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.

Ellis Williams

I started E Willz Entertainment back in 2017 but we didn’t come into our own until just recently. I’m 38 years old and, though I’ve had an amazing career as a performing artist, I do wish that I started this business MUCH sooner and for two reasons. 1. You don’t learn nearing as much as you need to about the music industry in any school. I believe I would’ve been further along my journey if I took the leap of faith and seek alternative methods to entering the field.  2. Although music licensing has been around for decades, only now are people just starting to realize how lucrative this part of the music industry can get. Either way I’m happy for where my path has taken me and I might not have gained the wisdom and confidence that I currently have at this point in my life.  Read more>>

Tink Rainbow

If I could go back in time and start my business sooner, I certainly would! Growing up, I lived in a world where you checked off all of the boxes. You went to college, you got engaged, you got married, had a baby…it was all part of the plan. The problem was, it wasn’t my plan, people-pleasing can take years from your life. In 2019, just as the world was being flipped upside down by the pandemic, so was my idea of the “perfect life”. I started to ask myself more questions. It was crazy to me that at almost 40, I couldn’t think of anything that I really enjoyed doing. I was a mother, a wife, a teacher, a coach, but in all honesty, I couldn’t think of something I enjoyed doing for myself. I didn’t hate my career, but it certainly wasn’t fulfilling. The world of education was changing and so was my desire to stay in the classroom Read more>>

Paloma Tillotson

I officially started my business three months ago after quitting my 9-5 to pursue my passion for social media management. I was a mix of excited, confident, and nervous, but I knew it was the right time. I’d worked in marketing before, both in Brazil and here, and always dreamed of running my own business. The timing just clicked, and with support from my amazing husband, I decided to go for it. Sure, I gave up job security and work-life balance, but I’m so happy I did. Every day is a learning journey, and I’m grateful for my incredible clients and the opportunity to do what I love. There is nothing I would change. I appreciate the journey and all the ups and downs. Read more>>

Stephanie Gibson

If I could go back in time, I would have started my business sooner. I officially started my business in 2022 even though I had been baking and selling for a few years prior. I had known for years that I wanted to own my own bakery and I knew if I should ever quit or get laid off from my job, I would start my bakery. In 2020, right before the pandemic, I got my chance. I was laid off from my job in the fashion industry after being with a well-known retailer for 17 years. I was not upset by it at all. I knew this was going to be my chance to live my dream. The only regret I have is that I had 17 years to do as much research and gain as much knowledge as I could possibly get and yet I didn’t do that. I wish I had started while I had a full-time job so that I wouldn’t have been scrambling so much once I wasn’t working. If I had my business operating while I was at that job. not only would I have been making extra income, but I also would have been prepared by the time I had gotten laid off. With that being said, everything happens as it’s supposed to, when it’s supposed to. Read more>>

Zoe Dolack

I get asked this frequently, I left college after one semester to pursue creating full-time. I officially launched my business two years ago and had no clue what I was doing. All I knew was that I wanted to create. Photography had been my chosen medium since high school when I first picked up a camera, I had experimented in every niche imaginable. I started working with couples about a year into officially being in business and I just fell in love. I’ve always been a romantic at heart, and I think when the heart of creation was rooted in love stories something just clicked into place for me. Read more>>

Stacy Braga

While sometimes I wish I was further in my business, I’m glad I came into it with the experience I did. Spending almost a decade in classrooms, earning my leadership degree, and building hundreds of relationships with families in my community — shaped the way I run my business. Looking back, I’d start at the same time. I value my experience as a teacher and it makes me a better, more empathetic business owner. Read more>>

Kristin Schaapveld

‘All things in due time.’ You know, I’m grateful to be able to reflect back at many chapters of this life and see so much purpose in timing. I am someone that truly believes I’m put in each moment, conversation, chapter of my life on purpose. The preparation personally, faithfully, academically… in all things, is SO purposeful. Read more>>