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.

Stephanie Singleton

If I could go back in time I absolutely wish I had started my business sooner!

I unofficially started my business several years ago and and at that point my children were grown and I had been working in the corporate world for over 25 years.

Had I started sooner I definitely would have been a full time entrepreneur and have no doubt that my coaching business would have been thriving. Also, the opportunity to create a schedule that suits my life would have provided the opportunity to travel frequently and to spend more time with my family. Read more>>

Ashlee Stancill

When it comes to wishing I had started Abiding Cakes sooner, I am a bit torn. One thing I wish I would had started sooner, was believing in who God says I am and the assignment He chose me to do.

I was scrolling through all the notes I had written in my phone, and if you’re anything like me those don’t ever get deleted. I happened to stumble upon a note that was created on November 25, 2021 at 7:35am. On that note was an entire business plan, menu, and to-do list to get a cookie business up and running. Read more>>

Sarah Allen

If I could go back in time, I honestly wish I would have started my business years ago. For years I’ve wanted to be a wedding planner, but I never had the guts to actually take the leap. For years, I kept putting it off—fear of failure, not feeling ready, or not having enough confidence held me back. Read more>>

Ivy Sbaiti

I started my business in my early 40s, during the midpoint of my career. Looking back, I sometimes wonder what it would have been like to start earlier. There’s definitely value in starting young—the earlier you dive in, the more time you have to learn and grow. But no one is ever truly prepared for the realities of running a business. Entrepreneurship is messy, stressful, and unpredictable, no matter how much experience you have. Read more>>

Zach Bauer

My studio began officially in 2018, a tough year riddled with injury, car trouble and emotional strife. Recovery always had me very creatively busy, but my activities in nature provided my spirit the most inspiration. The community provided a great impetus with a few large sales and comissions that year to get kick started. And a stead amount of smaller sales in the preceding years indicated a good opportunity to work on my passion. I’d have loved to start sooner but I was still growing into the artist I am now. Thus, it seems everything happens when it needs to. If I’d started sooner I feel I might have bitten off not what I’d be able to handle yet it also could have galvanized my studio into true organized purpose sooner. Who knows. Read more>>

Shengze (mark) Ma

If I could go back in time, I would choose to start working earlier while continuing my studies. As a film production major specializing in cinematography, I have come to realize that this craft relies heavily on practical experience. Mastering camera requires constant hands-on practice and real-world application—something I didn’t fully grasp at the beginning of my academic journey. Read more>>

Katasha Thomas

I absolutely wish I had started my business sooner. The level of creativity and self-discovery I’ve experienced as an entrepreneur has been nothing short of outrageous, in the best way possible. It’s fascinating because I never even considered being an entrepreneur until I became one. My focus had always been on climbing the corporate ladder, and I was excelling at it. I achieved the role of Vice President a full decade ahead of my timeline, which I thought was the pinnacle of success at the time. Read more>>

Karolina Aguilar

I started my business earlier this year, in February—I remember it very clearly because it was right after Valentine’s Day. At that time, I was in a period of confusion but also felt a deep conviction to create something new and take a leap forward. I had been working a full-time, 8-hour-a-day job for almost two years by then, and while I was stable in my routine, I was ready for a change. Read more>>

Ruichao Jiang

Recently, I often recall what my high school physics teacher once told me: “Give up on physics early and pursue art instead.”

Perhaps he saw something in me even back then. Perhaps he simply had no confidence in my abilities in physics. Or perhaps it was a mix of both. As an educator observing from the sidelines, he offered his candid assessment of me. At the time, his words hurt me deeply, as I was ambitiously dreaming of becoming a biologist focused on genetics. In China, if you want to enter a good university to study biology, you must choose physics, chemistry, and biology as your core subjects for the college entrance exam and perform exceptionally well—especially in physics, which carries the highest weight. Read more>>

