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.

Caroline Paradis

I started my Reiki business when I was 38 years old. That may seem young to some, but by that point I had already spent what felt like a lifetime in another career. Read more>>

Adamary Fernandez

In one word, yes, I wish I did start my business sooner. The joy my business has brought me in the last four years is unmatched. Dainty Hands Co. began in 2019 on Christmas Day just before the pandemic. I was decorating for a Christmas party and I decided to pick up a chalk board sign I had and create a welcome sign. Needless to say, everyone kept asking me who I hired to make the welcome sign and when I would say I made it, they instantly said I should open a business. Read more>>

Callista Mei-Miller

I think everyone gets really caught up in the perceived timeline of life, especially when it’s associated with success milestones. But as cliche as it sounds, I really do believe in everything happening when it’s supposed to. Technically the origin of my brand launched in 2018, but I had a lot of personal factors I needed to attack first before I could really feel ready to give it 110%. Read more>>

Laura Salcido

I’ve always believed that things happen in their due time. Do I wish that I would have started sooner? ABSOLUTELY. I’ve loved art and drawing for as long as I can remember. I did it never thinking of it as a career or business since I was made to think it is not a “real job”. I started to actually dive in 5-6 years ago around 2017, only selling small drawings here and there. Read more>>

Valerie Lucey

I absolutely would have liked to start my business sooner, but with that being said, you have to wait for the right opportunity that matches who you are. Read more>>

Gina Garrett

was 25 years old when I opened Sweet Pineapple. I was married, just completed my Masters in Information Systems, and fresh off an internship with an IT company. I was lost. I knew I didn’t want to work at a job where I was miserable 9-5 and living only for the weekends. One night I had dinner with a precious friend who encouraged me to explore opening a store. I discussed it with my husband and we agreed to take the leap. Read more>>

Corissa Saint Laurent

I was laid off in 2017. I knew it was coming. My company had been acquired a year prior and two-thirds of my team had already been let go. I had wanted to leave this job for a couple of years, so I felt ready for this change. What I wish I had done was start the building of my brand and all the early stages of building a business in those years when dissatisfaction with my job had struck. Read more>>

AMY LUCK

If I could go back in time, I would not have started SWS VINTAGE any sooner. I felt like I was ready and my previous career experiences would help me with this business. Before I started SWS VINTAGE , I was working as an engineer for a fortune 500 up until 2021, when I decided to leave. I don’t know what it would’ve been like if I had started this company later, but I do know what it would have been like if I had started earlier. If I had started earlier, I don’t think I would’ve made it 3 years in. I think I would have failed a lot sooner. Read more>>

Donnett Mitchell

Throughout my journey as an entrepreneur, I’ve had moments where I’ve contemplated starting my business earlier. I took the leap into this venture at the age of 38, while still holding a senior corporate position. At times, I’ve pondered if I should have taken the leap in my twenties, when I enjoyed more flexibility and fewer responsibilities. Read more>>

Abby Carver

I wish I had really started being more proactive earlier. When I was younger, all I wanted was to be a musician and singer in a band. I went to college for two years for acting but after dropping out right before the third year, I felt burnt out and uninspired for awhile and really just focused on getting by as a nanny. Read more>>

Ryn

Being of the age of teen sensations like Miley Cyrus, Justin Bieber, and Billie Eilish, of course I wish I started younger! By the time these icons were my age now (22), they had entire shelves dedicated to their Grammy’s, millions in the bank, and their entire careers made. I started singing around thirteen but didn’t take it seriously until I found songwriting at age fifteen. Now seven year later, I just barely have an idea of what I’m doing. Read more>>

Chanelle Wesley

Absolutely! I spent the majority of my life playing it safe. I have worked in various fields and have positively impacted the people I’ve served. But nothing compares to living in my purpose. I am using the talents, skill sets, and abilities that were given to me by the Creator. Although what I do motivates, encourages, and inspires others it provides me the chance to operate at a level that allows me to live my calling. Read more>>

Derrick Credito

Naturally, I do. My idols had spent their twenties creating rock & roll records like Appetite For Destruction and Nevermind. Instead of recording my own magnum opus, I spent most of my twenties living in the Asia-Pacific, where I worked as an English language teacher in Bangkok, Taipei and Seoul. In a more perfect world I would’ve spent those years making rock & roll. But prior to spending six years abroad, my band Mad Tea Party, in which I sang and played bass, had fallen apart after a year of gigging in Baltimore’s club scene. Read more>>

Tori Puente

I don’t necessarily know if I could have started any earlier (I’ve been doing art-related things since I can remember), but as far as it goes professionally, I wish I’d found my niche sooner. It was overwhelming to try and connect my photography classes from college along with new techniques and styles I discovered afterwards, along with my own ideas. In my experience, I felt kind of trapped by a more rigid way of thinking about art and photography during college and right after that. Some distance from that environment brought back the urge to experiment with my art, and I don’t think that’s ever disappeared again. Read more>>

Nikita Hamilton

The answer for both careers is “no, they each began when they were supposed to even though I don’t always feel that way.” I came to realize that I wanted to be a TV Writer in my late twenties, which felt so late to be starting at the very bottom as an assistant. However, the truth is that I wouldn’t be the kind of writer on paper or in the writers’ room that I am without all of the experiences I had leading up to the day I was staffed. Read more>>

Terry Chacon

I started my professional career as an artist when my son graduated High School. Before I worked as a Medical Transcriptionist and created part time working in sculpture and learning all about oil painting. I started my professional career as an artist when my son graduated High School. Before I worked as a Medical Transcriptionist and created part time working in sculpture and learning all about oil painting. Read more>>

