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.
Saraya “charli” Charlton
I started my business around 2019. I was working a corporate job and I was somewhat happy but definitely not fulfilled. My passion has always been art. At first I just made shirts and hoodies with my logo and sold them to friends and people in my community. Then I started making custom shirts and quickly got burnt out because it wasn’t what I wanted to do. I wanted to paint. So I started getting more involved with the art community in Nashville. I set up as a vendor to sell my art at some of the local art markets and that’s when I started feeling like I was heading in the right direction. I began meeting other artists and it felt like I found distant relatives I had been searching for. Sometimes I do wish I would have started my business sooner but I believe everything happens when it is supposed to. I wouldn’t change anything about the journey. I am thankful for every lesson I’ve encountered. Read more>>
Tiera Johnson
If I could go back in time, I wouldn’t change a thing, I believe that the path God laid out for me was the right one. My only wish is that I had more business knowledge back then. I started taking clients at 14 through Craigslist in 2008-2009, and by 16, I had turned my room into a salon. If I had understood the value of business and marketing, I would have branded myself early on, skipped joining the military, and fully committed to my craft. But everything happens as He sees fit, so I wouldn’t change a single thing. Knowledge is power. To all young entrepreneurs: gather as much knowledge as you can, and make the most of it! Read more>>
Joshua Montemayor
If I could go back in time, I wish I had started my business sooner. I officially took the leap and went full-time earlier this year, but for a long time, I hesitated. My previous career was in City Planning—a path I was deeply committed to. I earned my undergraduate degree in Urban Planning and, during the pandemic, pursued a Master’s in Public Administration. I was passionate about being a public servant, working to shape thriving communities. And for nearly a decade, I did just that. Since 2014, I worked for various cities and municipalities, served as a public official on a City Commission, and spent countless nights sitting in City Council and Planning Commission meetings. I worked hard and moved up to an Assistant Director position. On paper, I was exactly where I should have been, but in reality, I was burned out. Read more>>
Grace Emmons
I started my business at the exact right time for me. Once in a while thoughts pop into my mind like “if I’d started sooner, I’d be farther along…” or “if I’d waited until my children were older, I would have more time and could get further faster.” But hindsight is 20/20. And in reality I know there could have been no better timing than the crazy, unexpected way my path unfolded. I started my company when I was a decade into a career in biotech. I already knew I wanted to make a big career leap, but I didn’t expect it to happen so soon. I had a timeline in my mind. And then I unexpectedly found out I was pregnant. That accelerated everything. Did I want to spend 60 hours a week away from my baby doing a job I didn’t really care about? The answer was no. Suddenly it felt like this now or never moment to take control of my life and begin to create a legacy I would be proud of. It wasn’t exactly easy to take on entrepreneurship the same year I was birthing and nursing a baby, let alone launching my second business around the time of my second baby, but I know the timeline was the perfect one for me. Read more>>
Maeve De Voe
I believe everything in my life has lead me to this one moment. I’ve always known since I was little that this was my destiny, even wearing tiaras every day back then like I do now. I decided to start pursuing making music in 2015 at the age of 13, where I’d write lyrics and make original songs on GarageBand. I’d work devotedly with the notion that this was my one and only life path. In 2018, I decided to start college at the age of 15 to train my voice classically, so that my vocal talent and my music could elevate to a higher level. When spring 2020 arrived, I saw this as my opportunity to take a break from school, and fully dive into my dream career. I’d produce and work on originals almost daily, and start promoting myself online as the next big thing. In 2021, I became a princess full-time, began my journey of princess fashion that I have now, along with working endlessly on preparing for my debut. Read more>>
Kimberli Davino-wilson
Honestly, I am glad I didn’t start my business sooner (or later for that matter). I think the opportunity and desire to do so came about in the right season of my life. I decided I wanted to take the entrepreneurial journey in 2017, after my endometriosis diagnosis. I was working as a behavior therapist at a small center for Autism. We did therapy sessions and also had a Pre-K school program. I truly loved it and really did think that was where I was meant to be and what I was meant to do for the rest of my life. Or at least a very long time. But whenever I started having more sick days than healthy ones, and when my body started to be in so much pain daily, and discomfort and overwhelm ruled my life, I knew I couldn’t do this job anymore. I knew I couldn’t work for anyone other than myself. Because I knew I had to be able to call the shots on the days I wasn’t feeling well and needed the day off or time to rest. Read more>>
