Almost every entrepreneur has had to decide whether to take the leap now or wait– perhaps they wanted to acquire more capital, experience or connections. Given how common this predicament is, we asked some successful business owners to reflect back on whether they wish they had started sooner or waited for a better time.

Renata Bass

I believe I started this business exactly when I should have. If sooner, I would not have learned all of the lessons and skills necessary to be great at what I’m doing now. If later, I would still be unhappy in the rat-race of it all, hoping to find my next great gig. None of my years in corporate were wasted. It was time well spent. I am now primed, ready and fully equipped for such a time as this. Read more>>

Vincent Aguirre

I’ve often reflected on this very question. I began my professional culinary journey at 45, later than many in this field. If I could go back, I do wish I had started this career path much sooner. I was in a completely different industry before turning my passion into AZC13 FOOD, LLC. While that experience had its merits, the fulfillment I’ve found in cooking is unparalleled. Had I started earlier, I would have had more time to refine my skills, establish myself in the industry, and perhaps explore different culinary avenues. Starting later, while still rewarding, has meant playing catch-up in some aspects. Read more>>

Danielle Lynn

Yes. I for sure wish I had found this career earlier.

I have always been a creative but I was never informed reading or writing, it was always being creative in other ways.
It wasn’t until I needed to find a hobby to help with my anxiety that I found reading. The a random joke with my dad prompted my first story after a dream I had. Read more>>

Marco

I started cutting my own hair at 16, so honestly I think the timing couldn’t have been better. I was in my second year of school at O’dea High School and I was on the basketball team. I realized early on that going to the NBA wasn’t in my cards so I needed to find a way to be useful and known by my community. A lot of my teammates had several offers or opportunities to play after high school while I was on the bench. If I hadn’t made that realization that life was going to get real here shortly, who knows where I would be today. I went from cutting my classmates, teachers, coaches and friends, to traveling the world and meeting people who have shaped my life to what it is now. Read more>>

Florencia Rodriguez Lomeli

If I could go back in time, I would start my photography business sooner! I officially launched FlorenciaRL in 2021 when I moved to Florida, working with an amazing design studio to develop my branding and website before taking on my first clients—mostly friends and collaborations to get my name out there. Since I wasn’t originally from Florida, I had to build my client base from scratch, which was both exciting and sometimes very challenging. Read more>>

Terrence Spencer

There was a time when I wished I had started my writing career earlier. More time could have meant more books, a deeper connection to the writing world, and perhaps a different level of success. But looking back, I realize that my life experiences have shaped my stories in ways that wouldn’t have been possible otherwise. Without those experiences, my writing wouldn’t have the same depth or authenticity. So, no—I don’t wish I had started sooner or later. My writing career began exactly when it was meant to, and I truly believe that. Read more>>

Andy Keown

I believe I started my travel PR business at exactly the right time, however the world had other ideas as the Covid-19 pandemic hit three months later, shuttering virtually the entire global travel industry. So, that was certainly a setback on my path. It took me another couple of years of freelancing and eventually joining another PR agency before I found the confidence again to go back out on my own. I was about 15 years into my PR career when I first started thinking about launching my own company, and I do not think I would have been as successful if I had done it earlier. By the time I was ready, I had worked in a variety of settings both in-house and at PR agencies, so I had a well-rounded perspective on the industry and what clients need. Read more>>

Sarah

I wish I had established my production company earlier. I founded Anane Productions LLC in September 2021. With over 20 years of experience in the entertainment industry as a Producer and in various other roles, I had long aspired to own a production company. However, it wasn’t until 2021 that I took the necessary steps to create it. My focus had been on advancing my career and securing financial stability for retirement. Establishing the company earlier would have provided me with more experience as a business owner and increased the capital in my business account, lol. Additionally, I would have gained further education in business management. Despite the delayed start, I am very grateful for the opportunity to now own my company. I continue to progress and expand my knowledge as a business owner. Read more>>

