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.

Elena Hallen

If I could go back in time, I think I would have started my business a little sooner—but only by a few years. The timing of everything taught me so much, but looking back, I realize I had the foundation and skill set long before I gave myself permission to fully go for it. Read More>>

Aire Stillman

I started my first business as an online fitness coach, which later expanded to in-person sessions. But when COVID hit, I had to shut down one business and began working with my ex-partner at a gym while trying to scale things online. Everything felt like it was on pause. Read More>>

Janice Carte

I tend to believe life unfolds exactly as it’s meant to – and there’s something really beautiful about that. When I started working with personal chef clients, my full-time job had begun to feel creatively stagnant, and since growth and creativity are what truly fuel me, I knew I needed a new challenge. (Honestly, if I hadn’t found one, I was bound to start stirring the pot at work – in a bad way!) Read More>>

Abigail Vaden

If I could go back in time, I think I would have started my podcast sooner. When I launched it, I was working full time and figuring out how to turn my ideas into something that actually made an impact. I didn’t have a background in broadcasting—just a voice, a message, and the drive to create something real and relatable. Read More>>

Chelsi Bartlett

I like to claim I officially started my business in 2017, despite freelancing for years before this. However, I didn’t feel like a real business until 2019 when I rebranded into Laurel & Ives from my previous brand. Read More>>

Shawntelle Flanders

I do sometimes wish I had started my photography business sooner; however, I also know I needed time to grow into the confidence it takes to put myself out there. That said, I’m proud of where I am now. Read More>>

Gina LoPinto

My business partner Kristi and I started Vibrant Aura Photo in January of this year. We are an aura photography business that does pop ups at local businesses and also private events. Aura photography is a visual representation of the aura or energy field that surrounds the human body. We take our colorful portraits on film, pull an oracle card for a message from the universe and then do a reading that explains what each of the colors in the photo mean for you. Read More>>

Danielle Murray

Looking back, I believe I started my business at just the right moment. Alignment has been a recurring theme in my journey, and it all began with an unexpected layoff. In early 2020, at the height of the pandemic, I was working in sales support at a startup, handling lead generation. After eight months, my entire department was let go. Read More>>

Connor Cassidy

So I started working in the food industry when I was 15 years old, I immediately fell in love with the intensity and sense of urgency produced in a kitchen. I became a sponge and absorbed as much as I could every day and all day while on the job, then outside of work I fell in love with cooking shows and chef competition shows. Around the age of 17 I got a job as a sushi chef as a prep chef spending the entire day making rice, sushi roll mixes and sauces, learned how to hand sharpen knives to a razors edge and was addicted to the feeling of a blade just gliding right through anything and everything with ease. Read More>>