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.

Amaya Lawton

If I could go back in time, I would have started my business sooner! My family and I decided to start the business at a time when we thought it was best to start making something stable for ourselves. But being pregnant and wanting to start a coffee stand full-time was not the greatest idea! Due to pregnancy, we had only served our community a couple of times before my child was born and then we stopped business for a while. Now we all work full-time jobs and run the coffee business on the weekends, but having less time with my child is definitely hard. Starting sooner would have allowed us to jump in and not worry about the sleepless nights! We would have had more time to put into the business and less worry about needing to be home by a certain time. The amount of events we would have been able to attend would have increased dramatically than where we are now, but we had to start at some point! Even though we started later, it has still been an amazing experience and we hope to only continue to grow from this point forward! Read more>>

Jesse Zavala

If I could go back, I would have started my business at the same time. Not sooner. Not later. I’m a believer that everything happens for a reason and when the time is right. I started my business in 2018 as a side hustle as I have a full time job! If I would’ve started earlier or later, my business probably would not have grown to what it is today. The timing then allowed me to meet and become friends with other Coaches and entrepreneurs, which helped me learn many small business lessons from them that they had to learn the hard way. This has allowed me to add more tips/tricks into my toolbox and I am always happy to pass on that knowledge to other upcoming entrepreneurs who reach out for advice! Read more>>

Rebecca Renner

If I could go back in time, I really wish I had started sooner. Originally, I thought I had to go to college for photography, which isn’t the case at all haha. Unless you’re going for a job that requires a degree in photography, you don’t need it for a wedding and portrait business. In 2017, I was 24 years old, living in a new state on my own, and I was a waitress and really wanted a way out of that industry. I had an interest in photography from a young age, and I always envisioned doing something with it for my career. This is the year I started thinking how I could turn that passion into a career. After moving to a new state and knowing absolutely no one, I wasn’t sure how feasible it would be, but I needed to try. I started advertising and slowly taking clients, networking with other photographers, and navigating the legal side of owning a business. Read more>>

Megan Larkins

While I’m proud of the time frame in which I started my business, if I could go back, I would prioritize marketing my brand more strategically from the outset. In the first three years, I relied solely on word-of-mouth and direct referrals to attract new clients. While this approach proved successful and enabled me to scale my business to a full-time operation, it also limited my brand’s visibility and organic reach, allowing competitors to gain an edge in those areas. In hindsight, I would have invested earlier in a comprehensive brand strategy and identity while dedicating time to mastering SEO. These efforts would have significantly boosted my online presence, expanded organic reach, and increased brand awareness. Read more>>

Jordan Hill

After 2 years of nursing school, I realized that path was not for me and decided to pursue a degree in film. While debating between schools in Los Angeles and Nashville, the global pandemic took place, taking those options off the table. During quarantine, I used my free time to make videos for fun or mess around with my cameras. I often wonder what would have happened if I started posting my work online during this time. Amidst the worldwide chaos, this was the rise of TikTok and overnight virality. What would my life look like now if I had taken advantage of that time to share my faith, creativity, and positivity? On another note, what would my life have looked like in 2020 if I had originally pursued film instead of nursing? Over the last few years of running my business, these thoughts would often surface when I was facing a major roadblock. What could I have done differently? Am I even capable of a job like this with no degree? Who do I think I am to be able to pull this off? In times like these, you must refuse to believe it could have happened any other way. You must separate your own perceived reality from the truth and gain control over your thinking process. Anytime you pivot in your business or life, you must remind yourself that you are not starting over from scratch but from experience. We are the sum of all our life experiences, the good and the bad. What a privilege it is to capture, celebrate and share these experiences through a camera lens. Read more>>

