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.

Shatavia Luck

I often get this question, sometimes in the back of my mind I wish i would have started sooner. However I’m a believer of “when it’s time, it’s time”. It’s been awesome so start something in the middle of a pandemic and people still support you. Read more>>

Shirel Hernandez

I started my business two years into motherhood. I was just 25 at the time. Career wise, I was working less that 10 hours a week teaching ballet to elementary aged kids and dabbling in creating Dance for the Camera videos. Life-wise, I was a new mom and wife who spent most of her time at home. Starting my business sooner, I am sure would have been a nightmare. I had no experience with children beyond teaching an hour long Ballet class. The lessons that I learn spending so much time and energy with my own toddler really informed my teaching. It was invaluable. Read more>>

Megan Black

I started really getting into taking photos almost 5 years ago, after my daughters 1st birthday session went south I decided to pick up an old camera I had and take her out my self the next day and fell in love capturing those memories my self! I have always had an interest in photography but never thought I could make a living out of it! Read more>>

Tonya Civiello

Sometimes I look back and wish that I would have started this business so many years prior. Namely, when I was living in the Orlando area, living my dream of being able to go to Walt Disney World and Universal whenever I wanted to. Had I started my photography business in Florida, my life would be vastly different than it is today. Read more>>

Gabriela Carreon

This is a great question because I have thought about this before! I started photography in May of 2017, I was tired of losing jobs because the work schedule wouldnt line up with my sons schedule. My grandpa who lives in Mexico and my dad were photographers for a newspaper in Mexico and my brother was a wedding photographer in San Antonio at the time. So I thought “I CAN DO THIS!”. I decided to start my photography business and it’s been nothing short of amazing since! I feel that I started when I needed to. Read more>>

Tyrone Wilkens

Knowing what I know now do I wish I started my business sooner? No, what I do wish is I explored different avenues a lot sooner to confirm that this was indeed what I wanted to do. I stumbled across photography based on the financial ability to afford a camera. The repetition and growth in the area created an interest and seeing myself go hard for this medium made me love it. Like any relationship the love had to develop over time because the initial pursuit was genuine curiosity. Read more>>

Becky Morris

I feel that we started this business at exactly the right time – during Covid lol!!! But seriously, it was good timing because I was at a point in my life where my kids were more than self-sufficient and my daughter was even excited to partner with me on opening the store. Although it was Covid, the timing was actually good because there was more of a ramp-up period rather than hitting the ground running. Examples like – market vendors being a lot more willing to work with new stores, vendors being more open with merchandise being available (since there was a whole previous season they hadn’t really sold) and landlords being more open and flexible too. Read more>>

Darius Martin

I certainly wish I started on the path of entrepreneurship alot sooner than I did. I always loved cooking but didn’t know it was a passion that I could build on and turn into a career until my mid 20s . I often look back at the experience and relationships that could have been learned and built on over the years. I was fresh out of a relationship needing something productive to occupy my time and energy. The more I focused on my skill and want to get better the more I realized I wanted to cook everyday and share it with others. Around 2018 I decided officially that I wanted to make a business of it. Read more>>

Garrett Gardner.

I’ve had multiple people ask me about my journey with my business in terms of when I started it in life, when I took a sabbatical from it, and when I relaunched it, and if I would change anything about the time-line. I got into lutherie *instrument building* during my senior of high-school and immediately decided that was what I wanted to do with my life, and that is what I did for the next 4 years of my life. It was a great time full of learning more about the craft and honing different techniques, Read more>>

Whitney Huff.

If I could go back in time, I would have started my business sooner! I started freelancing in 2019 as a side hustle. I was working full time as a Public Relations and Social Media Specialist for a small certification school. While I loved doing that 9-5 at the time, I knew I wanted more for myself. My side hustle grew and grew. I ended staying up later, working around the clock, and it took over most of my weekends even through the pandemic. Read more>>

Paula Cruz

I wish I had started pursuing my work while I was still in University. I felt like I couldn’t because it was “the next stage” and something to look forward to. I could have started doing work outside of my art classes, but I didn’t and saved my ideas for later. It wasn’t until my last semester that I started doing my own thing. I had my work shown in a gallery in school and I realized that I could have been doing that for a while. I feel that not only did I miss out on that, but I also could have grown my early portfolio and experimented more. Read more>>

