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.

Ram Dettmer

I kicked off my web design business in 2016 and got it up and running by 2018. Looking back, I sometimes wish I’d started it earlier. Read more>>

Jaime Calsada

OH most definitely sooner! You know, it’s always that whole should’ve, could’ve, would’ve thing, right? But personally, I think I’ve gained a lot of wisdom and maturity over the last 15 years, accumulating tons of work and social experiences. If I were to list everything, it’d write a book! I got married, started a family, bought my first home, and switched from part-time jobs to a full-on career, got divorced, went through bankruptcy. I literally felt I was thrown into dark hole. Life’s way of nudging us forward really threw me into some pressure situations that forced me to grow, both personally and professionally. Some intense situations, but I don’t see it all as a negative. Challenges are like the pillars of growth and without failures we can blind our visions and perspectives. Sometimes we get too comfortable in places that don’t really push us forward. Looking back, I wish I had explored entrepreneurship sooner, even if it meant facing some expected failures. I believe having a realistic mindset keeps us grounded. Read more>>

Jessica Smith

I started my photography business the first time in 2014. I was young and had not idea how to run a business! Things were also a lot different in the photography world at the time. Needless to say, I didn’t make enough money to survive and always had to have a full time job while running my own business. I burned out very quickly and decided to focus on my full time job that I had. I explored several different career options, but could never shake the passion I had for photography. I tried starting it back up a few times with no success. Finally as I got older, and gained knowledge from all of my previous jobs, I decided to take the plunge again and things started to gain momentum! I wish I had all of the tools and knowledge I have now back then, because I feel it would have been an easier path to success. Read more>>

Ora Lockett

Embarking on the journey of entrepreneurship with THE GR8FULL COMPANY in 2019 has proven to be a transformative experience that I fervently wish I had initiated sooner. The impact on my family’s well-being has been profound, turning what initially felt like a leap of faith into a blessing. The business not only provided financial stability but also allowed me to discover my true passion. In the subsequent year, I founded THE BUILD GR8NESS, further expanding my entrepreneurial pursuits. This venture, in turn, opened unexpected doors, leading me to explore my creative side and resulting in the authorship of several books. Read more>>

Rachel Burch

MUCH sooner! I started my business back in 2017 after working a variety of customer service/support jobs ranging from entry level to management and I would 100% prefer to a) work for myself b) do something creative and c) have my work/life balance on my own terms. Read more>>

Tasha & Dale Rosemond

It’s easy to say we wished we’d started our business sooner. But, we are firm believers in everything happening at the right time, and not a moment sooner. Before we started our business, it was a hobby, just a pastime Dale had done after dinner each night. Creating was his way to decompress after sitting at a desk all day. We had often talked about having a Plan B because as we’ve seen too many times, no one is irreplaceable or safe from restructuring at their place of employment. So, like many, once Covid lockdown started, we were able to use the time we’d spent commuting to and from work or shuffling the kids to and from school and activities to hone in on our craft. Dale had already done tons of research over the years and would keep me in the creative and technology loop. I’d worked in Finance for years and never thought I’d had a creative bone in my body outside of the Pintrest projects I’d executed. My intention was to remain “back-office support.” After some convincing by Dale, I was finally comfortable using our Co2 laser and and quickly moved from back-office to creator. Read more>>

Clift Hart

I started my business in 2011 or at least the idea behind it. After trying to grow my own food on a balcony in a small apartment I became obsessed with the idea of replicating food farming in indoor spaces. It took a very long time to get from there to where we are today. Along the way, the cannabis industry rose from a collection of small businesses into the growing behemoth it is today. That has unlocked affordable, efficient, LED lighting for pretty much any kind of food plant you want to grow indoors year-round. My only regret is not building a digital product earlier, but I’m not sure the timing would have been right until recently anyway. Read more>>

Trish Macias

Timing is everything. And everything has it’s own time. My husband, Larry and I had been looking for a restaurant that we could open together since 2018. Larry has been in the restaurant industry his entire adult life either as an owner or General Manager. I had bartended for a few years but working in restaurants wasn’t my background. I have a law degree and my real estate license. But we make a great team as we compliment each other’s strengths and weaknesses. Read more>>

Rocheal Matthews

Neither… Although I spent most of my life interested in photography, I never imagined a career in it. People tend to ‘want’ things differently or ‘regret’ what they’ve done, but there’s so much value in the journey. Read more>>

