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.

Starr Swift

I started my business in June 2020. Literally during the Covid lockdown. It was a crazy time to say “let me start a business”, considering that most jobs were online and in the home. My business required me to be around people. It started because my family was suffering during the pandemic and more was needed. I was a stay at home mom of 3 children with needs that required me to be fully present daily. Being a photographer gave me the opportunity to be there for my family and still have the time for home. It’s changed my life dramatically. Read more>>

Nicholas Kusnir

I have definitely wished that I started taking control of my own time much sooner, but there’s nothing I can do to change that so I don’t dwell on it.

I’ve always found myself attracted to creative roles, and what started as fun ended up turning into a job. I worked in Television and Film, helping design sets or organize shoots, for a number of years before turning to marketing. I had worked a number of odd jobs while attending University, and realized I had a knack for creating engaging content. I was then offered jobs in hospitality and tech, creating viral videos to boost sales. It got to a point where I realized I could be doing this for myself instead of giving my time to someone else. Read more>>

Tess Kazenoff

This is something I think about often! I first started thinking about starting a travel blog 10 years ago, when I initially fell in love with traveling.

Sometimes I beat myself up a bit about not going through with it then — in those days, it was so much easier to grow a blog and social media following, and it’s so hard for me to not wonder where I would be now had I not allowed fear and insecurity to hold me back. Read more>>

Jess Brownsberger

I really wish I had started creating content way earlier, and I also wish I had focused on multiple platforms instead of just sticking to one. I’m the kind of person who hates juggling multiple apps, so I usually just stick with one that I like. But, with how fast social media changes, it’s so important to be active on all fronts. I began creating TikToks in 2020 when I was pregnant with my first baby. It ended up being a great decision because I was able to share my entire motherhood journey with the world. The downside, though, is that my followers now only know me as a mom, and it feels like that’s become my whole identity. I can’t stray too far from mom content, or else the algorithm doesn’t push my posts as much. Read more>>

Breonna Pulphus

I started my business in 2020 in a college dorm during the pandemic.
I was an ambitious but indigent college student that simply was looking to increase their income.
I’d say I started my business on time, divinely. Entrepreneurship is a journey of self discovery & spiritual gain. If I had’ve started it sooner, I’d be too immature to understand the organic lessons that are taught throughout this journey. If I had’ve started it later, I’m not sure if I’d have the same advantage & be able to make the same sacrifices. This testimony is happening at a time it’s supposed to, Read more>>

Dean Rhetoric

I’d have probably wished to have discovered poetry a little sooner than I did. There are so many schemes for young poets, and it’s great that those opportunities exist, but it can sometimes feel like you’re expired as soon as you hit 35 years old and above. I’ve always written – whether that’s song lyrics, film scripts, or short stories. I was determined to write scripts and do it for a living, but it didn’t happen that way. I ended up writing on some poetry sites around 2013 and it just kind of stuck with me.  Read more>>

Sonjja Baram

As a teenager, I wanted to write a book about the adolescence challenges I was living; all the insecurities, fears, and hopes of a teenager girl but I didn’t believe I could write a book because I had not finished my education. Little did I know that all those hormonal moments if I had put down on paper could have answered a lot of questions for young adults. I wish I had taken the chance and written that book. If I had been able to share my experience and insight with young girls experiencing similar difficulties, I would have been able to help them. I could have given them insight from a different perspective and maybe guidance during difficult times. I could have given them the courage to stand up for themselves and make positive changes in their lives. I could have provided comfort and guidance to others going through the same struggles. Read more>>

Jarrod Langwinski

Whereas many actors begin their craft in their childhood, I did not take my first acting class until I was almost midway through my college education. My transition to film began even later, when I was 26. In this time, acting has become my unequivocal passion. I often wonder, had I started sooner, how much farther would I be right now? How fundamentally different would my life be? Read more>>

