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.

Mecelin Kakoro

If I could go back in time, I would start the business sooner. Mulogo Safaris began during the COVID pandemic. The organization I was working for opted to downsize and let go of some of their employees and I was among those who were let go. Since I enjoy writing and traveling and decided to set up a travel company, to help people find places to visit and to also tell them about these places and aspects of sustainability taking place in these areas. Read more>>

Lauren & Jesse Stuart

We started Wandering Stu’s as a way to keep our family updated on our travels abroad. We love photography and writing so it was a little bit of a no brainer and an easy way to keep folks back home in the loop. We did not take a second to think, “hey, we could actually make a business out of this one day.” Instead, we just dove right in. It wasn’t until later, it dawned on us, all those travel guides we wrote, we could actually use those to create a business. Except, they we’re poorly written, not SEO optimized, and just needed a lot of work. Read more>>

Kassandra Davis

I started my photography business 8 years ago. I was a mom to a newborn and a toddler at the time working full time at a dealership. I started by offering shoots on the weekends while still working full time during the week and I do wish I would have gone full time with photography sooner. I let the fear of not being successful stop me from taking the plunge for the first 4 years I was in business. Read more>>

Christine Racheal

I attended Douglas Anderson School of the Arts as a high-schooler in Jacksonville, Florida. There, I studied Creative Writing. I wanted to see my stories on the big screen. At the time, I was impressed by the film school at Florida State University. I remember receiving a folder of information detailing the requirements and benefits of attending. However, as someone who grew up in poverty in some of the most dangerous communities in my city, no one spoke the same language. Read more>>

Bruce France

I wish I would have started sooner. I started the business in 2005 and was working for an IT company. I had a good career, but I wasn’t happy with my job. Starting my business sooner likely would have given me a leg up in building my customer base and becoming profitable sooner. Also, as I get older, the labor is more physically demanding and starting sooner would have allowed me to take more advantage of the energy and stamina I had when I was younger. Read more>>

Kelisha Perry

Orange Pop Media started running as a business in 2018, but back in 2013 I was filming and had the intentions of making music videos. I was just starting college that year, yet my focus was on my family’s well being (since I was away) and relationships that no longer exist. I did not put my craft first and lacked that “go getter” mentality. If I started sooner I would’ve built more skills in film, though I remain a student of my craft. Read more>>

Stephanie Markunas

(THIS MIGHT BE A BETER RESPONSE FOR THE RISK PROMPT) Hindsight is always 20/20, but knowing what I do now, I should’ve taken the step to create my own business sooner. In 2021, I chose to walk away from leading the kitchen at a very established, successful, restaurant. At that point in my career, I had positioned myself to buy into a part ownership (and eventual sole ownership) of the restaurant. Salary was good, bonuses & benefits were admirable for our industry, but it wasn’t enough. Read more>>

Ta’sha Henry

I wish I would have started my business as soon as I graduated high school back in 2003! I allowed fear to distract me for years! I started my business in 2015 when I finally took a leap of faith and moved to Atlanta GA from New Jersey. I was working remote as medical coder during the transition. Read more>>

Jennifer Fry

Sooner- I decided to take my hobby photography to a more professional level. And this was around the time when everyone else decided to become a photographer as well. Plus you had the increased surge of the instagram and tik tok craze that just blew everything up. Young adults these days are just way more advanced in technology, and app use. I found it extremally hard to keep up and compete with that. So, its has been hard to advertise a business when you aren’t up to date with the newest trends on the apps. Read more>>

Cadrea Scarbrough

My make up business started in 2016. I was at a standstill in life at the time, so that day I decided to post my work for prom on Facebook and I got so many great feed backs. That’s the day I decided to do make up I started in my hometown Eutaw, AL. They supported me and I’m so thankful for my clients, they helped me get to where I am today. I feel like if I would have started sooner, I would be in a different place right now, I would have had me a contract by now. Read more>>

Jerrica Griffin

To be completely honest, I wouldn’t change a thing, and here’s why. Everything in life is designed to propel you forward at the right time and at the right moment when you are ready to receive it. With that being said, if I had started my business any earlier than when I started, I probably wouldn’t be here at this very moment, because it’s all about timing and preparation. When I first started my business, I had no clue as to how I would actually reach my target audience or how to monetize my business on multiple platforms. Read more>>

Jonathan Thompson

I originally approached my talents from the hobbyist mindset, so I never truly made any profits. Music production was something I loved, as well as DJing, but I had never considered the business aspect of those interests – just the creative aspect. Had I been more aware of the business aspect, I would have transformed these “hobbies” into businesses much earlier. Read more>>

Pinki Umer

If I knew then what I knew now, I would not have hesitated to start my food blog page when I first grew interested in it, way back in 2014. At the time, I was still in high school, but I loved visiting businesses and always had a fascination for amateur food photography. Crazy thing is, I didn’t even start my page until spring of 2020, right when covid-19 was running rampant. I gave a lot of excuses on why I did not start sooner, but the reality was that I was scared. Read more>>

