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.

Deborah Olushina

If I could go back in time, I would’ve started my business sooner. If I had started sooner, I would be much more successful than I am at this moment. However, I lacked the confidence and motivation that I needed to start the business. At the time that I had this amazing idea, I was just not prepared to execute it. Read more>>

Phil Harrold

We (my brother Steve and I) opened in September of 2020 thinking that the presidential election was going to come and go and take Hurricane Covid with it. When that didn’t happen, we pivoted to doing livestream concerts until the coast was clear enough to start doing regular, in-person events. Read more>>

Michael Thompson

So I’ve been shooting for the past 8 years but my business officially started last year with the formation of my LLC. Since then, I’ve been consistently wishing that I had started much sooner. There are many but the biggest reason was because I wish I had more time to really establish and promote myself within the community. Read more>>

Jaimi Bailey

I started being a full time boudoir photographer in 2020 (Middle of covid, oddly enough). After seeing how much Boudoir has changed my life, I definitely wish I had started sooner. Read more>>

Shanna Eilers

Fear and change go together like peanut butter and jelly – they just can’t seem to stay apart. But when fear starts running the show, it’s like being stuck in a “Groundhog Day” loop of the same old, same old. Read more>>

Charlene Lindsay

Until recently, I wished I had found this passion and path sooner. But I’ve realized that the only way I found it was through my journey thus far. Read more>>

Jaron Cass

If I could go back I would have started my business a lot sooner. I think that a lot of business owners in the creative field start out doing free work while ironing out the expertise of their given craft. Read more>>

Robin Dodd

Being a 35 year old woman and just completing cosmetologist school and state board, is a wonderful feeling. It feels great because I didn’t give up and my children are my biggest motivation but as I look back I had this opportunity back when I was 23 when my auntie paid for my admission at MATC in Milwaukee, WI. Read more>>

Kelsea Johnson

If I could go back in time, I 100% wish I could start my business sooner. Though I believe everything has happened at the right time, I truly wish I could tell my younger self to just believe and go for it. Stop thinking about it and just do it. Read more>>

Nanaekow Stiles

Yes. So when I was younger I knew I wanted to be an artist but the idea was discouraged because at the time not many people knew of the many avenues you could take in becoming an artist. Especially since the type of art I wanted to make was drawing and painting. Read more>>

Madison Dufour

At the end of 2020 my husband and I sold our home and everything we owned and moved into a vanlife lifestyle. We had decided before we were married that we would not want to look back and wonder ‘What if…?’ ever in our marriage. If we were going to try tiny living it would be then and there. Read more>>