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.
Jen Bilger
Timing is always important when starting a business. In my experience, I launched my business in 2019 and with the events and business landscape over the past few years, many people ask me if I wished I had launched my business earlier or if I would have stayed in corporate longer had I known. The answer is always a resounding NO! Read more>>
Nathalie Williams
I started my business six years ago, when I was at a crossroads in my career. I was almost done completing my degree in business and was deciding whether I wanted to stay in my field or pursue something different. Starting my business seemed like the perfect solution to explore my interests without committing to a job or career path. The job I was in was becoming depressing. I felt trapped with and had no creative space to grow. Read more>>
Vickie Gray
Before becoming a professional photographer I spent over 25 years as a law firm marketer, managing the reputation and brand of several major law firms throughout the East Coast. I enjoyed my jobs but was DONE working in an office. Read more>>
Yaritza Rojas
If I had the chance to start my business sooner I would but then again no..Just because I think the process of getting to start one was like an entire learning experiences. Specially working in retail it kind of help me as a person to grow and shape me Today .I feel like different jobs help me to be were I I’m at today specially skills . I feel like every job has a purpose in my life In different ways . Read more>>
Alex Brown
Rising Action Publishing is definitely a labor of love. My business partner, Tina Beier, and I met in 2018 during grad school. While we connected initially on something else, we developed a great camaraderie. It wasn’t until May of 2020 when we started talking about the idea of a publishing house. Read more>>
Rockwell Stringer
We started our business in 2020 when, just like many others, I was laid off of my hospitality job due to the pandemic. I was working as an area manager when it happened. Although it was a great job, I’m an outdoor enthusiast and it felt unnatural being trapped in an office all day. Once I had the opportunity to change things up, I searched for opportunities that embraced more of my interests. That’s how I ended up with two jobs – pest control and personal training. Read more>>
Melissa Kelly
I come from a long line of self-employed entrepreneurs. My grandfather started a business that still employs generations of my uncles and cousins. After decades of steady W2 employment, my parents also struck out on their own and started businesses they believed in. While I started my LLC at the end of college, I really could not figure out how to make it anything more than a “side hustle.” Read more>>
Alexis Vantrees
I started my blog and social media account Exploring With Lexi in February 2021. I wish I would have started it several years prior. In 2018 or 2019 I was working as a hostess and started posting for the restaurant I was working for at the time. I had always had a passion for planning activities, trying new foodies, and traveling. When I started posting for the restaurant it make me realize how I might be able to combine my passion for travel/planning with my passion for social media. Read more>>
Love Nye
I am a Strong believer in everything happens for a Reason. So my business was started right on time. It takes time to grow, learn & improve. As long as I started the process I can see what works & what doesn’t work. I started my business 2021. During the pandemic it gave me time to brainstorm & prepare myself. Read more>>
DAN CASTELLO
Yes. Read more>>
Jeff Veliz
I love this question, it lets you reflect on everything you’ve done until this point. I decided to join the music industry about 5 years ago and started my record label about 6 months now. Read more>>
Andy Sharpe
I wish I had started my business a few years sooner than I did. When I was in design school I thought it would be a dream to use my skills to do my own thing. Build my own business. Then as I went through my career, it felt unrealistic, irresponsible, and just a pipe dream. So, I tried working my way up in agencies and even taught at a design school for a few years. Read more>>
Shonovia Phillips
I actually took the initiative to start my own business when I was in college around 2017. I started creating my own eyeshadows (loose pigments), but I didn’t take it seriously back then like I am now. I wish I would’ve taken it serious though because I definitely believe I would’ve been further than I am now. It was just hard to remain focused being that it was my junior year so the timing was a little off but, I believe everything happens for a reason and everything technically worked out for me. Read more>>
Stephanie Lamb
I absolutely wish I had started Quillkeepers Press many moons ago. The quick version of how Quillkeepers came to fruition. I earned my Bachelor’s in Business Accounting and later switched gears to further my education in Creative Writing. I’ve had a lifelong love of literature, which led me to study classic and contemporary writing forms. Read more>>
Rachel Lessenden
Looking back, I wish I had started my business sooner. I dabbled in blogging about healthy living back in 2013 but I didn’t know how to turn it into a business at that time. I was in grad school getting my MBA so my blog was more of a hobby than a side hustle back then. Read more>>
Veronica Hynes
If I could go back in time, I definitely would have started my business sooner. I wanted to join the beauty industry but I was influenced by everyone’s opinion. Everyone always said, “you can’t make money in the beauty industry” or “get a real job you’re guaranteed a paycheck.” So, In 2014 I enrolled in Pharmacy school and didn’t think of the beauty industry for the remainder of that year. Read more>>
Kyliah Baird
I absolutely wish I would have started my business sooner, yet I understand that the timing of when the business started is a part of my journey. Read more>>
Halley Prince