Anthony Repetti

Reflecting on when I kicked off HomeView Media, I often wonder whether starting it sooner or later would have been more beneficial. I began my professional photography career back in 2014 shooting a wide spectrum of photography and really found my niche in architecture and real estate photography in 2019. I battle with the fact of if I had launched HomeView Media right after college, I could have had a longer runway for growing my business. However, an earlier start might have meant facing the industry with less experience and fewer connections, presenting a potentially steep learning curve and the risk of missing out on honing my skills. Conversely, had I waited longer to start my business, I might have gained more experience and a broader network, leading to a stronger and more informed beginning. But, this delay could have meant missing out on certain market conditions and opportunities that benefited my business in its early stages. Read more>>

Marek Cornett

At the end of 2019, as I was in my third month of working for a new agency, I found out I was pregnant with triplets. With a 1 1/2-year-old son already, going from a family of three to a family of six changed my view on what was important for us. Rather than working for an agency where my salary was capped and I was dedicated to a desk, 8-5, I valued flexibility and limitless growth. Only after securing my first clients and earning more than I did at my full-time job did I start thinking it was worth the challenges. Looking back, I think I started at the exact right time. Earlier, and I wouldn’t have the experience that’s been necessary to run a successful business. Later, and I don’t know that I would have ever made the leap! Read more>>

Nicholas Valencia

I do wish I started my clothing brand in highschool of 2016-2017 where I was just designing cover art as a hobby and my main focus was expanding my knowledge of design related to website creations, 3D, logo design, marketing materials and more. Read more>>

Anna Pearson

I believe that everything happens at the right time. I do think though that if I gave it a go right after school I could be way further ahead now. So many misconceptions about the artist profession! I myself was under the impression that it’s impossible to earn enough as a creative. You know, this “starving artist” stereotype. This is not true, you can be very successful financially along with creative independence. I would even say that the more you are creatively independent with your own unique and bold style that sets you apart from others the higher your chances for success. But back to the point: I started my artistic career pretty late, only after moving to the US and even though I wish I started earlier I also think there’s no such thing as “too late”. So if whoever is out there reading this thinks it’s too late for them to start, trust me, it’s not! Even more so, I believe that all my previous life experiences helped me to find my artistic language and my audience because I actually have something to share. Read more>>

Kathy Zhou

I think I began my creative career at the perfect time for me. I was 29 when I first decided to try performing and gigging as an Indie-pop pianist and singer-songwriter in my city, Memphis, TN. I think as a society, we put pressure on people to begin creative pursuits while “young.” There’s certainly nothing wrong with beginning a new creative pursuit as a child/teen/early-twenty-something-year-old. However, the right time is whenever YOU feel ready to take that leap, and for me, that was at the age of 29. Read more>>

Melanie Collup

I didn’t make the decision to pursue a career in the entertainment industry until I was in my late 30s. I have often felt like that put me at a disadvantage, because many of the people who are my age had been in the industry for a decade or more before I ever came on the scene. They had more time to build up their training, experience, and contacts. But truth be told, I think the industry would have chewed me up and spit me out when I was younger. In order to persevere in this business, you have to really know yourself and be confident and comfortable in your own skin. This business is full of judgement and rejection. I’m not sure I would have been able to handle that when I was in my 20s. Read more>>

Jason Lai

My name is Jason Lai, Principal Designer and owner of JL Interiors. My company is a full service residential interior design firm located in Santa Monica, CA and my team is made up of strong diverse creatives. JL Interiors empowers homeowners to design their dream home that they can be proud of! Design isn’t just about making things beautiful; it’s also about making things work beautifully. My design firm offers services such as planning & consulting, new construction & remodels, interior design & project management. We pride ourselves on space planning and design, we never like to waste precious square footage in someone’s home. Read more>>

Erin Drago

Sooner. It’s funny if I look back….my younger self said she’d never work in an office. And then I stumbled into a 20 year career in business operations, and there I was behind a desk all the time. It became normal, and those dreams of a creative career were buried. That is why I started Farmhouse Glass. I had a craft that I knew was unique, a reignited creative fire and a desire to build something for myself and my family that was outside of the box. Read more>>

Erica Calhoun

For years, I secretly held a desire to become a blogger, but never seriously pursued that desire for a number of reasons. Then I finally realized how easy it was to make your own website, and I was instantly filled with regret for not trying to do it sooner. Sometimes I think of where I would be with my blog if I had started it years ago. However, I also think everything happens at exactly the moment it is supposed to. The one thing I learned from not pursuing this passion sooner was not to let fear or other obstacles get in the way of MY desires. Read more>>

Constance Willoughby

I’ve always been a late bloomer. My entire life I’ve watched peers, friends and family pass me in areas like puberty and finding their gift in life; the “thing” that they were really good at. I was smart, an honor roll student through college, but I struggled to find a path of purpose, one that I was naturally good at that didn’t require an instructor and a textbook. Read more>>

Duskin Wayne

I wish that I had previousky become as self-aware and motivated as I am now, however, I feel great about my current state as being a successful artist. Read more>>

