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.

Andrea Romero

If I could go back in time naturally I wish I would have started my small business sooner. Although if I’m being honest I feel like everything in life happens for a reason. I started my business in 2022 right after having my last daughter Sunny. The maturity and knowledge I had from my previous carpentry business helped me properly navigate Rock N Scroll. Read more>>

Lorrie Davidson

Ah, that’s the million-dollar question, isn’t it? Honestly, starting a business isn’t just about chasing profits; it’s about following a calling, building something meaningful, and carving out your own little corner of the world. For the three of us, each had our own reasons. My dad saw this venture as a way to make his retirement savings stretch while creating a space where families could gather, just like ours has done over the years. My brother? He craved a hands-on business where he could unleash his creativity and build something lasting. As for me, after years as a stay-at-home mom, I was ready to dive into a project that got me out of the house and back into the swing of things—reawakening skills I hadn’t tapped into for a while. I’ve always loved the idea of opening our doors to folks from all walks of life, creating a space where guests can make lifelong memories. Designing the space, crafting the brand, setting the vibe—it was a dream come true. We weren’t just building a business; we were crafting an experience, an atmosphere that would resonate with others as much as it did with us. Read more>>

Emma Dirolf

As a graduate student, I always dreamed of owning my own business. The thought of making my own schedule and working when it fit my energy and needs was so exciting to think about. After switching careers from education to GIS, I was able to really hone in on when my productivity was best. I found that I feel more energized when I can give my work complete concentration and take breaks that allow a brain shift, then return to focus on solving problems. Read more>>

Rebecca Armstrong

There are two answers to this question: I wish I had started my business sooner, and I know that it all unfolded exactly as it should have. Both are true. I always knew that I would one day start my own business, coming from an entrepreneurial family and always having had this dream of owning a floral shop, or a vintage boutique with a studio in the back… I dabbled in flowers for a time when I was younger, but knew I wanted to pursue a career in the visual arts first. So I moved to New York, went to grad school, and worked in arts education in museums for years. I am so happy that I took that time to build one of my dreams of working in the arts, working with communities and the public in educational programming- I hold that part of my life dearly. Read more>>

Pj Rosen

I think I started exactly when I was supposed to. I am 48 and I started almost 5 years ago, but I never started out intending for this to turn into a business. If this happened earlier in my life, I think it would have impacted the great work I did in education and child advocacy, maybe positively, maybe not. It would also have had an impact on the type of content I create. Most of the people working in the space I am are MUCH younger. I think that has advantages and disadvantages. It would also have advantages and disadvantages if I were exactly their same age. I am not the type of person to wonder about what could have been. I am more of a, “Here is the hand you’re holding. Play it to the best of your ability.” kind of gal. Read more>>

Matt Lefler

If there was a clock where I could go back and start this sooner I would. I didn’t start sincerely following this path seriously until my late 40s. Which is a funny story. In 2018 I was not playing all that much, maybe 3 to 4 hours a week. I lived on the west coast and had to go back to my home town in MIchigan. I ended up leaving my guitar on the plane and was looking at two weeks where I had no instrument and knew that would drive me crazy, so I stopped at Guitar Center in Grand Rapids, MI and picked up an acoustic guitar. I knew they had a 30 day return policy and I could either keep the guitar or return in once I got back to Seattle. All of a sudden I was playing about 3 hours a day. I couldn’t keep my hands off the thing. I kept it and still play the heck out of that guitar. Read more>>

Yeins Gomez

If I could go back, I wouldn’t change the timing of when I began my career, and here’s why. I started my journey as a tattoo artist around 2020, after years spent building a strong foundation in other fields. For six years, I worked in the construction trade, doing painting, remodeling, and restoration, while creating metal sculptures, drawing and designing in my spare time. That phase taught me invaluable skills—like time management, communication, financial planning, and, most importantly, how to work effectively with clients and collaborate with coworkers. These skills became essential assets when I transitioned into the tattoo industry. Read more>>

Alex S. Bradshaw

I would definitely start sooner! I have always dabbled in storytelling and writing but I didn’t really believe that I was allowed to write seriously until about ten years ago. Like I say, part of the reason was that I thought I wasn’t allowed to want to be a writer. Not really. That was for other people who were more creative or knew some secret formula. I could tinker with a few things here and there but they had to be for me or my friends and shouldn’t be mass consumption. I remember the moment when the lightbulb went on that meant it was okay for me to take it seriously: I was at the World Fantasy Convention in 2013 and having drinks with someone I’d met. They asked me about any creative projects I had going on and I said that I only had a few for fun things just for me as I was trying to get a job in publishing rather than write. I was putting together an anthology of stories that other people had written as a kind of portfolio of editing work. But he pushed me and wanted me to talk about the projects (which are now firmly in the trunk as they say!). As we talked about them I got more and more animated and they said to me that it sounded like I really wanted to be a writer. Read more>>

