The uncertainty of entrepreneurship causes many entrepreneurs to put off starting their business. For others, losing a job or other economic hardships push them starting their businesses earlier than expected. In our conversations with thousands of entrepreneurs we’ve seen so much variety in when, how and why people started their business and so we wanted to share a wide variety of views and reflections on the question of whether these folks wished they had started sooner or waited longer before starting their businesses.

Danny Lybarger

Part of me always wants to say “yes,” I wish The Well started sooner, but the honest answer is it started exactly when it needed to. If I had it my way, The Well would have launched years ago. On the other hand, I also realize that if that were the case, it would look nothing like the amazing church it looks like today. The people, the space, and the team that comprise The Well today all converged with perfect timing and synergy, and I think starting the church any sooner or later would have meant sacrificing the amazing pieces that God was bringing to the table to help start this church. Read more>>

Lexi Tuel

I started my cake “business” while in culinary school, I believe my first year. I’m surprised anyone ordered from me, looking back my stuff took awhile to look good! I truly started leaning into it once I graduated in 2018 and started growing from there. I always worked full time jobs, sometimes an extra job on top of that. But creating cakes and treats definitely brought me a sense of pride and purpose that nothing else did. It was only until 2 months ago that I quit my part time job and started working in my cake studio full time; Read more>>

Sadaiza Middleton

I say this a hundred times a day! If I could go back in time I would’ve started my business sooner right in high school or right after high school. I always had this mindset that I wanted to start a business some way or some how but, never knew the type of business I wanted to start. I have always been in to beauty and fashion my whole entire life so I knew if I did start a business it would have been in the beauty industry. Read more>>

Zwena Killikelly

I actually started my business In high school. At that time it was not official, but use to sell banana pudding and cheesecake cups to my classmates. That was my side hustle until Covid happened. When covid hit I honestly did not know what I wanted to do, but I knew I wanted to go to culinary school after high school. During the pandemic, I started really trying to perfect my craft. Read more>>

Allison and Yelca Tovar

We started the Simply Picnics DMV in the Fall of 2021. We began the business at the time that was right for us with where we were in our lives. We had left our previous job and were ready to begin a new endeavor. We wanted to have a creative outlet while allowing us to do what we enjoy most, working with people and being a part of their special moments. Read more>>

Perianne Louissaint

If I could go back in time, I wish I would of started my business earlier! I started my business back when the world was in complete chaos, in the middle of a pandemic! I know what you’re saying, who does that right? It was the craziest, bravest, smartest thing I have ever done. During that time in life, I was still working at one of the most frustrating 9 -5s, with one of the world’s most horrible bosses; literally wanted to quit every day. Read more>>

Haley Witt

I truly never anticipated starting my own business at 23. I took a Communications and Entrepreneurship class in college and knew I was interested in someday working on a business project of my own, but I assumed that opportunity was still many years down the line. But when I realized I wanted to develop a more diverse marketing portfolio, freelancing seemed like an excellent route. Thus, Awake Digital Media was born. Read more>>

Perry Robinson.

I started Athletic Scholars Brand about 10 months after being medically discharged from the military, unsure about what I would be doing with my life next, struggling with my mental health, and I asked God for my purpose. As clear as you could possibly get, God blessed me in placing this thought on my mind to start an organization and serve him. As cliche as it may sound, I honestly believe that God’s timing is perfect, especially in blessing me to start this organization and serve in my purpose, so whenever he would’ve put this on my heart, it would’ve all led to this. Read more>>

Portia Guillory

I would say timing is everything. I started my business in 2021 after my brother passed away Christmas Day in 2020. Before I started my business, I was working as an insurance agent but I wasn’t fulfilled in that career and I want to pursue my childhood dream as my own lipgloss model. If I had started my business sooner, it would have been an epic fail. My mindset at the time wasn’t ready. I’ve lost a lot of people in my life over the years, mental health wasn’t stable, and I wasn’t as mature now as I am now. Read more>>

Christa Black

This is a tough question because I feel like God has perfect timing. My family and I moved to Tennessee from Florida in 2016. After taking a year off from teaching to help my then 8-year-old son get adjusted to our new life, I decided to hop back into the preschool world where I belong. Read more>>

