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.

Nicole D. Scott

Looking back, I’ve really come to grasp the saying “timing is everything.” I remember starting different groups and businesses years ago, but none of them had the impact or stability of my current 7-year-old non-profit. Back then, I felt disheartened by the lack of progress and bewildered by how much I had invested personally without fruition of any progress. Read more>>

Alyssa Dahl

I wish I would of started sooner. The thing is I did start sooner, but even though I was designing in the fashion industry, bridal is it’s own world. I was a senior designer by the time I wanted to switch into bridal, and so that was tough. To have done the time of working my way up the ladder for years already, it’s hard to go into something starting from scratch again, especially when you are older. Read more>>

Stephanie Mathis

We opened our business in 2012. My husband, Dustin, and I decided to join forces to create our business, SB Body Arts. My husband is a professional body piercer and at the time had been piercing for approximately 15 years. I graduated from Oklahoma City University in 2005 with a degree in Entertainment Business. Read more>>

Annie Caspi

I wish I could go back in time and study metalsmithing and gemology in college. For whatever reason, at the time, it never crossed my mind that I could ever pursue a career in this industry. However, I am grateful that eventually I found my way here. It’s never too late in life to pivot. Read more>>

Julia Giang

I actually started my business around the worst possible time and this was during the peak of Covid in 2020, so you can just imagine what that was like. But then you also realize that birthdays don’t just suddenly stop and even if the bakery down the street closed, people still wanted to feel that normalcy in life. So while it was the worst time globally to start a business, it was the best time locally and I’m so thankful for the people that trusted me and still let me make treats and baked goods for their families. Read more>>

Sierra Driscoll

Back in 2019, while I was living in Colorado, I began crafting a website and drafting a business plan for a floral shop and boutique idea. Reflecting on that time, I’m almost relieved I didn’t launch things then, unaware that I’d soon relocate to Florida. The thought of establishing a clientele and business there only to uproot and start anew here would have been tough. I believe things didn’t align back then for a purpose, leading me to start up here when I did. Read more>>

Andrea Owens

In hindsight, I would have started my business sooner than I did. I started my business 10 years ago during a tumultuous time for me. I was in the midst of reluctantly leaving a job I had for 25 years, while starting a new career as an educator. I had mixed emotions and uncertainty about what was ahead of me. Read more>>

Sharon Alexander-Oscar

If I could go back in time I would have definitely started my business sooner. I actually got the “calling” into entrepreneurship 4 years prior to venturing out. Had I started sooner, I would have scaled my business and expanded into multiple locations by now. Read more>>

Jackie Hill

If I had the ability to go back in time I wish I had started my cleaning business sooner in life. I went to business management school and gained valuable knowledge and skills that could have been put to use earlier. Having served as a general manager and department manager in the past, I had already acquired the leadership and organizational abilities necessary to run a successful cleaning business. Read more>>

Danielle Blanton

I frequently find myself wishing that I would have began my entrepreneurial journey earlier. I was thirty the year our brick and mortar opened in 2017, and at the time it felt perfectly timed, and perhaps it was. Prior to taking the leap I had spent ten years in the bartending/service industry and had finally made the move to financial services to get out of nightime work. Read more>>

Diana Clark

This sounds crazy, but I feel as though I didn’t emerge from my chrysalis until I was 74, That’s when I finally decided it was time to fulfill my lifelong dream of being an interior decorator and launched Metamorphosis DESIGN. I think of myself as living proof that it’s never too late to start a new chapter. Read more>>

Vanessa Landa

I believe in the following phrase “God’s timing is perfect.” I say this because I lost my job in November of 2017, soon enough my father decided to step away from the restaurant business. I felt as if this was meant to be. It was early 2018 when I decided I would take over the business. I mean I had just lost my job and I thought … “we can’t stop serving our community” who my father had been serving since 2009. Read more>>

