The uncertainty of entrepreneurship causes many entrepreneurs to put off starting their business. For others, losing a job or other economic hardships push them starting their businesses earlier than expected. In our conversations with thousands of entrepreneurs we’ve seen so much variety in when, how and why people started their business and so we wanted to share a wide variety of views and reflections on the question of whether these folks wished they had started sooner or waited longer before starting their businesses.

Erika Stewart

Honestly, I am glad I started my business back in 2012– it wasn’t the issue of starting sooner or later, but rather going full-time instantly. I was always afraid of not being able to support myself, so for countless years, I would divide my time with another job while also running my business. I would find whenever I was slow with my filler job, I would get extremely anxious that time was being wasted- time that I could pour into myself and my business and make my dreams come true. Read more>>

Samantha Zimmerman

I’ve always loved baking. Some of my most favorite memories are in the kitchen with my mom or grandmothers. I didn’t truly step in to a “business” until 2019, but I wish I would have taken steps in my “early days” to really fine tune those skills. Taken the time before Army, marriage, kids to truly invest in me and my passions in the kitchen! BUT- IF I would have done that, would I have met my amazing husband and had these two crazy kids?! Probably not, so I think timing is everything in life and this is just the “season” of life to make Sami Kay Cookies truly happen! Read more>>

Khella Young

When I started my baking business, it was in 2017 after almost a year of corporate job searching. I had got let go from my first job that I had gotten right out of college in April of that year, and it was hard. I was really hard on myself and at the time I didn’t really know why. I hadn’t had any other “big girl” jobs and no prior experience than the part time jobs I held in college. I felt so stuck, but I also felt as if everything happened in divine timing. Read more>>

Kendra Hunt

If I could have started With Love sooner, I probably would have, but I can’t say it’ll be where it is today. I used to refer to myself as a creative serial entrepreneur and still do a little. At one point, I felt like I was “starting a new business” on a regular before moving on to another idea. I created a cleaning personal assistance service, custom designing accessories, and doing lashes. I was a modern-day hustler. Lol. Read more>>

Brittany Jones

If I had a time machine and I could go back in time, I would have definitely started in my career a lot sooner than I did. I always thought that I would feel more fulfilled choosing a different career path. cosmetology has always been an interest of mine since childhood I would watch my cousin do hair all the time . I loved the styling my dolls and practicing on friends. It wasn’t until I graduated college and after several failed job attempts that I decided that I wanted to pursue cosmetology full-time because that was something that was near and dear to my heart. Read more>>

Austin Alegria.

I started my business officially March 2020 during the pandemic, I was let go from my job due to the pandemic. My boyfriend said now is the time to do what you actually want and work on you and your business. I was scared as I hadn’t sold anything of mine or made anything in a very long time. But I took the plunge and decided to make crossbody handbags in an envelope style. Read more>>

Hester Parks

I started my business as a side-gig while working in accounting and finance in corporate America. My drive and passion for events gave me adrenaline during the late nights and early mornings. When I look back, I wish I had taken the leap sooner so that I could have helped many more people! My college degree in accounting and finance and later, a Masters in Business Administration, gave me a solid financial foundation for running my own small creative business. There have been bumps in the road, but for the most part, everything has worked out and I am smooth sailing into a long and successful future ahead. Read more>>

Eric Olson

When I was about 6 or 7 years old, I got my first ever drum set. By the time I was 19, I had been in a couple bands but not really made it anywhere. As it always does, Life happens and the dream of being that drummer guy never made it past the garage. I discovered the Djembe drum later in life, but I always knew about it since I went to larger music stores to get supplies for my drum set. I never realized the impact that drum has on people until I started playing it for my wife. Had I known sooner about the Community, the love, the Rhythms this wonderful drum creates, I would have left my corporate job a lot sooner. Read more>>

Ashley Williams

If I could go back in time, I definitely would have started my business when I was younger but it took some obstacles and self reflection to see that this was my purpose. It’s funny because I actually had just graduated from school as a dental assistant in 2018 but right after that I chose not to work in the healthcare industry and decided to pursue entrepreneurship in 2019. Read more>>

Ryan Henderson

If I could go back in time, I would’ve definitely started my photography business sooner than later. I originally started back in 2018 after some self reflecting and wanting a part-time hobby/passion. Knowing what I know now, I would’ve started back in college. Having way more opportunities to take pictures of friends, sporting events, and other campus events would have been easier. Read more>>

