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.

Taylor Berry

If I had a time machine I would wholeheartedly go back and start my creative career way sooner. Being a full-time content creator and makeup artist, I feel gratitude for having the ability to be 100% sure that this is what I was always meant to do. I graduated HS back in 2012 and like many, I figured it was only natural for me to go to college like the rest of my peers. Read more>>

Abdullah Konte

So its funny cause I think about this all the time. I started my adult career in Accounting (graduated with an Accounting degree from the University of New Mexico) and never loved it, but always figured that was just a part of growing up. When I jumped into photography I realized that I should follow my passion and try to do what I love for living. It was a rough up and down journey which continuously led me to think how my life would have been if I started it earlier and to be honest I’m grateful for those years in Accounting. Read more>>

Dale

As a kid, my parents had a camera that I would use from time to time. As I got older as a teenager, I lost interest in it. Once I got to community college I picked up a job with my school’s football team videotaping games and practices as a manager. I did that for two seasons and once I moved on to university I ended up taking an extended break again. During covid my interest spiked and I started taking portraits. And I’ve been in love ever since. Read more>>

Yung J

Honestly I don’t regret starting my business later. I’ve always wanted to do it, but I always wanted to do it right. I was still in the beginning stages of my career. But I knew then I wanted to start my own business. If I had started sooner, I’d probably would have made a lot of mistakes. Not saying I didn’t make any, but it would’ve taken longer for me to learn what I needed to know to be an entrepreneur. Looking back I don’t regret my experience. I learned some very valuable lessons and I not only applying those lessons to my career but my life as well. Read more>>

William Thomas

I started my businesses in 2021-2022 but I wish I started them in 2019-2020 or even earlier in 2021 because I had a lot more free time and disposable income due to me just being a college freshman with a part-time job reselling shoes. With all that time and money I had during that time to do whatever I want with it because I had zero responsibilities I would’ve been able to maximize the amount of time and quality put into my business and I would be in a better position than I am right now. Read more>>

Jewel Kingsley

If I could go back in time and start over, I wish that I had started laying the ground work for my business sooner. However I think I launched at the perfect time. I had the extreme privilege of being a full time stay at home mom for 16 years, and it was only when my children were older and more independent, that I decided to jump full time into creating my business. If I had started sooner, I would have lost precious time with my family and had to make hard choices surrounding how we raised our kids and the activities they participated in. Read more>>

Brittany Lee

If I could go back In time I do wish I would have started my business sooner. I started my makeup and braiding business at separate times. I started braiding hair back in 2016 after having my son. I enjoyed braiding and making extra money. Once I started back working in the corporate world I stopped. Then the pandemic hit and I began working from home, turned 30 and decided to pursue my passion in doing makeup professionally. I’ve always been passionate about makeup and hair since I was in high school but I wasn’t motivated at all to pursue it. Read more>>

Jasmine McGinnis

If I were given the opportunity to become an entrepreneur sooner than later, I would not have embarked on the opportunity at that time. I know that sounds crazy right? I am a firm believer that what is meant for you will be and everything that happens in life, happens for a reason, So let me give you a little history about myself and why I am very happy that things aligned exactly how they did and when they did. Read more>>

Meghan Hopkins Sokorai

I started And Here We Are after almost 10 years in corporate graphic design. I’d come to a point where I felt stuck in the middle of the corporate ladder and not really sure if I wanted to keep climbing it. At the same time, I fell back in love with the tactile nature of running a letterpress and creating physical goods instead of digital files. Read more>>

Leighton Hart

In 2014, I was very unhappy in my job. I started offering ghostwriting and social media management as a side hustle and booked a client who paid well. At the time, I had young kids and the idea of leaving my 9-to-5 (with its benefits, 401k, paid vacation etc.) was too intimidating. So I never went all-in on that business, and when my client didn’t renew his contract, it was all over. Read more>>