Timing is everything. If I could go back in time I wouldn’t change anything. I have always been ahead of the curve with my hustle mindset. However, I had to experience failure to understand what it takes to be successful. All of my losses have made me who I am today. Whether it be people I lost on the way, lost money, dropping out of college, ect it has all made me realize those losses equip me for what is ahead for me. Read more>>
Brittani L. Samuels
If I could go back in time, I would have waited to start my business. My book and podcast were perfect timing. My business, not so much. I do not have any regrets. However, there are things that I wish I knew sooner. When I started House Of Allura, I was fresh out of college. I always knew I wanted to be an entrepreneur. That was the end goal. The thing was, there were multiple things that I started and wanted to pursue. Read more>>
Jabria Howington
I’m the type of person that doesn’t live with regrets, but for the purpose of this question I do wish I would’ve started my creative career sooner. Growing up with an Asian grandmother made that difficult. She always pushed me to become a doctor or a lawyer (iykyk). Had I started sooner, I would’ve made a transition to California sooner to get a jump start on networking and propel my creative career even further. Since moving, the opportunities have been endless. Read more>>
Nella Khanis
I was a good girl. I obeyed my parents, who insisted I get a “real” profession. When we emigrated from the Soviet Union in 1980, I went straight to college, received my BS and later – my MS degrees. I worked in a medical field, disliked it immensely since all I wanted to do was paint! I regret the lost time of my creativity while I was young. I would like to see how I saw the world and how I would express it in my paintings. I would love to compare my young expressions with my mature ones. Read more>>
Deora Clairé
If I could go back in time with what I know now, I would have definitely started my music career sooner. Instead of releasing my first project Love Over Hate EP in September of 2018, I would’ve released music earlier because my talent show performance in Costa Rica, during the fall of 2015, boosted my confidence in singing and stage performance. Read more>>
Danielle Hunt
I would definitely have started my creative career sooner. I started in the creative space about six years ago, and I honestly should have started 12 years ago. I have always wanted to be a content creator but I guess I didn’t realize that what I wanted to be when I grew up was actually a content creator until now. I wanted to be a writer and editor and I am doing all of those things in the non traditional setting. Not to mention I’m writing and creating what I want, when I want on my favorite topics. Read more>>
Saki –
I wouldn’t change a thing. Even though I have always been interested in art since I could remember, I think my life journey before officially becoming a professional artist has filled me with more experiences, inspirations, and skills to draw from. It’s as if the pent-up creativity and the struggle to express it while being trapped in a non-creative career served as an incubation chamber for my art, like whiskey aging in a barrel. Read more>>
Lama Moppins
As we sometimes reflect on our life, you look back at many things you wish you could have changed. But if you changed those things would you be the person you are today? You never know. Now I’ve always been a jack of all trades when it comes to being a creative person. In my 20’s I was pursuing a career in music production. I knew I had the talent for it, but I did not fully believe in my abilities. Read more>>
Baraka McCann
I started my creative career later than I would have liked. I always knew that I wanted to be a model and Art director, but it took me a while to figure out what kind of artist I wanted to be. Read more>>
Justine Peñas
Ideally, I would have pursued the arts much sooner had I known I would have any artistic potential, which wasn’t exactly strongly encouraged growing up. My artistic career started in 2018. I was academically burned out, and I had just left graduate school in the Spring. After studying science for six years, I was looking to begin my career in the chemistry field. Read more>>
Cassie Rhoda
My creative career took a detour in my early twenties. Before I even got the chance to start, I had become a young disabled wife and mom from a severe, chronic illness. For twelve years, most of my days were spent homebound, unable to drive, and suffering with no answers or treatment. Sickness had progressed to a probable stroke at the age of thirty-two, and I thought my days were coming to an end. Read more>>
Ashlea Carter
I am a strong believer that everything happens in time, but I can’t deny that there is a part of me that wishes I started my creative career earlier. In a sense, I kind of did, but didn’t continue pursuing my dreams because doubt got in the way. About 5 years ago I ran my own virtual assistant business doing a wide variety of tasks for small businesses. Read more>>
Jessica Fiesta George
What began as a COVID / pandemic-led boredom project has now evolved into a full-fledged regular podcast. For over 15 years, I have advised friends, family, coworkers, jobseekers, and hiring managers on personal branding, interview tips, resumes, and the hiring process. I wish I had started much earlier in documenting my advice and expanding it to help even more people. The podcast is my way of continuing to help others on their career paths and businesses looking to hire top-tier talent. Read more>>
Avalynn Ly
One of my favorite quotes I often have to repeat to myself is “the best time to plant a tree was 20 years ago; the second best time is today.” I have always had a deep love of music and artistic story telling. Read more>>
Riley Bryson
My career kind of had a “false start”. I wanted to be many things as a kid – a marine, a writer, an actress, and more. When I was around 14 I started taking my dance training very seriously and there was no looking back, it seemed! I went all in with classical ballet. Moving away from home after high school and joining a trainee program, I was hopeful that things would progress in the conventional way, but things started to not go as anticipated. Read more>>
