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.

Paulette Piñero

I’ve been dreaming of my business for over 8 years. I remember sitting in my office, re-reading online articles and pulling leadership books from my desk library, trying to find advice on managing conversations with direct reports that I was only experiencing. It wasn’t that I was young or inexperienced; no one else was responding to questions like “did you only get this job because you are Latina?” or “why would you apply to be a manager if Latinos do their best work in the field?”. Read more>>

Sarah Rayburn

If I could go back in time I would absolutely start my business sooner!! I talked myself out of pursuing photography professionally so many times over the years. I was convinced I wouldn’t be successful, or wouldn’t be able to create and maintain a work/life balance etc. I made up every excuse possible to support my imposter syndrome and regret how much time I wasted. Read more>>

Anna Lipson

When I was a freshman at The University of Alabama, I didn’t know what I wanted to do with my life. The only subject in school I truly enjoyed was art and that was because it usually was a time to relax and put my mind on what I was working on. I know I was very interested in the sports and music industry because it seemed like you were on the go all the time and got to experience so many different things. I slowly realized that the industries were very cut throat and my self-criticism was at an all-time high. Read more>>

Teressa Mackey

I wish I would have started sooner. Maybe not the actual business .. but the part where I finally believed in myself and allowed myself to dream and that these dreams could actually be a reality. I think the moment I finally believed it could happen was when my business actually started . The moment when I allowed the dreams to rise up higher than the doubts .. that’s when it became real. That moment is what I wish could have happened sooner. Read more>>

Meric Mizrakli

I think everything happens in its own timing, when we put the intentions right, the path is always shown. We have to make an action plan and always believe. To me, I believe it was the right moment when I decided to build my own business and follow my passion. I love doing yoga and teaching it to kids and adults. So first I told to myself I am giving it a year to see the interest of others( it was kind of my market research with the target clients and different locations) and also I wanted to give myself a chance to see how I like doing it as a profession. Read more>>

Destini Jackson

I started my business in 2020. At the time i was grieving the loss of my mom. My father passed away 1 1/2 years prior to her passing. Legacy Sweets was birthed out of grief and a way to honor their legacy as bakers . There are times that i wish that I had started my business prior to their passing so that they could see how far I’ve come in business and also witness the love and appreciation that people have for our family recipes. However, all things happen in God’s perfect timing and i believe that my business started at the perfect time. Their legacy will continue to live through me. Read more>>

Morgan Nash

That is a difficult question. From a very young age, I’ve always wanted to be involved in fashion. The fashion industry offers hundreds of jobs opportunities and growing up I’ve had interest in all of them. My time in college was the spark of being an entrepreneur but waiting a few more years after college and building more knowledge would have prepared me more. So, if I could go back in time, I definitely would have started my business later. I don’t regret starting my business too early because I’ve learned from my experience as a young entrepreneur. Read more>>

Erica Blowe

I wish I would have taken my business more seriously when I started because the hardest part about business is starting. I started my business in 2013 and at the time I has just had my 2nd child and I couldn’t stay consistent not to mention I had a new job so balancing family, work and business was new to me. If I had started later it may have been a much less stressful journey as at the time there were not many entrepreneurs when I started that I knew only my husband. Read more>>

Latosha Bailey-McCutcheon

I wish that I had the courage to start my business sooner. I’ve always had love for fashion and modeling since I was a teenager I just never did anything with that passion. In the year 2020 is when I decided to move forward with my passion. I am also a hairstylist, and at that time the world was going through a pandemic in which I could not work. I wanted to find something that I would enjoy doing the work while bringing in a source of income. Read more>>

Marisol Morales

I started my brow journey almost 5 years ago but didn’t go full time with my business until about 3 years in. I was fortunate enough to work for a company that gave me a pretty well rounded learning experience to be able to open my business confidently. It was a retail environment but it also had services as well – so I was able to dedicate more of a focus on customer experience while not having to worry about paying for supplies or retail products. Read more>>

