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.

Rebecca Nash-Emerson

I wish I started earlier…because I love working with my clients and find the work I so fulfilling. It literally lights me up. If I started earlier, I might be further along. I might have learned things sooner about my craft and running a business. I would have be able to photograph more people, and impact more peoples lives with the work I do (and the relationships built along the way). Read more>>

Aly Shampain

I started Take a MOMent when my (now) 2 year old son was 15 months old. But it was something that was in my mind since before he was born. When I was pregnant I would walk around Hoboken, and when seeing all of the bumps and strollers, I thought to myself, “There must be so many mom groups to decide between, I can’t wait!” I was really surprised when my son came along and my options were limited to a breastfeeding group and a group located at the local hospital. These are both fabulous resources, but not what I was envisioning. I went back to work in education, both teaching and coaching teachers, and in the back of my mind was always this idea of a curated intimate moms group run in conjunction with local pediatric and postpartum experts. Read more>>

Quinn Wolverton

If I could go back in time, I wouldn’t change anything regarding starting my business sooner. I think everything happens when it’s supposed to and fortunately, Nova Cat Films became what it is because I naturally wanted to have it be that way. I technically started my business in 2015 but I’ve been making films with my friends my entire life so it has felt like I had a business my entire life. If I would’ve started Nova Cat Films earlier, I think my team would be different, my films wouldn’t be as interesting, and the passion for making films wouldn’t be the same. Like I said before, everything will happen when it’s supposed to. Read more>>

Amy Elizabeth Gorton

Before starting AE Events & Design, I never pictured myself as a business owner, and I’m the type of person who has a running bucket list. There’s so many things I want to do and try in my life, so looking back know it seems absurd that entrepreneurship wasn’t on my radar. Read more>>

Frannie McClester

If I could go back in time, I don’t think I would start my business sooner or later. For me, creating decorative cookies was a hobby to start. I had been watching so many videos on Instagram of cookies being decorated. Have you ever watched a sugar cookie get flooded (top covered in icing)? It can be quite soothing. To quote my eight-year-old, “It’s so satisfying”! So, I had been down the rabbit holes of different ways to decorate and wondered if I could do it on my own. My first set was for my daughter’s birthday. People seemed to like them. I got some positive feedback. My interest then went from the Instagram videos to blogs by people I was following. I began looking at different recipes for sugar cookie dough and royal icing. I thought about the texture I like and began trying a couple different recipes. To this day, the recipe I use for my vanilla sugar cookies remains based off a recipe I purchased and tried from Corianne Froese (@_cookie_couture). Corianne’s Instagram and blog are where I learned the most starting out. Feeling the success of a delicious recipe, my confidence began to increase. It was around eight months later when I finally posted my first presale. The presale brought me my first paying customers, some of whom weren’t even friends or family! Custom orders followed from there! I definitely wasn’t ready to start my business any sooner than I did. If I had waited longer, the timing of jobs related to my teaching career would have interfered with my availability to complete orders. When I began, I was teaching online and making my own schedule. I was able to plan cookies around teaching classes (and everything else in life). Having that flexibility was imperative to building my decorating skills and gave me space to take risks in trying new things. Now that I am back teaching in a traditional classroom, I am better able to manage cookies and teaching because of the foundation I was able to lay from the beginning. Read more>>

Jacklene Creekmore

I wish that I had started my business sooner, but I also think you have to wait until the timing is right. I spent years working in a corporate advertising job that I was very unhappy in, but it gave me a great experience that I would later utilize to build my company. After the birth of my first son, my husband convinced me to take some time off work and think about doing something that brought me more joy. It took me over a year to finally take the leap into starting my own business with a friend. I knew that I always wanted to work in a more creative field and also have a job that gave me the flexibility to be a present Mom. Part of me wishes I had started earlier when Instagram and social media wasn’t so demanding and competitive, however that break from work allowed me to realize how much I really wanted to work in fashion and run my own company. It also gave me time to educate myself and build up courage to put myself out there. As a business owner you definitely need a lot of courage! Read more>>