Charity Dyck
If I could go back in time, I truly wish I would have put more emphasis into my business and started it much sooner! Going back to the beginning, before I had my two beautiful children (and had, what it seemed, all of the time in the world), I was putting in full time cosmetics retail hours. Retail attests entirely to working weekends and holidays, so the ability to be present in my business, at the time, side hustle, limited me greatly. Retail can also be draining and mentally exhausting, which often demotivated me. I have no regrets on the retail hours I put in. They gave me experience to aid in working as a makeup artist, as well as relationships and connections I’ll forever cherish. It was when I became a stay at home mom, I was able to solely focus, improve and become empowered to grow and work my business as a freelance makeup artist. Anyone in this industry will tell you, the more work you do, the more you get. So at 36, of course I wish my success would have started much earlier, I couldn’t fathom where l’d be now, but I do believe my timeline all happened for a reason! Read more>>
Sara Stone
Everything in life happens for a reason. In 2019, I started looking at how I spent my time in a new way. At the time, I was working as an executive for a corporate cosmetic company. I spent many years working hard to grow in the company. I am very grateful for my time with this company, however something was missing. I was reading “Rich Dad Poor Dad” and found myself reflecting on my life. It was time to take a risk and start my own business. In 2021, Activate Your Impact was launched. I left my steady corporate job to invest in myself and start my own company. There is never a good time to take a risk like this, you just have to do it. It is easy to find reasons to delay or push back on a dream. We all have those moments of over thinking things. I truly feel the timing was just right for me, I got started and that was the first step. In addition, I had a friend take a chance on me. Marisol owner of La Bonita Beauty Shop was where Activate Your Impact products had its first start. Without this start the brand would not be here today. Timing is everything. Read more>>
Cheryl Boluch
For me, becoming a jewelry artisan came at just the right time in my life. After finishing my undergrad degree, I pursued a career in elementary teaching. I taught in Ontario, Canada for 10 years until I had my first son. I returned to work part-time but eventually stepped away completely when my second son was born. For six years, I embraced life as a stay-at-home mom. In 2015, my youngest son started school full-time, and with that came a shift in my role as a mom. Around the same time, I began experiencing headaches, something new for me, and I felt more anxious than usual. I went to my family doctor, who asked me, “Have you gone through any big changes in your life?” After thinking it over, I realized the biggest change was my son starting school. My doctor suggested I find a hobby—something that would give me a fresh sense of purpose. Since I had always loved working with my hands, whether knitting or crocheting with my grandmother or taking classes with my mom, I decided to explore something creative. Living in a big city gave me plenty of chances to try new things, and that’s when I discovered jewelry making. It quickly became a passion of mine! Read more>>
Rebecca Hansen
There are moments when I wonder what my journey would look like if I had started my interior design business earlier. When I decided to transition from my career as a choreographer and Pilates instructor, the advice I received from professionals in the field wasn’t encouraging. Many warned me that making a living in interior design was difficult despite my comfort with running a business. I also understood the challenges of being an artist without a stable income, which made their words resonate a bit too much. At first, I chose graphic design, thinking it was a safer creative path with broader opportunities. But deep down, I wasn’t fulfilled. I found myself gravitating back to my true passion, and I finally decided to trust myself and pursue interior design—the field I had always dreamed of. If I had listened to my heart, I’d have over 17 years of experience in this incredible industry. But every step of my journey happened for a reason. My background in graphic design has equipped me with valuable skills that enrich my work today. Though my path was unconventional, I am deeply grateful for the experiences that led me here. I’ve learned never to let others’ doubts deter me from following my passion. Now, I’m fully immersed in the work I love—crafting beautiful, thoughtful spaces for my clients. Read more>>
Grigorii Butrin
Starting my own business now feels like the perfect time because I’ve gained enough knowledge and experience to do it right. I’ve learned what works, and I’m ready to apply that. Looking back, I don’t have any regrets about starting now. I’ve taken the time to gather the necessary skills, and I feel confident in my decision. Starting earlier might have been more stressful without this experience, and starting later would have meant delaying something I’m already prepared for Read more>>
Gioconda
Today I say yes, I would have liked to share my spiritual work before. In the past I did it with those close to me, but the feeling now is totally different and comforting. Read more>>
Kendall Udofia
