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.

Ela Ozturk

Great question! I’ve been an artist my entire life, however I often think of how my career would have panned out had I started a bit sooner. I try to have grace with myself by knowing I did the best I knew how to at that time in my life and that everything eventually led me to where I am now. So I would say I have no regrets at the end of the day, but if I was given a choice I think I would choose to start my creative journey/career sooner because I believe you can’t live for tomorrow, you have to live for the present. Read more>>

Amanda Amore

I don’t like to live with regrets, but yeah —sometimes I wish I had started my business sooner. I went to law school and then practiced law as an entertainment lawyer in NYC for 2 years. I felt like I was living someone else’s life the whole time. I knew my creative potential was so untapped in that career, but I felt like I couldn’t get out. Then 2020 was the wakeup call I needed to start living life as the true “me” before the world told me who I was supposed to be. Read more>>

Heather Bunker

If you could go back in time, do you wish you had started your business sooner or later? If I could go back in time, I wouldn’t change the timing of starting my business. I trusted in the peculiar sense of timing and divine comedy that aligned the birth of my child with the birth of my entrepreneurial journey. It allowed me to embrace the joys and challenges of motherhood while building my own empire, proving that creativity and success are not mutually exclusive. Read more>>

Gigi Good

Even though I trust that everything has happened at the right time, in the way that it’s meant to, I can’t help but reflect on how far along i’d be if i’d found Chinese Medicine sooner and had been cultivating my craft all these years. While I did work for myself as a personal trainer for a couple years before going back to school, I would have loved to start my journey in holistic medicine earlier because the medicine is so vast and there is so much to learn. Read more>>

Iris Savoy

If I could return, I would have started my business sooner. I started my business in July 2010. I was in the middle of selling real estate, working on the 2010 Census, and looking for a full-time job at the same time. I was laid off from a company I worked for six years. If I started sooner, I would save my time on things that did not make me happy. Starting sooner, I would’ve had my business started before the economy crashed, wasting by being on the fence and getting distracted by other things. Read more>>

Kaci Nelson

Let me preface this by saying, I definitely believe that everything happens for a reason and I am grateful to have had the experiences I had prior to starting my business because they helped me grow a tremendous amount. That being said, I wish I had started my business sooner because I spent so much of my early adult life trying to force myself to fit into a box of “safe” and “reliable” careers which ultimately did not fulfill my desire to create. Read more>>

Sarah Barnett

This is something I think about a lot. On one hand, I wish I had started my business sooner so that I could be younger in my field, learn some of the lessons I recently learned a bit earlier, and most of all, so that I could have worked alongside my mother who was an interior designer in Atlanta for over 30 years. She and my dad owned their own architecture and interior design business that they ran out of our converted garage offices in Decatur so I grew up in and around the business. Read more>>

Tania Barton

I definitely wish that I had started my business a lot sooner when I was younger. I was a lot more creative. It just came naturally now I feel like I have actually have to search my brain but it’s fun. Read more>>

Isaac Middendorf

If given the chance to begin my journey earlier, I would have undoubtedly seized it. The inception of Promethex Productions took place in the autumn of 2021, during my junior year of college. Over the course of the past seven years, I dedicated myself to refining my production skills, and it felt like the right moment to utilize my musical creation abilities outwardly. Read more>>

Caroline Schmidt

During 2020 when the Covid-19 virus outbreak was beginning, the dental office I worked at shut down for two months. Being at home every day without much to do, my creative side began to flourish again. I was painting, gardening and restoring and cleaning some vintage wicker pieces I had collected that were making their own collection of dust in my garage. Read more>>

Tonya Cross

I’ve pondered over this question several times! I’ve been creating things by hand since childhood. Creating things by hand gives me joy and peace; it’s a creative outlet for me. The art of accessory making was a hobby for me that turned into a business. I’ve embraced my choice to start my creative career later than sooner. When I launched my brand, I was transitioning into an empty nester and had more time to focus on my passions Read more>>

James Gregory Jr

I definitely wish that I would have started utilizing my creativity a lot earlier. Instead of trying to find a career in something that I’m not really passionate about just to make a dollar. It would have saved so much headaches and unnecessary stress in my life. Read more>>

Crystal Green

I used to wish that I’d started my creative career sooner but these days I understand that I am exactly where I am supposed to be and that every experience that I’ve had has brought me here. But that mindset wasn’t always easy to turn on. I’d get caught up comparing my journey to others’ and I’d make myself feel awful because where I was wasn’t where it looked like they were, Read more>>

Karen Rosenfeld

This is a huge issue that weighs on me all the time. I worry all the time that I’m running out of time to do everything I want to do, and I just wish I had started sooner. However, I know that is not true and I tell myself all the time that everything I did prior to starting my creative career this time was important to go through to help me realize what I wanted to do. Read more>>

James Dewayne

Of course everyone wishes they started earlier but I think I started this new channel [James Dewayne] at the perfect time. I’m a firm believer in the butterfly effect, meaning if I were to change anything in the past I wouldn’t be where I’m at right now or certain things wouldn’t have happened. If I started earlier or later I might not be doing this interview right now. Read more>>

Keith Thompson

Wow, great question. Yes I wish I would have started my business sooner. Only because I see how well my business is doing now, imagine how well it could have been doing when I was 24 years old. I was definitely moving way better back then than I am now. I started my business at the age of 26. I was already an athletic director at the time. And this was also the same year covid-19 happened. Unfortunately I had gotten let go from my position due to covid. With all the free time I had, I decided training. Read more>>

