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.

Hannah Evans

Hairchaos Studio began as just as a thought for my Instagram handle. When I created the handle, I felt the name needed to fit my personality and vibe. I went through all these names and thought about what stylists have to go through during the service when formulating color and deciding on the technique to use in order to achieve the final look. This can be chaotic and yet the end result is beautiful. Read more>>

Lauren Garrison

It’s hard to say when my business began. I’ve been a working photographer since I was 17 years-old. For the past 13 years, I’ve been paid to photograph sessions and weddings, but I waited until January 2021 to “go full time”. In my experience, photographers often get asked “Do you do this full time?”. For years, when asked the question, I said “yes”. Because yes, I worked on my business more than 40 hours per week. It became a full time job long before 2021, but while building my business, I had another job as well. Read more>>

Mandy Hopp

I quit my full-time, very cushy marketing job in the tech industry in February 2020 to launch my design studio, Hopp Creative. I loved the team I was working with, but was struggling hard with burnout and overwhelm. I’ve known since I was in high school that *someday* I wanted to work for myself eventually – which is a large part of why I had pursued design and marketing. Read more>>

Sonya Welch

I used to regret not starting my business earlier on in life. My thought was, had I done so, I would be much further along than I am at the present. When I was younger, I changed jobs a lot as I would easily get bored. Nothing I did seemed to fulfill me. I knew that I enjoyed writing, but I didn’t see it as being a stream of income. Back then I would only write if I was asked to do a skit or play at church. This was mainly because the bulk of my time was spent trying to find a career path that fulfilled me. Read more>>

Paige Ratterman

I wish I would have started my business much sooner than I did. I let thoughts like am I good enough, will people hire me, can I do this, run my motivation right into the ground. I always let things like it was never a good time or that I didn’t have enough money stand in the way of starting but really all of these things are just excuses. Things we create in our mind to keep us from achieving our true potential. Read more>>

Rachelle Keith

Im a firm believer that everything happens for a reason. I think i was exactly where i needed to be when i started, scared, nervous, lost, unhappy. In the madness of COVID and being on lockdown, the only upside was having lots of free time. I still worked my 9-5 corporate job of 6 years when i started, and I sought out a new venture. I started out slow, i worked full time for my company and part-time for myself. I was miserable clocking in to a place everyday being told what to do, and no matter what position i was “Promoted” too it never fulfilled me. Read more>>

Shauna L

I definitely wish I had started my business sooner. Prior to entrepreneurship I was working two full time jobs in the medical field. I missed a lot of time with my family and children because I had to work so much. Entrepreneurship has given me so much freedom and flexibility to live the life I want. Read more>>

Nashey Perry

I started my business at the peak of the Pandemic, and to be honest, I wouldn’t change a thing! Before May 2020, I spent most of my career in corporate freelancing my marketing services and waiting for the “right” time to take the leap and start my business. As fate would have it, my dream soon became a reality once laid off due to staff reduction. Initially, I was scared, but after much thought and prayer, I knew this was divine confirmation and alignment. Had I done it sooner, I would have crumbled because I did not know how to pivot and if I had waited, I would have played it too safe. Read more>>

Sherita Smith

I started my business during one of the most difficult times in my life. I lost my sister to breast cancer. My youngest sister. And at the time I started a new job out of necessity, that I didn’t go to school for. And at her wake, one of my cousins asked a question, “Who will be there for me?” And I told her that I would be. Understand that I am not my sister, and we had different personalities. So I’d been to the University of Houston to get my degree in Accountancy and I knew that she had a business. So long story short, I ended up doing her accounting for her business, and that was 7 years ago. Read more>>

Klarke Taylor

I have been writing short stories since I was in elementary school because I have such a large imagination. I wish that I would have taken my writing seriously from the beginning. Of course it was fun, but I did not realize that I could actually make a living off of it. Art and creative services are a lot of the times looked at as JUST hobbies, but they can also be careers where you are allowed to have as much control as you want. Having that control while benefitting from my very intimate work is freedom to me. If I would have had more information and support as a child I would be in a much happier position career wise. Read more>>

Gretchen Baker

As a young girl, I always liked seeing pretty cakes. Growing up, I lived across the street from a wedding cake designer and I remember thinking that one day I wanted to do what she did. Fast forward many years, I started to just decorate some of the cakes my mom used to bake, jut to make them pretty. I did that for friends and family, and one day I got to make a wedding cake for my husband’s cousin. At the wedding, I heard so many people saying that I should do that for a living because that cake was amazing. Read more>>

Jenn Rodriguez

There were definitely moments I wished I had started my creative career sooner. I was working a lucrative sales job for a wireless company when I realized I wasn’t 100% passionate about it. I decided to leave my job and make a career shift pursuing cosmetology. I had no clue where it would take me, but somehow I was confident it would pay off. Read more>>

Ron Blake

I am happy this creative journey began when it did. I would not change a thing. The greatest things in our lives happen just when they are supposed to. It all began for me with an unexpected moment of laughter I had on a suicidal night. At 10:44pm on November 2, 2015. That spark of hope started my now seven-year cross-country journey of creating social practice artwork. With the colorful contributions of 32,101 complete strangers I’ve met one by one along the way. Read more>>

Tiana Darling

If I could go back in time i feel i would start my career sooner, Just because I’ve been writing songs/lyrics since a child. My first ever rap was written when i was in 5th grade. That Era was the MySpace Soulja boy era and his come up was crazy! I believe if i started performing around like the age of like 15 i would have been on more stages. A better stage presence and many more opportunities. I believe i would’ve had the confidence instilled in me at early age. But ultimately I’m ok because i still feel I picked up writing so early it has helped my lyricism and to find my sound. Read more>>