I do wish I had started my creative career sooner! I had fallen in love with calligraphy about 9 years ago but I did not realize the potential for what my work could be. I had dabbled in trying a few different ways to use my skills for business throughout the years- like products, digital designs, print on demand, etc. – but none of those were truly fulfilling. I missed the tangible aspect of calligraphy doing it with my hands. Then I realized the potential for wedding signage! I started creating beautiful signage for weddings in 2022 and that was such a fun business for a little while. I had to step back though once I got pregnant with our third child and realized that business model wasn’t going to work for me after our baby was born. And then, I started to hear about the possibility of engraving and live events and that greatly intrigued me. But I thought, how can I possibly do this with a baby and 2 toddlers? I didn’t know how I could make it work. And part of me wishes I had known about this avenue years before when my plate was a little less full even though on-site customization wasn’t near as popular as it is now. I say that only because I would have more time to build up my business, make contacts, and other things but that is alright because I’m doing it now and that is so much better than not doing it at all! So I decided that after being 6 months postpartum, it was time for a change. I pivoted and decided to dive head first into on-site calligraphy, engraving and hot-foiling! And I am so glad I’ve made this decision as it has been so rewarding and I am so excited especially for this upcoming holiday season. Read more>>
E D.rh
If I could go back in time, I still wouldn’t change when I started my creative journey. As a teen, I dabbled in sketching, especially after spending a summer in Boston with my great-grand aunt Vivian. It was during that time I learned her father had been an artist who sketched with charcoal, and that sparked my curiosity to experiment. There was this huge portrait he did that was in her home up on upper Beacon Hill in Boston’s Dorchester district. I spent a childhood summer there and that sparked an important milestone for me creatively. My father also had a passion for drawing and painting on canvas with oils and acrylics and had a profound interest in the arts. I grew up surrounded by creativity, and creative people in the family and our family circles but I didn’t fully dive in at that point. Music was my first love and passion most of my life, but I am finding that art and painting are making a presence the older I get. I balance the two these days among other creative talents under a series of aliases. It wasn’t until later in life, in my early 30s, that I truly returned to art. This happened after an accident and relationship that shifted my path away from music. Read more>>
Alexandra Camacho
This is such a great question because I think a lot of the artists I know ask themselves these questions: “Did I start too late? Should I have even started at all?” Some may even feel, “I wish I had more of my childhood back.” And I believe all of those feelings are valid. For me, I’ve known I wanted to be an actor since I was six years old. My mother didn’t want to expose me to Hollywood at such a young age, so I spent much of my youth acting in plays, performing in dance groups, choirs, and musicals—always dreaming of the day I’d turn 18 and move to Hollywood. Just before I turned 18, someone very important to me said something that shook me and my confidence. We were discussing my future after high school, and they said, “I don’t know, you’re not really one in a million, Alex. And that’s what it takes to make it in that business. You’re pretty, but not THAT kind of pretty.” Read more>>
Elinor Keyes
My career as a whole started much sooner than most people’s. I was accepted to college at the age of thirteen through Mary Baldwin College’s Program for the Exceptionally Gifted, and started studying full-time so I could earn my bachelor’s degree at the age of seventeen. This meant that a lot of my big decisions about the direction that I wanted my life to go in had to be made before I could legally apply for a learner’s permit, and those decisions had to be fully solidified before I could legally sign a lease. At the time, my one and only love was theatre. I had first gotten on stage through baby acting classes when I was four or five years old, and I had never really left. I declared my major in theatre during my first week of school, and didn’t waver from that path for four straight years. Read more>>
Chelsey Hall
Reflecting on my journey, I wouldn’t change the timing of when I started my creative career. It came at a pivotal moment in my life—after experiencing depression and going through a divorce. Those experiences were incredibly challenging, but they also gave me the push I needed to discover a new path, leading me to makeup artistry. I began this creative venture when I was a single mother trying to rebuild my life and sense of self. Makeup became a form of expression and a way to help others feel beautiful and empowered, which in turn empowered me. If I had started sooner, I wouldn’t have had the depth of emotional understanding and resilience that I do now, both of which have deeply influenced my work. Starting later, on the other hand, might have kept me from finding my creative outlet when I needed it most—when I was searching for something to hold onto and to rebuild my identity. Read more>>
Lord Of Horns