 Jonah Jimenez

I’m probably would have much ratherd to start my photographic endeavors much earlier but at that time my life was different, I was living in a different place, around different people, in a different environment that was not conducive to the type of artistry I love. Read more>>

Ray Roberts

I think everyone has the feeling of wishing that they would have started stand up comedy sooner than they did. It seems like a great idea until you realize that if you weren’t ready to do an open mic at an earlier age, you’d definitely not be ready to handle the “business” side of things at an earlier point in their lives. I think I’m one of the weird people who is happy that I started when I did. If I had started earlier, I would have definitely flamed out by now if I hit this low level of success with my bad habits and views on life. But if I would have waited later I may never have done it at all. So like most things, I feel that comedy pulled me in when it was ready for me and vice versa. Read more>>

Lupe Mendez

No, actually – I can safely say that everything happened/happens as its supposed. My day job informs my art work and my art work informs my activism and my activism informs my art and and my job as an educator. Read more>>

Optimus Volts

Yes, of course I wish I started earlier not had to deal with 9 to 5 jobs. But it’s hard you can’t just go to a university or college and become a full-time artist. Even if you go to an art school, you still have to work hard and build up Your following. The only way you learn is to get out there and show your artwork to the public even if you have to use the streets to do it. Read more>>

Jacki Fisk

I left teaching in August of 2022. I was working 40+ hours a week, juggling classroom management, conferences with parents, and leading meetings as the Union Steward all while navigating a “post” covid world. I was burning out… no I was fully burnt out and running on fumes without realizing it. I spent my free time sleeping or trying desperately to catch up on my To Do list. It was as long as my forearm and full of mundane things other folks seemed to magically have time for throughout the work week. But that version of me didn’t think there was another option. That version of me thought that if she could just catch up, catch her breath, catch a break, she would be able to make it work. That Jacki thought that she would one day be able to do 40+ hours of work, have clean laundry, washed dishes, time for brunch plans and that she’d get her creative drive back. Thankfully the only thing that Jacki and I have in common is our Husband. He saw what was happening and he told me to quit, and I listened. Do I wish I had given up all of that sooner to start my creative career? More than anything. Read more>>

Kelly Rose

My influencer career just kind of happened. I was not intending for it to become a big part of my life. During COVID I was on limited hours at work and just kinda started posting more since I had the time and just having fun with it.. and the results were amazing. I wish I made the leap and took the time to focus on it way beforehand. Read more>>

Amy Stricklin

I will always wish I had picked up a paintbrush earlier in life. Even though I’ve always been a creative person in some way, deep down, I feel the need to catch up! My mother was an excellent seamstress and taught me to sew at a very young age, so my first creative endeavors in college involved fashion design and tailoring. My only formal art training was during this time at Memphis State when I took a few figure structure drawing classes. Instead of continuing to pursue that path, I got married and took a job at a local bank. During those years of raising two beautiful daughters, I sewed. A lot! I made home decor, my clothing to wear to work, I made girls dresses, dance costumes and altered almost everything we wore. It wasn’t until we cleaned out a storage building by our house for my daughter to use for paint parties, that I found my love of painting. Now, I’m either traveling, looking for beautiful images to paint, taking a class or workshop, or just painting in my wonderful little studio. I jokingly say that being an Artist is my fourth, final, and most fun career! Read more>>

Phyllis Klein

I was trained and worked in a completely different industry for a long time. I wish that the younger me would have gone into broadcast journalism at the beginning of my career path than later. Read more>>

Gabrielle Howell

This might sound cliché, but I genuinely believe there’s a right time and place for everything. I feel that I’ve embarked on my artistic journey at the perfect moment. If I had started any sooner, I don’t think I would have been able to develop the images that define my work today. The initial piece that sparked it all was a compilation drawn from various life experiences, reflecting the emotions I was experiencing at that moment. Read more>>

Destiny Williams

I do wish I had taken my creative career more seriously sooner. When I graduated college in 2021, I was so excited about continuously making art and making sure I had an impact on my city and the people around me that I felt like I should’ve taken the business side of things more seriously. Though I feel like the projects and art I curated are sustainable, I should’ve geared toward projects that are more timeless and also personable to reach people outside of my city and even impact the world. I wish I had applied to more grants, and shows and even worked on how to price my work and to be even made business cards sooner lol. I took a long break from photography and now it kinda feels like catching up but also rebranding but it’s been really fun. Read more>>

