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.

Cynthia Luttman

If I could ride the Hot Tub Time Machine back I would definitely jump into my cookie business sooner! My first passion and career, veterinary medicine and horse breeding, was science based. I was always drawn to creative outlets but time to explore them was very limited. Horses don’t know you’re tired, it’s a holiday or the weather is terrible. It wasn’t until I retired from my equine business that I was able to pursue outside interests. I wonder how my skills could have improved if I had started designing and decorating cookies earlier. I’m so glad I took the leap to put myself out there and let others see my work. I’d definitely start earlier if I could! Read more>>

Nina Romer

I personally wish I would have started my journey as a travel content creator earlier. But at the same time I am very well aware of the fact, that I wasn’t ready. When I started my New York travel blog in 2022, I had been dreaming about a free-roaming life for many years. I think my fascination with Influencers on Instagram partly comes from my internal desire to live an equally free life filled with opportunities, growth and a community. So when I moved to New York in September 2022, I started to freelance as a marketing consultant. I basically did the job I had before, just out of New York instead of Germany. But I felt a sense of insecurity I had never felt before and at the same time I had gained a lot of free time in my new job. After speaking to a friend of mine, who was equally travel addicted as I am and who had started her own travel blog in 2019, I was hooked. Maybe it was finally time to pursue my calling an share everything about my passion for travelling the world? Read more>>

Kelly Butler

If I could go back in time, I wish I had started my business sooner, but honestly, I didn’t have the confidence. Starting something on your own is intimidating, especially when it feels like there’s so much you don’t know yet. When I finally took the leap, my second child—of four!—was about a year old, and for the first time in a while, I felt like I could take a breath. I wanted to do something for myself. At the time, I was working in oncology non-profits, which I loved, but I always wanted to pursue interior design. It was something I was passionate about, but the idea of venturing out on my own felt overwhelming. Looking back, I wish I had started sooner because I’d be that much further along now—more experienced, more confident, and more seasoned. Read more>>

Danisha Greene

I definitely wish I had started my business earlier. Although in January I will have been in business for 15 years. However, I feel if I had started sooner that I would have been much farther along into where I’d want to be at in my career. After graduating college I was more focused on trying to work in television production because that’s what my degree is in and then just getting stuck working entry level jobs in corporate America. Fashion was always my hobby but I had no idea that there were career possibilities for me to pursue. I was unable to move around initially like I desired because I chose to help my maternal grandmother raise my very young siblings. However I know that even when it seems you are going through a setback you’re actually being set up for better. Read more>>

Joey Clark

So I began shooting in 2016, but round early 2019 is where I started networking more heavily and confidently reaching out to various teams who were passing through Texas and festivals across the states. Overall I believe I started at the right time and I’m exactly where I’m supposed to be honestly. The only thing I wish I had done a little bit more of earlier in my career was network a bit more. Networking is an absolute key factor in the music industry to succeed and I feel like I passed up quite a bit of opportunities to excel my career further. I just wanted to make sure I knew what I was doing before putting myself out there and taking on more challenges. Read more>>

Meredith Styer

If I could go back in time, I wouldn’t change a thing about when I started my creative career. I began comedy during my midlife pivot, and honestly, it felt like the exact right time. Looking back, I realize that if I’d started 20 years earlier, I wouldn’t have had the same depth of connection with my audience. The past 25 years taught me how to truly relate to people—how to understand their stories, emotions, and experiences. That makes me a better comic. Sure, there are dreams I had, like being a cast member on SNL, that feel less attainable now as a woman in her late 40’s. But less likely doesn’t mean impossible! I trust the path I’m on and the timing. I don’t regret a single moment of the journey—because this is exactly where I’m meant to be, doing what I love. Read more>>

B’nathaniel Orlu

Looking back, I wish I had started my creative career during high school and stayed consistent with it—especially with my funny content and singing. In high school, I did begin making videos, but I stopped because I was too worried about what my so-called friends and the world thought. When COVID hit, I started making YouTube videos since there was more time to focus on creativity. However, I stopped again because I was graduating and preparing for college. My freshman year at Morehouse was a big adjustment, so I had to prioritize academics. Read more>>

Portia

If I could go back in time, I would have started my creative career sooner. I started my journey as a creator in April 2020. At that time, I had recently left my full-time role at a media agency, and I was back to pursuing brand ambassador roles. Shortly after, the Covid-19 pandemic took the world by storm, which led to my brand ambassador gigs to be canceled – leaving me unemployed. I had thought of starting a YouTube channel prior to the pandemic, so once I was out of work, I decided to just go for it and bring my idea to life. This then led to “That’s So Portia” YouTube channel being born on April 5, 2020. Read more>>