Francis Glynn

At 39, I decided to become self-employed and started a business renting a chair in a salon. It was the next stage in my career, and one that I haven’t regretted. Being able to give my clients the attention they deserve while becoming more relaxed and flexible in my work has been a win-win so far! It’s definitely something I wish I had done sooner, but I still feel that 39 was the right time for me. It gave me those extra few years to work abroad in Amsterdam and Milan, gaining valuable insight into how salons operate in different environments. Now, I can focus more on achieving a better work-life balance, spending quality time with my friends and family, and working in an amazing atmosphere. Read more>>

Catie Greene

I really feel that the timing of this business is so grounded in the timing of my life at that point that I could not have done it any sooner even if I had wanted to. I learned necessary skills and had the experiences needed to culminate in this point in life where my work and passions truly integrated. Read more>>

Janell Norris

If I could go back in time, I would have started my business sooner. Before starting SelfieSkin Co., I was an independent consultant for major skincare brand. Initially, I started selling these dermatologists-developed products because the results were conversation starters amongst friends — I figured why not continue using these products and get an “employee discount” and make some side money in the process. So, I did. In my first year, I hit the top 2% in sales and reached a coveted level in the network marketing business. As I got more invitations to have a “seat at the table,” I started to realize that women of color were not the product development priority, and we certainly weren’t the marketing focus. It seemed like my raised concerns were met with deaf ears. Read more>>

Mai Akdeniz

Looking back my path, I feel that I started the business at the right timing. My brand The Picnic Day started in 2021. Before that I used to support my husband’s food business for years but it was my dream to start my own one day. The turning point came when our son was born. It made me question what kind of role model I wanted to be for him, and if I felt ok that I was not following my own path. Then the pandemic hit the world and there was a long lockdown period in NY. It was enough time for me to make a commitment to my passion. It is not easy to run a business while raising a little child, and maybe I could have started earlier. But the fact that I was able to listen to and to be true to myself makes me confident that it was the right timing for me. Read more>>

Avidon Respes

My current business was started in late December of 2018. I was actually in the middle of trying to open a clothing store with a previous business associate when I was met with a very serious problem… My “partner” had changed the terms and conditions of our agreement after we had come to a disagreement about certain operations within our agreement. All of the drama ramped up and pushed me to go all in on my OWN business. That “partner” knew that I was building my own business separate from our proposed collaboration before we even had a discussion of what “we” would do, yet it became a much bigger issue for them. Read more>>

Cole Cipriani

As a young entrepreneur in my twenties, I’ve discovered that success is LESS about avoiding failure and more about LEARNING through it. My journey has been a testament to “failing forward,” embracing each setback as a stepping stone toward growth. I spent five years in corporate America, two of which felt stagnant like I was going through the motions. During that time, I learned one of the most critical lessons of my career: leadership can either propel you to new heights or hold you back in ways you never imagined. Unfortunately, I didn’t know my worth or how to align myself with a leader who shared my values, and that cost me valuable time and opportunities. Read more>>

Kaiyissa Ambriz

I was working a 9-5 that felt mundane when I started my business, and the desire came from needing to release creative energy. I think that at whichever time you decide to do something, whether the circumstances be ideal or not, it is the right time. Sometimes sitting on an idea causes us to plan it thoroughly and have proper execution, but other times it only results in procrastination and loss of excitement. There is beauty in just doing, even when the unknowns can seem more prevalent. Read more>>

Angel Abad

If I could go back in time, I don’t think I would have started my business any sooner. I’ve always believed that what’s meant for me will happen at the right time, and starting my business in August 2024 felt like the perfect moment. This journey has taught me a lot about myself, where I was at that point in my life, and how I envisioned my future career. Before starting my own business, I worked at an engagement ring company in Washington State as a social media manager. Although my title was Social Media Manager, I brought additional skills to the table that I introduced and offered to help with, as the company was a small business. I didn’t mind taking on these extra responsibilities because it felt right to use my knowledge and skills to support the company’s growth. Beyond my assigned tasks, I assumed multiple roles, contributing wherever I could to help the business thrive. Read more>>