Tali Leda

I started my music career much later in life than most people. One of my biggest regrets is not starting my music career when I was young. I worked in film and television casting after graduating from college for several years. I had a grueling schedule – sometimes 60 + hours a week. After casting, I segued into Talent Management and represented actors for a few years. These hours were less demanding than casting, but I would have to read client’s scripts and attend plays and film screenings almost every night, so I had little time for any hobby or creative endeavor. I was mentally and physically exhausted from years of working in the stressful and high-pressure entertainment business. Read more>>

Liana Ratner

I began my content creation journey in 2019. However, I’d been a casual Instagram user before then – sharing vacation photos and celebrating friends’ birthdays like most people. While I’d been inspired by other creators and dreamed of starting my own journey, the fear of not succeeding held me back. Read more>>

Hilary Brock

I’ve been creating and making art as far back as I can remember, even if it was only in my head. I knew I had a gift, even as a child. In school I took as many art classes as I could, and in college I had to make a pivotal decision. Do I major in art or economics? The scary route or the safe route? It doesn’t come as a surprise that I chose the safe route. I majored in Business & Economics. To hold onto a small sense of pursuing my passion, I minored in art history and it was by far my favorite part of my college experience. Read more>>

Malana Bouarouy

If I could go back in time, I would have wished I had started my creative career a lot sooner than I had. I started creating content back in March of 2020 when the covid pandemic began. At this time of my life I was working at a retail job that I was able to acquire new skills and challenged myself to be in a management position. The longer I had stayed at this job, the more I was craving to do something more creative that felt more to my calling. If I had taken this leap sooner, I believe I would have been able to really master my social media skills before the social media industry got more competitive. Read more>>

Kris

I think one of my biggest regrets is not taking that leap of faith sooner.

I’ve been drawing for most of my life, but it’s only in the last few years that I decided to start seeing if I could make a career out of it. It would be easy to put the blame solely on mental health issues and learning/developmental disabilities for why I didn’t put myself out there sooner, and to be fair, this was a pretty substantial chunk of the reason I didn’t start taking things seriously sooner… but one of my biggest mental blocks to exploring this path was my own insecurity. Read more>>

Destiny Kalinowski

If I could turn back time, I would have pursued my creative career earlier. My introduction to the modeling industry began during my teenage years in New York, where I first started exploring my passion. However, life took an unexpected turn, and at 17, I relocated to Florida. At that point, I needed to prioritize stability, taking on full-time roles in customer service across retail, sales, and health insurance to ensure a steady income. Read more>>

Marckson François

If I could go back, I wouldn’t think twice—I’d start my creative career sooner. For far too long, I let the weight of other people’s opinions hold me back. It wasn’t until I realized that confidence starts from within, no matter the circumstances, that I truly began to thrive. Read more>>

Agata And Warren Attersoll

We only started our Travel Couple journey less than two years ago. Initially it was just a platform to connect with other travel creatives but we soon realized the potential for growth and a myriad of opportunities that exist as a creator.
Do we wish we had started sooner? Absolutely. Like any career, one does not start as a CEO but rather, one has to build up to be at the top. Read more>>

Altodzi

I actually had no interest in music growing up. I was born in New York and raised in Korea, moving constantly back and fourth. I always felt like I was a foreigner in either countries and spent more time trying to get used to my surroundings rather than pursuing my interests. It was not until my first year of college where I started having an interest in music. It was by complete coincidence that I started on this path. I was playing a game on a live stream when a viewer reached out to me and asked if I wanted to try making a song. I said yes and he became a sort of mentor to me. I made my first song with his help and things moved fast from there. Read more>>

Tom Wiggins

The answer to that is yes, sooner for sure. The Bitz is one of the best cover bands I have been involved in. We are a relatively new wedding/corporate/variety band and this category is very competitive, more than being in the bar band category. I have been playing music in various bands most of my life and have only attempted running my own business once before as the owner of The Copy Cats back in the late 1990’s to the early 2000’s. Things went well, but I took a short break from the business side to adopt a child from a foreign country. I kept playing for other bands, but just didn’t have the time to run my own business. Read more>>