Almost every entrepreneur has had to decide whether to take the leap now or wait– perhaps they wanted to acquire more capital, experience or connections. Given how common this predicament is, we asked some successful business owners to reflect back on whether they wish they had started sooner or waited for a better time.

Danielle Barker

When I created Crowned Radio Station it was 2021 and I finally decided that I wanted to pursue radio as not just a passion project but eventually make it a global digital broadcasting company. It was during this moment my mom was diagnosed with breast cancer at 65 and I was sitting at her chemo appointment telling her how I wanted to really make this one day make bigger than anyone could imagine because the whole goal is to share the love of God through music and Christian talk shows. I remember my mom in her pink gown and her smile that looked over at me and simply said, “do it!” When I was in college and in high school I had an internship at a local radio station in Fort Lauderdale where I was from but it was hard being able to get passed the arena I was in which was editing commercials and shows for broadcasting. Read more>>

Tam Truong

At 46 years of age, I sometimes look back and wish I started my sweets journey just 10-15 years earlier. My family immigrated from Vietnam when I was only 3 yrs old. Growing up as the oldest daughter of 3 being raised by a single mother, I had a lot of pressure and responsibilities. A career in one of the common jobs, such as doctor or lawyer, was emphasized in order to achieve a happy and successful life. After graduating college and going through various jobs in corporate America, it wasn’t until I discovered baking that I found my true passion. While I had always loved eating pastries and baking, it wasn’t until I became a mother at the age of 34 that the passion began to do more than simmer. With the prevalence of social media I began an obsession with watching 1 minute cake decorating videos. After my second child, I began to experiment with cake decorating. Using those 1 minute videos to teach myself, I began making cakes and posting them on instagram. Read more>>

Jiya Monee

I had the thought my business in September of 2022, I didn’t really act on it until October 2022. I had just quit my full time serving job at twin peaks, a sophomore in college getting ready to come back home for 2 months because my lease was ending and the earliest time I could move into somewhere was January 2023,. I feel like starting earlier would’ve prevented me from wasting so much time in school doing something that I never wanted to do anyway. Looking back I’m actually glad that I was able to see what I didn’t want to do in life to push myself to see what I actually wanted to do. Read more>>

Rochelle Bailey

I started my business less than a year ago after being inspired by the artists I work and connect with every day. Through my full time role in communications and community programs with INTERFORM, the organization was given a grant to support local artists and designers by providing a retail store called the Atelier in Springdale Arkansas for artists to sell and share their art. I’ve always wanted to have something of my own, something I can do my way without anyone telling me what I should and shouldn’t be doing. Freedom to just…be myself. I never saw myself as a business owner. I thought it would be out of my wheelhouse, too stressful or just too expensive. I thought I wouldn’t have the time to devote to it, I feared rejection and worried about if people would receive it well. Read more>>

Meagan Faison

When I look back, I definitely wish I would have started my business sooner, but I don’t know how successful I would be if I had. So many of the skills and experience that I have needed to get my business started and grow, I learned throughout the course of my career. I started my business in March of 2024, so it’s still fairly new. Before starting my business, I worked in news and PR for ten years. During that time I learned many of the foundations of my business, from social media management, to interviews, to production. Even mentally, I feel like who I am now is more mature and better suited for being a business owner. So while yes, it would have been great to start sooner, I think that everything happens at the right time.  Read more>>

Jasmine Melvin

If I could go back in time, I would absolutely have started my business sooner. The idea for my French toast business began over a decade ago, but I was held back by misconceptions and fear. I believed I needed a full team, a brick-and-mortar location, and a significant amount of capital to launch a restaurant. These perceived barriers kept me paralyzed for years. Life-wise and career-wise, when the idea first came to me, I was in a very different place. I was working in a traditional job, feeling unfulfilled and yearning for something more. I had the passion for creating delicious French toast and sharing it with others, but I lacked the confidence and knowledge to take the leap. The COVID-19 pandemic became a catalyst for change. Witnessing others around me starting businesses from scratch, driven by necessity and ingenuity, inspired me to overcome my fears. I realized that I could start small and gradually grow my business. Read more>>