Michael Poe

I have had the dream of owning my own business for years and was searching for what that might be and look like. Over the years I’ve had different ideas, but I kept coming back to the thought of starting my own photography business. With photography being such a broad subject then I had to write out all the different types of photography there are and determine which one’s I was really interested in by basing it on photos I’d taken over the years. Read more>>

Echay Jackson

I started my business 2 years ago, in hindsight I wish I would have started sooner simply because I think I would have a larger clientele. Starting sooner I believe I would have the food truck I’m planning and saving for now. When I started my business it was during the height of Covid most offices and restaurants were closed or take out only and I seized the opportunity to have great tasting food available for pick up and delivery. Read more>>

Bre Lang

A lot of times I hear people say they should’ve started a business idea or hobby sooner, when they haven’t started at all. Or, when they felt like they have started too late in life. I think I started video production at the right time. Prior to getting into the business of it, mentally I wasn’t in the right spot. I wasn’t thinking of what a business or skill could do for my career. If you are not mentally ready for something, it doesn’t matter if you start now or later because you have to be mentally prepared. Read more>>

Leslie McBride

I would have absolutely started my business earlier had I known just how fulfilling my business was going to be. My husband and I were living in a tiny apartment in Savannah, Ga. We never saw each other due to conflicting schedules and I just didn’t have the space to create. I was waiting tables and putting myself through the dental assisting program at Savannah Tech. Unfortunately due to health reasons I had to stop but I never ever thought I would be living in Charleston, SC., happy and running a small successful business. NEVER SAY NEVER…. Read more>>

DeEtta Gleason-Conway

If I could go back in time …..I probably would have started my business sooner . I’ve always been known to be “girly” or “diva” by family and friends (not in a negative way). I am the one who everyone can always expect hair to be on point ,accessories perfect and can’t forget about lashes to envy (lash extensions)lol. But seriously,I’ve always had a hustle mentality,desire for business but most importantly providing things ,services ,experiences to make others feel good . I noticed outside of own personal battles with hair thinning people would always ask ,”where did you purchase your hair extensions ,who installed them, Read more>>

LaShanda Melton

I definitely would have started my business sooner. I really started putting an effort in getting work and name noticed in 2019/2020, essentially right before the pandemic. At the time I was working as a social worker and a therapist with some local hospitals. I really wanted to empower women to feel their absolute best & most beautiful. The look on a woman’s face when she sees herself & is satisfied with the outcome, is something I can not put into words, but when you love what you do, it does take your breath away. I originally began my journey in 2009. Read more>>

Wendy Shaia

I wish I had started writing earlier in life. I tried writing in my twenties, but I was not successful. I now know I didn’t have enough life experience; thus, I didn’t have much to write. Twenty-five years later, life has given me a lot of material to write about – some good, some not so much. I read a story about a woman who began writing in her seventies and wrote tens of books before she died. That story inspired me so much that I decided it wasn’t such an odd idea to begin writing later in life. I would love to write full-time (while still being able to eat and pay my bills), and I hope to grow towards that someday, hopefully before retirement. Read more>>

Samantha McRoy

I definitely wis I had started my business sooner! I feel like this is a loaded question though, because if I would have started earlier I wouldn’t have, nor did I have the support I have today. My success would have looked a lot different. I truly started my business about 2 years ago, however I have had interest in photography since high school. I asked for a camera I could learn on as a graduation gift, and received a point-and-shoot film camera. I played with it a bit, but soon bought my first DSLR camera so I could adjust settings. In 2015 I bought a camera you could change lenses! Read more>>

Christopher Oropeza

I first began the Idea of starting my own DJ business in late 2018. I first began my professional DJ career in 1999. The same year I graduated High School. I worked for, at the time, one of the only Nationwide DJ company’s in the US. I retired in 2016 after 17 years and countless awards and recognitions. I was the most requested DJ for 15 of those years. Read more>>

Zuri Hill

I honestly can say I have no regrets. I started my business in the 8th grade, and my brother was a senior in High school. I had always had a love for photography. I took pictures on family trips, asked my parents for a Polaroid for Christmas, and got my first digital camera. The day before my brother’s senior prom, his photographer canceled on him. When my mom explained what happened, I immediately said I could take his photos. Read more>>

Annie Fuller

It was summer of 2020, I had a two-year-old and a six-month-old at home with me full time. I was going stir crazy. I wasn’t ready to put my kids in daycare full time, but I was ready to get back to work. Instead of going the traditional route, I decided to start an online, product-based business. I took classes, hired a mentor, joined a community of other like-minded women and Find Your More Fashion launched. Just a few months into starting this business, my husband and I were surprised with baby #3! Read more>>

