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.

Melanie Snyder

If I could go back in time I honestly think that I would keep things the same. I was very fortunate enough to get a job right of college with another wedding planning company in the area and honestly, I never saw myself wanting to start my own business. After working for the company for a while, the Owner gave me an opportunity that allowed myself to open Melanie Paige Events + Design. I am a huge believer that things always happen for a reason and I truly believe that I was meant to start my business when I did, which was a little over 5years ago now (6years in January 2023). Read more>>

Mercedes Burchett

I started creating prior to starting a business. This was in 2020 at the beginning of the pandemic. I had no thoughts of running a business at all. I was dealing with personal issues, anxiety and just sadness because of how much was changing so quickly. I had also began a spiritual mentorship so my spirituality and my creations have me something to focus on that was solely mine. And I dove deep. I remember thinking that my pendants at the time were trash lol but I continued creating anyway. I have pieces away to family and friends often. One day, someone asked if they could make a purchase and even though I was not as confident in my work then, someone else was. I made my first sale mid September 2020. Read more>>

Tony Martino

I wish I would have started my business sooner. I had the idea for Fido Insido years ago, but I thought it would take too much time and effort to create social media accounts and build a following with a full time job. I told myself I was just too busy, when in reality, I had the time and bandwidth, I already had a ton of photos of my dog Ricky. How hard would it have been to create an Instagram account and share them there? Even when I was laid off from my full time job, I thought I had to do all this work before I could officially launch my idea. Read more>>

Lisa Clow

Hindsight is 20/20, isn’t it? On the one hand, I most definitely wish I had started my business much earlier in life, and on the other hand, I wish I had stayed in school longer to explore my interests or worked in a design firm, but all of that comes at many different costs. The years in between school and going full freelance were trying, but I can see how they were useful and formative. After a few years of floundering from attempting to earn a degree in Marketing, to dropping out of college, to selling women’s perfume in the mall, to singing downtown on the street corner, to performing for Dolly Parton’s Playhouse to promote her Imagination Library, Read more>>

Nicole Choate

I’d like to say that I wish I would have started sooner or jumped ‘all in’ sooner, but I truly feel that by being patient, I was able to set my business up in a more strategic way. I started my business when I was still working at my corporate job. I had been working in Talent Acquisition for 8 years, and was at a really stable place in my career. I had been promoted twice at my company, first to a Manager, then to a Director, and I was overseeing a nationwide team of 5 employees, and managing an internship program with 50+ interns a year. Read more>>

Allison Iannone

I started out teaching Art and I taught every grade level from Kindergarten to twelfth grade. I was working in New Hampshire at the beginning of my teaching career and because I was new, I would be the first one cut due to budget issues. After a few years of being cut and then rehired in a different position in the same school district, the opportunity came along for a job teaching Photography. After the current Photography teacher retired, I started taking classes and learning how to teach film in anticipation of interviewing for the job. After a year of teaching in Photography, which I realized was my dream job, my husband and I moved to Delaware. Read more>>

Hannah Johnson

Hindsight being 20/20, I feel like a lot of business owners look back now and would consider starting their business before a global pandemic would take over everyone’s lives for the foreseeable future. But, even looking past that, I still wouldn’t change a thing about when I started my company. It was May 2020, and at that time I was at one of the lowest in my life in regard to my mental health. The full-time job that I was working was draining and taking up a lot of my time. I had been working in childcare for almost 10 years and I needed a major shift. So, I sat at home and started to research something that I had always been interested in and that was weddings. Read more>>

Angela Freeman

I think I started my business at exactly the right time in my life for me. I’m originally from Scotland, where I worked as a graphic designer/printer for 25 years in the local library service. I loved my job there, but because it WAS a library and my bosses were librarians, I basically had free reign over the Reprographics Department. This taught me how to work on my own, scheduling jobs and being able to follow a job through from the initial idea to completion. Read more>>

Ilaya Brown

Looking back from right now in my career I would have started selling insurance when it was 1st presented to me in 2018. March of 2020 my contracting job with the federal government stopped abruptly due to COVID. We didn’t know if we would be eligible for unemployment or what the world would look like while we quarantined. The uncertainty of what the world would be had everyone on edge. I wasn’t unemployed for long but I didn’t have to shut down my online clothing store, And Amazed, due to the inability to get merchandise to sell. I started my insurance career in 2021. Read more>>

