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.

Dena Jane Leone

Looking back, I absolutely wish I had started my business sooner. While I’m grateful for my journey, the biggest lesson I learned is that you can’t fight your innate drive to create. I had the urge to be a designer and business owner as soon as I graduated college, and I spent years battling imposter syndrome, telling myself I wasn’t good enough just yet. I kept waiting for the perfect moment—to be better, to have more experience, to have a long list of reputable clients—but that perfect moment could’ve taken my whole lifetime if I let it. Read more>>

Amanda Fullam

I had been trying to buy my own bar / create a bar since 2017. I was six months into the process of buying my first bar when I had to abandon the location due to environmental reasons. This was a costly attempt, costing me about $10,000 between lawyers and environmental testing. It just wasn’t meant to be. My next attempt was in late 2019, we were 6 weeks away from closing on a bar that I thought was perfect, when I was unexpectedly let go from my full time job as a restaurant manager. Without proof of employment, my loan could not be funded. This second attempt cost me around the same, $10,000 between lawyers and a deposit that wouldn’t be refunded. I was devastated. Read more>>

Renee Cummings

I began creating book reviews in 2022 when I left my radio job to become a stay at home mom and I wish I would have thought of doing it sooner. I have always been a book worm and I joke in my opening of the podcast by saying I wouldn’t be where I am without Scholastic Book Fairs and the Pizza Hut Book It! club. If I would have started it sooner, I could have been able to get into podcasting before everyone was into podcasting. It’s an easy thing to start, but with so many people doing it these days, it’s difficult to get the exposure you want right away. While I’m happy with where I’m at right now with the podcast and content creation surrounding it, I’ll always wonder “What if I started 3 years sooner?” Read more>>

Margarita Vazquez

Starting a business wasn’t on my mind. It took COVID, losing my sister, my son’s heart surgery, and all the grief that came with those experiences to push me forward. Out of that pain, I found purpose in creating something that would become a lasting gift for my family, my granddaughter, and the generations after them. Read more>>

Samuel Johnson

I wish I had started sooner because I was young, energic, vibrant and I had no responsibility. Read more>>

Kat Kwueen(Hill)

I used to kick myself about how I could’ve started my career sooner! How many followers could I have by now? How much further could I be? How much different could my life really be? How many people feel overwhelmed or even get depressed at the thought of who they could’ve been or should’ve been? I’ve met countless “almost pro athletes” or I “I almost made it but then…” type people. And I almost became one of them. Feeling like my life circumstances held me back. “If only I’d made this decision”, I would often ponder past mistakes. Beating my past self up for doing the same thing people have been doing for thousands of years…just being human. Read more>>

Divine Play

Creativity is always in us. It is our connection to divinity. The closer one is to the source of all things, the more in tune they are with their creativity. Acknowledging and Embracing it are the keys to nurturing a vast healthy endless supply of creativity. Read more>>

URIEL BRG

I released my first full song when I was 21, but it wasn’t because I lacked interest or passion—it was mainly because I didn’t have the right connections, access to instruments, or knowledge of music theory. Sometimes I wonder what it would have been like if I had started my music career in 2015—perhaps I’d be much more established by now. Read more>>

Miyaeva

I think when I started it was perfect timing. I started content creating for TikTok when I was 18 years old and it was the start of covid. Nobody was working. Everyone was scrolling & I believe the time I started was perfect. If I had to go back I would start the same time as I did! The app was pretty new and nobody was really posting like they are today! Read more>>

Brit Spencer

I grew up in generation where being an artist wasn’t really considered a career path. As a child I was always drawing and writing poetry, playing cello and piano, those were the things that made my soul shine. Although I spent my spare time involved in these creative processes I never once thought that a career as an artist was a viable option. I was taught at an early age that those who were successful in these areas were troubled and lived hard lives in which their talents were not discovered until they were long gone. Maybe this is still the case in my story, as I always had anxiety and depression as long as I can remember. I spent most my adult life trying to find a career path that allowed me to be creative and also have success in this lifetime. Read more>>

Marta Swierczek

I feel like I entered real estate at the right time, bringing with me years of experience from the construction industry. My background has allowed me to work closely with clients, manage projects with precision, and understand homes from the inside out. This knowledge, combined with my passion for helping people, gives me a unique advantage in guiding clients through every step of the real estate process. Read more>>

Michelle Holmes

If I could go back, I would’ve started sooner as a side hustle while still working in corporate America. I didn’t fully grasp the freedom, fulfillment, and responsibility that come with building something of your own until I had to.

I started my business during a pivotal time in life.
I wasn’t chasing entrepreneurship, I was answering a call, because the truth was no one was calling after applying for countless entry-level to senior-level positions and hearing nothing back, I realized the door I was knocking on wasn’t mine. So I built one. I had spent years leading operations, customer service, ecommerce fraud, managing mergers and acquisitions, and stabilizing multimillion-dollar teams and departments. Read more>>