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.

Cynthia Lint

Let me tell you about my life, I always loved film and photography. My daughter Sydney Lint and I decided to open an acting/ film company named “Film and Talent Productions”, where we produce, photograph, film and teach classes for 10 years. My daughter Sydney and I decided to write, produce and direct a horror/drama film, “The Chime”, which we completed in two full years with our determination. During that time I also taught Spanish in public school. Read more>>

Samuel Bushi

I don’t think when you start your business matters as much as how you start your business. Do you have business plan? Having an intimate understanding of the market and your ideal client is paramount. Knowing who your competition is and what your niche is will help keep you focused on the right details. Once you have a blueprint in place, execution will follow naturally. A business cannot be run just on hopes, aspirations and dreams. Read more>>

Carmen Andersen

If I could go back in time, I wouldn’t wish to start my business sooner or later. In fact, I believe I started my activewear line, at the perfect time. JMC FIT APPAREL was born during the quarantine period, which was a challenging time for everyone.. I realized that many people were also seeking ways to stay fit and maintain their well-being from the comfort of their homes. Read more>>

Braxton Fuller

I definitely wish I would’ve taken writing and art more seriously growing up. I always had a knack for poetry and writing but I never really thought of it as more than just a therapeutic release. In high school, I caught my first glimpse of talent while doing my senior yearbook. Years later I actually tapped into that talent and started writing full time. I quit my 9-5 in 2018. It was such a hard time trying to grow on social media. Read more>>

Patricia LeGrow

I think about this every so often, funny enough. But even though I have thought about what would’ve been had I started my business earlier, I know that I started it officially at the right time. Technology has come so far in the past couple of years and there are tools and products that would not be available to me had I started sooner. I’m grateful to have started where I did because I’ve been to use those tools to help further my success in not only photography but also editing and gallery delivery and so forth. Read more>>

Julian Crosson-Hill

I started my business in 2019. At that time, I was 49 and had built a solid career in software engineering. I was leading multiple teams and managers. Throughout my 25-year career in software engineering, though, I’ve always had a strong desire to do more with my spirituality. I often volunteered at various spirituality festivals and conventions and taught workshops and classes. I just hadn’t figured out how to make a living at it or use it to help people live better lives. Read more>>

Tiffanee Bines

If I could go back in time, I wish I would have started my business sooner. If I would have started sooner, I would have accomplished a lot more because I had more free time before Nursing school. I paid people to do what I know I could do. I started my business October 2019, right on my grandma’s birthday the 21st. During that time, I was in the middle half of Nursing school (Med Surg to be exact. If you know, then you know). Read more>>

Julie Novak

I worked for other people for my entire career. But, I think things happen exactly when they’re supposed to. Read more>>

Brenna Kelley

When we started Lively Up Kombucha Zack and I were both only 21 years old at the time. Personally, I was a high school drop out with no diploma in hand and Zack was a high school graduate with no college experience. We really had no foundation to start a sustainable business with. So, we just went for it, and let fate decide the rest. Somehow from this, we are a success story, Read more>>

Courtney Warner

To be honest I understand everything happens for a reason, when I started my brand I believe I was 22 years old still trying to figure out who I was but I still knew what I wanted out of life. I sometimes wonder if I’d started my business a bit earlier would I be in a better position than I am now or would I be more successful. If that just happened to be the case, and I did start earlier and became more successful? Read more>>

Jason Patanjo

I am a professional educator and worked my tail off in grad school to get my teaching license in a handful of states. Moving to Florida and teaching was very expensive due to the low salaries, lack of respect and high debts of trying to succeed in my chosen profession made me think outside the box and start something new. Read more>>

Emily Taber-Moore

If I could turn back time and choose when to start my business, it’s an intriguing question. The answer is both yes and no. Yes because isn’t that what we all wish? To independently be our own bosses and call the shots is the dream for many people. In all honesty though, I would have to say no. All the experiences I have had throughout my design career provided me with essential knowledge of running different aspects of an interior design business. Read more>>

Kathryn Allen

I would not change when I started my own business. I started my business at a time when many people were also in transition, right after the pandemic. Returning to normal life motivated me to find a new adventure, and I overcame my fears and left my long-time job. This motivation carried me to embrace the challenge of learning new things, of making new connections and of taking risks. Read more>>

Nicole James

This is a great question because I don’t feel like it should have happened sooner or later. It happened when it was supposed to happen. I was an Event Director and Marketing Director for diffferent country clubs. I loved my jobs and even past jobs, because they all taught me different things. I now use those things and excute them daily with my own business. Read more>>

Adria Marshall

Now that Ecoslay is a successful business, it’s quite tempting to wish that I had started my business sooner. But when I realistically play out the movie that is my life, I begin to see that all of its twists and turns have led me to where I am today. If not for this journey, the outcome would have been less than stellar. Read more>>

Beth Sink

Yes, I wish I had started this business years ago but I do believe that everything happens for a reason. I don’t think I would go back and change anything from a career stand point. My previous corporate life, in sales and marketing, taught me so much that I apply to my personal business every day. Without those life and business lessons, I don’t think I’d be designing the way I do. I set goals yearly and have for over 20 years, so if I started Claude and Coy earlier, I’d be where I know this small company can be in 5 years. Read more>>

Jae Baldizzi

Great question. After pursuing my degree in Business Management & Marketing, I landed an incredible opportunity with a serial entrepreneur who owned a conglomerate of businesses in the Tampa Bay area. They had their hands in everything from a shopping mall to restaurants to theaters to sports teams. As Executive Marketing Director, it was my responsibility to manage all aspects of marketing across the organization’s businesses and work with a small team to execute the vision. Read more>>