Madhu Sharoff

I started Kimbala in 2019 but the idea came about in 2018 after I left my career in the wine industry. It was time for a change and I had always had this, ‘what if.. [I had my own Brand]’ at the back of my mind. Life-wise I had just gotten married, was living in the Bay Area, life was good and it felt like it was now or never to address that ‘what if’. So, I decided to make the move to Entrepreneurship. Knowing what I do now about starting a brand – starting sooner in my life (early-mid 20’s), perspective is different, energy levels are different and willingness to jump and take risk without thinking much is also different; which I think are all positive things. Read more>>

Alisha Needum

I Fancy Safety first came to mind late January and launched March 2nd, 2022. Now I am 6 months into business, and I couldn’t be happier with the outcome. I wanted to start another business that I am passionate about, something that can be shipped, and something that can be personalized. I remembered seeing a TikTok video about a self-defense keychain, and right then I knew that is exactly what I wanted to do. The idea of making women feel safer and more confident in this crazy world just made sense. I had been running my first business, I Fancy Sweets, doing event decoration and props for a few years at the time. Read more>>

Hydia Baldwin

Hmm, that’s a fair question. I don’t wish anything far as timing-wise. If I would have formed my company sooner, it wouldn’t stand a chance today. I had to strategically design my company, plan when to launch, and do intensive research; I didn’t tell anyone about my idea except for my now fiance. So, I began my online vegan bakery in January of 2021 during the COVID pandemic. I was still in college, had just relocated, and was still trying to figure life out. Not to mention I just left my work-from-home job in December of 2020. You can pretty much say, I was juggling a lot. Read more>>

Eric Lucas

If i could go back in time i wish I would’ve started my business sooner. My passion for photography started in college. I had just transferred from Alabama A&M University back home to Birmingham to attend Lawson state community College. I bought a Nikon Coolpix point and shoot camera and you couldn’t tell me nothing lol. I thought i was an instant professional, this was back in 2005 or 2006 and cellphone camera quality wasn’t what it is today so Im at every family function taking pictures of friends and family. Fast forward to 2018 i was approached by my brother to start a photography company, since he knew i was once into photography. Read more>>

Gabrielle Martin

No, I don’t. I truly believe that everything happens for a reason. I’m right where I need to be. I started NailedbyGee June 2020, right in the middle of the pandemic. The salons were closed and I’ve been into nails since I was 13 so it was honestly perfect timing. I feel like if I started sooner, my business wouldn’t be here today or I wouldn’t have been as consistent with it. My daddy was killed in a hit and run accident in 2014 while I was only 20 years old and I had just graduated college 3 months prior. Read more>>

Logan Boaz

I never thought there was the “perfect” or “right” time to start my business. I knew from a young age that I was a very creative person, I just didn’t realize I could make a career out of it. Around the time of my wedding is when I started thinking that I could actually make a career out of my passion. My husband and I made all of our wedding decorations to help save money and ultimately bring our vision to life. We were really good at it; he would cut, sand, stain the wood and I would dream up the pieces and paint on the designs. I received so many compliments and it boosted my confidence and confirmed that this is what I would love to do for work. Read more>>

Brittany Finn Cropenbaker

We feel that we were fortunate enough to start Blushery Events at the exact right moment – both in our lives and businesswise. Two out of three of the Finn sisters had already planned weddings and were married, and Kelsey, the third Finn sister had just recently gotten engaged. So with the knowledge of two previous brides, and a future bride, we were able to curate Blushery Events to meet both the wants and needs of someone throwing an event, as well as someone who would take the place as the guest of honor at a Blushery Events event. And yes, Kelsey had both her bridal shower and bridal suite at Blushery Events earlier this year. Read more>>

Bernice Loman

If I could go back in time, I would have started my business sooner. I started my business while working a 9-5. It was a leap of faith for me. I was nervous yet excited at the same time. Later in my entrepreneurial journey, I learned about the business capital, grants and resources available for minority business owners like myself. I would have love to have started my business during my early 20’s but I believe that all things work together for the good. I now take my experience and share with others including young entrepreneurs. Read more>>

Ben White

Currently, I am extraordinarily happy with where I am in life. Do I wish I did anything differently? Not even a little bit. Maybe a few tiny things here and there like not trying to steal gummy snacks from the elementary school cafeteria, but everything I have done has led me to a very happy place in life. That being said, I think it is very, very important to start a business sooner rather than later. If anybody has been toying with the idea for a while, then you’re already late to the game, but not too late to start. Read more>>