Jill Hellman

I believe we live the lives we’re meant to live, yet sometimes I wonder where I’d be if I had pursued my art career sooner. To be clear, I’m thrilled with my life now as a mixed-media artist and psychotherapist, but I’d be lying if I said it was easy or straightforward getting here. My life has been a zig-zag of choices and experiences, and I wonder where I’d be if I’d been able to go for it as an artist sooner. Would I have a huge career? Or would I be an artist at all? The part of me that allows me to make the art I do requires me to bare my soul and be vulnerable. Life has helped me develop a tougher skin, but as a sensitive young woman, I might not have been able to tolerate criticism or stand on my own with my art. Maybe I knew that and knew to protect myself.  Read more>>

Gina Cas

I have often asked myself this question for the past 7 years. Well, I realized there are no rules. From when I was a little girl, I strived to be perfect and obey all the rules and ironically enough, my life story turned out to be anything but a ‘by the book story’. I became the exact opposite of what I was in my childhood. Shy, obedient, fearful, conservative, with a low self-esteem, people pleaser, sensitive, I was willing to trade my authenticity for approval anytime I was asked to, for the sake of being accepted as part of a group and I did so relentlessly, until losing myself was more painful than the loss of others, or their approval. Read more>>

Erica Carr

I wish I started my creative career sooner as I always had innate creativity and talent and lived in a supportive creative environment and landscape in the NE where I would have had more opportunities and been able to progress quicker/maneuver easier. I started in my late 30’s privately and mid-40’s with public exhibitions and studio space in South Florida. I was an Executive career-wise when I started in my mid 40’s. Starting sooner would have allowed me to use my network for more exposure as the college that I attended and sphere of influence were very pro-arts. The success and traction that I’m enjoying now would have been accelerated and been greater based on geography, culture and value of the ARTS. There would be less sweat equity and a clearer path to being a successful full-time artist following my bliss. Read more>>

James Rogers Jr.

I started taking content creation seriously the beginning of 2023 but I actually did a couple a videos way back in 2008 – 2010 with animated music videos I posted on YouTube. I was in college for I.T. and working at Food Lion as a cashier. I wasn’t focused on making the videos but at the same time I wish I had the confidence to stick with it. The videos weren’t performing well and I wasn’t handling my classes well and I ended up dropping out, partied way too much. Then a few weeks later I lost my job and needed to figure something out quick and content creation wasn’t nowhere near the level it is today so it didn’t even cross my mind to take my videos seriously. I ended up joining the Army National Guard and getting deployed to Iraq which landed me in the care of Veterans Affair so now I can commit to content creation. So everything has worked out but I do still think, What if? Could I have really been one of the pillars of YouTube if I just decided to stick with my videos. I think if I buckled down and learned the ins and outs of creating videos I could have been one of the driving forces that brought anime to the limelight here in the states. But it wasn’t my time, I wasn’t mature enough to create that game plan and stick to it. Read more>>

Riesa Sumida

That’s a great question! Looking back on things though, I think that I started just at the right time for me. However, I also think that if I had started posting sooner and taken things more seriously at the beginning, I would have been able to form better connections with content creators in my niche. I definitely missed out on some fun opportunities to meet up and connect with similar content creators early on because I wasn’t very attentive to my account. Read more>>

Tushar Joshi

I certainly could have used the time I would have had if I had started sooner. After years of practice and hardwork being part of multiple successful bands one of which was also featured on TV, at 22, I was at crossroads to choose my career. I really wanted to take up a music course but convincing my father to let me pursue it was impossible at that time. He figured a more (or what he thought was)”stable” course would be better so I ended up doing a MBA degree in Finance. Two years later I completed it, worked at a world-renowned corporate company and, by that time, I had the confidence to say, “Okay, I did what you wanted me to, I think I’ve proved that I can take care of myself. Now I am going to do what I always wanted to”. So I left a corporate job and took up music full- time. I was 26 by that time. Read more>>

Ramiro Losada-amor

I believe we started our firm at just the right time. I launched the business in 2018 after a referral from a friend (the classic start), but everything took off exponentially after 2020. COVID changed how people see their homes—they’re no longer just where we eat, sleep, or spend time with family, but they’ve become our offices, schools, gyms, and everything else. Spending so much time at home made us all notice how our spaces weren’t flexible enough for these shifting needs and lifestyles. Read more>>

Jerry Carrillo

If I could go back in time and tell myself that to take that risk and the idea of starting the podcast sooner. I would believe that things would be different, also have the chance to build growth of the podcast. Me and my close friend, who I now call a brother, name Marlon. Me and him been talking about starting a podcast while back in January of 2023, but we just didn’t have the equipment, the time, or the location of where we should do it because for me, I’m currently in college, both of us have work, basketball training and lastly, I’m a father of two kids and with being said, it’s a time crunch. We wanted to get started back then but of course we had that fear of being judged or make fun of. But now looking back at it, we wished we should have done it and took it to the chin and just post our first video, even now, when we first started our podcast channel in August of 2024 when we first posted our YouTube video for our podcast. We were nervous but very excited and so far, we saw our channel slowly growing in the YouTube community and it’s just a huge motivation for us to keep on going with our goals and tell future selves that we are proud that we did this decision. Read more>>