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.

Aurora Kretsch

I started my business at the end of 2018. I ended up leaving my full time job to pursue my dream of being a photographer. A lot of the time I wish I would have started sooner because I can’t imagine a time when I didn’t have my business. But, with how my life was going at the time, it really was the perfect moment in my life to be able to leave my job and have my husband handle our expenses while I built everything up so it ended up being the perfect time to start and I wouldn’t change a thing. Read more>>

Katherine Reed

Looking back on the past 16 years, I definitely would have started my business sooner! Here is a little back story on how things got started for me- my husband and I got married in the autumn of 2006. Here I am a high school senior, focused on walking across the stage to receive my honors diploma, so I could focus fully on walking down the aisle. During this time, my mother and I didn’t know that people actually made a living to take on the stress of planning a wedding day, so we did it all ourselves. Read more>>

Brittney Crain

This is something that I think about often. I absolutely wish I would have started my business way earlier in life. Knowing what I know now about my career and path I would have done a lot differently. I wish I would have had the small business bug back before I started college. I always had a feeling college wasn’t for me, but at the time that’s just what everyone did. They went to college and then pursued a career. Read more>>

Alora Caminiti

I started Sweet Shoots at 27 years old during a very transitional time in my life. I had just left one Human Resources day job and was starting a new one with more responsibility, I was doing a lot of work internally on my mental health, and I had a big handful of things going on with my home, vehicles, you name it. These factors could have made it the best or the worst time to start a small business, depending on how you look at it. Read more>>

Taylor Mobley

I always believe that we get ideas given to us when we are ready for them. It’s our choice whether or not to act upon them. I started my business in 2015, my junior year of college. At the time, I was engaged, living in a tiny apartment, and I just wanted to talk about the things I love on the internet. I sometimes wish I had started sooner only because Instagram and Pinterest were in their prime 1-2 years prior to when I started, and organic growth was huge. But that didn’t set me back completely – and I was still able to grow my platforms to a respectable size, and there are always new platforms being created, like TikTok, to jump on. Read more>>

Gillian Tietz

I got sober in November 2019. On day 2, I immediately started learning everything I could about addiction science. I wanted to understand why this happened to me and not other people, and if it was really my choice to not be able to control my drinking. Quarantine happened about 4 months later and this gave me more time to learn. I had been working in a lab, and when we were all send home I obviously couldn’t bring my lab work home with me! Read more>>

Andrea Solomon

Honestly, I think I started my business at a good time.. there really isn’t a “right or wrong” time for anything. I felt it within myself that I was ready to explore more of what I always dreamed of. I grew up in my godmother’s hair salon watching her and assisting when I could. And I had a friend I used to share mannequin heads with. We played with those things everyday after school.. lol I remember like it was yesterday… in our kitchens after school with 3 heads. Read more>>

Nicole Stassinopoulos

I do with I had started sooner, but I’m not sure I would have stuck with the process. I have been thinking about blogging since 2011. I just didn’t know where and how to start. I had just discovered Pinterest and loved it! I feel in love with the creativity of the platform and realized these ideas ideas and pictures were linked to blogs. I was in the thick of parenting and was completely overwhelmed so I decided to be a passenger and not a creator. It wasn’t until Instagram took off that my interest really piqued. Read more>>

Denise Schumann.

I am so glad I started my business when I did because my whole goal was to be a stay-at-home mom and wife. Originally, I only took the jobs I had time for and thought would be fun. This actually helped me so much going forward, because I never had to take a job I didn’t believe in or want to do. This ensures that I give all my clients my full attention and my very best work. That is really important to me. Read more>>

Cheylaina Fultz.