Christie Yau

The timing was truly serendipitous. I had just left my previous role as an early employee at a successful venture-backed wine start-up and I was ready to take on something new, but felt insecure about moving from wine (fun and easy to talk about) to toilet paper (arguably less cool and a lot less natural to talk about). I shipped my 1st honeycomb order in Sept 2019. By December, I was already seeing crazy demand so I took a leap and placed my first large custom order. Read more>>

Katie Whitaker

I love this question because I wish I had started my business sooner but I know I started Handyma’am at the perfect time. I moved to NYC in 2011 and immediately got hired by West Elm as a visual manager – my role eventually expanded into something like a brand carpenter. I worked there for 8 years and loved my time with the company but there was no career path for me. In late 2018 I met my now wife, Madeleine, and we started talking about what my life would look like without a traditional job. What if I worked for myself? Where do I even start? Read more>>

Alishia Lee

I started my business after I quit my full-time job of 8 years. I was the head of my department and preparing for the next level of my career and felt completely unfulfilled. I had the opportunity to leave and It was terrifying. My job was embedded as a part of my identity. I knew I wanted to work for myself and take fashion seriously, but I had no idea where to start or how to start. After I quit my job, I dove head first into teaching myself how to sew more effectively and how to run a business. Read more>>

Sanya Kerney

Looking back in time, if given the opportunity, I would’ve undoubtedly started my business even sooner. Beginning my business in May of 2014, I was scared, confused, and frankly, completely lost. Having a 4th grader of my own at home, I knew that I had to be a role model to her young self and accomplish goals that I now knew were attainable. Read more>>

Aleatra Dimitrijevski

Wow… I definitely wish I would’ve started baking sooner. They say everything is clear in hindsight, right? Firstly, I would have to say that although I have been professionally trained and educated in almost all aspects of Culinary Arts, I do not consider myself, in any way, a Pastry Chef. I am a Baker/Treat-Maker or how I choose to identify myself… a Dessert Designer. Read more>>

Katie Cahn

I started my career as a metalsmith the end of 2017 – I was 37 years old. I always knew I wanted to create and be my own boss but I never found the right medium. I was a terrible student and skimmed by grade school with C’s and D’s. I worked restaurant jobs and was a raft guide for 14 years until I finally decided to get a degree. I earned a special education degree and graduated with a 3.9. It took everything I had to earn that degree and would ya believe I only lasted as a teacher for one year! Paper work and legality and meetings and bosses – I was in way over my head. Read more>>

Tamara Thomas

At the beginning of 2020, like the rest of the world, I made my plans for the new year. I just purchased a home, but my 20 year long career in fashion, was stagnant. I was entering a season of revolution. 2020 was supposed to be the year I made a shift, or, at the least, find a new job. Then there was the quarantine. Read more>>

Lisa Gantt

Yes, I wish I would have started my writing career as early as high school. I have always had a passion to write but my consistency was a major problem. My grandmother believed in me and published one of my poems in a book of poetry when I was a child. She believed in my work. This year I have been the most consistent with my Blog. I stepped out and believed. I just kept writing. It is freedom for me! I always had this desire in me and I will continue to write. My writing and transparency helps people in life. Read more>>

Jennifer Brooks

I don’t have any regrets! In fact, as I have grown older, I have come to appreciate the roads that have led to my current season. I actually started a custom cake business many years ago, called LKO Creations. I am mostly self taught, so I spent years practicing different techniques and finally decided one day to give it a go. I came up with a business name and just started taking orders from friends and family, coworkers, etc. Read more>>

Kristen Rutkowski

I believe that everything happens in the timing that it is supposed to, whether I can see that at the time or not. Dip’t Cookies started in 2022, however prior to that, I did own another bakery, which morphed quite a bit before Dip’t Cookies was born. Read more>>

Mike Olinger

I absolutely would have waited at least another year! I left my full-time job in November of 2019 with big hopes and ambition to start a microbrewery in a really cool, historic building in downtown St. Joseph, MO. I had a good business model, was paying for most of the business with my own money which meant no loans, and I had a good lineup of beers too. Buildout happened early 2020 and just as I was preparing to open to the public, Covid shut everything down. Read more>>