Flawless Flames

Edward : I’m stuck in between most times. Sometimes I wish I started younger to have an advantage but sometimes I also think about what my career would look like if I stayed in school and waited to wrestle. I don’t regret anything though. Kaizen: I wanted to start my wrestling career at the age of 19, but I had family worried that I would hurt myself and kinda discouraged me. I took the college route and after graduating I fell in love with martial arts and professional wrestling again. Thats when I started competing worldwide jiu jitsu tournaments. I then moved to Georgia from Louisiana to start professional wrestling in 2023. Read more>>

Arica Avery

When I think about STL’s Pot Chef and when we started, I truly feel like the timing was just right. We officially kicked things off in November 2023, with our first event planned for April 21, 2024. If I could go back in time, I wouldn’t change the timeline. Here’s why: everything I did before this moment was necessary to make this brand what it is. Before launching STL’s Pot Chef, I was juggling multiple businesses and growing my skills in media production, event planning, and connecting with people. Those experiences gave me the confidence and knowledge to create something unique in the cannabis-infused space. If I had started sooner, I don’t think I would’ve had the resources, connections, or clarity to execute the vision at this level. If I had waited longer, I might have missed this sweet spot where infused dining is really taking off, and people are hungry (literally!) for these types of experiences. Read more>>

Miguel Jose Matos

Around 2014 I watched a movie titled Radiant Child. The movie was about Jean Mitchell Basquiat. By then I was in my early sixties and retired from a fruitful career in Finance. Fascinated by Basquiat’s work I decided to visit the art supply store and started painted on large canvas paper that fit on top of the dinning room table. Soon thereafter I had painted over 100 pieces and could not stop. I can’t say what would have happened if I started painting earlier because I did not attend art school or have received any kind of art instruction. I came so naturally to me that I got into a whole period of discovery. Where did this all come from? Read more>>

Rob Mabry

This is an interesting one. I’ve dreamed of being a filmmaker since I was a kid running around with my dad’s 8MM camera making silly movies with my friends, but it didn’t happen until I was in my fifties. When I was in my twenties I did make a half-hearted go at being a big time Hollywood screenwriter. That was back in the day when Shane Black sold “The Last Boy Scout” screenplay for nearly $2 million. I’d been writing stories my whole life. I was a journalist in the Army. Writing and filmmaking were in my blood, but at the time (1990s) you really needed to be in Hollywood to have a career in film. Read more>>

April Ruiz

When I reflect on the timing of when I started my business, I truly believe that launching it during my undergraduate studies was the right choice. I was at a crossroads between my engineering coursework and considering a major switch—a decision that ultimately led me to pursue international business and eventually earn an MBA. At the time, I was juggling several roles in engineering jobs while still figuring out where my true passion lay. I often questioned my decision to not complete my engineering degree, but in hindsight, I see that the path I took was integral to my growth as both a professional and a business owner. Read more>>

Emily Bradford

I have been a licensed massage therapist since 2006, and I’ve always worked for someone else until 2023 when I decided it was time for me to go out and rent a space. I worked in a spa, a chiropractor’s office, and eventually started my own mobile business. I would mostly do my mobile business on the side while I also worked at a chiropractor’s office. I didn’t have a business name and treated it more like a hobby than an actual business. In 2020, during the Covid-19 pandemic and we were on a state wide shut down, I spent a lot of time thinking about what is next for myself. I was out of work for six weeks, two weeks of being sick with the Covid-19 virus, and four weeks being on a state shut down. No income for six weeks. During this time, I thought about how if I created a business name and really started treating my business as a business, what other opportunities could it bring me. Read more>>

Dee Evans

If I could go back in time, I would follow the same exact steps. I needed to experience everything I had before starting my business. My prior experiences helped mold and shape me into a capable, resilient business owner. With my faith in Christ, I am assured that I am walking in alignment with His purpose for my life and my business. Before starting Rise2Write Publishing, I worked part-time as a Life Coach for a practice I founded called “On the Go Life Coaching LLC,” and I worked in Corporate Sales for over 15 years. I gained experience in various industries, including Fortune 500 companies in Wireless (Verizon Wireless), Consumer goods (Coca-Cola Beverages), Non-profit (DonorPerfect), and FinTech (Fintainium, WorldPay). While I appreciated the unlimited earning potential in corporate sales, I felt stagnant in my career as a young Black woman with several degrees and certifications. My passion for my work had diminished. Read more>>