Cristian Cativo

I absolutely wish I had started photography years earlier. I’ve always been the family photographer just never on a real camera but always on phones but I’ve always been told “cris is the one who takes the best photos have him do it” it wasn’t untill a couple years ago that I said let me get a camera and do it for fun. Then one lens turned into another and soon to a professional camera and lenses and next thing I know I am being paid to do what I love, capture memories and freeze them digitally forever. Read more>>

Christina Duzan

If I could go back in time and make a change, I wish I had started my business sooner. I started Fox & Flamingo Creative in late 2022 for the virtual assistant work and Fox & Flamingo Clothing in January 2023 for graphic tees. I was working full time as a communications specialist, still am actually, and my daughter was almost 2-years-old. I started both of these businesses in hopes that the combination would generate enough revenue for me to leave my full-time, corporate job. I wanted to work fewer hours and specialize in the areas I like most about working in communications while also getting more time with my daughter. Read more>>

Gabrielle Mackie

I actually first started my business in 2020- I know. My husband and I had just moved to the small town we live in and I knew nobody. I was also writing content as a freelancer for another small marketing company while bartending at a little bar. My idea was to chat up the local patrons and pitch my social media services. It was destined to fail, as every business owner was struggling and marketing budgets get cut very quickly at a time like that. Read more>>

Cassandra Hill

When I started my company Holistic Living Consulting it was the best for me. Before starting my business I worked in corporate America for several years which provided management skills, insights on business operations, crisis management skills, and tons of other valuable knowledge that proved beneficial when I started my own company. Additionally the health challenges that I experienced while working in corporate America was the fuel needed to develop a regimen that transformed my health and sparked the desire to transform the health of others. Read more>>

Kristina Truluck

I began my photography journey in 2009 as a Combat Cameraman for the Army, capturing training and combat.

I started volunteering at a horse rescue about a year after returning home from a deployment to Afghanistan. I had always loved horses, but didn’t have the opportunity to grow up with them. When they learned that I was a photographer, I was invited to bring my camera out to document the lives of the rescue horses and their interactions with the volunteers. In 2014, I wasn’t aware of any resources or education for equine photography, so I learned equine photography through trial and error. Read more>>

Darren Haskins

Yes and no. It’s been a long journey of realizing where to focus my energy. I’ve known since I was a kid I wanted to entertain, but growing up in Los Angeles with so many distractions it was difficult for me to understand where to invest my time when I was spreading it out too much on having fun. Originally, I thought I’d focus mainly on acting, but once I learned the basics to screenwriting I jumped right in because I had so many ideas going through my head. A screenplay is the foundation to any film project so, I started writing features, but I didn’t realize how difficult and expensive it would be to get them made or even read. Then I discovered I can learn to hone other skills doing short films. I can write on a budget, keep the characters and locations limited, and use the short film as a proof of concept to anyone interested in expanding the idea. I produced, directed, acted in, and edited a few shorts and comedy sketches on my phone, and posted them online which I was able to attract a producer to help create my most recent shorts HARD AS IT GETS and WHERE IS MY MIND? that are now in the festival circuit while having my next project, BINGO in pre production. Overall, I’m very thankful for the progress and improving the production value of each project. It’s a timely learning process and you have to love it. Creating your own path can be frustrating due to how slow the rise is, but we must enjoy the journey moving towards our destination at a pace we are comfortable with. Move too fast and life can become overwhelming causing stress and that’s a silent killer in many ways. Read more>>

Ashon Ruffins

For most of my life, in one way or another I had a creative hobby of some sort. I develop recipes and cook which is an art in itself. However, in regards to writing, I definitely wish I would have started a little earlier in life. The process of developing entertaining stories that also carries a message to my readers that can be beneficial to them personally is rewarding. Writing is a challenging process. It’s not always fun. But if you really enjoy the process of developing stories, flawed and relatable characters, and storylines with consequences, it is a great avenue of expression. Honestly, I never knew becoming an author and starting up a small indie press was in my future. Read more>>