Joey Withinarts

I was born in Norfolk Virginia DePaul Hospital. As a kid I always loved to draw pictures with my brothers and sisters. art ran deep in our family.Back than art was just a hobby.I attend John Rolfe middle school and varina high and received many awards like central office exhibit black history month 2007 central office exhibit youth month 2008 Central office exhibit black history month 2009 also the scholastic Virginia of fine arts 2012. Read more>>

Chris Cade

If I could go back in time I would tell myself to keep going. I was always creative and loved being in front of the camera. Even as a middle schooler I was creating little movies with my sisters. I always had the talent but what I lacked was the confidence. The confidence to say, “so what I don’t have the camera that this person has,” or “so what I have never seen this idea, I’m still going to do it.” Read more>>

Susanne Kretschmer-Schmidt

I feel I that if had started sooner I wouldn’t be the person I am today. I’ve learned so much from my past decisions and mistakes and it’s so funny how things start to click with the passage of time. Things I learned that I thought I’d never need, became useful years later and I wouldn’t change that experience at all. I believe I am right where I’m meant to be and have learned that the best moment is the present. Who knows where I would be if I had started earlier or where I’d be if I had started later on. The hardest thing is to focus on the now because that’s what you’re living! Read more>>

Tahiera Brown

In many ways I wish I’d started my career sooner. I was in my late twenties when I began my career. I really started out in film in cable television. At the time it was like a new frontier. I was fresh and I was primed to try new things. There are many things I would have loved to experience and places I would have traveled. I can only imagine my life facing the new horizons that would have come my way. Looking back I would have been more daring. I was a very shy young woman. Read more>>

Makala Muhammed

My name is Makala Aayana. I am a Caribbean-American, mixed-media, sustainable artist in Durham, NC. In the fall of 2020 and 2021, I graduated from The Georgia Institute of Technology with an undergraduate degree in Industrial and Systems Engineering and a graduate degree in Health Systems, respectively. Although I do not have a formal art education, I have marked myself as a creative person since the moment I was able to hold a crayon by myself. I credit my proper ‘start’ as an artist to my experience crafting my submission for the 2016 Advanced Placement Studio Art Exam during my senior year of high school. Read more>>

Emily McClain

People are sometimes surprised when I tell them I didn’t write my first play until 2017. I had been teaching high school theatre since 2005, and I had my children in 2012 and 2014 respectively. Full time teaching and raising small children was the sole focus of my life for a long time, and while it was incredibly rewarding in many ways, I felt like I was losing myself artistically. I found it hard to get excited about what I was working on with my students and I struggled to maintain a healthy work-life-art balance. Read more>>

Angelique Bates

This is a tricky question. Normally I would say I would never have chosen to be in the industry if I knew even 1% of what I know now about it. But then with that knowing I also know everything happens for a reason and we are all on a path do good. And we are in control of our destiny. There are lessons that are supposed to be learned and a lot of us fail to learn those lessons. So until we do we have to keep on repeating cycles until the lesson is learned and then progress. Read more>>

Elle Ann Brown

“For everything there is a season, a time for every activity under heaven.” I’m a firm believer that the talents buried within us will emerge at some point in our lives, whether on a small, personal scale–like singing in the shower–or a grand, public scale–like reaching accolades and fame. I’ve always been a creative person in regards to signing, dancing, writing, and acting (yes, I was a theater kid), but reading, unlike many authors, wasn’t part of my life until I’d jumped with both feet into my thirties. Read more>>

Leighshana Barrett

I would have started my business sooner for sure. I love what I do and I love sharing what my business stands for with others. Getting those messages from clients telling me how my products make them feel and how much they enjoy them make me even happier. I started my business in October 2020. It was the height of COVID. I didn’t have a job then and I wasn’t interested in putting myself in a situation to get sick. I realized many people were indoors and needed items they couldn’t get to with the lockdowns and COVID going around. Read more>>