This is a rather interesting question. I started fairly young, but got into music in general way older than most of my peers. I was 16 when I bought my first bass and it took a year before I understood how music actually worked. By the time I was 19, I played in several local garage sort of bands and then I founded the project that would eventually become Lord Of Horns. We called it Acryptylyse, it was a blend of black and thrash metal with haunting keyboard melodies. We were never a full band and we had a few line up changes before I found myself the only member. Determined to go on, I learned all the instruments and recorded the first album myself… it was atrocious; but while promoting it at venues and concerts, I would meet more musicians who would later fill the line-up. In 2009, we released Oktober Myst and added a violin to the mix. Read more>>
Jul!et
Writing songs and making music is my true passion — I would do it even if no one else were listening. Besides that, I’ve always been an entrepreneur at heart, dreaming of starting my own business one day even before I had an idea compelling enough to give my all. While working in the tech industry, I realized that every path is challenging in its own way and that nothing beats internal inspiration. I became more comfortable taking risks and started releasing my music as a fun side project, which felt way different from my day job. At the same time, those years were well spent! I learned a lot about managing a product and being a good colleague, and I saved up to fund my early music career. Read more>>
Manuel Fuentes
If I could go back in time I wish I started my career in content creation in college. I feel like during my college years I wasted valuable experience focusing on other subjects rather than my creativity. I started my career back in 2020 when I worked with videographers who helped me launch my own influencer page. At the time, I had my own show interview people with interesting careers called 9 to 5. If I could’ve changed my perspective back then I would surround myself with artists, start posting on social media as I begin my work tribulations of trial and error. Read more>>
Joy Marie Hallare
I started drawing since I was 9 in Qatar. I continued to pursue my art when my family and I moved to America. I studied and enhanced my skills in school and work. Each company I worked with gave me experience in craft and business. As I was using my talent for them, I started to slowly lose myself. Although they funded my art, I didn’t have time work on it. My biggest regret was turning down opportunities when my art was starting to gain attention. Now that I am receiving more gigs , I thought it is time to start anew. It is a challenge to turn a hobby into a career, but I know in the future it will be considered an accomplishment. Read more>>
Kalpna Bora
I have always known and felt that creativity is the core of who I am and I am happiest when I create something or express myself through different mediums. I have spent a major chunk of my life learning and experimenting with different mediums like dancing, acting, painting, drawing and sewing. I started working as an actor 15 years ago back in my home country India. I have been creatively active all my life in some way or other. Looking back, If there’s one thing I would change, It would be to view art more from a business perspective, balancing my passion for creation with a focus on growing as an enterpreneur. Read more>>
Sweetie Shumaker
If I could go back in time I wish that I would have started my career later. I’ve been writing music since elementary school but in 2017 my junior year in college, I decided to take music seriously and pursue it as a career path. Once I began writing music with my new found identity as an artist I wrote songs for fun, making songs that I could dance to. None of the songs had any substance behind them, they were vulgar & lots of profanity was being used. For a time I was successful but in 2022 things started to slow down & I began working on my relationship with God. I was no longer satisfied with my life & I started going through an identity crisis. I decided the HipHop/R&B music that I was writing needed to have a message behind it & I also wrote a few Gospel songs here & there. Read more>>
Daniil Romanov
This is probably the biggest dream that I have to work through with my therapist. To go back a few years, and preferably with the same knowledge, which I have now. I’ve been told many times I should start making funny videos for my social networks, but I refused, saying it doesn’t correspond to my status or expertise. This was probably due to the framework of society in my home country. And now, having moved to the United States, I’m faced with the problems of creating a new personal brand and even more so promotion. However, if I could turn back time, I would have started releasing such content back in 2019. Having abandoned my prejudices, I started releasing this content on my Instagram, testing it on YouTube and TikTok. The results are not the best yet, but I’m not stopping. Sometimes I take a ‘digital-detox’, during which I analyze what I should focus on. At the same time, I do not give up on the global dream that should lead me to my own media business in Los Angeles. Read more>>
Marisella Bodrero
