Almost every entrepreneur has had to decide whether to take the leap now or wait– perhaps they wanted to acquire more capital, experience or connections. Given how common this predicament is, we asked some successful business owners to reflect back on whether they wish they had started sooner or waited for a better time.
Howie Withrow
I think one good thing you can say about getting older, its gets a little easier to focus on the things that are important to you. I would like to think that if I started earlier, then I would be further along. But if I stop and think about it, I didn’t have the discipline that I do now. Call it ADHD or whatever, but as soon as I lost interest in something then I would just abandon it and jump to the next thing. Read more>>
Jordan Bray-Burns
Looking back, I wish I had started my business sooner. I was always worried about failing, or what other people would think. I was having a hard time picturing myself doing what I was currently doing for work forever. The moment I stopped caring about what others think is the moment I experienced the most personal growth. The personal growth gave me the confidence to start that business, and Fight for what I wanted. Read more>>
Julia Street
While I’ve gained valuable insights from launching my business later in my career, I also wish I had ventured into the food industry much earlier. I never granted myself the permission to fully immerse myself in the creative process, even though it was a recurring passion. I was afraid that dedicating myself entirely to something I loved might lead to a sense of disillusionment. Read more>>
Dana Martin
I had originally picked up a camera and started to learn photography as a stay at home mom. It was something I had always been interested in, but I needed something that was mine while knee deep in motherhood. I quickly fell in love with the craft, and it slowly evolved into something I believed might actually be “something.” One year after picking up a camera, I opened my own LLC, despite pushback from people at the time I thought had my back. Read more>>
Justin Torres
I was always told “you can do anything in life that you put your mind to” but this statement did not settle in my reality until I took the leap of faith and decided I was going to bet on myself. You see I always wondered what life would be like owning my own business but I was too busy playing tug a war with fear. For many years I was paralyzed by fear but I knew deep down in my heart that I did not want to work for someone else my whole life. Read more>>
Amanda Duque
I believe I started Amanda Kay Photography at the right time. I just wish I had started taking it more seriously in the beginning! I was 18, just finished high school and knew I wanted to do something to involve my artistic interests in a career. I was going to go to college for graphic design. Read more>>
Lisa Gray
Hmmm. It was during Covid I had finally decided to take the leap and start my own agency. I have been in marketing in some capacity for well over 15 years. During the time of Covid, I was a commission paid employee and had lost a great portion of my income. So I started LEGS Media and it took off. Read more>>
Steffanie Harrison
There is never a straight line to success, and what qualifies as success? The idea that entrepreneurs are born and not developed is an idea that interferes with deep desire. Sometimes, the idea of what something should look like gets in the way of cultivating our thoughts and refining our gifts into what is our creator’s plan for us. Read more>>
Akira Robinson
Although I always wanted to start a business and enter into the entrepreneurship world, I spent most of my career being driven by stability and working my way up using the skills I had been verified as good at, which in my case was science and math. So, I started AKI THE LABEL after having gained the stability I needed to feel secure and honestly, I wish I would have taken the leap earlier. I had a mindset of going “all-in” because that’s what I’ve seen work. Read more>>
Ivan Ormuž
If I could go back in time, I’d probably have opened my business way sooner. This time I was almost 30. I had been living off my life savings while trying to ‘find myself’ and figure out what I wanted to do in life after quitting my 6-year corporate job. If I had opened my business sooner, I’d probably have had the enthusiasm of a young age and wouldn’t have been so burnt out by the corporate work. Read more>>
Zhané Thorpe
If I could go back in time, I would start my business at the same time that I did. Mainly because, I was actually ready to bet on myself. I’ll never forget laying on the couch and saying the prayer I said before I submitted my resignation letter. It just felt like it was time to stop being overworked and underpaid. I always wanted to make an impact and I knew I wasn’t going to be able to do that working in the role I was in. Read more>>
Luara Pinon
I definitely wish I had started sooner, but life had other plans. I started wrapping out of my poorly insulated, definitely not dust-free home garage. I remember one night it was so cold in my garage that brought car parts into my living room. I wrapped some car handles in bed super late into the night and woke up with vinyl in my hair. Read more>>
Vara Kaiser
When I started my business in 2022, I had been a stay at home parent for 10 years. My background was in social work, and we had become foster parents in, but I was not working outside of my home to make income. Foster care is actually a big reason for why I became interested in Reiki-I was raising kids who were very young but had a lot of trauma already, and it was hard to find interventions that supported their level of need. Read more>>
Imank Elke
Sometimes I wish I started my business sooner and sometimes I am okay with how everything has transpired. I say this because I started my first business in December of 2016. At this time I was focused and made my businesses’s growth a priority. If I would have began before 2016, I would have acquired more experience and retained more seed funds. Read more>>