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.

Sara Knetemann

I love this question! I started Arcadia Yoga & Wellness after a major career change. A year after having our second child, I started to feel an intense calling to prioritize myself and my passions. Read more>>

Sarah Elder

I started my business at exactly the right time. Okay, the truth is there’s no such thing as “exactly right” when it comes to making any major life decision, whether you’re thinking about having kids, buying a house, starting a business, or selling it all to travel the world nomad-style. Read more>>

Toccara Samuel

I started my business in 2018. At the time I was working a full-time and part time job as well as building my business. I would have started my business sooner if I had the knowledge I have now. Read more>>

Britna Savarese

If you asked me at 10 years old what I dreamed of becoming, then I would’ve unequivocally said “a mortician!” Growing up, I was deeply moved by time spent in the local funeral home for occasional visitations and funerals. Read more>>

Christina Martin

I started my business a year ago but I have been speaking at women’s empowerment events for years. I have been helping moms for as long as I have been one. I wish I would have had a name behind it sooner. Read more>>

Daniel Ortiz

I definitely do wish I started my business sooner when I was younger. I still look back when I was in highschool, wishing I should’ve started back then. But I remind myself that everything happens for a reason. I am grateful to have started my business when I did. Read more>>

Sipho Gumbo

Starting a business is one of the toughest things I have done, besides parenting. There are several decisions one must make to start a business, and they are all very big decisions. Read more>>

Margaret Kasper

I started my business in 2008, my last year at Art school. I think I started it the best possible time I could have. he investment to start my business financially was low risk. Read more>>

David Slobotski

Man do I wish I would’ve started my business sooner. Looking back I was in an amazing job at an amazing company, but there was just something missing something else I wanted to do or accomplish and I couldn’t quite put my finger on it all of a sudden one morning, my wife had a stroke. Read more>>

Kirstie Freimuth

I first dipped my toes into the business of graphic design when I was a stay-at-home mom, approximately 16 years ago! It took some time for me to hone in on my passion for wedding stationery design and creative business branding. Read more>>

Sofía Castro

I never thought about it, this is the perfect moment for me. My husband and I started our company Max Xperience in August 2023, at that time I was working for a local channel in South Carolina producing around 12 varied shows and before emigrating in 2018, in my country Venezuela, Read more>>

Phil Breeden

I spent 25 years working in electrical distribution starting when I was a young 19 year old pup. I wish I had started my business much earlier in my working career. I started competing in competition BBQ in 2015 while I still had my “day job”. Read more>>

Zack Mitchell

In 2022, I embarked on the journey of starting my own business, spurred by a pivotal transition in my life. Exiting a serious relationship and feeling unfulfilled at work led me to question the direction of my life. Read more>>

Kididia Rose

I had the vision for J Sanay Wellness Retreat around 2015 after I became an esthetician. I didn’t start J Sanay until 2021. I’m a “things happen for a reason” type of person, so I normally don’t question the obstacles in my life. Read more>>

Monica Kubik

I started my current company at the age of 35, and I believe the time was just right. I needed all the experience from before – and I am a firm believer that things come to you when you are ready. Read more>>

Nick Meador

I started my business on the only timeline I could have. But that was in some ways determined by what came before. It’s tempting to look back and wish I had made some different decisions about my education. Read more>>

Walter Boza

I officially launched my business in January 2024, two months after turning 52. I have been a senior executive in the advertising business for over 20 years, leading teams and companies across continents. Read more>>