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.

Linsi Taylor

I believe that timing is crucial when starting a business and the opportunity presented itself when I was ready to take the leap. That being said, I would not have chosen any other time to have started then when I did. For me, it was more about being emotionally prepared. Fear and lack of confidence held me back from starting my business earlier. I feared that I wasn’t skilled enough, that I didn’t have the proper equipment, and that I didn’t know enough about business to start one of my own. Read more>>

Geoff Cummings

Well, I started my business, in June 2015, so I am coming up on 7 years. Where was I at life-wise? Well, it had been just about a year and a half since my divorce. That was by far the most traumatic thing I had ever gone through. It came as somewhat of a surprise, yet now looking back there were signs and I am now happier than I have ever been. When you go through such a life-changing thing you step back and look at your life. I was finally finding out who I was and for the first time beginning to gain some self-confidence in myself. Read more>>

Jeff Biggars

I started in my industry when I was 19. By 20 I was in management, and I will always enjoy having that opportunity at such a young age. I had many employees who were much older than me and certainly had more experience. There were definitely many challenges, but I wouldn’t have learned as much as I did if I hadn’t have started so early. At 23 I became the Manager at a high-end custom hat store where I also began making hats. Again, my employees were much better at what we did than I was. There is a loss of respect for sure when you know more than your boss does. So, I made it a point to not only learn how to do every single job but to also be the best at it. Read more>>

Jameson Ray

Looking back on things I definitely wish I would’ve gotten serious about my craft sooner in life. I’ve had a camera for about 3 or 4 years now but I didn’t start getting serious about photography until about a year and a half ago. If would’ve been more serious about photography earlier on I would think I would be a lot further along. I used to have a lot more time on my hands back then, but these days it just seems like the weeks are flying by. I’m grateful to God that my business is doing as well as it is doing right now but I still find it hard to find time to keep growing my craft and manage my business simultaneously. At the end of the day it is a pretty good problem to have so let me not complain too much! Read more>>

Shelby Henderson

.It all started in February 2012 when I just graduated from culinary school and thought it would be appropriate to start my own business. I was working as an Executive Chef in a senior living community at the time. Entrepreneurship has always been my dream. It wasn’t going well for my business, and I had so much going on personally that I moved to Australia for a while to take a break. It was during my time there that I realized waiting a little longer to start my brand would have been the better decision. Read more>>

Deanna Lopez

No, I honestly wouldn’t change a thing! I feel like the timing for starting my business was perfect for me. When I got started I was a single mom with a 2 year old son. I was in a direct sales company and wanted to meet new people. So I started hosting a weekly ladies night type event at a local restaurant to help myself, and my small business owning friends, market our businesses while helping local charities. They were a success and I met lots of amazing people who have helped me grow my business for the last 9 years! This was around the time that my mom and I started our non-profit no-kill animal rescue (Mutt Mesh Animal Rescue). Read more>>

Brandi Richards

I do wish I had started my business sooner; however, I believe everything is in God’s timing. I think I needed to reach a point in my life when I knew having passion about my work was needed and figuring out what that was in my own life. I had always been passionate about photography, but it had only been a hobby and not something I thought I could build a business on. After my dad passed away in 2017, I was searching for what my career purpose was. I thought it was selling life insurance since I realized how important it was for families to have. Even though I saw the importance in it, I did not enjoy what I was doing. Read more>>

Lauren Arkin-Malacsina

I started my business LA Boudoir Miami in Spring of 2010, I was newly graduated from college and with working only about one year with the Florida Grand Opera costume department. Since I was in high school I always dreamed of having my own shop and started collecting vintage pieces since 9th grade. I was always drawn to this one very quant building in the MIMO district of Miami and envisioned my shop occupying a space there. I met the owner of the building when I was having lunch there one day with my mom while I was a senior in high school and he we talked about the idea of me opening the shop but unfortunately for me it wasn’t the right time being in school and going to start college, but I wished it was. This was prior to the recession of 2008. Read more>>

Lakiesha Thomas

If I could go back in time I would have started the journey of entrepreneurship much earlier, I believe I could have been more focused on my future and not so much on my marriage that was up in an uproar which you could read more about in my 2020 Title “Married With Broken Pieces”. I allowed it to deter my focus from several of my dreams and goals of being a business owner/entrepreneur and furthering my education as I am now, learning the detailed ins and outs of it all, working to set up a space that would have allowed my children to follow their goals and dreams without all the hiccups or struggles that I may have endured. Read more>>

Monique Renee Catoggio

After so many years taking both small and huge leaps toward my desires and life purpose, I’ve realized that although I wanted to take the leap much sooner, I WAS starting my business one small step at a time. This Aha moment was not only beneficial for me, but also for so many of my clients who also desire to leap into the world of entrepreneurship. We can choose to believe that doing it fast (or sooner) is the best way, and we can judge ourselves for not being able to take the risk sooner, or we can see how we were “becoming” all along. Read more>>

Vicki LeBlanc

If I could go back in time, yes, I would have started my photography career a lot sooner. If I could only tell my younger self to have more confidence and not waist time with nonsense, wouldn’t nearly everyone choose to do that? In the early 80’s, I was on the other side of the camera. I lived a short while in New York working as an editorial model. New York was a very different place in the 80’s and very rough for a young girl just out of high school. I worked all the time, met some truly amazing photographers, andI regret not taking the time to learn more of their craft. Read more>>

christianne dowd

I’ve been in business for 12 years and I wouldn’t have changed a thing. I’ve always enjoyed stories of individuals who changed careers later on in life or decided to enter college after their own kids were done with it. I’ve always admired their courage. But I never thought I would be one of them.
Growing up in Brazil, most people I know were proud to have stability, security at work, and that meant working for the government or a big corporation for their whole lives. My dad worked at the same place from his first day at work to the day he retired. Read more>>

Maya Juarez-Pena

I used to think that if I started my business earlier I would be a lot much further along. However, would I have had the right mind set? Would I have had the experience to start? Who knows….I had ideas of starting a business in 2016, but was going to college and working a full time job. I knew I wasn’t happy and this wasn’t my purpose, to sit at a desk and be on a computer all day. Come to 2017, I got started on my business. Though not much came of it as I was about to graduate and still working full time. Read more>>

Mo Cross

There are moments where I wished that I put down my criminal Justice degree and went into photography and set designing fulltime…yes. But honestly, I don’t regret much of it. For the energy that is put into my art are details that come from my experiences through my previous career. If you pay close attention to some of my work, you’ll be able to notice where each image is rooted from. I hope to continue to do this in the future. Read more>>

Alexa Tokich

If I could go back in time I would have definitely started my business sooner. I had started doing photography about 7 and a 1/2 years ago and in the beginning you know we are all just learning and growing. Over the years of being self taught I progressed pretty quickly and I felt that I should start my business, but I never fully had the confidence in myself. Ive worked with many amazing and talented individuals. Many people throughout my journey supported me and believed in me more than I did in myself. During COVID it was a difficult time, but it gave me the opportunity to take time to reflect on my life and myself. Read more>>