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.

Robin Compton

We started just about a year ago and I sometimes think about where we would be had we done it a decade ago but I always remember that God’s timing is perfect. The changes we’ve made and how we’ve grown in the last ten years has made all of this possible. I’ve learned a ton from the owners of the previous companies that I’ve worked for but more than that, my temperament has changed. I’m more equipped now to deal with the stressors and issues when they arise. I also know that when I’m hearing from the Lord, he directs our steps Read more>>

Brian Garcia

I wish I started a lot sooner but there were several reasons why I was afraid to make the jump to a Fulltime Wedding Videographer. The first thing was this stigma with other filmmakers back in college that would laugh at wedding videographers because many of them had this image that weddings are not creative or they’re just filming that boring out of touch uncle dancing to the Macarena. I also had no clue what the industry was like so I assumed it was something that wouldn’t be a thing for me. So I was doing a little bit of corporate work and short contract jobs right after college, then I went into teaching video because I thought a full-time salary job would be easier. The problem is that it felt like I was working more for less income. Overall, I taught for 6 years and 5 of those years was teaching high school students (2015-2020). Read more>>

Shannon Kung

I started my businesses in my mid-30’s after leaving my corporate job at Disney, where I had been for 7 years after getting my MBA at UCLA Anderson. Up until that point, I had only known working in the corporate landscape, and it provided prestige, stability, and a regular paycheck, but I knew deep down inside that I wanted to do more, say more, be more. So, I took a leap of faith to start a heart-centered boutique consulting firm called &etc (www.andetcco.com) and simultaneously built a family-run tea business, Wild Orange Apothecary (www.wildorangeapothecary.com) I used to feel that I wish I had started my businesses earlier, but in reality, looking back, everything happened as it should, in perfect timing for me and my journey. I had always wanted to be one of those people who could balance a 9-5 while nurturing a thriving side hustle – it would have been a less risky, more stable way of transitioning into entrepreneurship. However, in reality, my 9-5 was more like a 8-7, and I didn’t have the emotional or mental capacity to dedicate to a side hustle.  Read more>>

Bonnie Elgueta

I wish I had started my graphic illustration career sooner! Right out of high school, as a matter of fact! But at the time I was not clear about my life goals, or maybe I was, but I was too scared to admit to myself, and the world, that I wanted to be an artist. Like many before me, I didn’t dare call myself an artist. However, the rebel inside me kind of muscled her way out and I made the decision to go to fashion school. It wasn’t art school. It was fashion school. It would provide me with at least some classes in drawing and painting and various styles of fashion illustration, and it was more affordable than art school. At the time, my favorite thing to draw was the human figure, portraits and beautiful clothes that I saw in fashion magazines. I adored fashion photography; the styling, the lighting, the makeup, the magic in the color composition of all those gorgeous photos. I was obsessed with recreating those lovely textures, lines and contours and capturing the drama of the light and shade by way of paints and brushes and pencils. I loved challenging myself to recreate the beauty of the human faces and bodies revealed in those photographs, showing authentic emotion and dramatic poses, using pencil or anything on hand. Read more>>

Drew Martin

If I could go back in time, I would say that starting my business when I did was the perfect timing for me. I launched Martin’s Credit Doctors in 2020, right at the onset of the COVID-19 pandemic. At that time, I had overcome significant personal financial challenges—my credit score was at 444 and I had $25,000 in debt. Instead of filing for bankruptcy, I took the opportunity to learn about credit repair laws, rebuilt my credit, and ultimately decided to help others who were going through similar struggles. At the time, I had already been involved in corporate business and had tried real estate in Dallas, which didn’t pan out as planned, but these experiences built the foundation I needed to truly understand the needs of my clients. By the time I launched Martin’s Credit Doctors, I was fully ready to provide real value to my clients because I had walked in their shoes. Read more>>

Aldino Sambaho

I always had the Entrepreneur’s mentality. I always wanted to work for myself because I don’t like to be told what to do and I like to make the most out of my time. The most precious thing we have is TIME. I wish I had started my business earlier but I didn’t have the resources and ability to do so, even though I always wanted to build my own business. I came from a hard-working generation and nobody taught me how to become financially independent. So, I had to figure it out, reading books, attending seminars, watching YouTube Videos, and hiring mentors. I would be in a way better place by now if I had started my business sooner. My business should’ve grown exponentially by now because the sooner you start something, the better. As the world of business and entrepreneurship evolves, I would be a better Entrepreneur, businessman, and possibly a greater investor because it takes years to build a stable and rewarding company. It’s okay because I am on my way there.  Read more>>