Cortney Costanzo

I come from a family that sings “Happy Birthday” in three part harmony so singing has always been a part of my life. My mother and aunts took piano lessons starting at a young age and most of them didn’t enjoy it, but their mother wouldn’t let them quit. Because of my mother’s experience as a child she didn’t force me to learn piano. At the time, that was fine with me since I was a competitive dancer and had very little extra time. I didn’t realize how much singing would dominate so much of my creative outlet as an adult. Now in my mid-thirty’s I’m regretting not picking up an instrument sooner. As they say, it’s never too late! About 5 months ago I started acoustic guitar lessons. I wish I started 5 years ago but, better late than never. Read more>>

Colleen Kennedy Premer

With my artistic career (as well as life in general), I do believe that the universe has a plan and the timing is exactly what it should be. I have always been a creative person, guided by visual clues and observation. Early in life, I wanted to be a writer, so I spent much of my teenage years and college training pursuing that vocation. My mom, Elaine Kennedy, was a prolific artist, so I grew up surrounded by her work and a witness to her process. I always felt like she had the role of artist in our family. But behind the scenes, she was always encouraging me to draw and paint and be creative. When I was in my mid twenties, my mom bought me a weekend at a printmaking workshop, and I fell in love with that medium, and felt like I had found my artistic voice. When my mom passed away at a young age, I sensed it was my job to carry on where she had left off. Even though I was a stay at home mom with three boys, I always found time to work on my printmaking. It wasn’t until my youngest son went to college, however, that I jumped into my work with both feet. While technically my work as an artist didn’t really get much traction until I was older, it was a consistent and evolutionary process that brought me to the point were I am today. Read more>>

Josh Evans

I wish I started “Snake Edge” sooner because I went through a couple other projects before it that I didn’t get as much pleasure from whether I wasn’t in a big enough role in the creative process or financial reasons. Read more>>

Aline Humbert

That’s a question I’ve been asking myself a lot since I started on this path in 2014. I had just turned 17 and graduated from high school in a small town in France. Where I come from, movies and actors weren’t seen as “real.” They aren’t actual people; it was very far from where I come from. We don’t do extracurricular activities; there isn’t such thing as “theatre kids” because there aren’t theatre programs, especially at school. Even if I spent most of my time watching movies and shows, only in my teens did I realize it was an actual job and that even I could maybe do it. I realized I had never been able to choose just one job for my future because they all looked great on screen. I wanted to do them all. That’s when I realized the only way I could experience everything was to BE on the screen. That may have been the first time I was excited about the future. So, at the end of junior year, I dropped the bomb on my mom. I wasn’t going to medical school anymore. I was finishing High School and trying to become a professional actress. Read more>>

Shannon Lee

In the past, I might have leaned towards wishing I had started my content creation career sooner, considering the idea of potentially having less competition and the evolving landscape of the internet. However, my perspective has shifted. I’ve come to realize that everything unfolds at the right time. Divine timing is crucial. While starting earlier might have presented certain advantages, I now firmly believe that what unfolds for us does so in its due time. I trust that my audience will find their way to me when the timing is perfect, aligning with the growth and evolution of both my content and myself. Read more>>

Juliet Parisi

I wish I would have started my creative art business sooner. I have always loved making art and drawing all over my work & notes. Having 2 kids now makes having a full-time art business much more difficult, as most art opportunities are on the weekends. This means I don’t get to spend much time with my family as I want to. Additionally, if I were to have started my business sooner, I would have been up and running before Covid hit. Having had a solid business model prior to Covid would have helped with budgeting, annual show planning, and much more. Read more>>

Kathleen Roby

From a young age, I have always had a desire to explore the world, drawn to the unknown and constantly seeking to push my limits. At the age of 18, I seized the opportunity to fly to England to live there for a whole year, with the goal of learning English. However, this journey exceeded my expectations in terms of learning and went beyond just the language. Read more>>

Sam McNeil

I imagine a world in which I was much bolder as a kid. I didn’t know any better, and I didn’t know anyone else that knew any more than I did. (Pertaining to music production) There was almost this feeling that, if your recordings weren’t very good, you just weren’t very good. The level that was “good” also was loose, because what is “good” for a 14 year old kid that is recording songs with a gaming headset microphone? Well that answer is probably anything recorded with something that sounds better than a gaming headset. Read more>>

Benjamin Conrad