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.

Tyra Hall

If I could I would have started my business earlier. I feel like 100% of the time we don’t take leaps of faith because it’s human to fear of the unknown. Starting earlier would have only benefited me in the long run, I would have had more experience in the industry, in business and financially. I am a firm believer in divine timing, so I do feel that I started my business at the right time for me. After you get through the “scary” parts it’s pretty rewarding! It’s literally nothing like having your own business. Read more>>

Veronica Smith

My business started as a hobby to give a gift to say thank you for those that supported my nonprofit Wewalkforjuan to help raise money for Autism research. My son juan was the motivation for me to stared WristRock. Once I started giving bracelets to all my supporters,they wanted more colors and designers and asked how much I charge. Read more>>

Lawanda Givens

If I could go back in time, I would have started my business about 13 years ago. I came up with the idea that I wanted to become a boutique owner before my son was born in 2009. I drew up a plan and looked for resources to fund this idea, but to my surprise, there was little to no help for up and coming business owners. Most resources that were available were mostly loans and I didn’t want to start the business out in debt. Read more>>

Dee Pearson

If I could go back in time, I definitely would have started my business years ago. I have always had a passion for creating memories or making any moment a memorable/meaningful one. As a young adult, I would maximize any moment of celebration or just pure joy. Read more>>

Stephanie Padilla

Since I was a little girl I always dreamed of owning my own business. It was a leap of faith that I took in 2020 to finally make it happen. I was still working in the corporate world but the pandemic left me with a lot of uncertainty in life. I was fortunate to keep my job, but so many friends and family members around me were out of jobs Read more>>

 Jamiece Spears

My eldest daughter was born February 2012. Shortly after I started making baby gifts, blankets, custom wipe cases, and even bibs. I loved creating and crafting for my client’s special arrivals. Cuddlies by Jay was my first stab of entrepreneurship. It gave me the best feeling. Read more>>

Melo

I definitely wish I would’ve started my business sooner. It’s wild because I’ve had a passion for imagery since such a young age, but where I come from there aren’t many outlets or avenues you could pursue as a kid interested in the arts. So because of that, I spent many years treating camera work like a simple hobby because just as most parents do, my dad was more focused on me securing a “real” job. Read more>>

Kate Rogers

I absolutely wish I would have started my business sooner! Owning a boutique has been a lifelong dream of mine, I can remember when as a little girl, wandering the stores with my Grandma dreaming up the inventory I would carry and the way I would design the store. I sat on this dream for 25+ years and as an adult even though I continued to dream of it, I was always so afraid to take the risk and put myself out there. Read more>>

Mya Douglas

I wish I had started my business straight out of college. I believe fear stood in the way because as creative as I am, I didn’t always have the confidence I have today. I remember when I was at Temple University, people were talking about how big YouTube was then and I often think, what if I had started my channel then? What if I had started to build my influence as a writer back in 2006 rather than waiting until now? My professors would even tell me how good I was whenever I did a journalism project requiring me to interview people. I had the on-camera personality, I just didn’t have the faith. I believe starting sooner would have allowed me to have a platform that pays me. Read more>>

Tabia Kuntz

If I could go back in time I think it would have been more beneficial to start my business much sooner. I have learned a valuable lesson in birthing ideas but not allowing them to flourish and grow to their fullest potential. I have always had the idea of starting my own denim line for tall girls. Read more>>

Ben Carter

In the Summer of 2019 I officially launched Play 2 Win. I was a freshman in college with a new found passion for the clothing industry. I had very little experience with designing a clothing brand, marketing and manufacturing products. I ended up in various situations where I could’ve did more research to get a greater outcome. Read more>>

Cassandra Doxa

Sometimes, I wish I had started my business sooner, but I’m confident I started it at the exact right time. I always had a passion for food and cooking but I spent many years trying to find my footing after graduating college. With a business degree, I knew I wanted to start my own business, but first wanted to gain experience in Corporate America. Read more>>

Vanessa Messer

If I could go back in time I would go back to 2016.. I had a successful t-shirt business Ruffles with Love. Business was great and it was the perfect time to kick off my influencing career. I would have been able to grow my t-shirt business while breaking into the influencing field before it got really inundated. Read more>>

Delma Gomes

Personally talking , I think that I started a business at the right time , during the most unfortunate moments of humankind. When I first decided to star the business, I basically did it out of boredom and wanting to do something during the quarantine period. Looking back , I realized how bold of a decision that was. People are literally avoiding eating out as much as they could , and there I was , starting a baking business. Read more>>

Marliee Rose

I wish I would’ve started my career as a nail technician sooner than I did. Being my own boss, making my own hours, being available for my children when I want, and of course the lucrative income that came with my career has been life changing. I didn’t know I had a passion in this industry until I was 25 years old. I got my nails done frequently and was never satisfied. Read more>>