Cassidy Burel

In November of 2019, I launched my business with the start of my biggest commission to date. Although I had alway wanted to own my own brand. I felt like it made the most sense to work/study under another successful designer to gain experience before truly investing in a business of my own. 2019 was also my senior year studying at the University of North Carolina at Greensboro (UNCG). But the next year brought so many challenges. As we all know, during the year 2020 came the rise of the pandemic. Read more>>

Mark Pinkney

I definitely wish I started Mark’d By Mecca sooner ! I actually waited 5 years before actually getting my LLC and launching my website. But here is a little backstory- In 2012 I enrolled at the Illustrious Clark Atlanta University and started dancing, modeling, directing, styling, etc. I became the president of the leading fashion organization; E2S. I founded the first modeling troupe at CAU; EPIC Modeling Troupe. I directed 3 CAU homecoming fashion shows and I used every designer I could find in ATL. If I had the knowledge I have now, I would’ve have not only started Mecca during my junior year of college, I would have also changed my major from Psychology to fashion design. Read more>>

Sydney Johnson

I definitely wish I had found the inspiration to dive into the creative world sooner. I wasn’t exactly sure what I wanted to do with my life in my early 20s, so I went the “safe” route and completed my Bachelors degree and got a job in corporate America. I thought that I would have one of those lightbulb moments at some point and magically know what my calling was. However, I found myself getting caught up in the day to day of work and life and not giving much thought to “what’s next?”. Read more>>

Dieter Meza

I grew up when YouTube and myspace were the dominating social media platforms. Back then we didn’t have “influencers”, and you didn’t have the plethora of vloggers on YouTube that you do now and the ones that were vlogging were small, unknown, and it was relatively easy to know who they were, even if you were not subscribed to their channel. Read more>>

Tymarri Holmes

I wish I would have started modeling sooner. I wish I would have took a leap of faith and started in high school. Modeling has really helped me come out of my shell and be more confident and I wish I could have experienced the same confidence then I have now back then. I think the biggest thing that would be different if I started earlier would be experience and the photographers i could have worked with. Read more>>

Joletta Sells

I would say that my “career” as a Christian artist began in 2014. That’s when I noticed a shift from a very long season of preparation into a season of artistic creation and corresponding career pursuits. My season of preparation lasted about 30 years. From the very first piano lesson at age six, through all the church music practice I had with my local congregation during my teens, then all the years I wandered away from music, and finally through the life struggles that brought me back to music and kindled healing in my soul. All of these experiences served as invaluable preparation for the creative work I do now. Read more>>

Kaitlin French

I’m originally from Brooklyn,New York but I live in Atlanta, GA currently. December 29th, 1995 #Capricorn What got me into modeling- Growing up I was different. I got teased like many other small kids. But being around my fashionista older sister, I have always had a keen interest in fashion, but never felt confident enough and like many never really knew where to start. She always had a closet full of designer clothes and purses and I would always play dress up in her closet. Read more>>

Lana Adams

The human part of me would say that I wish things happened for me sooner. Because I believe in divine timing, I know that going back in time would not produce a different outcome. Thought it’s hard to truly believe this at times, I have an “innerstanding” that all things happen when they are supposed to and that I’m right where I need to be. Read more>>

Peter Prankster

I wish I had started my creative journey sooner! So I’ve known for a long time that I wanted to be an entertainer. It wasn’t until a couple of years ago I discovered what that might actually look like. I started a TikTok page when Covid started in March of 2020 and I began uploading pranks. I really had no idea what I was doing. At that time, I had just been let go from my part time job due to the Pandemic. My page began to grow abnormally fast and I wondered if I might be onto something! Read more>>

Derek Jefferson.

This is a good common question. I would obviously state that everything is divine timing but to be more specific, everyone would like to think starting something sooner would mean you would be further now but without the experience I learned from mistakes, failed attempts, missteps and even the glorified moments. I would think then I would have never matured enough to achieve success in my field. I doubt a doctor would regret all of the time he spent just learning how to become their best version of a doctor they could be, you can apply that to anything. Read more>>

Ashlee Hightower

In my 20s, I stayed on a pretty traditional post-college career path. I graduated undergrad, attended law school, graduated at the top of my class, and went on to work at a top-tier law firm. After practicing law for a few years in Birmingham, Alabama I decided I needed a change and took a job in the publishing world in Washington, D.C. While I thought this change might scratch my itch to do something different with my legal degree, it mostly provided a temporary reprieve and relief from long, Read more>>