Amy Proffitt

I am a true believer in the notion that all things happen in life when they are supposed to. Our business began in the thick of the pandemic. The world was dark, and people were feeling sad about the state of affairs. Most of our family worked in service industries and were home and out of work. My husband had previously made candles, and he decided it would be good to make some as fun gifts for our friends and our daughters’ friends. When family and friends received them, they encouraged us to begin selling them. With one post to Facebook Marketplace we had our first wholesale client, and it blew up from there! We began just wanting to make people laugh and bring joy in a dark time. WIth every shipment that was sent, we included a handwritten note, amethyst and rose quartz, to deliver peace and healing vibe to every customer – along with some belly laughs. Read more>>

Katie McVicar

I think we both agree that we wish that we would have started our business sooner. Working with animals has always been a dream for both Jen and I for a long time. When we finally decided to take the plunge and open up J & K Pet Services we were both working full time for the government. It paid the bills but wasn’t our passion. Jen and I along with her husband Brian decided to quit our regular 9-5’s and focus full time on our business venture together. Starting sooner would have given us more creative freedom in our lives as well as being able to maintain a work life balance. Truly doing something we love has been a life changer for our family. Read more>>

Matthew Kulewicz

I constantly think back and wish I figured things out sooner than I did. I always knew I wanted to work in SOMETHING audio/sound related. My mother still has a pin I made in middle school for a faux company called ‘Matt’s Music’.

In high school I took an internship at a radio station, and learned I didn’t want to be in the world of replicating/playing back other peoples music, I wanted to be part of the creative process of making it. Then in high school and college I worked for a number of live concert venues, and learned while I loved working with musicians (and sometimes playing with them), it still felt like I was there to service other people’s creations and not my own. Read more>>

Paula Pötry

If I could go back in time, I wouldn’t change when I started my creative career, but I would have done things a little differently. I began my journey at 21, but I’ve always had an entrepreneurial mindset. My first job was cleaning a hair salon every Sunday at 16, which taught me hard work and responsibility. At a very young age, I also came up with my first business idea—a bikini line. However, looking back, the business plans and financial projections I had were far from realistic. If it had gone forward, it would have failed quickly. Read more>>

Marco Romantini

The short answer is I’m glad I started when I did. When it comes to a firm start date, it’s a little blurry. I’ve made art my whole life and worked in the arts in varying capacities since I was a teenager but for functional purposes, I’d say my “career” started somewhere around 2021. I spent a big chunk of my twenties in and out of school, bouncing around jobs, and making art that I would, on occasion, actually do things with. Read more>>

Yung AJ

So I was 16 and I got my first show and I was living in Duluth,Ga and I was feeling like all my neighborhood friends were gonna buy a ticket. Nope they was just saying nope and my brother came to me and he told me don’t give up and from that day I never gave up. I wish I did take time and really pursue earlier but I believe that things take time and I’m going to keep pushing. I know my gift and I know my talent and I’m willing to keep it going. Read more>>

Erin Anderson

I started learning calligraphy in 2016. At the time, I was working a corporate job that I didn’t love and I really needed a creative outlet. It quickly turned into a little side hustle for me! I continued working and doing calligraphy on the side until 2021 when my son was born. Then, I quit my full-time job to stay home with him and focus on ECLetters. It all worked out well and I’m so grateful to be able to do things this way, but I do sometimes wonder what it would have been like to be a truly full-time calligrapher pre-covid and before becoming a mom. I think I would have been able to take on some opportunities that are harder for me to do now, like additional classes, additional travel, etc. Ultimately though, I think that things worked out well as they did and I wouldn’t change it! Read more>>

Lulu Winkler

Young Lulu Winkler was an artist. I attended an art-focused high school and college, even showing my work in galleries around Seattle. But a tough economy and imposter syndrome pushed me off course, leading me into the world of restaurants—and away from my artistic dreams.