Edwin Rivera

I started my business in August of 2021, and officially opened for business in January of 2022 after I finally received my Federal Firearms license. If I could go back into time, I would not change a thing about when it started my business, because my employment prior to set me up to be the successful business owner that I am today. Read more>>

Von Thomas

If I could go back in time I would have most definitely not started my business sooner. If I would have started sooner I believe I wouldn’t have learned all the life lessons I’ve had the chance to learn. And I honestly would not even be half of the woman I am today I’m very grateful for my business and all that’s it’s taught me about life. It’s been such a journey but I would not have it any other way! Read more>>

Vanessa Deets

I started my business when I was 6 months pregnant with my third child at the start of the Covid 19 pandemic. Up until I was about 3 months pregnant, I had worked for other small businesses from home. My third pregnancy was very hard on my body yet inspiration struck me and I had a yearning to try something new for myself. Read more>>

Norma Cisneros

If I could go back time yes definitely I would of started the business earlier. I started my business after working in the logistics industry for 8yrs and realized I’m making money for someone else when I can be making my own money. Looking back I would of change my ways of spending money when we are young we don’t think about the future we just think about the moment we are living but like I always says only god knows why I started when I started and thanks to him I’m here I don’t think I would change anything I happy with my achievement Read more>>

David Burns

I have been an avid photographer/videographer for over 15+ years, however, it wasn’t until 5 years ago that I truly grasped the idea of what ‘freelancing’ was. In those 5 years I have learned an incredible amount from a lot of very incredibly talented people. I have also had the opportunity to work on a lot of fun productions and with cool clients. Read more>>

Miya D

I started my business a year ago in July of 2021 , I’ve been working at my current job for about 3-4 years then and just wanted more for my son to have one day. But life got really stressful, body was feelings off, was having family issues, and then a hurricane came and destroyed about 60% of my business products. Read more>>

Teri Lee

I do not regret starting my business at that time. Family-wise, my daughter just graduated from high school and my son from college. It was a good way to stay busy during my free time. However, if I could go back in time, I would choose to start my business earlier. I was restricted and had to spend most of my time accompanying my kids until they grew up. Read more>>

Dominique Van Ausdall

I know for a fact that other breweries like us were doing unreal numbers out the gate before 2020. Unfortunately we missed that wave. If we opened our brick & mortar in 2019 or sooner things would be much different. We’ve had an uphill battle from the start. Read more>>

Courtney Nguyen

Honestly, when I was in 7th grade I took one of those career aptitude tests and it told me that I should be a chef. I was so steadfast and hung up on becoming a doctor so I totally ignored it and went on to university on a pre-med track. It wasn’t until my Senior year in college that I realized I could not continue going to school for 8-10 more years so once I graduated I took a job in the medical field but hated it. Read more>>

Latasha Williams

Great question, I wish I would’ve started sooner than I did actually! I was always waiting for the right time, to have the right amount of proof, the perfect client story to share, etc, etc- instead of just starting because I was already getting proof. Oftentimes, when we start our business we want things to be perfect but I’ve learned that done (or rolled out) is better than perfect especially when our mission, our vision, or company origins are about helping people. Those people you want to coach or support do not care about your polished logo they want to learn what you’ve learned in less time and with your support! Read more>>

Lisa Zinna & Sylvia Troconis

Lisa: I came from a family of “IBMers”, so that was the path that was expected after college. I didn’t necessarily have another passion to pursue, so after a few years of random IT jobs, I finally landed at IBM as a technical writer… for 27 years. During my last few years of that job, I became increasingly curious about creativity, art, and photography, especially photo editing. I was known to decorate the dull hallways with photographs and Damien Hirst-inspired dot collages. Read more>>

Tony Ohara

I can’t say that I got started too late in pursuing the career of actor/ stuntman but I can see how starting younger would have it’s advantages. When your 18 the body can handle a lot more damage and you have more then enough time to perfect your craft. I don’t regret when I started because that’s just part of my journey and it gave me time to accomplish other things. If I had started when I was 18 then I probably wouldn’t have created a card game, wrote a book, or traveled to the countries I’ve been too. It’s all give and take and I’m more then happy with where I’m at. It will all come together Read more>>

Jena Brown

I feel I started my creative career at the right time, but I wish I had the tools that people have now, then. When I first started getting into blogging and sharing my creative outlet, I didn’t know where it would go or what all I can do from it or how to utilize that platform to gain more visibility — Read more>>

Selene Salas

I would say everything was right place, right time, right mind. Being in the Culinary Industry, I barely had time for my family let alone starting a business. When My Daughter was born I started to question my career choice. Can’t forget to mention that we don’t have family locally to help out if she ever got sick. Right as I’m feeling the pressure, COVID changed everything for the better. Read more>>

