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.

Ciara Burton

Honestly if I could go back in time, I would’ve started my business sooner! When I first launched my business, I was in a hustling mindset to make a living and ends meet for me and my two kids. I lost everything, house, job, car so I didn’t think of how challenging running an business while being a single mother could be. My drive to get my income flowing, helped me sell the product, but my will to fight off depression due to my living situation I was in definitively helped my creativity flow! Read more>>

Sarah Montgomery

I don’t know if I could have started my business any sooner having not grown up with an entrepreneurial example or abundance mindset, I never really saw this for myself. I was about 10 years into my career as an artist/designer and the company I was working for doing product design was no longer creatively challenging, although I was able to hone in on leadership and project management skills. Read more>>

Ja’Cole Tabor

If I had to choose, then I honestly wish I would’ve of started my business SOONER! So originally, I started selling sunglasses in 2018 along with other “fur” accessory items and I called my business ‘D,Foreman Frames & Fashionwear’. In the spring/summer I did sunglasses, while in the fall/winter I did fur coats, hats, & etc. I had just graduated college in 2017 and was working for the City Dayton Recreation & Youth Services Department, so my business was really just a ‘side hustle’. Read more>>

Jules DeLorenzo

It’s funny when I look back at the trajectory of my life, now that I’m standing here at 30, living some of my wildest dreams, being able to intertwine such a strong passion for photography and make money doing it has been life changing. I worked as a barber in NYS for close to 10 years. Which led me to understand humans in a very close up way. It’s said your doctor, your dentist and your hair stylist are the top 3 services that actually have to touch another human being and its true. Read more>>

Kendall Frost

I certainly wish I had developed my business sooner. I spent my first few years in film making and photography as a freelancer and not a business owner. I found myself working for others rather than working for myself which led to a bit of instability when it came to income and the direction of my craft. As a result my career took more of a corporate route rather than creative. Read more>>

Jackie Dallas

**Do you wish you had started your acting career sooner or later? Great question! It’s tricky answering that because on a gut impulse, of course I wish I could’ve started acting earlier. Of course I wish I could’ve spent more of my life doing what I love! But the honest answer is, I’m glad I started when I did because I don’t know if I would have found the same kind of success if I had pursued acting earlier, or if I would have been able to handle the challenges of being an actress if I were younger and not had the life experiences that I did when I chose to pursue it professionally in 2014. Read more>>

Jenny Araiza

If you could go back in time do you wish you had started your business sooner or later? Give us the backstory Before I started in the permanent makeup industry, I was in the fashion/beauty industry. I owned and operated a front store and online boutique that also offered makeup services in house for 5 years. About two years before transitioning into permanent makeup, I had my eyebrows done and loved the process. Read more>>

Jeffery Mullins

We all have the FOMO of what could’ve been. But in essence, what really matters is your willingness to do the thing. If you’re able to mix your instances of preparation and opportunity, and by the graces of reality are able to take some of those moments of curated luck, I believe that that’s admirable for anyone to experience. Read more>>

 Jay Coleman

I definitely wish I had started my business sooner. I launched Sincerely, An Introvert just over a year ago. At the time, my career was going incredibly well. I had achieved success and recognition in my field, but deep down, I always felt that there was something more for me out there. I had a burning passion for creating a brand that catered specifically to introverts, acknowledging their unique needs and providing them with comfort and solace in the form of loungewear. Read more>>

Greg Lytle

I sometimes wonder what it would be like if I had started my business back in the late 2000’s. I was working at a vehicle graphics company at the time and getting my hands into some paint pinstriping cars and truck lettering when the jobs came in. I didn’t think you could make money painting signs. I was told it was a dead craft. Read more>>

Paul Hairston

I would have definitely started sooner. But I feel when I 1st got started back with photography was the perfect time. Though I wished I had gone from free work to charging sooner. And had I done that sooner it could/would have made my transitioning out of current day job happen sooner. If I had I would be I would be much closer to achieving my goals and dreams. Read more>>

Nina Martinez-McCaslin

At the time when I first started my business I was nervous on how everyone would react to not just seeing my personal pictures with my hair loss but also how would they feel when I mention I have a ‘all natural hair growth product’. I started my business at a time in my life where I was having to build everything from the ground up. it took a lot of courage to put my story out there but I knew if this product helped myself it could help anyone. Do I wish I could’ve started my business sooner? Of course. But during the pandemic I had plenty of time to think this through an finally push myself to do it. Read more>>

Marie-Laur Killebrew

I would have liked to have started my business earlier and differently knowing what I know now. KlassyKillebrew was started a little over 4 years ago. I was a Paparazzi Customer and my consultant, Davida Clay, asked me if would like to be a consultant. I hesitated at first but eventually I agreed and KlassyKillebrew was born! At first, I could only do it part time because I was the Pharmacy Buyer for the local hospital and I had been working at said hospital for over 25 years. Read more>>

Jana Orr

I was an infant teacher for five years prior to launching my business. I never knew what a postpartum doula was until I was an infant teacher helping parents get some sleep. After spending time with a family and helping them out at night time I knew the story wasn’t done yet. I soon realized my heart wanted more than just to be a teacher in a classroom. I wish i would have know about this amazing career sooner. Now I get to change lives on a daily basis and still get to work with infants. Best of both worlds. Read more>>

Ray Sauter

Yes and No. I first got the opportunity to open a food truck in late 2020. Food trucks were never on my list as I just didn’t have an interest in them. But after what we all know happened in 2020 things changed. I wanted to do smoked meats or pizza. However I was opening this first food truck with a former partner of mine so we decided on Mexican food instead as everyone loves Mexican food.. Fast-forward a year and a half from then things had changed. The Buisiness was fine but our partner relationship was incredibly sour.. Read more>>

Cody Eggleston

If i could go back in time and start my business sooner I definitely would. I started my actual business about 5 years ago and like a lot of contractors used it as a nights and weekends gig. I fully pursued it full time about 2 years ago, and to have started it sooner would have meant building a client basis and overcoming all the new company problems earlier. Read more>>

Zuri Sanaa

When it comes to starting my business like anybody else Id say I wish I started sooner. If Im being honest I started my business at a crazy time in life but it was actually the perfect time. Ive always wanted to be an esthetician since I can remember it was the skilled trade I planned to take on upon high school graduation. Read more>>

Tonya Rivens

Looking back, I would have started my business later. I was a single mom when I started the business in 2003 and my son was born in 2003. Two births in the same year! As a senior in college, I had a vision that came in the form of a dream, to keep my grandfather’s legacy going. The following morning, I documented the dream by drawing pic of a diner & barbershop. Grandad died when I was 3 therefore I had no memory of him. Read more>>