S. Duvall Thornton

I wish I had started my career as an actress much sooner. I’ll preface the remainder of my response by stating that the life decisions that I made at a very early age dictated my career path. I deferred my career because I became a mother as a teenager and I knew my children were my first priority. I was 17 years old and became pregnant with my first child. Shortly afterwards, I had my second child at 20 years old. I’d gone from graduating high school two years early and being the winner of a county pageant (Miss Indian River County) to being a teen mom thrust into poverty and scared as hell that my choices had led me far off the course of life that I’d dreamed of. I began to recognize that I was not living the life I desired. Read more>>

Jeremiah Coyne

I really feel like I would have been more true to myself earlier on. I spent much of my writing days early on trying to replicate what I thought was great or trying to write what I thought people wanted to hear. I have come to find out that the impact of my music is found in its strangeness and uniqueness. Read more>>

Jo Miller

I started pursuing my art in my mid-forties. I had gotten laid off from my twenty-year job as a physical therapist assistant. I was burnt out with the job anyway and decided it was the perfect time for me to change careers.

looking back, I wish I had started pursuing a creative career sooner. You see I had always had an inclination to be an artist at a young age. i was a very creative child. I loved making my own paper dolls, making things out of clay and finger painting was a favorite thing for me to do, when i went on a school filed trip to an art museum with my class in the sixth grade, I had a longing to be a painter. unfortunately, my erroneous thinking was I could never be an artist because I didn’t draw very well. It never occurred to me growing up that drawing was a skill I could perfect with practice. Read more>>

Kimberly Pack

I actually took steps to launch my business in 2022. At that time, I wanted to offer a signature two-day experience specifically crafted for professional Black women. I had an incredible agenda and relevant speakers all of whom had impacted my career or personal life. Everyone I shared it with thought it was unique and exactly what the intended audience needed. However, all of my speakers except a friend either declined or never responded. I was crushed and suspended all business activities for more than 2 years until I relaunched as Ascend Together in April 2024. From my first year of working in a Fortune 50 company, I felt called to help others navigate corporate America’s terrain. Read more>>

Aaliyah Nitoto

Honestly, it wasn’t the right time for me when I started. Looking back, I wish I’d had the courage to start earlier, but one of the biggest things that held me back was the perception of what it takes to start a winery. Most wineries begin with hundreds of thousands, sometimes even millions, of dollars. I didn’t have that. When I finally did take the leap, I started with $10,000 of my own savings and $20,000 from a friend—a total of $30,000, which, by most standards, isn’t enough to start a winery. Wineries are traditionally built around owning land, buying expensive equipment, and having significant resources. I didn’t have any of that. Read more>>

Lindsey Ikeler-reinking

Looking back at my timeline and story there are no regrets on when I started this company. The moments are brief when the shoulda’/coulda’/woulda’s creep in but the whole WIN is that I started. Not when. I’m proud that I did.

I became a personal trainer in 2013. I started training at a commercial gym, and I value everything I learned from this place. They taught me the business side of training, such as sales, time management for sessions, designing a structured program and I was able to shadow other experienced trainers and take pieces of their good stuff and tossed the bad stuff. I later started contracting out of smaller private gyms. Read more>>

Nicki Voss

With respect to a creative career, surprisingly no, as I do feel that I’ve been a creative person my entire life, and I’ve always prioritized making art. Creativity has been a daily practice for me for decades, and I have both undergraduate and graduate degrees in art. I’ve come to the view that many of the skills I acquired in my professional career, prior to launching my small arts business, Textilepop, are in fact assets that have absolutely helped me navigate my role as a sole proprietor. For example, I worked for many years as a Director of Operations in a fast-paced academic environment with tight budgets and complex scheduling in an ever-changing dynamic department that was also focused on accountability. Read more>>

Michael Cobb

my parents’ love of music, their excellent collection of vinyl records, and high quality radio stations. This instilled a deep love of music in me.

I always wanted to play guitar and be in a band like my rock and roll heroes. I played air guitar for many years, which helped me learn quickly as I spent many years visualizing playing guitar. My parents bought me an acoustic guitar when I was 16, but it was in bad shape, and I couldn’t really play it. Read more>>