Tennile Friday

when I started my business in 2021, although I wish I would have started the business much sooner, I am glad that I waited. I am building my portfolio on a daily basis now. When I started my business I had just finished obtaining my four-year degree, and life was much less hectic, as far as time management. If I did start my business sooner I would have had to manuvere around my hectic schedule. So in the end I feel like I started the business right on time because I can dedicate my energy to my clients. Read more>>

Henry Mahome

I wish I had started the brand earlier, I started in or around 2016 with the foundation of the brand and it has evolved to what it is today. I was in College and and wanted a way to do art work, community service and have a company that is an overall artistic expression that was unique but I was not ready, as I was entering post graduate school, I realized there were still things that needed to be learned that if I had learned them sooner I would be at a more productive level. Given the opportunity, I would have taken classes specifically designed for my business that would have maybe given me more structure in the beginning. Read more>>

Bekah Blagg

I LOVE what I do, so it would be easy to say that I wish I would have started sooner! But in reality, I’m very aware that my past experiences and the people I’ve met along the way have played a huge role in where I am today. After college, I worked in the oil & gas industry for several years where a learned a LOT about problem solving, deadlines, performing under pressure and working with a team of people. That’s also where I met my husband, who is my biggest supporter! When we had kids, Read more>>

Jonathan Sams

I definitely wish I would’ve started my business earlier. We really started our business in January of this year . This year has everyone has been impacted by inflation. So it wasn’t the best time to start a business but we took a leap of faith. We are very grateful for coming this far , but we could only image how far we would be if we started earlier. Read more>>

Jessica Green

Although it may not seem like it, I feel like I started my business at the perfect time, in February 2020. I started out as a Portrait Photographer, but I was initially interested in product photography. Some people told me that I should just do portraits instead and I took their advice. The pandemic hit like two months after I started and I felt like I was stuck. No one was going outside let alone booking shoots! Read more>>

Stuart Singleton

I’m a big believer in “everything happens for a reason”. Before I started Cake Records, I had several other businesses that I had run. While I wish I had more of a specific vision for what I wanted to do when I was younger, the experiences and lessons from running businesses from the day I turned 18 are the reason I am able to have more of a focus now. Without trying out a ton of different aspects of the music business, I never would have been able to find what I love to do. Some people get too focused on the destination that they forget to enjoy the journey. Read more>>

Adedotun Adeniji

Shortly after I bagged my Bsc, reality hit me and I wanted something more for myself and I didn’t know what to do at the time but I surely wasn’t set on been average. 2019 was a year to process my entire life and look into some areas I could harness. What motivated me was the urge to do more and better, and more importantly to have a legacy. So I took the leap of faith and started and haven’t looked back since then . Read more>>

Shayla McGhee

If I could go back in time, I would have definitely started my business sooner. I have always wanted to be a writer but honestly did not know all of the career paths writing could bring. I started really taking writing seriously and pursuing my dream of becoming an author right before the pandemic in 2019. The upside to beginning there is that my husband and I had finished paying off all of our student loan debt, so we had a lot expendable income to put into a business. Read more>>

Ebony Walker

There are some people who know they want to become business owners. Then there are those, like me, who are forced into entrepreneurialism – and it actually works! That was my story. I was working an amazing job, making good money in my field. With a degree in Criminal Justice Technology, I was employed as a background screener. This opportunity allowed me to check the backgrounds and experience of those in the military, as well as those applying for fortune 500 positions in various companies. Read more>>

Sophia Starnes.

I think I started my business at the right time. Everything happens when it is suppose to. I had lessons to learn before I could pursue certain aspects of the business. I learn something new about my business and how I can make it better for me and my clients daily. The experience is very rewarding. Read more>>

Elisa Harold

If I could go back in time I would start exactly where and when I started, I am a firm believer in everything happens for you when it is suppose too. I started my business journey in 2015 right after I graduated high school, I wasn’t sure of what I wanted to do but I hated school. I knew working long hours for someone else’s company wasn’t what I trust wanted to do. I wanted to put those long hours into my own business and I started to do that. Read more>>