Maygen & The Birdwatcher

This is a great question that we often have dialog about internally. We are both in our mid to late 30’s, we both have families, Maygen has two kids, and Noah has a full time career. As we continue to move with momentum it’s more and more apparent that being 20 and having no responsibility would make much of this way easier. It makes it difficult for us to travel or take chances on opportunities when we have to dramatically shift our life around each time. Read more>>

Melissa V Neal

So first I believe that life is all about timing. I feel like right now I’m in a great space to actually be prepared to receive all of the amazing things that have been coming! Now I wont lie, I lost a lot of ground by taking time off and also not giving my all when I first started. When I first started music and fitness I really just seen it as a hobby, and never thought much of making a career out of it. I just knew I loved to sing and exercise, but I played around a lot with my craft/gift. Read more>>

Morgan Hyde

One of the most important foundations for a successful creative career is understanding that there is no time limit or expiration date on self-expression. It’s easy to conceptualize artistic success as something which can only be achieved at a young age, but your work at 30 will differ vastly from your work at 20; likely for the better. Lived experience is integral to the creative process, and though I don’t regret pursuing an early education in filmmaking, it’s only in the latter half of my 20s where I’ve found the confidence, perspective, and emotional maturity to channel my effort into what I would consider “serious” artistic endeavors. Read more>>

Melissa Torres

I moved to San Antonio, TX in 1997 from Newburgh, NY after graduating college with a BS in Nursing. I have always loved art whether it be drawing, painting, or working with clay. I grew up as an only child and art was my way of entertaining myself, but I never showed my work to anyone. In high school, one of my art teachers suggested to my mother that I pursue a degree in it. I was a young mother, having had my son my Senior year. Mom felt art was a hobby, I needed a steady income to support myself and my son. I took a few art classes in college. Once I began working full time, I stopped. My life was sleep and work, mostly because I worked 12-hour shifts at night.. Read more>>

Dee Soo Pretty

Honestly, I thought I was too late. I didn’t start taking my modeling serious until I was 30 years old. But it was perfect timing. I feel like if I would’ve done it sooner I wouldn’t have been as successful. In my 30s, I am more aware of the projects that are a right fit for me instead of accepting any offer thrown my way. I am able to create firm boundaries with companies and peers in a professional yet assertive way. I also know my worth now and the value of my time. It really pays to understand the business aspect behind the pretty face in the pictures so definitely grateful that I waited until I was a bit wiser. Read more>>

Yong Takahashi

I grew up in an Asian household and we were encouraged to get a traditional job that paid well. Accounting came easy to me so I accepted a business scholarship. It was a great career choice as it provided for a new house, car, and almost all other luxuries I wanted. However, I didn’t aspire to be an executive for a corporation. When my supervisor said he wanted to promote me to assistant controller, I lightbulb went off. I told him I wanted to leave. Read more>>

Yael D.

I so wish I would have started sooner. Since forever I knew I wanted to be an artist and be on stage. When I was little I forced my poor younger sister to do plays with me using the window curtains as curtain and the tiny space in between back stage. She hated it but I forced her! In elementary , mid and high school, I always participated in plays and musical (never got a lead part though !!!) Read more>>

Daisy Jve

Well, I actually started doing hair when I was in the 10th grade. I had just turnt 16 (I think) and my first client name was Nique Nique . I remember like yesterday I did her hair on the first day of school in my room . So I started really young but I didn’t start taking my craft serious until after the pandemic. I was doing hair because I loved it , but then I started getting good and it shocked me honestly, so I told myself , “ Read more>>

Markethia Bankston

I finally found the courage to push my business and get my LLC license around the fall/winter of 2019. Then boom, covid hit the following months. That was a very crucial time for me. Not only was I just in the beginning stage, but I was also trying to find a way to manage the business, still working in the education field, be a mom and wife, all while covid is happening. Read more>>

Sha’Keisha Hendricks

If I could go back, I would have started my business later. When I first started my business, I was working my 9-5 while making custom wigs as a side hustle. It was kind of a spare of the moment thing. I didn’t take it as seriously and shortly after, took a break while I transitioned to a mom. Looking back, I would have pushed it off while I educated myself more on business, branding/marketing and studying my target audience. It definitely would’ve saved me some time. I also would’ve waited until I was at a point where I could truly and was ready to invest in myself. It is a true statement that it takes money to make money. Read more>>