Looking back, I wish I had started my creative career sooner, ideally in my early 20s instead of my 30s. While I appreciate the lessons learned from my corporate jobs, starting earlier would have been more fulfilling and advantageous. Here’s why: 1. More time for experimentation: Starting sooner would have allowed me to take more creative risks and explore various content formats without the pressure of immediate success. 2. Early audience building: Launching my creative endeavors earlier would have given me a head start in building an audience and establishing my brand in a less saturated market. 3. Skill development: I could have honed my content creation skills over a longer period, potentially leading to higher quality work and a more refined creative voice. Read more>>
Candace Dyches
If I could go back in time, I believe I would have started my creative career sooner, but with a different educational path. My parents, coming from humble beginnings and limited formal education themselves, believed in a traditional path to success. They saw a four-year college degree as the surest route to financial stability and a better life – a perspective born from their own experiences and the wisdom of their generation. However, this well-meaning but narrow focus on conventional academia meant that alternative educational paths, such as trade schools or specialized creative programs, were inadvertently overlooked, which I now realize might have provided me with more hands-on experience and diverse opportunities earlier in life. Read more>>
Hopeellen Turner
Ironically I decided to invest more time and effort into my art business after having my first child. After having my son I decided that maternity leave would be my best shot at trying to prove to myself that art was something I could actually pursue as a career. I envisioned my child peacefully rocking in a swing while I painted, but that never happened. Prior to having my son I was a full time nurse and I remember feeling like I never had any free time to paint. The joke was on me because after having my son, I TRULY have no free time to paint. In hindsight I wish I would have made art a priority prior to having my son. The biggest thing I’ve learned during this process is that creating an art business is truly a daily grind. You have to build your following organically. Read more>>
Santiago Cubillos
My plans while I was finishing high school were to attend La Sorbonne in Paris for which I prepare studying French and relating on my own natural skills as a fine artist. Unfortunately life had other plans and move me away from my original Colombia to Madrid and finally NYC when I’ve been a resident since the beginning of the century. Fortunately because this turn of events I ended up studying at Hunter college, first Art History and finally Fine Arts to reach graduation by 2019. Since approximately 2014 I’ve been working professionally in my Art and doing sales and it’s getting more demanding and difficult but fulfilling in the past years right after the pandemic. I think we all have a specific paths to follow and this was mine, so far I’m grateful and happy where I am. Read more>>
Allison Ragle
If I could go back in time, I wouldn’t change when I started my creative career. I initially began pursuing biology with the intention of making it my career back in 2016. I was deeply invested in the field, but as time passed, I found myself burning out. The heavy coursework and constant pressure gradually drained my passion, and I started to lose my sense of direction. When the pandemic hit and I found myself in online classes I hit a mental low. During this low point, I was asked by a garden id been volunteering at to paint a mural. This 500 square foot mural was what kickstarted my path back towards art. Painting again felt so freeing, I promised to myself I’d never take a break again. The more I allowed myself to create, the more I realized that I didn’t have to choose between art and science. In fact, blending the two not only revived my passion for biology but also opened new doors. I learned scientific illustration and began studying softwares to blend the two fields. Bringing art back into my life led to more opportunities in the sea turtle conservation field because I had skill sets a lot of conservationists lacked. It felt like I found myself again, and the balance between the two disciplines restored my energy. I now do sea turtle rescue and research half the time, and paint half the time. Read more>>
Daniel Herrera
I wish I could’ve started my DJ career a lot sooner. I didn’t find this craft until I was in an outpatient rehabilitation program. My love for music has always been there, and my curiosity about djing has always caught my interest. However, I never stuck with it or fully committed myself to it until I realized I had a drug and alcohol problem. Drugs and alcohol were really my coping mechanisms, but when I got into committing myself to djing, my whole life changed. Djing became my next coping mechanism and it’s helped me so much with my mental health, which is exactly why I was turning towards those two things. I’ve only been a DJ for a total of three years, so I’m still managing my life instead of “it” managing me. I can say I wish I would’ve started this craft when I was about 24 years old, but six years later I’m now here as a DJ, (I know do the math lol.) Thinking about it, my entire life would’ve changed if I were to start being a DJ a lot sooner at a younger age. I could say my life would be a lot more manageable as far as life choices and decision makings. I keep referring my life back to being a DJ because this is still my coping mechanism til this very day. Not only having that title or occupation, but being able to hop on the decks takes my mind off of things for just one hour or two hours, sometimes even all day! Read more>>