It was during the lockdown of 2020 that I was 5 months pregnant, stuck at home with my husband, our 3 year old and 1 year old that I remembered the vision I had the year before to start a movement to increase the awareness of HBCUs through fashion. When I realized the children’s collegiate market didn’t have what I was looking for, I designed it myself. Sometimes I find myself saying, “Ugh why didn’t I start this business a long time ago…I’d be so much further by now…etc.” Read more>>

Nick Italiano

Starting a business is the greatest yet most difficult thing I’ve ever done in my life. I often ask myself if I should have done it sooner. I spent a long time working corporate, and some independent jobs, in the financial industry. As a whole I found in unsatisfying despite the pay being good. So I set out in 2017 to build a “side hustle” that I found more rewarding. Read more>>

Blake Summy

I started my business very small, out of my house in January of 2021. I took over a section of my garage because our home office was already being used by my roomate. Making paintings can also be very messy —so being in the garage seemed like a good fit. I had been making art and posting them in my free time since college ~ 5years —so I had a couple of leeds for commissions. I saved up my money from some good investments aswell as working, so my goal with these interested people was to simply make them a product. Read more>>

Kathleen Mickey.

I retired from the military in 2017 and later started my business in 2019. Starting a business had been a goal of mine for 15 years. While I was always confident that I could make it happen, there was also a fear that kept me from taking the plunge sooner. What if I failed? What would people think of me? The questions went on and on, but eventually, I decided to just go for it. Read more>>

Deshawn Smith

I definitely wish I would’ve started my business sooner. I started my business in June of 2020, during the pandemic and that literally showed me that there’s no perfect time than now. Prior to launching I spent almost 2 years trying to create a “perfect” business & today use little to none of those things or strategies. At the time of launching my business I was working for a company that got government contracts & I had just got back on my feet financially from going through a cycle of finding a job, then losing it. Read more>>

Carolyn Cherry.

We started our business six years ago, and while I wish we had done it earlier, it all works out for a reason. I had run the local Chamber of Commerce for years and had met a lot of great people. One of the yearly events was a townwide festival, during this festival I met a lot of talented artists. I thought how great it would be to have access to this work all year long. This was the impetus behind “The Purple Aardvark”. Read more>>

Gilda Alai.

When we finally find our passions we all wish we could have started them sooner. Throughout my life I had tried different things that never stuck however I was always doing something creative or building things with my hands. It wasn’t until my kids had started driving that I found more time to try some new things and decided to take a pottery class at the place I always passed when dropping my kids off at their swim practice. Read more>>

Paola Ochoa

Hi my name is Paola Ochoa and I am a teen entrepreneur and content creator. I started my journey at 16 starting a social media agency in high school. When people ask me if i wish i could start earlier, I wish i did. When i was 9 years old I had started my first youtube channel and showed how much I loved youtube and what it was for me. I was so creative at a young age creating videos and being in front of the camera until I was bullied for doing it. Read more>>

Kevin D. Benton.

If I could go back in time I wish that I had started Acting earlier. I believe that with all that I have accomplished to date, which is alot, I would even be further ahead and established. Research has shown that the average Actors career length is 28.4 years and although there was wide spread of careers, 46.5% of Actors had a film career between 20 and 40 years. To add to this, the Acting journey is a process full of rejection and layers which in most cases takes time. There, the earlier the journey and process starts, even with all the rejection that awaits, the better. Read more>>

Justin Jaye Vorise

I do wish I would had started my creative career a lot earlier but to behonest I did not really believe in myself so I just enrolled in college to take the safe route. I grew up in a mainly white area and was the only black kid in my class for years so I did not get a lot of attention from the girls because there idea of an attractive black guy was to be light skinned with color eyes which was not me. So it took a toll on my confidence because I didn’t have a lot girlfriends and stuff throughout elementary and middle school. Read more>>

Brandon Carpenter

I wish I had started much sooner. My channel is focused on cooking and I cook nearly every day. I began my journey as a content creator after I retired as a Firefighter. My reason for starting a YouTube channel was to document my recipes for my family. I don’t typically cook from written recipes, and seeing the way something is done usually translates better than an old index card in a box. My mother was an amazing cook, and sadly she passed away before I could document her recipes. Read more>>