Akisia Belvin

I wish I would have started my Baking Business earlier in life when I first noticed that I was good at it and it actually can be a great Career that I love . When I started my Business on the side while working a 40 hour a week job , I didn’t have much experience in baking or chocolate making . I would watch a lot of Baking shows to perfect my craft . If I would have had the confidence back then that I have now I believe I would be further but I do understand timing is everything and to be great in your field takes time and experience . Read more>>

Ashley Saunders

Dark Raven Products was established in 2020 during the pandemic. At this time in my life I was looking for more ways to make money and also a way out of working for someone else. At this time every job I’ve worked I’ve never received a raise, at each job I was able to work independently while also preforming different tasks that wasn’t in my job description. I worked hard and did not receive the pay to reflect that, so I started to research on how to start a business doing something that I loved to do. Read more>>

Kim Miller.

In January of 2020, I found myself between jobs and trying to decide what I wanted to be when I grow up. While I was exploring career options and searching for my next opportunity, I found a post on Facebook from a childhood friend. She posted about a new business she was starting. As I looked into what she would be doing, I learned more about Chefs For Seniors. Read more>>

Kia Conyer

Haha! What a great question! I will start by saying that I have no regrets. For many years I have struggled to find my passion and if I even had one at all. I am a student of life and love learning and growing. I graduated college in 2011 with a Bachelor of Science degree in Electrical Engineering Technology, and a Master of Science degree in Engineering Management in 2018. I’ve spent years in the engineering and project management industry. Read more>>

Jae Hussain

I definitely wish I would have started my business sooner than later, however I do believe that all things happen when they are suppose to happen. I believe that life experiences we go though help keep us on track to where we’re suppose to be. We never see it that way in some moments but time always tell. When I stared my business I had completed my Bachelors degree a few years prior and had already built a lengthy career in my 9-5 work, but I was looking for more , Read more>>

Serena Teakell-Rigby

I do wish that I had had the financial stability to have started my business sooner. I would have loved to be young and childless with much less life responsibilities when starting out. Haha! I started my upcycled clothing business in 2019. I was a new mother and wanted to be a stay at home mom while still maintaining some financial independence and making a difference in the world. It was a difficult start for me, simply because I had a baby on my hip while trying to sew and alter clothing. Read more>>

Craig Lawrence

Honestly, I wish I’d started sooner. I got into photography shortly after my (very sudden and unexpected) divorce. It started as something to fill my time, something new to focus on, but I quickly fell in love with the storytelling aspect and the way you can connect with people through photos. Working with models and clients, learning new and creative ways to make art with these tools (camera, lenses, lights, photoshop) really meant the world to me. Read more>>

Heather Schultz

Mato Tomato Girls began as a way to support my daughter Selah with her hopes to attend 4-H Camp. I taught her how to bake when she was 5 years old and we began to really push for her to make something great out of it when she was in 4th grade. 4-H Camp was her goal and she met the goal above and beyond! After seeing herself achieve what she set out to do, she was inspired to continue on and begin saving her earnings for the future. Read more>>

Caitlin Lo

If I could go back in time and start my business sooner, I would. In high school, I freelanced makeup for about 5 to 6 years. Beauty school was always on my mind, but everyone tells you that you need to go to college to make money and be successful. I ended up going to college because my mindset was that I could go to beauty school anytime. College wasn’t for me and I wasted a lot of time when I could’ve been an esthetician already but I love the memories and people that going to college gave me. Read more>>

Zayne Ward.

I would have liked to have started my business sooner. I’m much happier even though it took longer to achieve my goal. I believe I learned a lot by waiting. I believe it helped to wait to have a true direction. I don’t know if it would have meant as much to me had I started sooner. I’ve been licensed as a cosmetologist/barber for j 12 years now. Before my career in hair I was licensed as a massage therapist. Read more>>

JJ Gibson

When I was younger, I thought I would grow up to be an engineer. Then, I thought I would be a musician. The concept of me pursuing a career in animation didn’t surface until I was well into high school, and every piece of art I ever created before then had been purely for leisure with zero professional education. Read more>>

Bone Zone

Rollin: I so wish we could have gotten started with Bone Zone earlier! All of us in the band have a blast together and have so much fun playing music live that it would have been awesome if we could have done this sooner. I’ve known Zack since high school and Jeffrey since just after high school so it would have been rad if we could have gotten together sooner, but I’m thankful for the time that we’ve had together regardless! Read more>>