Adrian Pollard

They say hind sight is 20/20. That is actually true. For many years I regretted not stepping out on my own sooner. I mean look, the music industry has changed drastically and I can’t say it for the better. However, In the time that I have spent grooming my skill and educating myself I cant say that there would have been a better time for me to start than when I did. I’ve met many people during my long pursuit. Yet I’ve only met a few who I would say were actually beneficial. The truth is, had I started sooner I would have been thrown to the wolves. It is after all a dog eat dog world. Read more>>

Summer Taha

I think I started this business at the perfect time in my life. It all happened so fast and it all fell into place perfectly. In 2019, I found myself with an intense urge to start buying plants. I felt like I needed something to look after other than myself. During the pandemic, that urge grew stronger and my collection grew larger and I found myself with no more space for my green babies. They all lived in my little egress window and I had the idea to find a plant hanger on Amazon so that I could fit more plants into the small stream of sunlight I had in my room. Read more>>

E-Roc

I didn’t start making music until 2017 when i was 19. A lot of my peers started when they were even younger. So i feel like if i would have started earlier i would be a lot further on in my career than i am now. Read more>>

Dominique McNeil

Of course I wish I started my creative journey sooner than I did. I picked up modeling all on a whim. I had finally got my life back on track after uprooting and leaving my toxic 8 year relationship. I was living at my best friend’s house for months before and then I was finally was able to save up and get my own place. I felt like my whole world had crashed around me but at the same time I wanted to pick up the pieces. For so long I had felt so insecure about my weight and my appearance. In fact, I don’t think I had ever felt content with myself before modeling. Read more>>

Tessa Emily Hall

I began to pursue both of my dreams to act and write when I was a teenager. I wanted to be an author since I was a child, and frankly, writing (and acting) were my only two passions. I couldn’t envision myself pursuing any other career. Since I knew that the publishing process took a while, I didn’t see any reason to delay. With the amazing support of my parents, I enrolled in a virtual school in high school so that I could fit creative writing into my schedule and go to acting auditions. Read more>>

Evan Small

I’ve been at least producing some form of visual art since childhood. In middle school I fell in love with Photography. In middle and highschool, Art Class was never something I chose as an elective. Looking back, I don’t know why that was, because I drew or took out my camera every day. There were about 5 years in my Twenties where I stopped pursuing any sort of Creative form of expression altogether, but when I started painting again, it felt like I’d gotten better, and it didn’t take long to surpass where my skill set had been. Read more>>

Sheree Rabinovichh

the butterfly effect. If I had started any sooner or later, who knows what path I would be on now! Events in my life leading up to starting my business really shaped my creative mindset and gave me the inspiration and drive that has brought me to where I am now. Read more>>

Dalton Jensen

The short answer is yes. I do wish I could have started my creative career sooner. I started my podcast in January 2020 and quickly realized this creative journey was for me. I picked up everything quickly, from video and audio production to interviewing and sourcing my guests. Starting earlier for me would have probably meant a whole different life trajectory. I hold a Bachelor’s in Accounting and a Master’s in Business Administration, but if I had started sooner, I might not hold either of those degrees because I knew right away that I had something unique with my newly discovered talents. Read more>>

Jordan Ryan

I like to live life with no regrets and instead I try to learn from my choices that maybe weren’t always for the best. I started my makeup artistry career on the retail side of the industry. I worked 40+ hours a week as a manager in cosmetics and for years I put off pursuing my passion of working for myself as an artist we blamed it on my job. In hindsight I saw that it wasn’t that holding me back, but instead, I realized it was me. I lived in my head and unfortunately constantly compared myself to other artists around me. What is that saying? Comparison is the thief of joy? Speaking from experience I will say this is completely true. It took a big life change and a global pandemic for me to decide to finally pursue my passion of makeup artistry 100% and I haven’t looked back since. Read more>>

Vander Warner

I definitely wish I would have started sooner, hindsight is always a clearer picture but there were 100 different things I could’ve done to have jump started the career path I’m on now. I wanted to be a professional guitar player when I was 10-11 years old, I hadn’t been playing guitar very long but I figured there had to be people somewhere making music for a living and that began a very deep rabbit hole I’m still going down today. It took me a very long time to figure out how the music industry worked for somebody that wanted to be a sideman, and I don’t really think that part would have changed. Read more>>

