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.

Kayleigh Eilenberger

I absolutely wish I would’ve started my business sooner. I’ve always wanted to be my own boss, and have my own business. In 2020 I was ready to figure out how to have my own business, but I was overwhelmed and nervous where to start. I was working on an in-house marketing team at the time, and it was during Covid lockdowns. I decided to hire a creative coach to help get the ball rolling, which definitely helped. She helped give me some direction and goals to work toward that I wouldn’t of been able to come up with on my own.  Read more>>

Caitlin Mccall

I wish I had started sooner! I think so often aspiring entrepreneurs feel like they need more experience or aren’t skilled enough yet to go out on their own. In my case, I felt like my entire career was trying to fit myself (a square peg) into a traditional career (a round hole). I kept failing at working for other people, and it left me wondering if something was wrong with me, if I wasn’t able to work well with others or if I just wasn’t skilled or smart enough to keep these positions long term. I always quit around the 1 year mark because it just got to the point that I couldn’t stand being constrained any longer. The truth was, that I wasn’t meant to work a traditional career at all. I was meant to start my own business and provide value in a completely different way. Once I started providing value to the world in a way that was actually aligned with me, I was compensated at a rate that made sense and was far beyond what I could’ve made working for others in Marketing. I really wish I could hop in a DeLorean and tell myself that I had everything I needed and MORE to start my business and just get out there and do more! Read more>>

Aarica Smith

Infectious Design Co. was started in 2020, during the summer of the pandemic. At the time, I, like many others, was spending much of my time at home, away from the masses in hopes of protecting myself from Covid. With two small children under 5, I had a lot of time at home and a lot of time to think of creative things to entertain my children, as they were also home with me. While consistently planning for engaging activities for them to do, I started going through packed boxes and founded a business plan that I wrote in 2008, the summer after graduation. This was a business plan that I wrote 12 years ago of a greeting card business that I wanted to launch. I remember writing the plan, and shelving it, as I was getting ready to embark on my career in technology. To the advise of others, I had to put away my ideas of continuing my art so that I could fully focus on my new career and adulthood as a technology consultant. Read more>>

Jordan Scarzfava

Honestly, despite not realizing my potential for voiceover work until after high school, I’m glad that I was able to start it while attending community college. I’ve always loved drawing cartoons on paper, but little did I know until that point anyone could do that voice acting with the skills. I created my YouTube channel on April 12, 2013, and practiced different character voices a month later. Granted, at the time, I didn’t like the sound of my voice because it was always high-pitched for my age. But after finding the courage to sing and take voice lessons, I grew to embrace this passion. Read more>>

London Dior

I absolutely wish I would’ve started earlier,I was in already within the neighborhood of the career field with being an artist and a designer but I ignored it for a long time because my first thought was , “whose actually going to watch me ?” Especially with where I was in life , I had just went back home , I was sleeping on my moms floor and I was starting from scratch, working a high effort job with low pay out , I just felt my life wasn’t interesting enough . Look at it now I would’ve started earlier , my first really video was something I could’ve done on any day , if I could change anything I would change my consistency when first starting Read more>>

Alex And Jodi

Jodi: I’ve spent most of my career in both the corporate and start-up worlds, with a bit of experience in small business. But my true passion has always been creating. While we launched our current business a bit later in life, I’ve never stopped pursuing my creative interests. I’m really grateful for how everything lined up—having years of business experience has given me the balance to blend creativity with the practical side of running a company. If I could go back, I don’t think I’d change when I started. The timing has been perfect, because my experience has allowed me to approach this venture with a solid foundation, giving me the space to thrive creatively while managing the operational side of the business. Read more>>

Makenzie Farley

I’ve always been in the creative space since the beginning of my teen years. I started doing youtube at the age of 15. I always knew that’s something i wanted to do because i couldn’t stop thinking about that kind of life and the passion i had behind it was very strong. I have a very out going, goofy personality so i wanted to share that with the world. I was only a freshman in highschool so i had no job or other main hobbies so most of my videos were always school vlogs and school interviews. I really enjoyed what i did so i would say i would have changed the fact that i wasn’t as consistent with my content and didn’t take it as serious as i do now . I feel if i would have done that i would have gotten recognized much sooner and also would have a larger support base. Read more>>

Geraldine Bielke

I still knew how it felt when I discovered my passion for acting. I was 14 years old. Actually, I had a glimpse of it when I was 7. I was sitting on a stool, holding a puppet, and a lovely lady took photos of me. The photographer asked me if I was interested in becoming an actress. I wished I could revisit that moment to ask her why she thought that, or I wished I had been bold enough to say, “Yes, I am interested. What are the next steps?” But I just sat there shily and did what the photographer asked me to do. My parents and none of my relatives are in the show business. All of them are pursuing regular jobs. My dad used to be an Ingenieur, and my mom a nurse. The theme of being an actress never came up again. Read more>>

Jennifer Resurreccion

In a way, yes, but also I didn’t start of 2024 with the goal of being a content creator. I decided back in August. At the time I my beloved Papa had passed back in July and I was looking for something to fill the void in my heart so I turned to my absolute favorite anything: Pokemon! I wasn’t even sure it would really go anywhere. I just wanted to meet other fans that enjoyed Pokemon like me. Had I started sooner, even a year sooner, I think I would have had a stronger start as I was in Japan last year and had a lot of opportunity to create content. Looking back I don’t have any regrets about when I started. With the uncertainty of my Papa’s health I think past me just wanted to focus on being there and supporting him and now that he is no longer with us, I can move forward as he would have wanted for me. Read more>>

Jasmine Pugh

I honestly feel like I started right on time. Here’s why I say that: I created a plan for my creative career when I was probably between the age of 11-13 years old. Many goals on the list did come to fruition, but not how I expected them to. Content creation was not a thing during my childhood, so I had no idea I would be interested in it. I got into makeup in 2016 during the beauty community rise on Youtube. It was then that I decided, this is something I’m very interested in and passionate about, because I love art. I wrote out a list of over 100 ideas that I wanted to do, and the list continued to grow daily, but no action towards actually creating anything. Read more>>

Michaela “kayla Kay” Sterling

If I could go back in time, I often wonder what my creative career would have looked like if I’d started sooner—if I’d had the stability, love, and support that so many others take for granted. Growing up, I felt unloved and neglected, constantly shuffled between family members and later friends, never feeling like I had a true place to belong. Those experiences left scars that I still struggle to release, especially when I think about how much further I might have been if I’d had a foundation of support to build on. Read more>>

Daniel Jenkins

Looking back, I don’t regret when I embarked on my creative career. After college, I spent the better part of a decade navigating my way through a more structured and corporate career path. I held various positions in the construction, real estate, and asset management worlds. There were moments that I gave serious thought to “blowing it all up” and trying something new. It wasn’t until I discovered my passion for photography that I began to consider how I could take a creative hobby and turn it into a career. Read more>>

Joana Donovan

If I could travel back in time, I wouldn’t hesitate to start this business 10 years earlier. Back then, I was at an identity crossroads—like so many professionals, I was figuring out who I was while simultaneously reinventing myself. My career was a patchwork of experiences in different industries, each offering a lesson or skill that I couldn’t fully appreciate. Financial constraints limited my ability to pursue additional education or certifications, and finding an economic path forward was a constant challenge. Read more>>