Becca K

If I can go back in time I don’t wish I had started my creative career sooner or later. I believe in divine timing in which I was suppose to start my creator journey back in 2019 and expand onto another platform in spring of 2022. During this time, I was working towards my 4 year degree and graduated December 2021. Read more>>

Chantrice Rachelle

While I have been an artist my whole life, it wasn’t until 2020 that I actually decided to take this journey seriously (as opposed to it being a hobby). Within these last two years, there have definitely been moments when I wished that I had started earlier. I even sometimes wonder where I’d be in my art career had I pursued formal education in art versus business and technology. However, I have to always remind myself that I am exactly where I am supposed to be on this journey and timing is everything. Had I started earlier, there is no guarantee that I would be further, as knowledgeable, or even as prepared as I am now. Read more>>

Hope Obadan

If I could go back in time I would have tuned out that voice that told me being a creative does not get you anywhere. I typically had this stereotype in my head about artists and creative people that they were broke degenerates and could never become successful. This was because of my culture and where I grew up. I’m originally from Nigeria but I grew up in a country even poorer than Nigeria and the only thing that was fed to me was that the only way to make it in life was to become a doctor, lawyer or engineer. Read more>>

Cody Schultz

That’s a really good question, knowing what I do now I wish I would have 100% started way earlier! Content creation has come along way in the last 10 years, Nobody was really doing YouTube or Streaming back then. If you were one of those few who were in it early you probably have a drastic following at this point. The people who were the small group streaming had a lot less competition, now when you go to twitch there are millions of people who you are competing with, in thousands of different sub categories. Read more>>

Ichiban Tez

I actually decided I wanted to be a creative when I was 22. It was around the beginning of 2018 that I really started the learning process behind taking my hobbies and making them passions. My family always encouraged and pushed that I go to college, which now graduating this year – I don’t regret. I learned a lot of things being in college, indirectly: struggling and prospering. I finished a bit later than I wanted because of life issues at first, and then COVID on top of that although I think that made me even more excited about the future. Read more>>

Emily Anderson

My path as an artist has often been a sharply winding road, but ultimately I think everything happened with divinely perfect timing. Although I had an unfulfilled dream of being a painter for as long as I can remember, all seemingly unrelated life experiences led in one direction for me, guaranteeing that when I finally had the guts to try painting at age 40, I was ready to use my life experiences to be able to make smart decisions in my path towards becoming a professional artist. Read more>>

Gail Williams.

I began my life as an artist in earnest when I retired from my previous career in health care. Sometimes I think I would like to turn back the clock and have been an artist earlier, but I realize that my life experience has prepared me perfectly for this new career. I am an intuitive painter who lets curiosity, rather than logic, guide the brush. Read more>>

Tasj-Mari Myers

I officially started my creative career around February 2021. I had been playing with photography a couple years before that but in high school I was of two minds. I was fixated on either becoming a field biologist or an international business major. Once Covid hit, I fell into a deep hole and I pretty much forgot about any dreams I had. TikTok was booming during this time, and small businesses were getting a spotlight. Read more>>

Shannon Lee

I officially started my creative career exactly two years ago in the year 2020. During this time, covid19 locked everyone inside due to restrictions. I always wanted to start a youtube channel, but I never had the time nor patience to start! When I started my channel, it was pretty easy to maintain consistency since I wasn’t too occupied outside. Even though I started this journey two years ago, I wish that I started it sooner. I’m usually not the type of person to regret my decisions, but I really wish I started my channel in 2017. Read more>>

Ariel Niu

I love this question because I reflect a lot on this personally. My creative pursuits was a gradual process. I started it for fun on the side, and was in a completely different niche than what I am doing now. Throughout the first year, I felt the “I should have started sooner” energy all the time. However, it was because of all the challenges I had to overcome. There were many obstacles in the beginning, because I was learning, experimenting, and switching things up all the time. Read more>>

Toi TooTall

If I could go back in time and start my creative career sooner I definitely would!!! I started in 2012 doing stage plays but I feel like I took a more serious aggressive dive into pursuing my dreams between 2019-2021. It was a slow rolling start because we were there in the middle of a pandemic. But thanks to the Internet everyone was watching. When I start taking things more serious I was in a space where I didn’t want to be the 9-to-5 worker anymore. I was ready to quit my job without a true plan on how to go about things. Read more>>