Aurore Meleme

If I could go back in time, I wish I had not started my Art & Design business sooner. I registered Aurore Meleme, LLC in mid-October 2024, which I think is the perfect timing. It is often said that if something must be done sooner or later, the sooner the better; however, it took me a while to identify my vocational calling because of a lack of clarity and direction. Being busy and money were the “calling blockers”, but it should not be an excuse for inaction! The COVID-19 pandemic has given me time to re-think my career and life at that time. I realized that what I was doing was not enough and personally meaningful. With my life and work greatly disrupted and forced lockdowns keeping me at home, I had more spare time to start identifying my calling’s “puzzle pieces” and begin to act on it. Read more>>

Cayley Credit

Growing up, I never thought too much about being a business owner. It’s not that I didn’t want to, more than I didn’t think I COULD. Growing up in the early 2000’s, being an entrepreneur was essentially talked about the same as being unemployed. College and working at a large corporation was touted as the dream scenario. So, I did the thing. I went to business school, graduated, and got a boring office job. I LOATHED office life. Then, in 2020, I was laid off from my corporate job due to COVID. I spent about 3 months looking for work; I sent out HUNDREDS of applications and didn’t have a single interview. I was so incredibly discouraged and started to think I was worthless to the workforce. Then, a family friend who knew I was struggling presented me with an offer to help me build up a business of my own in something I was already good at–marketing. I started as a social media manager/strategist and over the last 4 years I have evolved into a full-blown graphic designer and illustrator. I wish I had started my business straight after college, and not even bothered with the mainstream workforce. Hindsight is 20/20, however, and I am still grateful that I started the business even if it was a bit later than I should have. Read more>>

Rachel Anderson

I would have totally started my business earlier-actually I would have gone to cosmetology school earlier! I started cosmetology school when I was 22 almost 23 years old. I initially wanted to go to school right after I left university (at age 20) but my dad wanted me to get some work experience (which almost caused me to not go to cosmetology school). I actually got let go from my restaurant job and decided to enroll for the November class & finished the following fall. I dealt with an eb & flow between corporate salons & private salons. The pandemic made me realize that I could do this on my own. I was presented with an opportunity that I was scared to do for so long— run my own salon with my own branding and my own everything! Initially- I was like “Great! I love this! It’s just me & my clients, that’s it!” But now, 4 years later, I decided to grow and have a team, and I wouldn’t change that for the world! Except-I wish I just did it all sooner! Read more>>

Casey Jordan

If I could go back in time, I wouldn’t change when I started my business. I firmly believe in the power of timing; every experience I had before launching my business shaped who I am today. I began my journey as a bartender, a role that taught me invaluable skills—communication, upselling, and customer care. While it paid the bills and offered consistency, I wasn’t happy. I reached a point where I felt disconnected from my work and knew I needed a change. It was a TikTok video about a UGC creator that opened my eyes to a new possibility. I had never heard of UGC before, but I was drawn to the creative lifestyle and the potential for income. I dove deep into learning about it, realizing that this path could be both enjoyable and financially rewarding. Read more>>

Ralph Anthony Sandez

I spent 11 years working at a popular smoothie company, where I built a strong work ethic, learned management and team-building skills, and honed my interview abilities. But deep down, I knew I wanted something more creative. I felt overworked, underpaid, and unfulfilled. After I quit, I finally had time to reflect. I noticed that many voices were out there, but most took a one-sided approach to topics like film and society, with little room for nuance. I wanted to create something different—a podcast that was both entertaining and unafraid to dive into complex subjects with balance and depth. That’s how the Scream Queer Podcast was born. Those 80 episodes were a journey, helping me become who I am today. The show was raw, messy, and sometimes you could tell I was still finding my way. I was cautious, often holding back for fear of cancel culture. By August 2024, I felt ready for a refresh—so I changed the name, streamlined the format, and committed to authenticity, giving birth to The Scream Society, my “variety show from hell.” Read more>>

Kristina Denzel Bickford

Entering grad school in my mid-forties wasn’t daunting. I was mostly in the presence of artists who could have been my own students, but my career in the classroom (23 years as a biology teacher) had instilled in me a deep sense that wisdom doesn’t necessarily come with age. I knew I had just as much to learn from my younger peers as they did from me, and it was ultimately an enriching experience to be learning in that age-diverse climate. At the same time, I still carried my 20-something self with me and I knew her as a person with much less confidence and originality than 45 year-old me had. In many ways, I was incredibly happy to be entering school again as a person with a lot of life lived. I knew more about myself, and that gave me a greater sense of clarity in terms of where I wanted to push my work. The risk I took to leave a career mid-stream and dedicate myself to something that had been a long-term desire (earning an MFA) also lit a fire in me to make the most out of my time in the program. I am not lying when I say that on most days, whenever I walked down the halls of the studio spaces, I couldn’t stop myself from smiling. I felt so incredibly lucky to be doing what I wanted and to be seen again as a student. The whole experience, even when challenging, was joyful. I felt as if I was in the right place at the right moment, and that I was and always had been an artist. Read more>>