Stacy Mootoo

At times I do wish that I had started my creative journey earlier than I did. I am also grateful for the lessons and experiences I’ve had prior to starting my creative career. Life has a way of teaching you things that only come with time, allowing for growth. Based on personal experiences, current events and things taking place on a global level, my perspectives, opinions and beliefs have evolved from what they once were. As such, I think that its allowed me to be more conscious and deliberate with my work as an artist. It’s always an eye opener, when I go back and take a look through my old sketches and art pieces. It’s a good reminder of where I was, where I am, and my potential for the future. Read more>>

Tim Furlow

Sooner, because I would’ve been the tattooer i am today 10 years ago as opposed to having to go through working in the medical field for 8.5 years, trying to figure out the next move. Read more>>

Nao Shirawachi

I can say that I have already had a creative career of about 35 years in the sense that I spend my days centered around the creation. However, if doing creative work as a professional job is what you call a “creative career,” then my creative career has only just begun. Read more>>

Hannah Rainy

I feel like I started it exactly when I was supposed to. Not a day too late, Not a day too early. No regrets (; Life is too short for that and life is too long to worry about what I haven’t started in my life up to that point. Although I think it’s a great question to think about. Read more>>

Sophia Flot-Warner

I absolutely wish I had started my creative career much sooner, like in high school sooner! I sometimes feel I’ve lost or wasted so many years working in other fields, but God reminds me that I have gained valuable experiences and met wonderful people throughout the many iterations of my life. Read more>>

Alonso Garcia

Considering that some people dive into acting right after high school, and I didn’t begin until I was 27, that’s a question that crossed my mind more times than I can count. Read more>>

 Jessica Heath

I think about this all the time! I am constantly talking about how nice it was to have a “regular life” before I found the entertainment industry. I got to grow up in a small, Southern town. I got to have a “normal” childhood with “normal” problems. I went off and had a “normal” college experience. I had the best life possible. Once I graduated (shout out to UNCW-woo!) and entered those lost years that all of us have where I had no idea what I wanted to do in my life, I stumbled into an acting class. Another shout out to a place that I am forever grateful for and wouldn’t be here without – ACTOR’S ARSENAL (love you, Allie & Ron)! The decision to sign up for this class catapulted me into my dream career. It started a chain of events that I believe happened for a reason. One decision led to another which led to another which got me here. So, sometimes I wish I knew at 18 that I wanted this life, but then I remind myself that I never would be exactly here without the journey that I took. I’m thankful for it because I love everyone I’ve met along the way and how it shaped me into the person I am today. Read more>>

Awesum

Its not so much that I wish I had started my career sooner, I actually wish I had the courage to never stray from what I was passionate about as far as my art career when I was younger. I wish I had more people who were supportive of my choices around me because that would’ve helped with all the doubt I had at such a young age going into a profession that wasn’t as thriving as it is now. Read more>>

Al Chang

In hindsight, definitely later on. I don’t think I was mentally ready to take on the challenges of being a filmmaker. There are two big chapters in my life, before my first born and after my first born. I’ve always had that itch to be creative in any way but it wasn’t until I had my son, lost my job, and joined the military that I honed in on what I wanted out of life and myself. I know for a fact my intentions were different than it is now. Fame and money is always enticing and if I had gotten into this early on, I know my reasons for doing this would not have come from a genuine place. The art of this means more to me now. The fulfillment comes from the journey and the relationships I build along the way, not the outcome. As corny as that may sound, it is the absolute truth. Read more>>

Tara Prager

I always used to think I wish I started earlier, but now I am so glad that I’ve waited. I feel so ready now to step into my artistry. I have been able to truly study and perfect my craft by going to school for musical theater. I feel like if I had started this journey and gained success at a younger age – I wouldn’t have the tools to help prepare me. I know how to find grounding and peace now. I have found sobriety and a healthy relationship with my mind and body. I am surrounded by people that I know support and love me. I am allowing the hard work to pay off. I have a more clear vision of what I want my life and my success to look like, and if that was granted to me any earlier I’m sure I would’ve figured it out – but now it feels like everything has progressed exactly the way it was and is supposed to. I am so blessed to have been given the life experiences I’ve had up until this point and it has taught me so much about myself as a human being and as an artist. I can write and perform so much better now. I think things happen for you, not to you. Timing is everything, and this timing has happened for me. Read more>>

Julie Eckert

I do wish that I had started my art career sooner. Circumstances in life sometimes branch you off in a different direction that you have no control over. It is never too late. Read more>>

Ivett Soto

Neither. I am a big believer in “everything happens for a reason”. I think that if I started sooner, I would have not been ready. I believe that I would have not been able to handle all the failures. I think that putting yourself out there is a scary thing to do. I remember when I created “photosbyivett”. I was like “what are people going to think?” “Are people even going to book me?” But at the same time, I didn’t care. I love photography. I love being creative. I was going to do what I enjoyed no matter how many times I failed. Read more>>