Kari Dern

This is an interesting question! My whole life until I founded this business I felt like a creator trapped in someone else’s life. As I was growing up I was always drawn to art, drawing, sculpting, crafts of any kind imaginable. At the same time I was determined to be independent from the moment I left college and I knew I had to pay the bills so I first worked at an insurance agency, then later had a career in sales in the beverage industry. All the while I woke up every day feeling like this wasn’t my life. Read more>>

Lurenny Franco

From the moment you decide to enter social media, it is the perfect time to start interacting and experimenting with your creativity, attract attention or interest with your message to the public within an environment that you can capture. The time is now. For me there is not a before or after, the important thing is to start and give flight to your creativity. From a very young age I wanted to venture into the world of social media. The only thing is that I doubted myself and did not have the right maturity to face everything good and bad that comes with the world of social networks. For many I have started very late. Read more>>

Emily “Emmy” Slager

In hindsight, yes, I absolutely wish I would have pursued this career sooner. I truly believe this is what I’ve always been meant to do, but it took awhile for me to stop doubting myself and to go after it. I spent a lot of my twenties jumping around from job to job, trying to make one of them fit. I also spent a lot of those years struggling with OCD and anxiety. I only decided to go back to school after a broken engagement and a bit of a quarter life crisis. I just wasn’t the best version of myself during that period of my life, and it has taken a lot of time, work and life experience for me to begin trusting myself and truly going after what I have always known I wanted. Read more>>

Ally Rose

I think it’s important to preface that it’s never too late to start pursuing your dream. Sometimes things fall in place when they need to, though I always think back on where I would be now if I pursued music seriously earlier. I’ve always been interested in creative work. I come from a very musical family where singing is a natural talent. Throughout my life I dabbled in fine arts, film, poetry, music, and creative writing. I wanted to do it all so I did. I thought illustration and film was my calling, as being in front of crowds always gave me severe anxiety. As I got through college music started calling To me, and I started becoming more and more comfortable being in front of crowds and performing. Read more>>

Stella Nicole

For me I always knew I wanted to be in music/a creative. I think the biggest part of why I didn’t start earlier was myself. I felt like I had to be at a certain level to start creating music or performing, when it’s actually quite backwards from that. I started music and recording music near the end of my college career but started writing much sooner than that probably around middle school. I would have started earlier and just reached out to people to collaborate with rather than do it all myself. I would have done more things with collaborators in my field. Just went for it and not let myself stand in the way. Read more>>

Jenn Bouchard.

I hadn’t written fiction since probably middle school. That was a long time ago! When I was in my late thirties, I had just finished a two year stint as the president of my college’s alumni association. It was all-encompassing and wonderful in so many ways. When it was over, I had a big gap in my life. My kids were still young, and I was teaching full-time, but still, I longed for something else. The idea of creating something was very appealing to me. I began to entertain this idea of writing a novel. Why that, I’m not sure! Although part of me wishes I had started earlier–my debut novel novel was published when I was 44–I do think there was something to starting when I did. Read more>>

Amanda Keltner

Well, this is a loaded question. I have started 2 businesses in the past 2 years, one, opening my own hair salon studio, has been extremely successful and the other, my artistic/creative business, while not at the level of my salon yet is also becoming more and more successful. Here’s the story of opening my own salon, Flora Luna Hair Studio. My career in the hair industry started in 2004 while still living in the Pittsburgh, PA area. I had a successful job at a large chain managing a couple of different locations but it was lacking the creativity that I was desiring. I then got a job as a senior hairstylist/manager at an Aveda salon and realized all of the things that I was missing in my career. Read more>>

Acacia Harris

I sometimes battle with the question of whether I should have started my creative career sooner than later. I have always truly loved creating, but I never knew how I could make a living from it. I was taught that I needed to have a career that would be able to provide a living for me. So, I went the college route and I attained an undergraduate BBA degree in Finance and Marketing. I ultimately landed an entry level job in the financial services industry that required no degree because I had no experience. I had a degree with no “relevant” experience. Read more>>

Brandon Dawson

I grew up playing basketball, and being an athlete meant that I couldn’t be interested in anything other than basketball. I thought that basketball had to be my highest priority; I even held basketball in higher regard than God. Books, art, and other things that I was interested in were somewhat off limits to me due to the culture of basketball. It was almost as if it wasn’t cool to read, write, or be interested in anything that wasn’t a round spherical object. For years I had the desire to create art through my writing but I never did because I was afraid of what my peers would think. Read more>>