For years, I worked tirelessly as a restaurant manager in Los Angeles. I endured long shifts, cried in walk-ins, navigated endless lines of hangry customers, and convinced myself that the chaos of “being in the weeds” was an exhilarating rush. But in reality, I was burned out. Read more>>

Emilie Doering

I think almost every actor grapples with the question, “should I have started sooner?” If only I had… gone to LA/NY instead of going to college, or gone to a Conservatory and made connections, if only I had started as a kid, if only my parents had been actors! Take your pick, and insert the alternate reality [here]. Sometimes, when I’m feeling particularly self-critical, I think about the years I “wasted” pursuing Opera as a career instead of going straight to on-camera work. Or the years I pursued degrees in Statistics and Political Science instead of moving straight to LA and getting started building my network and getting representation. Or, or, or. Read more>>

Symone Davis

No, I wouldn’t have become a creative sooner because I truly believe I’m right on time. Every experience I’ve had has led me to this moment as the CEO and Founder of Foodies Unanimous, a supper club that goes beyond just dining—we create unforgettable social experiences through food and drinks. Read more>>

Dee Alvis

If I could go back in time, I would certainly have become a voice actor sooner. In 2009 I gave some serious thought to becoming a voice actor. In my broadcast days, I had recorded hundreds of commercials from 2004-2014. I had also obtained a lot of side work doing commercial voice over for clients locally and regionally. Read more>>

Ewa Tamar Lewandowska

It kind of came full circle for me. I was very creative as a child and teenager, and drawn toward writing and visual art. But when it came to choosing a professional path, the messaging I received all around me was to be practical. After studying journalism and media, and later business strategy, I landed at a social media agency and then transitioned into tech startups. Read more>>

Crystal Lewis

When I let my mind wander back, back to my earliest memories of standing on stage with a microphone in my hand I admit I’ve wondered what it might have been like to have done things differently. I began singing in front of people around age 4 or 5. My father was a preacher and my mother a musician which gave me both a built in platform and an accompanist. I wasn’t a ‘showbiz kid’ or child prodigy or anything like that. But I was encouraged to take the stage. I ‘competed’ in singing contests, which honestly, I highly disapprove of. I believe that pushes the theology of judgment and comparison and leads young creatives AWAY from creativity. I started recording at the age of 15, so throughout my formative high school years I traveled and sang. Read more>>

Rayna Ali-Patterson

Oh my gosh! I so wish I started sooner, because…well I did! Let me explain. In 2009/2010, I started my Youtube channel where I was simply doing hair and makeup. I was in a one bedroom apartment, newly married and with a newborn on my android phone uploading short videos to Youtube. I was still in under grad after taking a break and had some free time on my hands. So, I randomly started a channel, no plan just vibes lol. A few months into it, one of my friends messaged me and told me they saw one of my videos pop up on Youtube, and I PANICKED. I have no idea what I was thinking would happen, but after she told me, I deleted my channel. I didn’t start back producing content until a few years later. Read more>>

Sayakat Cosplay

I actually don’t wish I had started earlier. As a cosplayer, there’s a lot of social interactions and nuances that being older helped facilitate. I have a weird entry into being a full time cosplayer, I started after I completed my PhD in biology (my thesis was actually in biophysics/biochemistry but that’s a whole different can of worms to talk about). I had also discovered that I liked teaching and instructing in grad school and that lead me into my current niche within the cosplay community, which is the educational space. I don’t think I would have gravitated to that part of the community without the experience I had and the age at which I started cosplaying. Read more>>

Michelle Francois

I began writing poetry in the sixth grade, not fully understanding the path I was stepping into. At the time, I was simply following encouragement from my mentor, whose feedback inspired me to keep writing. By the 10th grade, that same mentor took me to see a production called *City at Peace* in Washington, D.C. I remember sitting in the audience, captivated—watching kids my age share raw, personal, and powerful stories on stage. It struck me deeply, and I knew I wanted to be part of something like that. Read more>>

Marie Awn

While I was in college earning my BFA in painting, I worked in the salon industry as a makeup artist. I never intended on staying in that career for as long as I did (21 years!) and I often wonder where I’d be in my painting career had I started out of college. But I believe things happened the way they did to make me hungry for it. I don’t think I’d be as motivated to paint every day if I didn’t have my previous life not creating the way I do today. Taking care of a home and a family is also really challenging as I’m trying to carve out time for painting, but again it makes me want it even more. So when I show up in my studio, I’m ready and willing. I wouldn’t change a thing. Read more>>

