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.

J Manuel Ambriz-Varela

It’s been a few years that I started my business, but going all in into my business it’s been a tear and half since I decided to go on my own.
yes, I wish I had started my business sooner, I feel that If I done so my life and everything around me would be entirely different from what it is at the moment, meaning I probably will own my house by now and not have any debts , my mom would be taken care of and most important I would be able to tell my partner that she could stop working at any time she would want I would take over the entire household bills. Read more>>

Kendra Motley

I absolutely wish I could go back and begin my business sooner! I started my business in December, 2021. I always had a passion for finding affordable trips for my family travels. My friends soon caught on to the good deals I was finding, and began asking me to help them plan their trips and find them good deals as well. I had been following a few travel agents on Instagram, and one of them posted about their host agency hiring. I knew right then that I should take a leap of faith and apply. I didn’t really think I would get accepted, so I never even told my husband about it. A few months later, I got the news that I was on the team and I haven’t looked back since. Being an agent has truly changed everything for my family! Read more>>

Aaron Shriver

If I could go back in time, I would’ve never put the camera down.

I officially started my photography journey in 2021, but the passion began long before that. Photography has been a part of me since high school—it was a true passion even then, but like so many people, I didn’t chase it the way I wish I had. Life took me in other directions, and photography stayed something I did on the side, more of a hobby than a pursuit. Read more>>

Destiny Henderson

If I could go back in time, I’d actually choose to start my business later, which I know might not be the typical answer. I launched my business during a really difficult time in my life—I was in full-blown survival mode, financially and emotionally. I was struggling, trying to make ends meet, and looking for something that could not only bring me income but also give me a sense of purpose. Read more>>

Brooke Jennings

I do wish I started photography earlier, but I don’t think I would’ve been mature enough to make the decisions I needed to for my profession. All my life I was a beach volleyball player and nutrition gal. Studied nutrition and played beach volleyball in college, then coached as a job. Soon after two years I stopped and got into photography. It was the best decision of my life. I wouldn’t change anything about my experience or choices in the past. I believe that God had this plan for me all along and was just waiting for the right time to reveal it. Read more>>

Carlyn Bushman

If I could go back in time and start my business sooner or later, I honestly wouldn’t change a thing about when I launched. But not because it was perfect timing—far from it. (Progress OVER Perfection)

I didn’t land in this business all at once—it was an evolution. I left a corporate career, took a much-needed pause, and in that quiet space, I realized how deeply I craved more meaningful, purpose-driven work.  Read more>>

Teinye Boyle

So, in 2013 i officially started my modelling outfit, i started with just a sparse amount of industry knowledge and winged it up until its eventual and official closure in 2016.

Looking back, while i am grateful for the experience, people and lessons i learnt from, i felt i went in too early and ill-equipped.

It was just a spur-of-the-moment king of expression that i think i took too seriously for a novice. Read more>>

Hannah Dayton

I’m currently 26 and started my business at 17 years old during my senior year of high school. I was lucky to attend a school that not only encouraged creativity across all subjects, but also gave us a platform to pursue a passion project—similar to a senior thesis. Some students built things, others created art, some learned new skills—and I chose to create my own business. Read more>>

Tess Kania

This is such an interesting question, and the answer depends on a few factors. If I consider my first paid sessions the moment that this business started, the answer is no. I was in high school when the families of a few of my friends saw me carrying a camera around everywhere. They asked me to take family photos and senior photos. So, in a way, that’s when I started. Read more>>

Merve Ayyuce Kizrak

Looking back, I realize that timing was crucial in establishing HUX AI. The idea of ​​starting my own business had been in my mind for many years — sometimes more visible, sometimes overshadowed by other priorities, but never completely erased. It was a seed that was constantly growing in the background, waiting for the right time to sprout. This understanding of the importance of timing in entrepreneurship is a valuable insight that I gained from my journey. Read more>>

Dacia Zimmer

If I could go back in time I would have started my marketing business years prior. I had always been told I would do great running my own business and know the ins and outs. I have worked in the hospitality industry for over 18 years and have been doing marketing for 15 years. I have been a marketing manager for some big hotel brands like Marriott and Hilton and worked at a resort and Casino. I love to help make a difference and support local businesses. I know I would have been happier running my own schedule and working with clients that enjoy my help. Read more>>

Laura Thorne

On one hand, I wish I had quit my 9 to 5 to work for myself sooner. On the other hand, I don’t think I would have gained the same life and work experience or the motivation I got from years of gaslighting bosses that pushed me to succeed on my own and never look back.

I started three businesses in 2015 after hitting a glass ceiling in my 10-year government role and finally taking the leap to quit. At the time, I had been promoted to just under high-level management. I had strong relationships with my coworkers, and on paper, I had the best job in the world. I was leading habitat restoration, running the artificial reef program, and recognized as a seagrass and GIS expert. Still, despite the job title and its potential, government was not the right fit for me. Read more>>

Tiffany Harlan

If I could go back in time, I sometimes think I would have started my business full-time sooner—but looking back, I know that everything happened at the right time.

In 2015, I was juggling school and working full-time, trying to figure out exactly where I wanted to take my degree. At that point, I didn’t have kids yet, and I was gaining experience in different areas of fitness. I managed at Orangetheory while also working as a personal trainer and group fitness instructor at Wichita State University. Later, I transitioned into working at a mortgage company while continuing to train part-time. During that time, I even pursued my master’s in physical education with the intention of teaching, all while keeping one foot in the fitness world. Read more>>