Matthew Morris
If given the chance, I don’t believe that I would seek to have changed the point in my life in which I started along the career path of the creative. One’s art is a reflection of themselves, and it took into my 30s for me to be able to turn my experiences into meaningful pieces of art, despite always having an interest in music. Read more>>
Rutuja Gadkari
I am very passionate about my business. I believe that I started my business at the right time in 2019. It was a point in my life where I was able to dedicate the time and energy required to make it successful and maintain a healthy work-life balance. As all my family, friends, and clients will attest, I truly love what I do and hence am able to enjoy doing makeup & hairstyle as per the needs/wishes of my clients and make them happy. Read more>>
John OConnell
This is a real catch-22. On the one hand, I wish that I had remained serious about photography after learning it in middle school instead of only dabbling casually with basic gear and effort until 2018. In the time that elapsed, I traveled to many incredible places and saw many beautiful sights. Read more>>
Jeremy Jaeger
You know as a creative you hear all the time how people think the younger people have more of a chance to “become” something. But when I think about it, if I had became “something” at, let’s say 21, Im not sure I would’ve had the strength to last. The person I am today is more intuitive with who he is now more than ever. The things i’ve gone through, the lessons i’ve learned, have molded me into exactly who I feel I needed to be, not just for me, but for anyone else I touch with my art. Read more>>
Jacolbie Hicks
Is wish I would have been started I started my career back in 2019 . I have always been an entertaining person I just like to have my hands in multiple hustle and different thing that have always made it hard for me to decide what I really wanted to do in life . I started getting heavy traffic on my leg from artist and entertainers that inspired me so I decided since I have the attention why not gone and try it out . Read more>>
Saneequa Maddox-Barlow
Looking back, I’ve realized that every job I’ve had – has prepared me for where I am now. I’ve always worked in the field of customer service, and health care. During that time I was always working “just to get by”. I figured that “getting by” was good enough for the time being, and like many – I pushed my dreams aside because I couldn’t afford them. Read more>>
Nyleve Nyson
If I could go back in time, I would’ve not wished to start my creative journey sooner or later. I would actually say the creative journey started in my adolescent years, when I was attracted to videography and photography. Knowing my interests at a young age caused me to invest in myself back then without even realizing it at the time. Read more>>
King Ken
If I could go back in time I definitely would’ve started pursuing music earlier in life. I started writing music and poetry in middle school but I didn’t have enough confidence in myself at that time, I was more worried about what other would think. If I was as comfortable in my skin as I am today back when I was 12-13 yrs old I truly believe I would’ve been one of the youngest up there with Jay-Z and Lil Wayne. Read more>>
Valencia Snow
I’ve been involved with music for as long as I can remember. Whether it was church or school choir or even karaoke. But I didn’t start doing it seriously until I was 22 years old. I honestly hate that I waited so long because I believe I probably would be a lot further along in my career. If I had a Time Machine I would’ve pushed myself more in high school. But as much I wish I could’ve started earlier I believe everything happens exactly when it should happen & extremely grateful for the opportunities that I’ve come across. Read more>>
DuragDevTheGoat
I think there are pros and cons to both sides. The con is I know I’d be a lot further along if I took the time to start building my brand earlier. The pro would be that I took those years to work on my faith and relationship with God finding myself essentially. As I reflect on that time I think to myself that I would it be worth making it to the top of the mountain if you don’t remember who you are when you get there ? Read more>>
Jessica Browne
After losing my job as an executive chef due to the COVID-19 pandemic, I began my creative journey as a content creator in 2020. With the extra time I’d gained, I had more time to scroll through social media, which is how I learned about content creation. I saw others making money online doing what they loved while working with their favorite brands, and I wanted to do the same. Read more>>
Keyla Belvin
I started sharing snippets of my life years ago via YouTube and Instagram. The goal was always to create a safe space for people who may relate in some of the life journeys that I have experienced. I wanted to provide representation in areas that I couldn’t find for myself for things such as health and wellness or just daily living in general. Also combining all of those aspects into my family and what that looks like individually and as a whole. Read more>>
Emmanuel Castro
I have always been the sooner rather than later type of guy, but as life comes your path will always change, most of the time for good. I started music at a very young age (5 years old) and traveled the world with other children who share the same passion for music as me. Read more>>
Cindy Hoang
Definitely—I wish I took it seriously to explore my creative potential much earlier in life. I was already drawing everyday, doodling in the margins of notes, doodling for my friends and classmates, and creating mini comics for myself. The energy to learn, create, and make mistakes (emphasis on mistakes) was there. Thinking back on those days, that was pure freedom — not feeling pressured to create something perfect. But I digress… Read more>>