Khristin Brooks

If I could go back in time I would still wait to start my Comedy career. My Comedy career started after a series of events that nearly caused me to take my own life. I had been through so much emotionally and felt suppressed in ever area of my world. I had a truly spiritual experience that pushed me to even start Comedy. I know I started it when I was supposed No sooner, No later. Read more>>

Michelle Mueller

I love this question. It allows me to reflect on my journey and share that with you all. My story goes back to around 2020 when I was working full time as a teacher and pregnant with my son. My husband and I are lucky to have made the decision that I should stay home instead of work because of the pandemic and being pregnant. We had a lot of fear and uncertainty.  When the world opened back up again, we never took parks for granted again. We began exploring all the parks and libraries close to us. Over time, I began sharing these adventures on my personal Instagram page. I started getting a lot of questions about it and people telling me they really loved my content.  Finally, in March of 2022, I started Play STL. It is such a tremendous creative outlet for me that I wish I had started sooner. It allows me to do what I love (being a mom) and sharing some of that with my followers. It truly is the biggest blessing and I’m so grateful for this platform.  Read more>>

Shari Wiltshire

I’ve been creative all my life. Literally, I’ve been a fictional writer since childhood. But pragmatically, I am creative in finding solutions to solve problems; I like the trial and error process; I like to investigate and test what works and what doesn’t. I have embraced this approach to my work life, so when I say that my creative career began exactly at the right time in my life – I mean it. For a very short moment in my life I was good at math and computer programming and then one day I wasn’t, and I had to fall back on English and writing to graduate from college and not waste any more money. My first step toward a career was as a reporter for a local newspaper, but at that time, I had no idea I was learning about humanity and society and collecting human stories for my eventual creative career as a filmmaker. My next step toward a career was as   facilitator and teacher, but again, at that time I had no idea this skill would be effective as a film director. My next step toward a career was earning a Master’s degree in social work, but again, in the time I was working as as a case manager (and then a therapist). I had no idea that research, honesty, accountability and transparency – skills that I honed as a reporter years earlier – would benefit me now in my creative career as a film producer. To be honest, I have made films, but I don’t have a career as a filmmaker…not yet. Read more>>

Callina Anderson

I went to the University of Houston for acting in theater, but once I graduated, I was terrified to audition as a professional. I thought I might have talent, but the possibility of rejection seemed too personal and scary. I would audition at our annual city-wide auditions, but wouldn’t pursue any callback or open auditions. I, instead, picked up odd and end jobs, and became an actor at a children’s theater. I finally decided to pursue professional acting nine years after I graduated from university. I realized how much time I had lost being afraid, and determined to try, even if I got rejected. Soon after that decision, I was hired in three professional shows, and have been consistently working as a professional in the Houston theater market ever since. Read more>>

Scott R.s. Raphael

The true origin of my creative process came when I was around eight years old. I don’t think I could have started much earlier than that, but I do have some regrets about where I went from there. As a young child, I enjoyed drawing pictures and telling stories. It was after I’d drawn a (very poor) representation of a wolf with physical capabilities reminiscent of one of my favourite cartoon heroes, Inspector Gadget, that I realized the appeal of turning my storytelling into a lifelong goal rather than a childhood fancy. As I recall, the decision was made on the spot. “I want to be an author,” I declared, and that was that. What I wish I could have done differently is related to the years that followed. Yes, I wrote here and there—very short stories, first chapters that never had second ones. I never committed to the art, however. In a way, I think that being an author had become so ingrained as “a dream” that I had no concept of it ever becoming a reality. I wish I had applied myself then: reading more, writing more, looking into the processes to find agents and traditional publishers. Read more>>