Saunya Jones

I currently working as an HR manager and i do my business on the side – I do youtube, as well as massage therapy and I am an author also. I remember in college when I was on the dance team, we would post our videos to youtube but I never knew it could be a career path, I just knew I had to get through school and thats all I could focus on. It wasn’t until the year after I graduated I realized my other talents that stemmed from being on the dance team, I could create flyers, and edit music and videos and plan events. If I had somebody else to push me farther into my creativity I could have been more successful. Read more>>

Jamie Huber

If I were able to go back in time, I would start my creative career exactly how it has been laid out for me. I began teaching 22 years ago, so that allowed me to be creative every day. I applied for an Elementary Art position, but I ended up taking a 5th grade classroom position instead. While I was initially disappointed, it allowed me to build my strength as a classroom teacher with 30 kids a day before I transitioned to over 300 students per day. Read more>>

Nathania Guerra

I wish I had started sooner! When I was in university, towards my last year, lots of peers had started internships or getting small gigs here and there. I was so focused in school work and keeping up my grades that I thought working and studying was just an impossible thing to do. It wasn’t until the very end of my educational journey, that I started a job, not even in the graphic arts industry, but in aviation! I was a sales agent for an Ecuadorian airline, so I dealt with lots of people and angry customers with delayed flights. Read more>>

Doug DeAngelis

I started my professional career at age 18 while I was in my first year at Berklee College of Music. I got an internship at a recording studio that quickly turned into a paid position working around the clock on local and signed artists. That job gave me the opportunity to use my skills in electronic music and audio production, which were much stronger gifts for me than performance. It was “home” and the owners pushed me to thrive and be my best. Among the many great artists and records I worked on at SyncroSound, one standout was Pretty Hate Machine by Nine Inch Nails. Read more>>

Stephanie Henderson

Halfway through my 40s, I began to paint large canvases to fill the walls of my own house after a renovation created empty wall space. I had always loved to draw, paint, and make things with my hands, but I hadn’t painted a canvas since a college, when I squeezed in a couple of studio art classes as an English major. Read more>>

Nicole Garrabrant

To preface I want to say that I do believe that things happen at a certain time for a reason. Maybe there were lessons needed to be learned or personal developments that needed to come to fruition before a certain thing can happen in life. That being said I do wish I started my creative career sooner than I did. I think time and experience gives anyone a leg up in their career and that’s no different for acting and performing especially when networking is such a huge factor. Read more>>

Cait Maloney.

I actually started my creative career pretty early, doing some freelance work before I graduated with a degree in illustration. That was in 2008 and occurred around the same time as a big economic crash. I found a job doing more technical design work, with the occasional environmental design or illustration project sprinkled in. Read more>>

Malaiye

I’ve began training in the arts around 5 years old. First was singing in choir, then I went on to study violin, and after I was placed in dance class. I’ve been in love with training all throughout my life, however it wasn’t until I was out of high school I made any strides towards my career. By time I was ending high school acting became my love, and I began to put a focus on learning about the industry. From studying film in college to interning any industry event I could get my hands on, I began to experience life beyond the camera. Read more>>

Jeremy Wolf

I’m a painter and that to me is what I really am. At the same time, though, I’m also a buyer in a big retail corporation and in all honesty that’s how I pay my bills these days. While I’ve had good opportunities to show work over the last few years, sales have been hard to come by, so there had to be something else. For me, I guess I wish that I had truly committed to the idea of a career in the arts way earlier than I did. Read more>>

Kelly Hagen

Before I was officially in my “creative career” I had been creating art and selling it casually to friends and my local community while working in various other roles outside of the creative industry. While part of me wishes I had found my career in tattooing earlier, I don’t think I’d be where I am, or who I am, without working in all of those other jobs. I worked as a waitress for seven years while in college and a few years afterward. While I knew this wasn’t my dream career it was truly a humbling job. Read more>>

Brittany Marshall

I’ve always thought about the “what ifs” in life being an artist. I should’ve started sooner, if I did I would be in this position. But I had to stop saying that to myself because everyone finds their purpose on their own time when God has planned for you, but it happens at the perfect time. Read more>>