Alex Cloyd

If I could go back in time, I would have started my business sooner–I’ll take you back to tell you why and why you might consider it too if you’re on the edge of starting a business and need a sign. When I was 15 years old, I started my first job: site clean up at a large construction company who specialized in new tract homes. Dozens of houses under construction at a time in different phases in a sea of trades. I felt I was a good helper with a motivated, first job attitude. I wanted to learn as much as I could. I sought out several mentors on the job site and from them I saw what hard work and longevity in an industry looked like. It looked like confidence and efficiency. It looked like long days, but great accomplishment. It look like hard, honest work and I liked it. Read more>>

Addison Farrier

I started tattooing later in life by traditional standards (if a “traditional standard” in the tattoo industry exists). I spent a lifetime exploring all kinds of different careers and art forms until I was presented with the opportunity to become a tattoo artist (a lifelong dream if I’m honest). I was 32. Despite being the hardest thing I’ve ever done, tattooing was immediately the best thing that ever happened to me. It gave me a creative outlet like I had never known. It gave me community. It gave me purpose. I remember thinking, “Dang! Think about how much further along I would be if I had started this 10 years ago!” I remember being so hard on myself for not pursuing it with more fervor in my early twenties. Read more>>

Andrea De Los Santos

In short, yes. I started graduate school a few weeks after graduating with my bachelor’s, and through mutual friends met a guy who was making music. We watched him perform at a local open mic and I was so intrigued. I remember messaging him during a class the next day to learn how to start making my own songs. That night, I rented out an audio booth at the school library, with no idea how to work anything, and recorded my first song. He came at the end of the session, and we were both just laughing and screaming with excitement at what I started creating. We spent the next 6 months always together, making new songs, and collaborating. I got to perform at an open mic, and a show, and I loved it. I felt so fulfilled. Read more>>

Shela Solomon

I wish I would have started my music career sooner. Music has always been a very integral part of my life and who I am. I grew up with a very musical parent who shared their love for music with me from the moment I was born, so it feels that the path was almost inevitable for me. However, I didn’t actually figure out how to make this my career until a little over a year ago, when I was 21. I grew up taking vocal lessons and learning how to be in a band from School of Rock, and my passion for music only grew deeper as I got older. However, once I graduated, I felt a little lost and had no idea how I was going to continue my music career outside of the school. I took a hiatus from music for about two years and decided to pursue drawing and painting. As I continued down this path, I had a growing feeling that I was not headed in the right direction. Read more>>

Mavry

I can say without a shadow of a doubt that I wish I had launched my music career sooner. I was caught up in something before that I really thought was fulfilling my heart’s desire. I didn’t realize until the last two years that I’d only been burying this dream of being a music artist. I was never truly satisfied in life until now, though the decision to start fresh on a new career path has carried many challenges with it. I think starting earlier would have dramatically helped my self-esteem. I always had such low self-esteem but now that I’m creating music, my confidence has been restored. Read more>>

Kanude Lightstone

I like to tell people sometimes that I’m a “30-year overnight sensation.” It’s actually longer than that… Since the 1950s or so in the United States and beyond, with the advent of mass media and fueled by rock and roll, pop culture has been driven by youth culture. It certainly goes in waves and we live in a different time in many ways with the explosion of the internet, streaming culture, and the fragmentation of popular culture as a result. But the artist creates AT any age and FOR any age. Always remember that. And making one person cry is worth more than a thousand “ho-hum” sighs. Read more>>

Dave Marmon

Something I’ve learned now that I’ve been pursuing music & DJing over the course of two decades is that having a sense of comfort with oneself and one’s mission is essential. When I started in my early twenties in New York City, the pressure I put on myself often felt crushing. I was working to create the concept and art behind parties, promoting them, investing much of my nearly nonexistent resources into making the events the best they could be, and learning the craft of DJing on top of all that. This left little time for consideration of what I was trying to say, as an artist. In one circumstance I was driven pretty deeply into debt just trying to get an event series off the ground. These experiences put a fairly sour taste in my mouth around the entire endeavor. Read more>>

Raquel Arnette

I’ve been a photographer and videographer for over 15 years now, and looking back, I sometimes do wish I had fully committed to this artistic path sooner. After college, I found myself drawn more toward corporate jobs—payroll, administration, tech coding—but my creative side was always there, waiting for its moment. While I loved the structure of those roles, photography and videography were my true passions. My journey as a professional photographer really took off when I began covering events like New York Fashion Week, the Billboard Music Awards, Soul Train Awards, Celebrity Boxing, WNBA LV Aces, and the Grammys. Over time, this evolved into running RA ImageZ LLC, where I specialize in event, portrait, and fashion photography, as well as branding for small businesses. Working with celebrities, politicians, and major public figures like Former President Barack Obama, Denzel Washington, Jermaine Dupri, Jake Paul, Coolio, Floyd Mayweather, Hillary Clinton, Donald Trump, and VP Kamala Harris has been incredible. Read more>>