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.

Denali Geesh!

I honestly feel like my journey is right on time but if I must choose, I would have wanted to start my business sooner. The sooner the better is what they say! It would have given me a chance to work through the kinks, mistakes and lack of knowledge at an earlier stage and age. With those being handled earlier I’m certain GEESH! Society may actually be more well known worldwide. I started GEESH! Society as a way of transitioning my artistry into a brand. The music compliments the clothing and vice versa in my eyes. For the people that may not care for the music, they love the clothes. For the people that may not care for the clothes, they love the music! For the people that enjoy both, I continue to strive and grow to show my appreciation to them. 9 times out of 10 if anyone sees me they will see my brand first! Read more>>

Arlene Dizon

There’s a part of me that believes starting sooner could have opened doors to greater opportunities, more experience, and earlier financial freedom. I could have gained valuable insights earlier, build stronger networks, and had even more time to grow my brand. But then I remember that timing is everything. The lessons I’ve learned, the experiences I’ve had, and the person I’ve become all happened at the right moment for me. The challenges I faced before starting prepared me for the journey of entrepreneurship. Every step I took leading up to this was part of the foundation I needed to succeed. Starting my business when I did allowed me to align my goals, values, and vision with who I am today. It gave me the clarity I needed to build something meaningful and sustainable. Read more>>

Jennifer Balarezo

I think about this question a lot. See, I have always had love for art. I grew up drawn to different creative outlets. They varied from drawing, painting, and taking photos or videos, so I knew I had love for it but never thought about making a career out of it. When I first started my business in December 2021, I had just quit my 9-5 due to being extremely unhappy and constantly stressed. I knew I was good at my job, but I realized I was sacrificing more than just my time but my well-being too. When I started becoming more successful in my photography business, I would think to myself, “Man, where would I be if I had begun when I was younger?” “What if I never put down my camera to focus on school and finding a stable career?” These thoughts haunted me because I was getting older and wanted to make sure I was doing the right thing by taking a chance on myself and making this my full time job. Read more>>

Robyn Ashley

If I could go back in time, I would definitely start pursuing my music career sooner! Music has been my lifelong passion. I was deeply involved in my community, taking lessons to enhance my voice and hone my songwriting skills. Music consumed my thoughts; it was the first thing on my mind in the morning and the last before I fell asleep. However, I didn’t fully dive into my professional artist career until I was 27. Why the delay? I was incredibly self-aware, and I realized that fear was holding me back. I was so focused on achieving perfection and constantly questioning whether I was ready or good enough. I had a career I liked, but it didn’t ignite my passion. Eventually, I had to face that disconnect head on and it was a painful turning point for me. I firmly believe in the value of time currency, and I didn’t want to be the person looking back with a “what if.” So, I took the leap and jumped right in. It’s been a journey of putting one foot in front of the other, day by day. Read more>>

Jessica Arispe

I started the business in 2018 but knew about it since 2013. These were two different stages of my life 2013 I had no kids I was just trying to figure out how to be healthier and lose weight and figuring out my future in corporate America , 2018 I was I was a mom of 1 definitely started the business because I was desperate to spend more time with my baby. This is why I wish I would’ve started sooner. I wish I would’ve seen this opportunity and not been so afraid of what others might say it. because doing it with a kid it’s not impossible, but it’s a lot harder and I wish I didn’t have to wait till the pain Missing my baby be my driving force. Read more>>

Yang Qian

Looking back, I wouldn’t change the timing of when I started my creative journey. I first got into filmmaking about three years ago during my undergrad. At that point in my life, I wasn’t entirely sure why I felt drawn to it, but I trusted my intuition. I had no grand plan; I just felt the need to create and express myself through film. That spontaneity is part of what makes the journey meaningful for me. If I had started sooner, I might have been too focused on figuring out what it “should” look like, rather than letting it unfold naturally. Starting later, on the other hand, might have led me to second-guess myself or feel like I’d missed the window. I believe art is an organic process that happens at the right time when you’re open and ready for it. Starting when I did allowed me to stay curious and free of rigid expectations. So, no—I wouldn’t change anything. The timing of my journey feels just right, and it has shaped me in ways I’m grateful for. Read more>>

Gregory Johnson

If I could go back in time, I would. Starting earlier would have put me so much further in my career. Although I know Gods timing is everything. The dream of me acting started when I seen the movie grease as a child. From that moment I wanted it all! I acted on the dream when I was 20 in college. I did my first play called the angry 12 jurors. Shout to “Michele Davis” believing in me. ’m content with the time I started. It’s for a reason it was this way. Read more>>

Robert Vandewiele

I would have started getting into music way sooner. I always had a guitar but, I never really tried to play with people. I had friends in bands but, I never tried to get involved even though my life was always full of music. The main reason I wish I could go back earlier is all of the memories and the friendships that can be made. I could have 10 more years of experience and knowledge if I had just tried. Read more>>

Matt Kollock

All my life, I wanted to be a professional musician. Well, that’s 47 year-old me speaking. When I was a kid, I wanted to be a ROCK STAR. The music bug infected me at a very young age via exposure to older siblings’ records, the radio stations my school-bus driver favored and the early days of MTV. Right away, I could sense that music was a language, and I had a gift for understanding – and speaking – it. And I knew I wanted to perform on stages, travel on tour buses, make records in studios and hang out with others who spoke the same language of music. I excelled at piano lessons. Later, after finding an old nylon-string acoustic guitar in the basement, I advanced quickly on that instrument, as well. All the while, throughout childhood and into adolescence, I was obsessed with music. Not only playing it, writing it and performing it, but also absorbing it, integrating it and paying attention to all the things that make it work. I was expanding my vocabulary. I was beginning to find the others. Read more>>

Sydney Teare

If I could go back in time, I would have pushed myself out of my comfort zone much earlier. It would have greatly benefited my art career and helped it take off sooner. I have been drawing and painting since childhood and always knew I wanted to attend art school. When I arrived at Ball State University in 2016, I was surprised to see that many of my peers had already been submitting their work to local fairs and galleries. It wasn’t that they had been making art longer than I had, I just believed that I needed to keep practicing and improving before I was ready to show my work– but at some point, you have to start sharing your work with the world to truly grow. Even in college, I struggled with ‘putting myself out there.’ After graduating, I looked at my former classmates’ websites and realized they had been entering competitions and showcasing their work the entire time we were in school! Viewing the art you’re making now as a precursor to the ‘real art’ you’ll make in the future won’t lead to progress. What you’re creating right now is already real art. Read more>>

Paula Mans

I started my journey as an artist quite late in life – in my early 30s, after becoming a mother. As a child, I was always engaged in some form of creative work – from singing, to ceramics, dancing, playing instruments, and even performing on stage. I loved to create in many forms. My childhood home was also full of art – sculptures, paintings, and tapestries of Black artists from across the African Diaspora. As a teen, however, I had a negative experience in an art class that pushed me away from making art. The class was highly technical and largely drawing based. Learning about making art in that rigid environment led me to believe that I did not possess the facility or talent to be an artist and pushed me away from creating entirely for decades. Read more>>