Ronda Ramsey

Honestly, my business revolves around my personal life, Education and professional experience. I started my business in 2021 and at that point I was in my field of Criminal Justice, traveling a lot, no children and just loving the life. Even while working I would ask myself “is there more than just coming to work and doing the same thing? I need to be doing something bigger and helping people.” I was dealing with juvenile offenders whose crimes varied from assault, murder, sexual assault and more. I am watching kids anxious wondering if they are headed to prison or will they be on parole or simply be able to just go home. Mental issues were all over and some of the youth, you could tell some wouldn’t make it to see age 21 even 25. Many going right back to the environment that they were in. Now doing this 12-16 hrs a day being in leadership and work phone ringing constantly…..you have to wonder. With all of this came the question, How can I reach these people before their circumstances lead them down the wrong path and they end up in the system? Read more>>

Newt Wesley

The short answer is no, I don’t wish I’d started my creative career sooner or later—I believe I started at the right time for me. My journey as a content creator officially began in June of 2023, while I was still working full-time as a fitness instructor. Every day after work, I dedicated time to creating content, consistently refining my craft. Looking back, I realize that starting earlier wasn’t really an option for me. I needed all those seemingly unrelated experiences and steps to lead me here. Before this, I explored various creative paths—starting brick-and-mortar businesses with my wife, DJing at weddings, designing fitness plans etc..Each of those ventures might have seemed disconnected, but they were all preparing me for what I’m doing now. Every one of them taught me valuable lessons, building a foundation for this moment in my career. And honestly, I think that’s key: I’m not done yet. What I’m doing now is just another stepping stone, preparing me for what’s to come. This isn’t the endgame—it’s a process. Each past experience, each creative endeavor, has shaped my approach to content creation today. Read more>>

Jess

Twenty Sides Podcast “began” about 3 years ago, when our group of friends decided to take playing Dungeons and Dragons online and turn it into an actual play, story driven podcast (with amazing audio) for others to enjoy. Of course, we all would have loved to have started this journey together much sooner, however we started playing online during the pandemic, and so inorder to have the best audio and product possible, it was important for us to be able to record inperson together. When we first started playing, our lives and careers had all been upended somewhat, and so there was no way for us to homeschool our kids, while working from home, plus being responsible by social distancing and wearing a mask (effecting the audio). We are just really glad that the podcast started at all because it seems so few dreams become reality, and every day we are taken aback by the love and support Twenty Sides Podcast receives. Read more>>

Mary Steskal

I’m a firm believer in everything comes at you at the perfect time, so I don’t wish I would’ve started sooner or later. However, I do wish I put 100% of my confidence into Lotus Earth Lace sooner. I started LEL in 2018, but I’ve been an artist my whole life.  I have always had a love of gemstones and in my late teens/early 20s, dove pretty deep into the healing properties of them when I was living out in Arcata, CA (shoutout to Beads Supply Inc.!). I created my own gemstone mala after a friend showed me how, with no real plans to make any more. However, the knotting process between each bead was SO meditative for me, I made a few more and started to get the hang of it.  I moved to St. Petersburg, FL in 2016 and began creating gemstone malas again. It wasn’t very long before one of my pals saw my mala and requested one of their own- made with gemstones that would call in protection, creation and enhance psychic abilities. After that, it was like a domino effect of requests and Lotus Earth Lace was born!  Read more>>

Nina Polunina

I can’t say that I dreamed of drawing since childhood. Although I wanted to draw. I even started to study on my own as a drawing student. But… My parents bought me a piano and drawing was forgotten for many years. Either they didn’t know that art schools existed, or they simply didn’t pay attention to my hobby. Or they simply wanted their child to study music) In general, I had to finish music school. I remembered about drawing in 2015, when I accidentally got to a painting master class. That’s when it all started. Oil, watercolor, exhibitions, students. I often think about what would have happened if I had started my career earlier? Like all artists, I would have graduated from school, college, institute. What would I have done? There was not much work for artists in the Soviet Union. And it was difficult with exhibitions. Yes, I don’t have an art education. And I can’t get into an art university anymore. But today there are a lot of opportunities to study and show my art to the world. And I made my choice of profession independently and consciously. I think that God gives everything in its own time. Read more>>