Joselyn Rodriguez

I have always known I wanted to be in the entertainment industry, As a kid I would often create talent shows for my parents as well as get involved in arts in school. I was always part of the dance teams in my school. Also growing up I was part of the acting ministry in my former church. I also did pupeteering for the kids at church. I create content which is based on acting, roleplay and some cosplays as well. Read more>>

Demond Drayton

If I could go back in time, I would have I started my creative career sooner. I started around the end of 2017, beginning of 2018. Before I started take photography seriously, I was working at FedEx. I believe that starting sooner would’ve allowed me to be more dedicated and focused on my craft. When I first graduated high school, I didn’t know what I wanted to do but I always enjoyed taking pictures. I’m sure if I would’ve went to college or a school of the arts, I would’ve had a different experience in my journey. Read more>>

Tyler D’Shun.

I wish I would’ve started my career a lot sooner but I believe in divine timing and everything happens the way it does for a reason. If you just align your thoughts with your actions and just give your all in everything you do. I always knew I would have a career somewhere in the arts just never knew exactly where. I was very passionate about theatre and dancing at one point. Read more>>

Francesco Ponticelli

More than 20 years ago, when I was studying at the university, I had my side job as freelance journalist and content creator and I was doing really well but, for the Italian culture of having a better future with a regular job, I decided to gradually quit my creative career and get a regular full time job in marketing for telecommunications companies. Read more>>

Mr. Muzix

If I could go back in time, I would have definitely started my musical career earlier. At the age of 19 I was faced with an intense choice; staying in college or chasing music. I recall siting outside of my freshman dorm on the phone crying to my mother; mentally, I felt trapped. I knew that my purpose in life was to make music, and I felt as if I was wasting life by being in college and not having the time and opportunities I wanted to develop myself musically. However, my mother was extremely persistent in me becoming a college graduate. Read more>>

Kate Walker

No doubt, I would have started my career sooner. As a photographer, at times, it can feel hard to keep up with new technology, trends, and marketing. I also feel like I still have a long ways to go in mastering my tools such as camera equipment and editing software. Having to juggle these aspects of building a photography brand can be exhausting, of course I would love to have had more time to build my brand. Read more>>

Erika Timko

I guess I like to think that everything happens when it’s supposed to happen. For years I had been scribbling down random thoughts, one liners, and silly jokes, in hopes that maybe someday I might actually do something with them. Then in May of 2016 I started making videos for my comedic, puppet forward YouTube channel, Beaucoup Askew TV where I started incorporating all of the characters, parody songs, and storylines that I had concocted from over the years into my videos. Read more>>

Shelley Smartly

I’m a very late bloomer! As an arthritic widow, I became a stand-up comedian at age 69. At age 70, I was Creator, Writer and Actor in our first television pilot for THE SMARTLYS. We filmed our first pilot in front of a live audience in a senior’s center. We’d just begun shopping the pilot when the pandemic hit. So, we had to throw it all out and start over from scratch. Read more>>

Jiron Griffin

Truly I love how everything is unfolding right now at this pace and at this very moment. Yes, some times I think to myself like “dang I wish I would’ve started earlier” but I’m a firm believer that everything happens for a reason. I’ve learned so much within these past few months not only about my craft but also myself. That has helped me with ideas and bringing that idea to life. Read more>>

 Sky Janga

Time is not on our side. I learned that later in life. While others had figured out that they wanted to be athletes, nurses or doctors, I didn’t really know what I wanted to do as a profession let alone what I needed to do to find out the things that interest me. I never took the time to think about what I wanted to do or what I was good at could be a passion. Read more>>

Derek Brown

I definitely wish I would have started my creative career sooner. I didn’t officially begin my pursuit of being a full-time entertainer until I was in my 40s. Since I was a young father, I put all of my dreams on the back burner and became a union electrician in order to provide for my child. Read more>>

Enecia Miller

If I could go back, I don’t believe that I would have wanted to start a career in travel sooner. My father joined the Army when I was 5 or 6 years old. Just before I turned 8, he was stationed in Germany, so we took our first flight, 8 hours from Atlanta to Frankfurt on Delta Airlines. Read more>>

Zephaniah Jones

In being a creative there are many times that we wish we knew what we know now sooner. For me being a creative has always been about understanding how to reach people and help them on their journeys. So I think it’s fair to say I wish I would have started sooner, but I couldn’t say sooner would be the right time. Over the years of performing, teaching, Read more>>

Chatrea’l Waters

If I could go back in time, I do wish I had started my creative career sooner. Although I started modeling when I was in middle school, I didn’t pursue it long enough to really appreciate or receive any benefits from my craft. Since I was in middle school when I first began modeling, everything had to be funded through my parents. Read more>>