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.

Emmie Rotsky

Without a doubt I wish I would have started my business sooner. I started my business the summer after my senior year of high school, but starting it during high school would have been more beneficial. I think if I were to have started doing senior photos for students while I was also in high school, it would have gotten my name/business around a lot easier than it was right after, since I was amongst everyone daily. I believe my business would have been more established in the area by the time I graduated instead of just starting it the summer after. Read more>>

Antonia Royal Whitmore

I distinctly remember sitting on the colorful ABC carpet at school, legs criss-cross applesauce listening to If You Give a Mouse A Cookie. Every year at our Scholastic Book Fair, held in the school library, I saw new shining books with titles like There Was an Old Lady Who Swallowed a Fly, Clifford the Big Red Dog, Junie B. Jones, and Goosebumps. Read more>>

Brian Koz

For some, they know at a young age what they would like to do as an adult. I was in college and bartending at local Irish Pub- wishing I was spending more time outdoors. Often times I wish I had the motivation to start my own business in my younger years. I envy the young guides I see head off to Alaska or Chile each year, what a cool experience. But I had to wait to be in my late thirties. After a visit to my doctor for stress test, which revealed 90% blockage in my LAD, I decided to take the leap and become a full time guide. I am thankful for the motivation and treasure my time on the river with clients. Read more>>

Kevin Jackson

Even though I am still very new to the world of business and am just learning as I go, I would still have to say that I wish I would have started my business sooner. Coming out of high school, I had absolutely no idea what I wanted to do with my life. I remember when my senior year of high school began, and realizing during that time period, “Oh shit, I’m gonna have to do something with the rest of my life after this is over.” Read more>>

Hannah Sheridan

I wish I could go back in time and tell myself that becoming a professional photographer isn’t a pipe dream. In school I was never really interested in any one particular subject so when it came time to decide what I wanted to study in college, I chose Marketing. I chose it because I liked my high school teacher and the class wasn’t terribly boring. Not necessarily the best reason to choose a major but I rolled with it. And I although I don’t regret that decision, I do regret not keeping up with the hobbies that fueled my creative side. Read more>>

J’Metria Anderson

If I could go back in time, I wish that I had started my business much sooner. I started October 2019 which was right before covid really hit the U.S. I didn’t know the impact that covid was going to have to my business but it hit it pretty hard. However, had I started my business when I first started arranging travel I would be much further along than I am now as far as customers go. I have always been the planner of vacations and group functions but I didn’t have the business to do it, and get paid for it. Read more>>

Scott Shivelhood

I wish I had started my business sooner for sure! I held a few jobs in my 20’s that just weren’t right for me. I decided in 2016 I wanted to work for myself, but I wasn’t sure what I wanted the field of work to be. The first business I started was landscaping. I worked at it for a while, but it became tough because the market was so saturated with landscapers. I then moved to pressure washing homes and businesses. Read more>>

Karl Greene

Looking back at the last fews years of running my business, I really wish I had started sooner. Launching a business is hard no matter when you do it. It is more challenging when you have a family and financial responsibilities. Everything in my life prior to lauching my business was incredibly stable. My career in law enforcement had an upward trajectory. I spent my nights and weekends completely with my family. The only pressure I had was to get up in the morning and head to work. Read more>>

Sara Rosales

Coincidently, I began working in the corporate and business law space around this time and fell in love with it. I learned a lot about various business industries from the start-up phase to their dissolution and I advanced quickly. Legal colleagues and friends began reaching out to me for guidance on setting up their businesses, that’s when I realized there was a huge demand for it. Read more>>

Alisha Shumake

I am a believer that things happen when the time is right. I always knew I would own my own business, I just did not know what it would look like or when it would happen. I started my business in 2020 after many years of working for others. I was happy being an employee – until one day I wasn’t. I realized that if I was going to work as hard as I was, why not work for myself? Read more>>

CJ Bland

In 1998, I launched ATLInfoConnection and JobConnection e-newsletters to promote diversity organizations, job opportunities, and other robust career, economic, lifestyle and networking content, events, and resources. At the time, such vision and publications were widely viewed as highly innovative, unique, and forward-thinking. My audiences for these publications rapidly grew to tens of thousands of e-subscribers, and multiple people repeatedly asking me to move and expand this type of valuable and beneficial content from email newsletters only to a web-based online. Read more>>

Juda Hensley

It took me a while to realize that 9-5 is not for me and that I ignored my childhood dream to become a hairstylist (that inner voice wasn’t loud enough just yet). I was 27 when I started cosmetology school and haven’t left the industry since. Before then I was always looking for something new and different. I worked at a bank, oil company, cruise ship (as a personal trainer) so I always told everyone that I’m adaptable and like to try new things, but doing hair and makeup is my passion. Read more>>

Monica Walker

TenFiftySeven Media Group was started by myself, and my two business partner’s at the beginning of 2022. My son was heading off to college, so the life I had been living for the past 18 years was changing. He was planning his next chapter and so was I, not having any idea what a fun but crazy ride this would be. As I stated we started TenFiftySeven Media at the beginning of 2022 with the middle of that same year giving the option to bring back the Christian Country Magazine…Power Source Magazine. Read more>>

Scott Eakins

When I look back, I wish I had started my business sooner. I started my business in 2021. At the time I was leading a vinyl wrap team at a local sign shop. I was also doing wraps and graphics on the side for a shop I have worked at most my life. I love being able to be creative and applying that to vehicles. I got to be more creative in my side work and I was starting to get burned out by the same work in the sign industry. I was nervous to take the leap and turn my side job to my main job. Read more>>