Zach Reynolds

I started the idea of my, business in 2017 and officially started my business in 2019. During that time I was working a full time job as videographer in their marketing department. During that time I would learn and study up how to run a business while growing my video experience. Its hard to say if I started sooner how things would be because I feel everything happens for a reason and we all have a path we take. So everything I’ve learned along my journey was all part of the plan at the right time. Read more>>

Von Davis

Part of me says yes I wish I had started sooner and the other part of me is asking “Was I well equipped to even start at that time”? I started my business shortly after graduating college in 2017, although I have always knew my talent as an artist since I was in grade school. I didn’t know my worth until I witnessed others reactions towards my gift. I believe if I would have started sooner I would not know all that I know now-the good, the bad, and the ugly. Read more>>

September Carolan

A part of me wishes I started my business sooner and kept on going. In 2009, I had a small clothing and accessory line on Etsy. It did really well online and offline, with stores in San Antonio and Austin, TX selling my brand. The time spent with my day job, small business and family made me doubt if whether I could really continue working creatively. In 2013, I went on hiatus and in 2021 relaunched September Carolan Design. The persistence and determination to start new wasn’t without moments of self-doubt. Read more>>

Dr. Kristelle Beecher

As many of us do, I’ve dealt with many depleting situations with cultures, leadership, and roles that didn’t align with who I was, and ultimately these stressors added to the mental health challenges I was already trying to manage. Over time, I recognized more of what I really enjoyed doing, what contributed to my success, and I recognized “non-negotiables.” I’ve learned how to take ownership of my career and in totality, my life. Read more>>

Hillary

I started my business in 2017, doing alterations for my friends and making cute embroideries casually here and there. I had been an artist and a seamstress for years before but this was the year I established the name Hillsthreads. 2019 is when I really started to take it seriously and started making art more of a priority in my life. I was tired of being complacent with it. I had known for a long time making art made me feel extremely fulfilled and I wanted to create more than I had been. Read more>>

Derek Robbins

Owning and managing a construction company has always been a goal of mine, but as I worked my way up the ladder at previous construction companies, my goal was always in the background, as i learned my craft. One day I realized my contributions and “out of the box” approach at the previous company were not valued, I was often laughed at or ignored for my thoughts and ideas, the same thoughts and ideas that has made successful today. Read more>>

Dr. Lunide Adeeko

If I could go back in time, I would have started my business sooner. Growing up, I always had the feeling I wanted more, to do more and be more. I grew up in an immigrant household, was born in Haiti—the Caribbean, where 90% of the country is unemployed and lives in poverty. We moved to the US on a cold winter night in March 1995. When we landed at JFK in our Sunday best, we saw white stuff falling from the sky. Read more>>

Laura Meza Wulf

I wish I had started my business in real estate sooner but I also know that in life things happen at the right time. Was I ready to embark on this business 15-20 years ago? maybe not, maybe yes…but what I know now is that what I have been exposed to as well, has taught me that I’m not waiting any longer for what I want. I have that mentality of “if you can’t handle it, move out of the way because I will”. I gained confidence along the way. Read more>>

Kristen Hale

My goal was to always have my own store. I was just so scared to do it. In October of 2019 I opened my own online boutique and have loved every minute of it! When the perfect spot came available I jumped on it and opened my brick and mortar in the Fall of 2020. Read more>>

Ashley Starnes

I started Baked by Ashley in 2019 and was baking specialty cake and cookie orders out of my home. It wasn’t until February 2022 that I opened a brick and mortar and I believe it was the right timing for me. Career wise, baking out of my house wasn’t enough to pay the bills so I started working at The Different Twist Pretzel Co. in the morning and heading home in the afternoon to start or finish any orders I had for that week/weekend. Read more>>

AC Winston

I feel as if I started my business at the perfect time. I think I had to experience, learn and growing with in my craft before I could even consider starting my own. To give a little backstory, In May 2018, I graduated from Sam Houston with a Masters in Mass Communication in Digital Media, and finding a full-time job in my field was hard. Read more>>

Nick Battaglia

As a vintage seller and theatrical designer, I 100% wish I could go back in time and start WAY sooner. I started my vintage selling business in October of 2018 which also coincided with my new work as a Prop Designer/Set Decorator for professional theatre. I had just gotten sober, and was reaching my sixth year at a terrible restaurant when a few upcoming opportunities fell into in my lap. The notion of failure constantly haunted me, but that fear was keeping me chained to the restaurant for safety. Read more>>

Madison Dixon & Andie Nordstrom

We’re not sure there’s ever perfect timing for leaving the comfort of a steady job to jump ship and start something new! You obviously need to cover some practical bases—making sure you have some financial buffer and initial promising leads as you build your new business. It’s certainly quite scary to make the leap, but we haven’t regretted it at all. We’re close(ish) to the same age, so we had a similar amount of professional experience. Read more>>

camil williams

If I could do it over, I would have became a Barber sooner. It’s no secret. I tell people this all the time. While I don’t regret serving 20 years in the accounting field, I can safely say, “I love being a Barber”. The idea of barbering first came to me in my mid-20’s as I was going through lay offs with a major investment company. My older brother is a barber and influenced me a great deal but I wasn’t ready to take up the responsibility of other people’s hair and skin health and care. Read more>>