Kendra Littlejohn

I started my business at a time when I didn’t know what else to do. I had been laid off from my previous employer of 18 years, six months before launching my business part-time. I often say that I have no clue why I didn’t think to start my business immediately after my lay-off because I had dabbled in professional organizing in 2009, working for one client almost the entire year. It was the one thing I knew I would someday come back to. Read more>>

Brittney Kelsey

If I could go back in time , I wish I would have started my business sooner. I started my photography business in 2020. During this time I was still working as a health care provider from 2015 to currently. I stayed working countless hours on the ambulance for 24-72 hours. On top of working on the ambulance , I was also working in the ER and attending college. I am a mother of a 7 & 8 year old; that alone made me work harder. Read more>>

Isaiah Owens.

I honestly feel like everything happens for a reason, It was all Gods timing for me to really start my business in 2020 and to now see my success go big. I started photography winter 2020 after I graduated college. I needed something else to do since I wasn’t going to be able to do sports Video for awhile. I went to a photography event to see if it was something that I wanted to get into but also to really learn how to take photos. Read more>>

Trisha Badman

I started Essence Digital (formerly Take 5 Virtual Assistant) in September 2019. I had just moved to Nashville, TN to start my new healthcare job when the pandemic hit. Like many others, lost my job because of it. I have worked in healthcare as well as marketing for over 20 years. So because of that, I decided to use to experience and knowledge I already had to start my own marketing business. This journey of business ownership has given me such a learning experience and I only wish I had started it sooner! Read more>>

Tashay Taylor.

If I could go back in time I definitely would of started my business sooner. I was in High school when I first came up with the idea of selling hair , it was Me and my two sister who actually came up with the idea. but of course I was in high school with no money , My mom is a hairstylist so her clients would always ask her where to get good quality hair from and she would always say ” Ask the twins they’re always wearing hair” so that right there gave me the upper hand advantage of seliing hair. Read more>>

Angela Humphrey

If I could go back in time, starting my business sooner, would definitely be my first choice. When starting my business, it was 2nd semester of freshman year at Oakwood University. After switching my major from psychology to music, I still wasn’t satisfied. Before going to college, I made the decision that I would not work a job that wasn’t enjoyable. From 14-18, I was already doing hair for church members and their children. Read more>>

Teri Alston

For me – I would say later. I started my business in 2020 and given everything going on, I had amazing customers who want to support my business. However, with the rising inflation and the uncertainty around the pandemic, they had financial priorities – and I totally understood that. I wished I would have waited and started my business when I was financially secure and can devote the time to my business. Read more>>

Coranisha Warren

I have always had a passion for hair. As a little girl, I grew up wanting to pursue a career as a cosmetologist. However, my career choice was not thoroughly praised. My family wanted me to use my intelligence and choose a different career path. I mentally started my business in 2019, but I did not pursue my LLC until 2022. I put my hair desires on hold and attended school to become a physical therapist. After I graduated from physical therapy school and started my new job, it was time to execute my hair business. Read more>>

Lily Hansen.

I founded HappiLily Events at the start of 2021, and it was a long time coming! But, I’d say I started my company at the perfect time! It’s kind of a whirlwind how it all happened. Opening my business when I did, I had a little over 5 collective years of experience working in the hospitality and events industry. I had worked for several catering companies, served as an Event Coordinator for a venue in Madison and I also managed the entire events department for a venue in Minneapolis. Read more>>

Shantel Auguster.

Neither. I believe I chose the perfect time to start my business. I had been doing photography prior to buying my first camera in college. When I was in high school, I’d practice on my neighbor’s Sony and my ROTC instructor would let me borrow his camera for the football games so I had a good bit of knowledge ahead of time. My dad also did photography when he worked as a private investigator so he passed down a lot of his equipment to me. Read more>>

Darlene Taylor

I wish I knew I had this in me. I really had no idea I could make a living at painting all over the country on a large scale that I am now. Read more>>

Allison Costa

I started my business in October of 2022 as I found myself at home with my first baby about a year after leaving my previous job. After Covid hit, I was furloughed and then I took my baby bonding time before I “went” back to work remotely. I attempted to work from home while taking care of my baby initially and because of Covid, I didn’t feel comfortable having him in a daycare. Eventually it was too much with working and taking care of a baby so I decided the best option was to be a stay at home mom. Read more>>