Amanda Mitseff

When my husband Bill and I first got together, we had no idea really about the financial freedom possibilities when it came to investing in real estate. It was October 2019 when we bought our first investment property and we have got a couple more under our belt since then. Bill and I got married that next month after buying our first house and now have two precious boys both under three years old. It would have been great if we would have started the investing journey sooner but everything happens for a reason! Read more>>

Aliece Brown

If I could go back in time, man would I have started my business sooner. I first launched Cozy Universe Studio in the summer of 2020. This was such a wild time for me. I was finishing up my final year of college at Florida Atlantic University and I had recently moved back to Tampa since classes were online due to the pandemic. All of my closest friends were back in south Florida and I wanted a way to connect with so many of the wonderful creative people I had met during my time on campus in Boca Raton pre-pandemic. Read more>>

Jessica Stasik

Growing up, I always had a camera in my hand. Capturing friends, family, school extracurriculars, etc. I had decided to start my business in 2012 after my husband (then boyfriend) helped give me the extra push to start this new journey. At the time, I was in my third year of university majoring in music education. I truly believed I was meant to be a music educator. Read more>>

AuLora Record

Looking back now, yes I would have loved to start my career earlier. But looking back I would do it all the same one hundred times over. Because what I learned in the years prior to becoming a hairstylist was how to believe in myself. To have the drive and determination to want to work hard and not goof around. I took beauty school with all seriousness when some girls didn’t. I found myself excelling and getting more out of class than my other class mates. Read more>>

Darrell Kenny

I don’t think I would have started my business sooner , but I would have loved to have gotten into the craft sooner I find myself trying to learn everything I can about it and I just wish I would have been able to start making lures sooner just to have that much more experience and knowledge. I’ve been making soft plastic fishing lures for going on 6 years and have been a business for almost 5. We spent a few years watching and learning about the craft before we bought the needed equipment to start. Read more>>

Idara Barney

I started my business during the height of COVID, which allowed me a great amount of time to be creative and focus solely on my business, I was a senior in high school at the time so I did have to balance work and school. But I run this business with my little sister, so having another person to lighten the load made it easier and more enjoyable. I actually don’t wish I had started my business sooner or later, I’m glad I started when I did because I was emotionally mature and intelligent enough to dedicate my time to my business. And if I started it in college, where I am right now, I don’t think I would’ve put as much effort into it as I did two years ago. Read more>>

LaToya Simpson

I made my first greeting card sale on April 24, 2021 but my brand, The Candidly Speaking, started 2 years prior to a greeting card ever being drafted. When The Candidly Speaking was created, the mission was a blog that would provide me with an outlet for my thoughts and ideas. I was a full-time employee in corporate, like I am now, and was so unfulfilled. I dreaded work so much that on Sunday’s I would be close to having panic attacks due to stress. Read more>>

Aurscanta Mounger

I started my business, NGK Consulting, in July 2020, right in the heart of the pandemic. At that time, I was in a corporate position that I genuinely enjoyed, although COVID had complicated things. However, the idea of starting my own business had been on my mind for quite some time. The decision to start my business came about unexpectedly during a car ride back home from Chicago. Read more>>

Coach Jay | InnerGConnoisseur

Absolutely! If I had the knowledge that I have now I would’ve started my business as soon as I graduated from high school. Starting sooner in my opinion would’ve provided me with more time to correct mistakes and master my craft. I didn’t have any solid plans on going to college and I hadn’t quite figured out what I wanted to do with my life. Becoming a business owner would’ve been an outlet. Fast forward to the year 2021 and I’d gained the courage to finally take myself and my dream serious. I took a leap of faith and never looked back. Read more>>

 Zodiac Chenoweth

January 2020, I separated from my life partner due to unfortunate circumstances and for the safety of my children and I. I moved with them and began working at my father’s auto shop as a mechanic. In July 2020 I was getting tired of missing my children’s lives, so I decided to finally take the leap into starting the business I had been planning for years from my hobbies of drawing and candle making. Read more>>

Jimmy Star

I would have loved to start my three main businesses much earlier in life. I am a publicist, have been working as a publicist for the past 7 years, and wish I had the idea to become one in my twenties instead of my fifties. Having been named the best entertainment publicist in the United States, I am very happy with my success but would have loved to have done it many years ago…. Read more>>

Alan Johnson

Upon reviewing I wish I started this journey sooner. I started around 2017 where I worked as a material handler in a distribution center. I always felt like something was missing in my life. Although I cannot rewrite time I feel like starting earlier would have definitely helped me a lot.. Honestly though I would not change anything about the journey it was meant for me. Read more>>

Macy Krall

Well I am what you call a serial entrepreneur. I’ve lived many lives in my short 31 years. From going to college for Nursing, becoming a Medical Assistant for 5 years. I loved that, loved my job, co-workers, Doctors and patients. But the upper management was the issue I had. During college I also became a photographer to pay for college and have a hobby. I started photographing wedding and quickly loved the wedding industry. Read more>>

Anneliese Arend

I only officially started my business in 2020 and I started it because one of my (many) hobbies was sparking joy in people. Enough for them to approach me to sell my sugar scrubs and at the time it was a nice side source of income but I didn’t think anything of it. Fast forward to now; 2023; and I am running a full business with more products than i imagined i would sell. I am so happy with where i am but it also came with pains. Read more>>