TyQuan (Ty-Clef) Baskin

In all honesty? It’s quite ironic that you’ve asked this question. Wishing I started my journey sooner is an internal battle I face frequently. In this entertainment industry, they want what’s the newest, what’s the hottest, what’s the “Now”. And as a 27 year old, I often ask if I’m losing my spark. If my eyes have the same gleam as they once had… When I was younger, I was fearless! I was focused, confident, and determined! Read more>>

Jennifer Alvarado

Ultimately no. There are times I wish I had the confidence that I do now to trust God and move forward with music. However, there are lessons I have learned that I believe have made me more grateful. I think too many people want everything right now. I was very much that way. I have always been a hard worker, but it wasn’t until I chose to pursue music that I ever understood struggle. The road has not been easy, but it has made my passion for music even greater. Read more>>

Melissa Corpus

I’ve often asked myself this question so many times. Do I wish I had started my Samba career earlier? NO. I’m glad Samba came into my life when it did. It’s almost hard to imagine my life without Samba since it’s been a part of my adult life for over 12 years. Before Samba became a massive part of my life, I was still involved with dance and teaching Latin dances such as Salsa and Cha Cha Cha. I was also working a full-time administrative job and putting myself through college. Read more>>

Can We Talk Music

I definitely wish I created Can We Talk Music sooner. The brand is currently three years old, but I can only imagine where it would have been if I started it when I initially had the vision arise in my head. The only reason I didn’t push to start Can We Talk Music earlier is because I was still dabbling in songwriting and didn’t want to blur the two lines, but something told me Can We Talk Music was my true calling. Read more>>

Geoffrey Stein

I have always made art. I made wood and metal sculptures as a kid, worked as a photographer for the local newspaper in high school, and briefly studied product design at Parsons School of Design. I ultimately transferred to Bard College, completing a liberal arts degree. Having graduated during the recession of 1982-83, I fled to law school. Read more>>

Brittany Jones

This is a great question because I’m big on not regretting anything in life–everything happens exactly the way it’s supposed to right? But, if I had to choose I think I would’ve started later than sooner. I begin my creative career at 25, and now at 29, I’m a lot wiser and able to mentally handle the beast that is entrepreneurship. It’s certainly not for the weak and requires a great deal of patience and responsibility, two things I lacked at 25. :-) Read more>>

Veronica Gomez

When I look back sometimes I think of the opportunities that I had. I ask myself all the time where would I be now if I didn’t choose the choices I did at the time that I chose them. I have been trying to purse a career in Music for about 11 years, I had opportunities to work with celebrities, ghost write for artist and travel but due to my circumstances I allowed those opportunities to go away. Read more>>

Xiya D

I did not start making music until the Summer of 2020, even though I had been writing songs and hiding them in my closet for about 15 years prior to that. Now it sounds preposterous to me because I have so much fun recording and releasing music – it’s a part of who I am. Nevertheless, the more I think about it, I couldn’t make music the way I do now without that life experience. Read more>>

Mikey Lujan

Sometimes I get frustrated knowing that I started performing at age 16 as opposed to many of my peers who started when they were four or five, because it makes me wonder if I would be better at my craft had I started sooner. Growing up, my parents never really had money to enroll me in acting, dancing, or singing classes, so it wasn’t until I was old enough to work that I was able to go for my dreams. Read more>>

Ashley Charles-Bennett

If I could go back, I definitely would’ve started on my passion sooner! I feel like in my teenage years, I didn’t have much guidance or help finding what I love to do. I wasn’t exposed to many creative hobbies or culinary projects growing up. I oddly found my passion while grieving (that’s another story) when I was 24 and I’ve kept growing and learning ever since. I think if I started sooner I’d of course have a wider skill set, Read more>>

Monet Maxwell

I think things happen the way they are supposed too, but if I could go back with the knowledge I have now I definitely would have pursue being a creative much sooner. I decided at 23 that I was going to go back to school, but this time for fashion. I previously went to a community college for like 2 years, I had no idea why I was there so I decided there’s no need in going back. I always wanted to pursue styling but I didn’t have the resources and honestly didn’t know where to start. School seemed like the best option at the time, but I ended up learned everything from working. If I could go back I would have pursue full time freelancing in the beginning. Read more>>

Daniel Chan

I have mixed feelings about the start of my career. Knowing what I know now, I would have started my career later, not because of anything creative-related, but because I missed out on a financial benefit from staying at my previous job! After graduating from the University of California, Riverside, I worked at Paypal. All the employees were offered stock options at the time as Paypal was a pre-IPO startup. Read more>>

Baby Bishop

If I knew what I knew now back then, I would have started my career sooner than later. Music fans love seeing a young artist grow up in the industry grinding, chasing their dream. I lost a lot of time also by being in the streets, jail time, and putting my dreams on the back burner. I came up from a one- parent household but live mainly with my grandmother. From age the 10, I started writing poems. During that time, I was influenced by mother and step-father when it came to hip hop music. Read more>>

Maressa Roberts

I used to wish that I had begun my journey as a serious artist sooner. It has taken me a while to get to the place I am at today and even now, I feel like I am behind. If I could travel back in time, I would not change a thing. It has been a turbulent journey to my current mindset. A super bumpy road with highs and lows. I think that if I tried to do what I am doing now It would not work out as well because, over time, I have been able to build the confidence that I need to work as an artist. Read more>>