Priscilla Rathbone

You know those Deep Thought Questions about how to make a career out of what makes you happy, and they say to think back to your childhood and what brought you joy as a very young person? And I always thought about climbing trees and catching bugs (I grew up kind of wild in Florida with a single dad), and I didn’t see how I could make a career out of that. But I forgot about the hours I spent lost in creating imaginary worlds, and perfecting my own languages and fancy scripts. Even though I never played D&D, I was fascinated by the anthropological descriptions of different kinds of cultures and governmental systems. I drew the fantasy creatures I saw in the books. I developed a calligraphy script for writing down my ideas. Read more>>

Kimberly Liermann

I started getting serious about acting later in life, around 39. Career wise, I tried almost everything I was interested in except the one thing I was truly passionate about–acting. I just said, “Why not?” I didn’t really have a lot of things holding me back, so I started taking an acting class at The Actor’s Workout Studio with Fran Montano. It changed my life and I’ve never looked back. I’m actually very happy with the fact that I’ve started later in life. I feel way more grounded in life and I know exactly who I am. When I was younger, say in my 20’s, I would have been way too desperate for something to happen, too much of a rush to ‘make it’. Now, I’m just enjoying journey of being an actor. Enjoying making friends, collaborating, and taking acting classes. I’m in no hurry and I’m trusting the process. If I had started earlier in life, there’s a good chance I would have quit already!  Read more>>

Noah Conner

I was on the outside looking in for a long time. I always played music and was passionate about attending concerts and festivals. However, I guess I had a lot of growing up to do to realize life is just about doing what makes you feel alive. While I wish I started the journey a bit sooner, I don’t regret anything I went through on the way to this life I live now. Read more>>

Shaun Harris

I think I would not have changed anything. I started rapping out in Tucson as a Jungle MC after a chance meeting with Shock-G of Digital Underground. This meeting led me to an experimental band, “Satori,” the band’s drummer, and a drum and bass DJ named Clay Steele. Who let me Jungle MC with him and the Historic Club Congress in Tucson, Arizona. I was just getting an associate degree in computers from a trade school. At the time, I didn’t think 24 years later; I would still be sound music and enjoying what I love—starting sooner? I can’t imagine it. I believe the path I am on is the one I should be on. I quit for 10 years and reemerged with My Partner LUGO to do two remarkable projects. So, I guess I started sooner and later? Hahaha. Read more>>

Yazmin Garcia

I was born in Guadalajara, Jalisco, Mexico, and we moved to the States when I was just two years old. My parents, chasing the American dream, worked hard as a construction worker and at a fast-food restaurant. My mother repeated to me the belief that I would attend college and secure a good-paying job. As the eldest daughter in a first-generation household, I felt the weight of expectations, even though I had a passion for drawing and creating. In 2011, I faced a significant challenge when I was deported, returning to Mexico to fix my residency before turning 18. Heartbroken about missing my high school graduation with honors and leaving my life in the States behind, I struggled to adjust. However, I fell in love with the rich culture and arts around me. It was a transformative year, reminiscent of “eat, pray, and love.” Upon my return, I got back on track, graduated high school with honors, attended college, and found a decent-paying job. Read more>>

Xavier Torres

We probably started at the right time but would have loved to start sooner than we did. TooTaku started as an idea in August 2016 that we didn’t put into effect until 2017. At this time I (Xavier) had just finished my bachelor’s degree while Alton was still in culinary school until 2017. Shortly after Alton moved to Alaska for 6 months which made recording the podcast difficult, to say the least. Timing-wise starting when we started worked out for us because we were both available to begin the podcast that we probably wouldn’t have if we waited until Alton had returned from Alaska. But starting sooner would have allowed us to be much more prepared for the physical separation than we were because during this time we questioned if we should continue or just put TooTaku on hiatus until he had returned. Read more>>

Lucia Gallipoli

I’ve always had an interest in making visual art, but I wish I had taken my content career more seriously sooner, although not as soon as I initially wanted to. When I was 12 (in the beautiful year that was 2010), more than anything I wanted to be a beauty-guru/YouTuber. Every day I would do my makeup—which I wasn’t allowed to wear outside of the house—and talk to myself as if I were talking to a camera. (One time my mom overheard me and thought I was talking to her and was like “are you talking to someone right now” and I had to be like, ugh, you’ll never understand me!) My mom said I could start posting on YouTube when I was 13, which was, conveniently, the age when I started to hope that no one would ever perceive me, literally and honest to god, ever again. Read more>>