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.

Krystal Hudson

If I could go back in time, I would absolutely start my business sooner. I started my business in 2018/2019 following a health scare that I experienced. I was longer working full time, but am also not the kind of person to sit still so I felt the need to do something with my time. I originally just started out wanting to create an updated portfolio for my work, a new resume, and a website that I could use to showcase my work. Read more>>

Diane Latiker

I wish I had started it earlier because being 46 at the time I thought I was close to retiring from having any ideas of new adventures. Realistically, if I had been younger I probably would have not been ready to take on the responsibility of running a nonprofit full time. In my twenties my life was tumultuous to say the least, in my thirties life was settling down but still didn’t realize any passions of goals of importance. I often questioned why did my calling begin at this age, but understanding why at the same time. Read more>>

Patricia Cosulich-Smith

I wish I had started my business sooner, or to be more precise, I wish I had taken it seriously from the beginning. Let me share the backstory to explain why. Read more>>

Olivia Lynes

My entrepreneurial journey began in March 2020, just before the world was hit by an unforeseen global pandemic. At that juncture, I had recently transitioned into a full-time healthcare job and was keen to lay the groundwork for my business. Read more>>

Amber Rose Powers

I started my boutique travel advising business one year ago, and truly feel like it was the right time for me to branch out on my own. I have worked for other people over the past 25+ years in supporting roles, and it was time for me to finally take the lead, whether I wanted to or not. Read more>>

Nadine Collins

There are moments of life, especially when change is on the horizon; some people find themselves at a crossroads, challenged to redefine themselves and, sometimes, their purpose. For me, that moment arrived recently. After eight years of operating under the umbrella of my husband’s business, I felt the Divine leading from God to register my business as a woman-owned business. But, even though I knew that it was prompted by a sense of calling, the transition was far from easy, and now, I truly understand the significance of starting from $0.00, and it never felt so good. Read more>>

Loren Pullum

I think more than wishing I had started sooner or later than I did – that I wish I had taken myself seriously sooner. When I was contemplating this question I finally realized that Loren Kmp Photography started as soon as I had a camera I could use regularly, but that I didn’t take Loren Kmp Photography seriously enough to turn it into a business. I let my passion for photographer wain in those early years because it’s an incredibly hard business to get into, especially when you’re not able to find mentorship, or enough support. Read more>>

Terez Grace

If I could go back in time. I wish I would have started sooner. I was always helping planning family events and my mother’s dream was becoming an event planner it was something she loved to do. I actually got started planing my cousin baby shower and i realized I love wedding s when I was planning my own. Read more>>

Kristina Wolter

As much as I’d love to say “I wish I had started doing this much earlier in life,” I really can’t because I’m a firm believer in opportunities being presented when they are meant to happen. I started my commercial food-styling business in 2014 as the result of a few different paths all coming together at the right time. While food has been a passion of mine since early childhood, my opportunity to be a food stylist would not have been successful without the experiences that came before. Read more>>

Spencer Doepel

I do wish I started my business earlier. In the emerging black soldier fly larvae industry, some of the largest companies were founded between 2010-2020. Ecoflys was founded in 2020, so we’re not that far behind, but a 7-year head start is quite hard to catch up to. Sometimes this causes me anxiety that I started too late but then, I remember I can’t beat myself up about starting my business earlier. Read more>>

Jelena Radoicic

I believe that all small business owners wish they had started off sooner, and a part of me feels the same way. If I had not waited to start, I could be in the wedding industry for 10+ years, but I would have missed out on character building jobs and experiences. I began working at a the young age of 15 and have held a job every single day since. Read more>>

Jenna Griffith

I wish I had started my business much earlier than 2021. In fact, I began making body scrubs towards the end of 2015, but I felt that I lacked the financial resources and time to expand it further. During that time, I was primarily focused on my stationery designs and caring for my infant and preschooler. Read more>>

Danielle Nakeia

Career wise I was trying to find that one thing I was passionate about while working a dead end job! Once finding that passion, I wouldn’t say it was too late, but I do wish I would’ve made the decision or found the passion I had business wise sooner! Read more>>

Brandon Brewster

I started my first business May of 2021 with a couple of my friends called Normal Convos Pod. In November of 2022 I partnered with a childhood friend and became a producer at Matose Visuals. A production company with a myriad of ideas. April of ’23 I launched BrewsTees my pride and joy. Before starting any of these businesses I was just going through everyday life. Read more>>

Tayanna Nelson

Honestly, I think I started my business at the exact right time for me. Moreso decided to “go full-time” at the right time. I registered my business the year after I graduated college with my BS degree in photo. I floundered and barely made enough to even pay taxes, but I wanted to do everything right. So then every year I made a little bit more money, and I got a few more clients. Read more>>