DJ Wilke

Oh my gosh yes! I wish I would have just realized in high school that I wanted to be a hairstylist, and that I would have been good at it. In high school I was a sophomore in a senior film making class and at the end of the term we had to make a short film. And in my video, I was a super hero with the ability to move fast like Superman, and regular world identity was a hairstylist. Although I am happy that I have my business degree, I would have probably done things a little! Different. Read more>>

Addie Moore

Short answer: I wish I had the courage to pursue art a long time ago. I grew up in Tyler, Texas, a big town in a largely rural area not previously known for its vibrant art scene. I have always loved to draw. I used to spend all of my waking hours drawing and giving my little scribbles to friends or filling the margins of my school books with doodles. My creative drive was celebrated, but my parents, both creatives in careers that didn’t suit their many talents, discouraged me from pursuing a career in the arts. And seeing our family struggle financially, I was also convinced. Read more>>

Cara Leighty

If I could go back in time, I definitely wish I had started in VoiceOver YEARS ago! I know it was always something that I was interested in as a kid, teen & young adult so I wish I had started pursuing it sooner! I’ve just realized how amazingly fun it is & even though I have always been creative and done creative things career-wise, I wish that I would’ve jumped into it a little earlier than I did. I mean it’s better late than never & I’m thankful that God has opened the doors for me over the past couple of years! I just wonder where I would’ve been if I had started sooner. God knows what He’s doing, so it was probably supposed to happen EXACTLY how it did. Read more>>

Yani Sun.

I believe that I have chosen the best time to start my creative career. I was a big fan of pop music and music videos when I was a teenager. It inspired me to want to be part of a music video team. I’m lucky to have my parents who always support me in pursuing my passion, so I started to learn a mix of digital arts during college. By exploring visual design with new media forms in 2013 with a focus on creative brand identity, UI&UX design, and immersive interactive installations, I developed a passion for motion graphics and animation. Read more>>

Amy Williams.

Going back in time is something I used to think about quite often when it came to starting my creative career. It is one of those tricky questions because I know I got to where I am now because of what I have been through. I am just too curious to not think about having a conversation with my 7 year younger past self. Food blogging back them was purely a hobby I completely enjoyed sharing with others. Read more>>

Minda Gomez

When I was a young girl, it was my dream to be an author/illustrator of children’s books. I actually entered in a contest as a 10-year-old, hopeful that I would be able to have my book published. When I didn’t win, I was disappointed, as I didn’t see another path to becoming an author in the near future. Read more>>

DJ Simmy.

I always think about this question. When you’re in the entertainment industry, everyone has their own opinions about when someone should stop or slow down their craft because they’re “too old” or because another generation is stepping on the scene. To be honest, I used to regret that I didn’t start DJing and producing in my high school years because I felt that I would be in a very different position now. Read more>>

Heather c. Lou.

I have been a creative my whole life. My earliest art practice memories include drawing on typewriter paper, painting with water on the sidewalk, creating found poetry from my Ranger Rick magazines, or collaging from an assortment of newspapers and old magazines that my amah (grandmother) collected in her basement. I used to look at coffee table books with awe- wondering how someone could be so innovative as to display their art in public. Read more>>

Karen Morgan

I began my career in comedy in 2005 at the age of 40. Before that, I was a trial attorney specializing in criminal defense, medical malpractice & plaintiff’s work. I had taken a break from my law practice when I had kids, but staying home with 3 kids under the age of 3 inspired me to get out of the house once a week to keep my brain cells from atrophying. My friend suggested a standup comedy workshop at a local comedy club. I would have taken underwater basket weaving just to have some time to myself, but thankfully the comedy workshop also fit the bill. Read more>>

Madison Montgomery

There is an inherent association with pressure and timing in the creative field, specifically in the performing arts. It’s easy to get caught up in the comparison trap as we watch our peers and colleagues progress on their own timelines.. But I believe in the concept of Universal or Divine Timing, and I truly think everything happens when it’s supposed to. To me, the biggest indicator of Divine Timing is the people you meet along the way. Read more>>

Renée Crouser

My father recognized a natural talent early in my life. He encouraged my interest in drawing by throwing every medium he could at me. Dad never asked me to choose one, so I used and loved them all. Graphite is my base, almost always my starting point, but I’ve “drawn” with every medium I use as far back as I can remember. I’m a self taught artist, if there were a way to change my experience, I feel I would have benefited from an education in art. and would have started my creative career sooner. I won’t call it regret, I’ll call it a missed desire. Read more>>