Stephanie Vargas

This has been a question that has popped into my mind frequently over the years. I honestly feel that Emily’s Marvels would not be what it is now if I had started it later. A big reason for that is because of the pandemic. When it hit, it didn’t just hit the state of Florida, or even just the USA. It hit the world, hard. It was rough enough to not be able to do any in person events or conventions because that’s where, at the time, my sales were coming from. I had to come up with a new strategy and thus EmilysMarvels.com was eventually created. Read more>>

Kara Brown

Oh man, I totally wish I would’ve started much earlier! I’d always thought it would be so cool to be a travel agent, but in college and right out of college I figured they were a dying breed since you didn’t see too many storefront agencies anymore. It wasn’t until I’d gotten married and had a kid that I actually looked further into this career field and realized that travel agents (or advisors, as I prefer thinking of them) haven’t died out – they’ve just started doing more remote work! Read more>>

Krista Long

Looking back, I wish I had started my business earlier in life. It was in 2013, just two months after becoming a Certified Event Planner, that I took the leap. Naively, I thought clients would flock to me right away, allowing me to leave my day job within a month. Boy, was I wrong! As a creative soul, I’ve always wanted to avoid traditional jobs. Even in college, I steered clear of Job Fairs, feeling there was something more fulfilling out there for me. Read more>>

JessAnne Guzman

I feel it’s all about timing. In retrospect I wish I would have started my business sooner but I let fear stand in my way. Fear of failing, not knowing the back end of a business and how it is supposed to run. Now that I’ve done it everything has fell into place. Things I feared are easier than I expected. But what I come to realize you don’t really fail you learn and modify. Read more>>

Dre Johnson

If I could go back in time, I wish I would’ve started my business earlier. In the beginning, there were so many obstacles in my mind that kept me from taking the leap and getting started. I started my business in 2016, but I didn’t give it my full attention. I was still working a 9-5 job as a Purchasing Assistant and most of the time I was too tired (or lazy) to dedicate any real time to getting my business off the ground. Then one day it just clicked. Read more>>

Sasha Floyd

So when I started my business it was pre Covid. Originally Blackkribbon was a place where I’d sell my drawings, it wasn’t until once I noticed my witch hats where selling more is when I started making only witch hats. The first year was hard as it is with any business but when 2020 hit it was a lot worse. Because of Covid I barely made any sales since most of us were broke or dealing with life situations. During this time I spent a lot of days and nights wishing I did this sooner but unfortunately I couldn’t change that so all I could do was stick it out. Read more>>

Kim Johnson

If I could go back in time and change the time that I started my business, I wouldn’t. I started my business during quarantine in November of 2020. It was a time that a lot of us had a ton of extra free time on our hands. At the time, I was a newlywed and about a year into my Product Owner role at a FinTech Startup Company. My day job was no where near as challenging as my previous role so I felt I should be doing more outside of work to occupy my time. After all, I couldn’t take another virtual happy hour after 8 months of quarantine. Read more>>

Mark R. Hunter

First, “started” has to be defined. I’ve been writing since I was too young to write–thanks to my mother typing out a story I told to her. I “completed” a novel rough draft at age fourteen. It was just as bad as you’d imagine. Read more>>

Candace Parker

Have you ever felt this way? In 2019, I was working full-time doing what I love as a graphic designer, yet I was bored, wanted to grow and felt completely unfulfilled and unhappy. I knew I wanted more and that I was capable of more, but my environment was holding me back. Read more>>

Wesley Harden

The idea of being able to build your own business is far more common than when I had first begun, primarily because I had a lot to learn about the intricacies of all that would go into a feat such as starting to work for yourself. While developing my company, I spent countless hours after my eight or ten-hour shifts from my then job, well into the night, researching what I should be doing and learning from others who had already accomplished what I was now beginning. Read more>>

Autumn Nikol

Not at all! I truly believe I started at the perfect time, as it relates to my purpose in life. I started – what I did not know would turn into a successful creative career at 16 years old. This was the time I decided…that thing, I spent 10 years of weekly light therapy sessions trying to remove from my face because I felt it made me “ugly”, was the thing I should have been embracing, i.e. VITILIGO. My career started in front of the camera, and over the years I made my way behind the camera at, until I realized – “Hey! I can do both!” Read more>>

Oksanna Romanov

Yes, I wish I was given the opportunity to go to art school when my parents discovered I had a talent. I was 3 years old I drew on every wall and every floor, I found my element very early in life, however, born into disfunctional family in Ukraine, my parents were so young and unstable, too busy, constant survival mode & fighting… My art talent was neglected and fast forgotten. I intuitively fast found my other passion – dance, put myself in dance class and became a lead dancer and a teacher for younger kids. Read more>>

DeShawna Ladd

I really do wish I would have started my creative career sooner. I spent many years working for other people, doing stuff I hated, just to pay the bills. Often, I found myself in some “soul crushing”, boring, 9-5. It got to a point where I couldn’t do it anymore! Several times during that season of my life, I found myself daydreaming of “what ifs”: “What if I studied art like I wanted to?”, “What if I didn’t go to college, worked in retail, and did my art on the side?”. “What if I worked for myself?”, “What if I pursued music seriously?”. By the time I was 30, I wasn’t in a good place mentally or spiritually. It was time to break out of the matrix! Read more>>

Katie Cox

If I could go back in time, I would have started my business much sooner than I did. However, I also believe that God knew when I was ready and he made it so that I no longer had a choice. He held the door open long enough and decided to push me through! Read more>>

Angela House

I used to be disappointed in myself for not becoming a business owner when I was younger. I always thought starting a business at a young age would be a more rewarding experience and would have positioned me to provide my children with better financial security, education, as well as other benefits and opportunities that could have helped them have a step up in life. Read more>>