Brittany Franklin

I think I started You’re Not Finished at the right time. If I had started sooner without the mental or emotional capacity to run it, I would have given up. If I would have waited, I would have never started it. When I decided to legitimize You’re Not Finished in March of last year, I was finishing my last semester at Azusa Pacific University, working full-time, and getting lots of therapy to undo the things that I knew would hold me back from moving forward in my purpose. Read more>>

Rebecca Major

I wish I would have started my business sooner! I absolutely love being in business for myself and I feel so amazing when I hit milestones or make certain accomplishments. I officially started my business in February of 2022, but I had to wait until I finished esthetician school to actually use my license. Honesty, I wish I would have done this 10 years ago, but hindsight is 20/20 and I am still young! Read more>>

Mohammad Sadat

Honestly, I think I started it just at the right time. I’m a firm believer in everything happens for a reason, and everything happens in the time it’s been ordained to happen. Perhaps I wasn’t ready mentally or even emotionally to take on the challenges I eventually faced, and of course, still do. Read more>>

Niahisha Remy

Great question! I have always had the dream of becoming apart of the News Industry. To be more specific, I was most interested in being an on camera talent, News Reporter and/or News Anchor to be more specific. It all started in Elementary School when I was told to read the morning announcements and the Pledge of Allegiance. From there I knew that public speaking was my passion. Read more>>

Treisha Marcoux

Yes I definitely wished I would have started sooner. My world was a professional makeup artist. I got to do the make up for a mermaid one day and I decided to try myself with photos and did some gigs soon after. Read more>>

Sasha Owens

I am happy I started it exactly when I did. I am happy I invested in me exactly when I did. For instance, I’ve been in interviews and meetings and the moment I said, “I have six published books,” … eyes get big and start looking around the room. I have been releasing books since 2015 and counting. Each year I released a book it wasn’t the easiest. I didn’t feel the biggest. However, NOW❓I feel huge. And I’m just getting started. GET STARTED. It’s always significant. Read more>>

 ChrisCVine

I honestly do think to myself, “what if I started making music earlier?”, “what if I did this at that time?” or “what if I did something different along the way?”. Those questions do often cross my mind and though I could have made better decisions growing up, I’ve been content with the realization that most things will happen when the timing is right. Read more>>

Ric Westman

Sooner, as this would have allowed me more time to expand my skills, as well as give me more photographing opportunities. There are a number of places and sights I wish I had been able to photograph and print. Read more>>

Bill Wilson

I made my living for decades first as an engineer working within the property/casualty insurance industry then transitioning as an insurance expert speaking and writing about insurance coverage issues for industry professionals. But, while doing this, I was secretly an aspiring musician. I’ve always loved music and played a little guitar, but I let the demands of making a living inhibit my efforts to get better at playing music. I never played a gig as part of a band until I retired at age 68 and I’ve been doing it for over 4 years now. Read more>>

Suzanne Barton

I do not consider what I do as a “career” choice. I am just fortunate enough to follow my passion. It’s just the way I move through this life. I feel everything has unfolded as it should. All I needed to do was “pay attention” and “step out of my comfort zone” to continue to grow and move forward. Read more>>

Jaclyn Gordyan

I had about 15 years of wandering after I graduated college. I had been really active in my creative practice while earning my BFA. I studied art, art history, and design and it kept me inspired. But when I left and moved out to Chicago, I found myself searching for my medium. I explored every medium and style I could get my hands on. Realistic, abstract, digital, ceramic, textiles, realistic graphite, chalk, art blogs, furniture building, and photography. I was building skills that would ultimately help me build my art business, but at the time it felt like I was failing because I couldn’t define my art. Read more>>

Grace Scott

I like to think of myself as a late bloomer. I have always had a song in my heart and music in my soul but it wasn’t until my 30’s that I started writing and recording music. I never dreamed that I would have the opportunity to play music around the Midwest and to share my voice with the world through streaming services. I believe that it is never too late to realize childhood dreams. Read more>>

Tracing Paces

No, as a band we would not have had the needed skill and comfort with our instruments when writing and performing music. However, it would have been great to start playing music earlier so we could be more skilled present day. Read more>>

Rachel Reilly

While my past work experience has helped shape me in many ways, I absolutely wish I had started my cookie business, Bluebonnet Bakery, sooner. In college I found a passion for early childhood and elementary education. As a military spouse moving every few years, I thought this career field would serve me well. Teachers are needed everywhere, right? But the reality of military life also made keeping up with teaching certifications across different states and countries extremely difficult and discouraging. The frequency of our moves (most recently, Read more>>

Dolores Cruz

I am a firm believer that things happen when you are ready for them to happen, though I didn’t always see it that way. I used to feel I needed to hurry up and get things done and saw failure to do so as a commentary on my talents and abilities. Now I see that all our life experiences bring us to a unique place where we can express who we are in whatever manner we choose, and this creative place is constantly evolving. For me, at this point in my life, it is through writing. Read more>>

Ashley Anngora

I think about this question a lot. Sometimes I do wish I started sooner, because ageism can be a huge issue in a creative field – especially for women – and I often struggle with a sense of feeling like I’m behind. However, for me, I think I’m entering my creative career at the perfect time in my life. When I was younger, I don’t think I had the maturity, drive, or means to properly invest in a creative career or make meaningful art. Read more>>

Allen Carter

In life, we all have those “what if” scenarios, whether the situation is good or bad. When it comes to starting Carter Comics along with promoting and selling my work at comic book conventions, I’m always glad that I started getting my artwork and books out there at the time I did. My very first convention as an exhibitor was Anime Expo in July 2010, at the start of social media, YouTube, and online print-on-demand services. I don’t think that I would have been able to get Carter Comics started even five years earlier, due to most of those services either not being as accessible, or not existing yet. Read more>>