Amber Mitchell

I feel like where you are, is exactly where you are suppose to be. Things happen at the right time. When I was in my younger twenties I was not responsible enough to run a business, or even make the decision to start one. It also wasn’t the best time. I was a college student trying to figure myself out making mistakes bumping my head and figuring out life. I started my business at 26 years old and I feel like at that age I had a wake up call. I realized who I was and the things I like and disliked and what I was really capable of. Read more>>

Tracey Flanigan

I am frequently asked if I always wanted to own a floral business and the answer is, “no.” (I’m smiling.) The storefront was opened in July 2010 when I was in my mid-40’s and looking back, it was the perfect time for me, my family and the community. My vision was to formulate a full service floral boutique that showcased local artwork along with fresh flowers and brought the arts together for a fun, visual experience. Fine art and floral workshops became part of the business plan by the second year. Read more>>

Kevin Sebastian

Yes, absolutely. Starting my business has been a wild journey and I’ve made some mistakes along the way. However, I wish I would’ve started learning to code much earlier in my life and started freelancing my services much earlier than I did. I always suffered from the fear of failure and imposter syndrome. I always listened to those online that said “You can’t freelance until you’re an industry expert.” And I kept putting my dreams and life on hold. So yes, I’d say if you want something, just go for it. Read more>>

Christina Richardson

I wish I would had started modeling earlier when I was eighteen years old in college. I started my modeling career at the age of thirty-five years old living in Kansas. If I would had known about modeling when I was in college it would had made a big difference financially instead of being a struggling broke college student. If I would had started modeling earlier when I was eighteen I would had better modeling opportunities. What would I had changed was talking to an agent first instead of wasting my time with photographers who dont know anyrhing about the modeling industry. Read more>>

Alilia Toney

If I could go back in time, I definitely would have chosen to start my business sooner or later. I started my business back in my senior year of high school and I was in a place in my life of wanting to call something my own, but I truly didn’t know where to start. I was getting ready to head to college and was still confused on what I wanted to do with my career, but I knew I had a true passion for design. Personally, I feel as if I would have had a chance to start earlier I would be higher in my professional field and more aware of all of the obstacles that comes with being an entrepreneur. If I knew what I do now back then I would be greater than I am today. Read more>>

Ebone Marlowe

I started my business a good while ago (2010), however, looking back i wish that I’d invested in coaching earlier than I did. Although I started the boutique back then, I had to eventually re-brand because I had no idea what I was doing the first several years. I took a break in 2014 and when i came back a year later, I knew a little more, but still hadn’t grasped the idea of hiring a coach. A little after I decided to have a re-grand opening in 2018, I started to invest a little more in ecommerce education and and eventually entertained the idea of hiring the right coaches for my business, and it’s made a huge difference. Read more>>

Lindsey Pattee

I started a business in my late 30’s and I would say I don’t wish I would’ve started sooner or later! As cliché as it sounds, I am a firm believer in that everything happens for a reason. There’s a reason I had almost 20 years of experience in marketing, corporate settings, working for someone else, etc. It has taught me a ton of valuable lessons that have directly impacted my business today. Now, that isn’t to say that everyone should wait and choose the same path that I chose, to each their own! It was just the right timing/right place sort of thing. Read more>>

Skye Marshall

If I were to go back in time I would have definitely started braiding earlier. My mom taught me how to braid around 2012 when I left college and moved back home. I was working at AMC movie theatre and do not have a career in mind. Back then it was just for fun, like a hobby. I started doing my friends and family and realized I enjoyed it. While still working my regular jobs I was braiding on the side for extra money. I was even working 2 jobs and braiding to pay bills. Once my clientele started building up and I started touching real money I started to think back like I should have learned this before college or in high school. Read more>>

Joanette Aird

I started making beaded jewelry and eventually started making gifts for friends and family. Then I progressed to taking small orders and had my first jewelry show at my church in 2015. I took metalsmithing classes at Dougherty Art School and ACC, just for ‘fun’ and to learn a new skill. Life happened and I had a career as an engineer, but people were always telling me to start a business with my hobby, I never did …. until 2021. Read more>>