Martelle Graham

Reflecting on My Journey: Taking the Leap of Faith When I think back on my journey, I can’t help but ponder what could have been if I’d taken that leap of faith and started my business earlier. The progress I might have made! However, I must be truthful with myself; I was still inexperienced after graduation, so maybe it all happened at the right time. Read more>>

Shakerra Monét

Do I wish I had started my creative career sooner or later? Mmhmm, I go back and forth with this question often. Sometimes I do wish that I had started earlier or been more consistent, but then I wouldn’t experience what I have experienced as a young 20-year-old. I think where I am at right now my younger self prepared me for it, but I am still learning and advancing my skills each day. Read more>>

Garrett Hampton

Earlier, absolutely! I have always had a love for art, I have been a musician since I was 11 and working on my graphic and web design since 15. I knew that grab bag was what I wanted my future to look like and music has became the dominant one. I started releasing my own music in 2019 but I had been rapping for school projects or goofing iff with friends sporadically since 2012. Read more>>

Molly Golson

Sooner! about 36 years sooner, to be exact. I would have benefited from 4 solid years of learning the basics and technical aspects of the craft, gotten professional feedback and support and had a degree in Art. Instead, I took a meandering path, marriage, divorce, two other careers and then a very late entrance into what I knew I wanted to do an be my whole life. Read more>>

Michelob Williamson

I can’t lie, I think of this often. This has been one of the thoughts burning in my mind. Ive been musically inclined my whole life but never really knew what direction to take it or where to begin. Had I known these things sooner I feel like I could be much further with my career. I see all of these you get artists nowadays and just think to myself, where would I be ? Read more>>

Natasha Camp

I wish I would’ve started when I was a bit younger. I do understand content creation has no age limit, but I feel like I could’ve grown more back than. Im thankful for my platforms I do have, but I know I could be BIGGER! Read more>>

Ranier Acosta

I’ve never thought about this before. Honestly, no. I used to think I started late because, you hear about all these people and how they’ve been acting since they were eight or nine. But after working as an actor in these last few years, I realized that I might have started at the right time. Read more>>

Alex Petunia

At first I thought I should have taken my creativity more seriously sooner. I always enjoyed writing as a kid but put it aside to focus on my nursing career. Being a nurse has taught me how to invite healing with my hands and kindness with my presence, and how to use my voice to advocate for my team and my patients. Read more>>

Zople recently

Starting YouTube in my early twenties was always a love/hate relationship for me. Even while I’m glad for my fast growth and the love of many supporters, I am constantly reminded of what could have been if I had worked on my aspirations after graduating from high school. How far down the road to the greatness could i be? Would be a household name by now? Could i have retired my parents by now? Read more>>

Robbie Kenyon

When I was in my 20s, I was a filmmaker, and one of my only regrets in life is that I didn’t start a creative business much sooner. Looking back, it’s something I could have built for myself over time, while also working another job to stay afloat financially, which is much easier to do in youth than it is as you get older. I lacked the confidence and the know-how, and I’m hoping that others will realize how important it is to find a mentor to help them map out a plan for themselves. Read more>>

Jill Albino

I was never in travel, I came from the event/design world. I have always been a creator and I love small details, perfect timing and interesting concepts. Looking back this is what would help me build a career in travel. In 2018 I decided I was ready for a new venture. I had been home for 8 years with my children after working corporate for a luxury brand for 13. Read more>>

Holli Beth Clauser

My journey into entrepreneurship kicked off in a slightly different timeframe than you might expect. My LLC was formed in June, 2022 but I officially launched my business in November of 2022, and it wasn’t until February of 2023 that I hit a significant milestone by securing my first major client. The idea for my business had been brewing since 2018, and, like many entrepreneurs, I had my fair share of doubts along the way. Read more>>

Jermaine Lanos

Looking back at the path of my career in business I am glad that I started when I did. There are some things that i would definitely do differently but for the most part I am happy with where I am in business. I started this business during the middle of the pandemic with two close friends. Read more>>