Laura Carrier

I didn’t start painting until I was 18 and graduated high school. I mention painting because I think that was the first visual art, formal creative thing I had done, and the first thing I did that made me feel like an artist. I had always had many little creative endeavors my whole life, such as sewing projects, creating fun outfits, playing with makeup, and taking a lot of time to edit the pictures I posted on Instagram, but I didn’t register as art-making. I never took any art classes or joined any art clubs, which I think would have been a revelation. I saw visual arts as an incredible thing that I guess you were either born with or didn’t have or weren’t drawn to, although I knew I was creative, I didn’t make the connection until the labels and categories of high school were over. Read more>>

Lisa Nelson

I often think about how I wished I had started my art career sooner than I did. In hindsight, I hadn’t realized that it was an option. I didn’t start my creative career until I was knee deep in diapers and midnight feedings with my first born. Looking back I have no idea how I even had the brain capacity to try anything new like that. I think that if I would have started sooner, maybe I would have been able to give myself a more structured start. I would have been able to study my craft and all the parts of business. But sometimes, diving in head first is just the way it happened, and I think there are benefits to that too. I do think I would have been further along in my career, had I started before I became a mom. But I wouldn’t change it for the world. Read more>>

Harrison Sweeney

I started my circus career a lot later than most people – I was 24 when I began full-time circus training. Most others in my class were either younger than me, or had been training circus since childhood. I spent a long time believing I was playing ‘catch up’, and wishing I had started a lot earlier in my life. As I progressed in my training, I realised that this feeling made me a lot more driven, and kept me focused on my goals. I also had a lot more life experience to draw from when it came to act creation and show development. This breadth of experience really enriched my art. I felt a lot more sure of myself and what I wanted to present in my performances. Looking back now, I’m very grateful to have started when I did. Read more>>

Edward Abbott

I definitely wish I could have started my creative career sooner. I spent 15 plus years working as a designer, part of that in a corporate setting. While it was still creative, it was for other people. The longer I worked in that setting the less and less creative it felt.

I often imagine how much more experience I could have as an artist and illustrator if I had started 10 or even 5 years earlier. I could have found my style, networked with other artists, made connections and generally had more practice honing my skills. Building confidence is also a thing that takes time. It’s a great feeling, but I spent years doubting myself and on occasion thinking I had lost my ability to draw. Read more>>

Tania Tare

I do think looking at the way of the digital world now, i probably started later than usual. But my first priority/goal was always to be a player on tour. To compete. Being a professional athlete was always the dream i had since as long as i can remember. Initially it was tennis but when that dream was cut short (due to falling through a home window) it switched rather quickly to golf. Read more>>

Amanda Campbell

I didn’t discover I could sing until I was 43 years old and it was quite by accident. I had always sang, I just never let anyone hear me. I always wrote poetry too, but never shared it. Secretly, I fantasized about being a singer my entire life.

I would’ve liked to have started singing sooner because it gave me confidence in myself and writing gave me a way to express myself and to process difficult feelings and situations., but there’s always a balance between timing and life circumstances, Read more>>

Emily Maverick Shankman

I’ve definitely taken a very kaleidoscopic & winding path, but am so grateful for everything I’ve learned at every step of the way. I was always an artist, but didn’t get into comedy and acting until relatively recently. However, I feel like everything leading up to my blossoming as a performer and clown has brought me where I am today; and I can’t wait to see what’s next. Read more>>

Madeline Schmidt

If you had asked me years ago if I ever thought about starting my own business, the answer would have been a big, confident no. At the time, I was fully invested in my career, leading talent and leadership development functions across different industries and often building them from the ground up. I gave 150% to my work, and on top of that, I had two small kids at home. The idea of starting a business on the side, like so many people advise, felt impossible. Who has time for that? And honestly, the thought of leaving a steady paycheck was just plain scary. Read more>>

Faith Colello

As a game design student, I wish I had begun learning the craft at a younger age. I only found my passion for coding and environment design once I got to college, and didn’t even play a ton of video games growing up. Some of my friends lovingly poke fun at me for never having played online multiplayer games or having no knowledge of some classics (but I’m getting there!), so I wish that I was able to relate to what drives them in terms of being a game developer. Learning how to code for games has been nothing but fun for me – I truly do wish more high schools provided students with a chance to realize that this is a very possible career choice. Feeling the pressure of going to college and not feeling like I would enjoy what I studied was a very scary thing for me, and I didn’t start as a game designer. Read more>>