Asten Rey

If I could turn back the hands of time, I would definitely start sooner. I began slowly but also privately because I wanted to improve over time and give myself time to prepare for what I thought I’d need to know. My career was basically nonexistent because I was pursing other avenues, so it could be considered a hobby to more people. I think if I had started sooner it would’ve been beneficial as in opportunities, growth, experiences, as well as being more creative in where I am at this point. Read more>>

Kenny Boyer

Definitely sooner. I am the oldest in the band, and I often feel like a grandpa with these guys. It’s good though, because they tend to keep me on my toes, and we all know exactly how to push each other to make one another better musicians. That said, however, I definitely wish I had known these guys 10 years ago. Read more>>

Angely Martinez

Personally, I never think about this. My life as a jewelry designer and metalsmith has been a journey and will continue to be. I started by experimenting with different materials and learning a variety of techniques. I did ceramics, digital fabrication, glass, other alternative materials, and now fine metals. Everything I have learned, whether from school or from all my jobs on the bench, has led me to this moment where I am. As a professional designer, I feel like my journey has just started. Read more>>

Keisha Hester

When I first decided to start KD3 Enterprises, I had already tried once at the ‘entrepreneur’ lifestyle. Originally being a teacher for 7 years, I experienced a life changing car accident that made me have a different outlook on how I was going about my chance here in this lifetime. Therefore I decided to ‘retire’ early, and go after my dreams of building my own business. I joined what I thought was a great opportunity at the time, to work in financial services. Long story short, it was nothing of what I truly wanted to spend the rest of my life doing. I had to return to teaching, Read more>>

Bernie and Christy Auld

We had been married for almost two (2) years when we decided to start the blog but had been together for almost 16 years. We had plenty of stories and adventures to share with our readers but we both believe that when you do something you do it right. Even today we struggle with finding the time to sit down and work on a post. Actually, let’s correct that…every day we discuss something fun we just did or a memory of somewhere we traveled that would make a great blog post. However, talking about it and writing down our adventures are two (2) different things. Read more>>

Peyton Magee

I started my business in January 2019, when I was 11 years old. I was in fifth grade and was interested in starting a business. Looking back, I believe I started out at the perfect time, but I wish I was more prepared for doing so. I wish that I had learned more about what journalism is, how to be a good journalist, and what it meant to run a business. If I started my business sooner I would have been too young to handle the responsibilities that come along with it. If I had started it later I still would have been successful but I would have had less time to dedicate to growing a new idea. Read more>>

Victoria Ybarra

ABSOLUTELY! I wish I would’ve started seeing hair in a creative light earlier on in life. I grew up always loving hair and makeup but never really explored cosmetology as a career when I should have. I worked in the service industry straight out of high school and I wasn’t sure what I wanted to do with my life at that point. I started getting more into the craft of hairdressing in my early twenties so I decided to enrolled in cosmetology school. Once I entered into the program, I knew this was my path. Read more>>

Sandra Myers

Our business came to life when a life-altering experience occurred for my business partner. & CEO Amber Lee. Amber had a sudden cardiac arrest and survived driving across four lanes of traffic and into a brick home. When Amber woke up n the hospital after surgery, she reached out to me and said, “It’s Time.” Amber & I had worked in the matchmaking industry for over 20 years and constantly challenged clients’ limited opportunities with the firms we had worked for previously. We chose to take a leap of faith and go out on our own, knowing that if we provided a gold standard service and took excellent care of our clients, the clients would, in turn, take care of our business. Read more>>

Tyeshia Smith

In my opinion, starting a business would be better done sooner than later because it involves taking risks. In life, however, that decision can backfire. If not planned well, many obstacles can arise. On a late midnight day in early 2017, I was inspired to start a gourmet cookie bakery. Since I enjoy cooking in the kitchen, baking wasn’t my strong interest, the idea came to me as a surprise. My curiosity began to grow as this clever idea slipped into my mind, and I became interested in finding out more. In order to work out every step, I headed into the kitchen to test my hypothesis. Read more>>

Monique Burns

If I can return in time, I genuinely wish to start my business sooner. I have always known that I wanted to have my own business and be a personal/private chef, but fear has always stayed in the way. I started my business, and during most of the pandemic, my business was slowly growing while everything was shutting down. I have always wanted to start, and finally, it became a reality. But the pandemic pushed me into the unknown, and I was terrified. Once I started with my first client when things were moving in the right direction, and that’s when my business began to grow beyond my wildest imagination. If I could go back in time, I would’ve started my business a long time ago, roughly about five years ago. Read more>>