Maya Deanne

If I can go back in time, I most definitely would have started content creating sooner! I started to seriously think about content creation at the beginning of January 2024 because I just was not fulfilled at the job/role I was at. I always found so much joy looking at other creatives living out their dreams in the spaces that I aspire to be. I thought to myself, “ You don’t want another year to go by without at least trying, you know”. If I had started sooner, I definitely would have like to hope my efforts weren’t in vain and I see some sort of success lol. I would have gotten rid of that imposter syndrome out of my mind and straight to the trash for sure ,but hey ! better late than never! Read more>>

Rowan Lee

I’ve taken a circuitous route to get where I am, but looking back, I’m not sure what I would change. There are times when I wish I had been more focused in my younger days or had a better sense of what I wanted, but there’s a lot to be said for the wisdom that comes with age. Even though “writer” has been a core part of my identity since childhood, I’ve hardly had what anyone would call a creative career. I’ve been an educator at several colleges and an editor for a testing company, but I’ve only recently started to get paid (a token amount) for my writing. As a teenager, I attended a fine arts high school where I concentrated in creative writing, and later I got an MFA in poetry. Having a creative career was always the goal, but I graduated into the economic recession of 2008 and spent years struggling to make ends meet with part-time jobs–like a lot of my generation. Making a living in creative work is a challenge under the best of circumstances, but the last 15 years or so have been especially rough, and the introduction of generative AI has been really disruptive and anxiety-inducing for writers and artists. Read more>>

Lisa Selle

Isn’t time funny? It goes so slowly sometimes and too quickly other times. I wish I would have started singing and performing sooner. My insecurity got in my own way when I was younger. I used to have massive stage fright. I was terrified to be in front of a crowd. Like, kneecap-shaking terror. I’m an introvert for sure, living in a world of extroverts. Well, actually, it’s really not a world of extroverts; they’re just the ones who get all the attention. But us introverts have worthwhile content to share as well…it just takes us longer because we’re reluctant. I did a lot of playing guitar and singing in the privacy of my kitchen while daydreaming of one day being in front of an audience. I sort of knew if I could ever share the openness that I felt when I was alone with other people, they would enjoy it. But there’s something in me that really struggles with letting my guard down around other people. I’m getting there now, though! I played a show last weekend, and I was able to enter that almost spiritual state that music can guide you to. It’s something like zen? Or flow? I was playing a song I wrote, and I went somewhere else…in front of a crowd. The place got silent for a few minutes, which is really hard to capture as a performer in a bar setting. Read more>>

Tatiana Farmer

I began my creative career during my freshman year of college in 2016. It wasn’t something that I planned honestly. I would wear makeup around campus and people would compliment me and ask me to do theirs. I began doing makeup for different scholarship pageants, birthdays, and graduation. After returning to Cleveland, I began to find myself having doubt about my creative career and what it would look like had I began focusing on that instead of leaving to begin my college career. I watched people who didn’t go off to college pour fully into their businesses within the beauty industry and how they were able to do that full time and how they gained a large clientele. I started to have regrets but after a while I began grateful for where I was in my journey. As many say, comparison is the thief of joy. I realized that I was exactly where I needed to be in those times. Makeup did so much for me during my college career. It even helped me take a spring break trip to Miami. While I quickly realized taking clients in college was far different than building a business in Cleveland, I began to yearn for knowledge on how to deliver my services professionally and gain clientele here. This was the start of me really becoming a student. Because of this I don’t regret anything. Everything happens when it is supposed to and me beginning my journey when I did worked for me. I wouldn’t change anything honestly. No matter when you start its never to late or early to learn something new, reinvent, and focus in on your creative career. Read more>>

Blanca Frappier

I feel like everything happened for me at the time it was meant to. I’ve been acting since I was 5 and continued through my college years but took 16 years off to be a stay at home mom. When the kids were older, I discovered Audiobook narration and fell in love! While I do sometimes wonder what my life would be like if I had continued acting, I feel that this timeline allowed me to have phases of life that I have fully gotten to enjoy. And it feels like I’m in the right place at the right time right now! Read more>>

Tanya Gillie

I wish I had started my own business much sooner. However, I understand that everything has it’s own devine timing. Nonetheless, I wish I know what I know now because I would be so much farther. I do feel like I delay my own progess with the choices I made, the paths I have taken, and the knowledge I did not have. Read more>>