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.

MUKA No

If I could go back in time, I’d probably have started my career as an artist sooner. I’ve always loved art and took every art class or opportunity offered to me growing up but I never considered it as a career. It always felt like it would just be a hobby. Fast forward to now, I am 2 years in of being a full time artist and I only wish I would have nurtured this sooner. I would probably have been a lot happier, I would have felt more like myself, and by this time, I’d have years..even a decade under my belt as a career artist. Read more>>

Augusto Esquivel

This is a very tricky question. I was ready to do the things I did, when I did them. Like everything in life the point is not to spend time thinking about the past, but work on your skills (personal, psychological, physical, emotional, professional) to be the best artist you can be today. Read more>>

Lisa Davis

I am a firm believer that timing is everything, and the timeline of my career has happened exactly how it was supposed to. I applaud those who start successful businesses right out of college. However, personally, I think the value of working in a corporate setting for 5 years after college, before branching off to start my business, was the best path for me. Read more>>

Sharon Fletcher

I remember coming across planning documents for the business dated back in 2009, while I was completing the business formation documents in December of 2016 to start Chic Collective Group. I was in what I called the “thick of life” in 2009; being a wife and mother, focusing on our six (6) children who ranged from ages 3 to 15 and working full-time. At that time, I remember saying to myself, “This just is not the right time! Where would I find the time to start and manage a business?” Read more>>

Michelle Dennis

I launched adopting courage LLC in 2019. This was a simultaneous launch that was coupled with the release of my first book which was also entitled “Adopting Courage”. The timing couldn’t have been more perfect. I was in a season in my life where I prioritized healing and I was starting to benefit from doing the emotional and mental work to unpack childhood emotional injury as well as the negative impacts of navigating the foster care system and being adopted. Read more>>

Jaleesa Bray

I’m glad I waited to start all of my businesses so I wouldn’t just have dived in head first. My husband was the brains of the T-shirt business that we have in Dallas at Midway Towers during COVID-19. Beforehand though I started my work from home staffing agency that I built and now have a total of 55 agents responsible agents since 2017. After that I worked odd jobs on and off while I went to school for makeup and later after that hair school. Read more>>

Stefanie Haas

I started my home bakery in January 2020. I toyed around with the idea of starting a bakery every few years but just didn’t for various reasons: I didn’t feel confident enough, my kids were little, I had no idea how to run a business, the list goes on. But in January 2020, I made a cake for my niece’s birthday party and people asked for my card. Well, I didn’t have a card. Because I didn’t have a business. I decided then that it was time. Read more>>

Elda Marletd Sanchez

Since I was a little girl I remember looking at my grandmother sewing in her vintage Singer sewing machine. I knew since then that sewing was something I wanted to do. But for some reason I never did until couple years ago. Before sewing I did Baking Classes and Child Development. But around 5 yrs ago I got a fall Winter classes schedule on the mail and I check the classes and saw sewing and It started on that day, I went and stayed there until 2020 when the pandemic started and I had to stop. But I’m hoping to go back this Fall/Winter. Read more>>

Cristina Walker

I can say I am proud of where I am now, and where I see myself going, but if given the chance to start over I would have started sooner. If I’m being completely honest, the only reason I didn’t start sooner was due to fear. Fear of being judged, criticized, made fun of, etc. I considered and still do consider myself a self-taught makeup artist, and due to that I always felt I wasn’t good enough. I would question, why would anyone want to work with me? I’m not certified, I didn’t go to school for this. Read more>>

Solange McKenzie

Honestly, no, I don’t wish I started sooner or later. I believe things happen in each person’s own time. Specifically for me as a Tall creative encouraging other tall women to love themselves and their height, I needed to become confident in my body myself. Even though the journey of self-love is personal and on-going, I need to go through my stages in order to share my experiences and help my tall community as they experience their journey. Read more>>

Nick Price

If I could go back in time, I wish I would have had the interest and motivation to continue and stick with my creative career. I had gone to Indiana State University starting in 1999 – and majored in Graphic Design and Art History. At that time, I had been told by so many non-artists as well as professionals in the art space that graphic design WAS the future and that I shouldn’t waste my time on fine art or traditional art. Read more>>

Malik Norris

A question I’ve thought about this from time to time and I honestly wish I did. Originally, I started designing clothes and graphics in 2016. I was just your ordinary broke college kid studying to become a Computer Engineer. I had recently quit playing college sports and really just trying to find out what I could do to fill my free time. Which sounds easy enough still being in college, but when you think about going from having no time to all to having all the time in world was kind of scary. Read more>>

Jessica Valderrama

I always liked drawing, painting, and doing creative projects in school. I started art lessons in the third grade and as I got older, I knew I wanted to study art and be an artist. So I studied painting and drawing in college, worked in local galleries for a few years after that but never really knew how to make a regular practice for myself, how to value my practice or really investigate my work. I thought I could just do it on the side here and there, sell a few pieces at the gallery but nothing really stuck. Read more>>

Marcus Hanna

I normally don’t have regrets but thinking back on certain situations, as a 29 year old, I have learned not to waste seamless amounts of time. Some backstory, I started producing in 2009, juggling my last few years of high school, work and even extra curricular activities. The pressure of what something different than what your family wants can take a real toll. I loved music and everything about it but I was not the best idea according to my mother. Despite the friction, in 2011, I decided to go to college for Music Business. Ended up picking the wrong location for my job choice and that itself is very crucial. Read more>>

Stacy Olsen

I worked in my corporate career for over 25 years and for many years said “teaching yoga on the beach” would be my ‘retirement career’. Long story short: in 2018 I met and started working with a coach that shifted my timeline forward about 2 decades – in early 2019 I attended a retreat in Bali, sold my house, and left my corporate job to start my own yoga/coaching business. In February 2020, I hosted my first yoga retreat on the beaches of Lake Atitlan in Guatemala. Read more>>