Jaela Amos

I wish I would’ve started sooner. Since I went to a magnet school, I didn’t have the opportunity to graduate high school with a cosmetology license, but I knew how to do hair. It is seen as a tradition in my family, so I had plenty of people and examples around. What encouraged me the most, was wanting to help around the house. In grade school, I wanted to make my mom’s life a little bit easier by doing my sibling’s hair and my own. My father was an active duty Navalman for a good portion of my upbringing, therefore he was gone a lot while my mom, younger siblings, and I stayed in Houston, Texas. Read more>>

Jessica Strang

If I could stop time and make any changes to launching my online only jewelry brand, coco + peach jewelry, I wouldn’t change a single thing. That may surprise people who may say that they wish they started their dream job sooner but I needed to have lived before making my own creative dream happen. And it starts with my origin story: I launched this brand in 2019 but I already had a lifetime of connections with jewelry design and sales. My parents have owned a fine jewelry store in Chicago (they still do) since I was a child and so did most of my aunts and uncles. Read more>>

India Barnes

If I could go back in time, I would not have started my business sooner as I wasn’t ready. I firmly believe that everything happens for a reason and that God aligns our steps. If I had started sooner, I would have probably given up because running a business is complex and challenging, and I wasn’t aware of my calling at the time, so it would’ve been no reason to keep going. Read more>>

Kiara Juniorr

If I could go back in time, I don’t think I would have started my hairbraiding journey sooner. I’m a firm believer in perfect timing & everything will happen when it’s SUPPOSED to. I didn’t start taking on clients until 2020 when COVID hit. That was a hectic moment in history for EVERYONE but I’m actually glad I decided to step out on faith & start up my business during that time. I was working at a warehouse and the entire staff got laid off due to the pandemic so I figured “why not FINALLY start putting one of my many talents to use?” Read more>>

Jaèlaun Moses M.S.

Looking back, I’d like to believe I was before my time. Fashion has always been a passion of mine. In 2012, my sophomore year of college I started a styling page on Instagram of me styling people for different occasions or trends, creating looks to give inspiration to others and even posted some of the cutest pieces while out shopping. I didn’t think I would get anywhere, so I stopped. So to see how influencers are making it big for doing those same things I get so frustrated with myself because I let my doubt & fear get in the way of me sticking to what I love. Read more>>

Christy Campbell

After finishing art school I decided the best choice for me was to enter the corporate world, it was consistent money and I felt like that’s what I needed in order to grow. Several years later, I realized that job was completely unfulfilling for me. I started working part time in photography while doing other creative endeavors like co-owning a DIY craft store with my Mom. Shortly before the pandemic that business venture came to an end and it was time to move on. After years of self doubt of whether or not I could be a full time photographer, I took the plunge anyways. Read more>>

Yo-Annie Rosado

This is a question I have ask myself several times. Where will my business be if I would have started years sooner? I really don’t know, I do know that it started in the right moment and is where it has to be and I don’t know what the future departs. In many cases I have wanted to run instead of walking and this time I decided to go step by step to make a business that will last longer. My entire life I have been very crafty and I always created different pieces for my family and friends. Read more>>

Lynette Robinson

People often ask me if I wish I had started my business sooner and my answer is no. I am so thankful for the time I spent in corporate america. I got a sales job right out of college and looking back, it was the best thing for me. The experience helped me because: 1. I was constantly learning new things. Every time new technology came out, I had to learn it and learn why and how it was beneficial to customers, business, etc. I never stopped learning and I realized that things are always going to grow and change and you have to embrace it or you’ll be left behind. Read more>>

Shannon Moton

I first became interested in graphics during the end of 2019, but I didn’t start taking my graphic business seriously until I taught myself how to create logos, flyers, and other things in 2021. Although I was in a somewhat respectable situation when I started my business, I was stressed out and depressed. Because not everyone in the graphic industry is friendly, it was difficult to break into the industry. To be quite honest, I’m glad I launched my company at the time I did. The graphic business is no joke, thus I do wish I had more information when I first started. Read more>>