Chloe Kono

I have always given myself a hard time about the time I “wasted” before I made up my mind to pursue my working artist lifestyle. When things aren’t smooth, or when it’s simply one of those self-doubting days, I would get hung up on the idea of how much more progress I would have made by now. I would imagine that I must be a lot more “successful” all together. What I have come to realize, however, is that even if I did gather enough courage to start being my own boss earlier, I would not have the tools I have today. Read more>>

J Rodney Turner

From a very young age I always wanted to be an air traffic controller. during that time, and using my voice daily to perform the functions of the job I discovered that peers and pilots found my voice to be a subject of interest. It is when faced with mandatory early retirement (age 56) that I decided using my voice, post-retirement, would be the best avenue to serve the future of my family and our needs. Read more>>

Xiaodie Hu

I believe that starting my career later is more helpful because I enjoy figuring out what my decision is affected by. I believe in the philosophy that is the opposite of utilitism. And we need to waste time, make mistakes, and wait for a deeper realization. When I first tried to start my creative career, I faced many challenges because I was not sure how to set boundaries, advocate, and communicate my needs. Read more>>

Ariana Azoulai

I’ve been in the acting world for over a decade and have recently ventured into music. Reflecting on the timing, I have mixed feelings. Part of me wishes I had started music sooner because I feel like I could have learned so much in that time. However, I recognize that I wouldn’t have been emotionally ready. In a way, I’ve been learning and prepping to become a musician for a long time. Read more>>

Lynn Richards

In High School, I was bound and determined to pursue art. After all, my grandmother was an artist, I had been told I had much potential, and, most of all, I was happiest when creating. While in Jr. College, I took several art classes and had a lot of success with my creations. However, when I told my mother I wanted to pursue art, the “NO” boom was lowered. In my rather largely dysfunctional family, I was the one who did what I was told and so began the pursuit of a career. Read more>>

Keylonda Wheeler

I started my author journey in 2020. I was on maternity leave after having my second child and decided it was finally time to begin writing out the children’s book idea that I’d had for years. In some ways, I wish I had started sooner. In other ways, it was the perfect timing! Starting sooner would have allowed me the chance to jump into the growing market of self-published books earlier. Read more>>

Jack Rasmussen

I am glad I finished school and received my degree because that allows me to enter business or try to be a part of multiple companies. Being educated is excellent and offers many opportunities, creative or not. Delving into writing has been a great start for me, and I hope to do more. I started at the right time. Read more>>

Trevor Silva

I sometimes Ponder over the idea that maybe if I started dancing at a younger age things would have been easier for me. Starting dance at 18 and being thrown into class with girls who have been doing it since they were 3 was challenging, intimidating but most importantly motivating. Yes I wish I started dance early, I would have probably had better technique and better understanding of my body. Read more>>

Paola Cocchetto

Actually, I think I did it just right. Having pursued a non-art related career path after graduation allowed me to have experience in a completely different field, and having a plan B is never a bad thing. Plus, my office job allowed me not only to make very unexpected human connections that ended up in art-related gigs, but also to have a stable income to become economically independent at a very young age, to attend illustration classes and to buy my favorite art supplies. Which can be expensive, since I’m a traditional artist! Read more>>

Lance Cayko

I didn’t decide to pursue professional fishing until the ripe old age of 37 but wished I had started sooner because I’d be further along in it now. The later you start careers the more competition you’ll have contrasted by the fact that you will also be older. It will always be difficult starting a new career so starting it sooner rather than later is always a better option. Embrace the uncertainty in life. Read more>>

Jason Evanko

I think that a lot of people wish they had found their “thing” sooner than later, but in my opinion, it’s all part of the journey. I wouldn’t have been the person I would be without the experiences I have had. Those experiences have helped shape my way of thinking and how I create. I had never thought I would be in a creative career, having always had a passion in engineering and robotics, but where I am today, I can’t imagine another path. Read more>>

Barbara Kolo

Since I started out in commercial art and transitioned to fine art, I have often thought about a similar question. If I had started out in fine art, I would have had more time to develop the connections and relationships to help me in that field. There’s no doubt there would have been benefits. Read more>>

Mansi Bhatia

My acting career began at the tender age of 4 in Tollywood, which is the Bengali language film industry. I remember the creative bug caught me quite young, sparked by a serendipitous moment in 2002. It all began when a friend of my mother’s recommended me for a one-day gig as an extra on a television show set. Read more>>

Mi’Chel Bombshell

I think back and always wish I had started my career sooner. I’ve always loved beauty but would second guess myself and my makeup talent. I allowed fear of judgment from others to delay my dreams. However, I am a strong believer that everything happens for a reason, at the exact time it’s supposed to, in the ordained order it’s supposed to. Read more>>

Makai C.

Sooner. Starting my career at 18 was a wise choice but if I would’ve known what it was capable of I would’ve taken myself seriously a few years prior while I was still attending school. Other than that would recommend anyone find their calling and their gift early in life, chase it don’t let anyone tell you diffrent, monetize it for your family and your God. Read more>>

Neha Shetty

I would have definitely started my creative career sooner. Looking back, I realize that I shouldn’t have waited until the pandemic to fully invest in myself and take on content creation and dancing seriously. There’s this misconception that there’s a perfect time for everything, but in reality, you have to listen to your inner passion and start pursuing your dreams as early as possible. Read more>>

Sean Alan Mazur

When I think of my start, I think of when I began my training at the American Academy of Dramatic Arts. My first year I studied online since we were very much in the pandemic still. However I have no regrets starting then. If I had gone to college right out of high school instead of entering military service first, I would have attended Grand Canyon University and gotten a degree I wouldn’t be happy with. Read more>>

Kara Connolly

In all honesty, I wish I had started my creative careers later. When speaking of my creative careers, I am not referencing working on the crafts of either acting, singing or songwriting. I solely mean the pursuit of turning those crafts into a business. Read more>>