overachiever, so I love good competition. Read more>>

Beverly Carlson-Bradshaw

I sometimes do wish I had gone to college for a Finer Arts Degree and at least taken a few years out of high school to study with a mentor and seen if I should pursue the one passion I had. At that time I was so naive and felt I could never make money as an artist so instead I got a job and never quit working until I retired at 60 and then started full time. However, I did take night time classes off and on through the years. Painting and drawing from an early age it was the one thing I felt I had talent for and kind of wish I had pursued it earlier. I feel I only have so many years now to do as much of it as I can now. However, I did work as an Interior Design which was a creative outlet to some degree and I did that for years before retiring and moving to Arizona in 2018. Read more>>

michelle cortez gonzales

Although I didn’t change from one extreme career path to another, I feel my creative journey is a unique one that leads an avant garde path, where I have experienced the fruitfulness of it later than most. And I regret nothing. Do I wish I had the nurturing and guidance to make wiser decisions? Of, course, but everything I have experienced has led me to this great time in my life and there is no looking back. Read more>>

Yukako Ogawa

I started this journey at age of 35 with no musical background. Because of my age, I had to spend more time and energy. If I started it at much younger age, it would be very easy for me. Read more>>

Kendra Jones

Well first off I have to say I believe energy is precious and I don’t think it’s wise or beneficial to invest it in wishing. So there’s that. But secondly, it seems people tend to mistake the public part of an endeavor as the beginning or ‘start’, and that couldn’t be further from the truth. My journey to a creative career started the first time I picked up a pen as a child and wrote, “Once upon a time”. So no, I don’t look back and wish I’d started this phase of my creative career sooner because everything up to this point brought me right where I’m supposed to be. Read more>>

Quinn Elliott

The artistic calling has been present all my life, but I never thought I had “it” – whatever “it” is. From my teens onward I dabbled in creative writing and photography, but never anything else because I was convinced I lacked some innate talent for more. In late 2013, I left a job I’d had 10 years and was bereft- my sense of identity was so wrapped up in that career. My partner gave me a book on collage for Christmas soon after, and I knew it was time to stretch my wings. And thus the journey began. My friends and family immediately loved the work I was doing and I felt a sense of fulfillment that had been missing. Read more>>

Rebecca Robb

My journey to becoming a fine artist is rather unusual. I thought I had to jump through certain hoops before I could be a professional artist. Knowing everything I know now, I see how I could have launched my career as an artist much sooner than I did. Let me start at the beginning. I always knew I was an artist as early as I can remember because my family would be very impressed and praise me for each art piece I created. However, because my parents were missionaries, they did not have the means to invest in their blossoming artist. My artistic talents were never nurtured or developed academically. Read more>>

Shay Chenette

Choosing to be an artist as a career is a risk in itself…then to choose to perform while painting…that is just insane! Or so I have been told. Hi, I am Shay Chenette, a visual and performance painter on a mission to bring my audience into the creative process through speed painting, live painting shows and events. I have been into the arts for as long as I can remember and professionally since 2015. I am an oil painter at my core but also use mixed media, digital art, acrylics and exploring non-traditional surfaces like wood and metal canvas. Read more>>

Courtney Griffin

I started my artistic journey as an adult in 2018 — when I was gifted my first bullet journal by my husband. I began with illustrations in my bullet journal, which seamlessly led to sketchbook work and my first commissions with friends and friends of friends. My practice has evolved into one of non-subjection and intuition guiding my process. Read more>>

Barbara Nickless

When I was three years old, I had my first of what would prove to be many eye surgeries. The hospital was dreary, visiting hours were restricted, and I was bored and lonely and scared. That was when I had a flash of genius! I took all the get well cards I’d received, turned them over to their blank backs, and began writing. I didn’t know the alphabet. I couldn’t yet read. But I could imitate my mother’s cursive writing and make up stories to go with my squiggles. Read more>>

Jack King

I’m 71 (about to turn 72). While I wrote a ton of advertising and marketing copy during my lengthy business career, I only started writing as an author in 2007. It took four years to get my first book published with a traditional royalty publisher. I’ve gone through one literary agency and three royalty publishers, in total. My new BLOOD Crime Thriller series is with a small traditional publisher and my three earlier books are Indie published through IngramSpark. Read more>>

Karl Hibbert

This past April marks 11 years since the inception of Fortunate LifeStyle (FLS). In 2011, while a sophomore in high school, FLS was curated alongside classmates Ashley Hagopian & Tyler Harris through our personal influences and innate creative passion. In 2013, after distance made business hard for us 3, I took Head-chair position of the brand and never looked back. Having developed the clothing line in early in high school, none of us had access to significant capital to invest in bulk shipments or equipment so we were left ordering one off’s online for personal wear around school. Though we weren’t ready to sell any product at this stage, this strategy helped build social stature in the hallways and in town. Read more>>

Sarah Zabel

I don’t think I would have started my business later. My business was open in 2018. Timing in life is intuitive. When I started my business I new it was the right time for me. Although my business certainly brought my life full circle. As a lawyer I was in private practice which included being a Circuit Civil and Family mediator. In 2003 I became a Miami-Dade Circuit Court Judge for nearly 16 years. Sometimes I think had I stayed in private practice where would I be now as a mediator. Read more>>

Agatino Zurria

In hindsight, I have to say that I’ve learned this about myself: Everything I like or want comes to me at a later time than I expected. This is my tempo, the way I move and my mental process creates that way…it takes time, so there’s no use on rushing things. I learned I wanted to be a filmmaker very early in life. I was just learning to read and write when that happened, and I was watching a film with Barbra Streisand, I think it was Up The Sandbox, in which she played someone who woke up from dreams and imagination very often, so that we never knew what was real. As I was watching, I remember telling my mother “I wanna do that”. My mother asked me what?: I wanna make what they are making. Oh, she replied, so you wanna be a Movie Director! Read more>>