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.

Ryann Liebl

I launched my production company in 2019, called REL Films. I think I started my business at the right time but I also think I wish I had trusted myself enough to start it earlier. I was always looking for partnerships, rather than believing in my own abilities. But I’m now realizing confidence comes from simply doing, diving in, making it happen and that is the key in being successful. Read more>>

Megan Westers

Sometimes I think about if I had started my business earlier where I could be at this point in my career. The more I progress in my business and look back, the more I realize that the timing that I had in starting my business was exactly the right timing because I was at a point in life where had the right experience and connections to be successful that I didn’t have previously. Read more>>

Katelyn Kremlacek

If I could go back in time, I definitely wish I would have started sooner. I did not realize just how much opportunity there is on social media with content creation. I recently started taking this seriously within the last two months. I worked in retail management for about 4 years before this and have been a stay-at-home mom ever since. Read more>>

RaNae Andrews

Sooner! I acquired my first embroidery machine in 2005 just after my mother passed away. I started designing and creating embroideries for families and friends. I worked at that for two to three years but then realized that I couldn’t continue to supply just that group of people with my creations. I was bored and they were inundated with embroidery. Read more>>

Kayla Lassetter

I don’t think I would’ve started sooner or later. I believe the time that my business was born was perfect. I started my business in September 2020 right in the middle of the pandemic. I was at my 9-5 of almost 4 years & I was completely miserable. I wasn’t being paid or treated fairly, I had an idiot of a boss who had me doing a lot of HIS work, & it was a toxic environment. I had applied to what felt like 200 jobs & I never received any callbacks despite being more than qualified for the positions. Read more>>

Leah Wells

I started my Photo Booth business in March 2021 during Covid. I had been doing photography as side hustle for about 10 years and never thought about doing photo booths. I was working a full time in banking and had been doing so for 13 years but because I had always been a creative person by nature, working with music and sound, so I never felt settled in that industry or career. Read more>>

Andrew Laufers

I started my law firm on July 22, 2022. I had been working for various law firms for the bulk of my twenty-five-year career. I had my own solo practice previously in a small town which I shut down to pursue a job at a firm. Last year, I reached the point in my career where I knew I could provide better service to clients on my own than with a firm. On my own, I can focus on my client’s needs and do not have to worry about a firm’s needs Read more>>

Rai Smith

I definitely wish that I would have started earlier. I started unofficially in 2022 and officially this year but wish I would have just went for it in 2020 instead of being scared. I was fresh out of grad school but the idea kept eating at me so I decided to go for it. Starting sooner would have put me in a position help people sooner. Read more>>

Candice Clemens

When I started Witchcult in 2021 it was the perfect time. I had just graduated college with a Social Work degree a few months prior and knew that career path wasn’t for me. I have always wanted to own a business and be my own boss. Why continue to ignore that dream? I decided to finally put my fears aside and start working towards my goals. Read more>>

Brandi Karnopp-Clark

If you would have asked me this 4 years ago right after I quit my regular job and decided to open up a boutique, I would have told you that I wish I would have taken the leap years ago. Now looking back, I realize and appreciate the timing. I was working at a label factory since I was 18 years old. My husband and I met there, so I do not regret all of the years I worked there. The last two years that I worked there I was miserable. It just wasn’t where I wanted to be as I was coming up on my 30th birthday. Read more>>

Christina Carney

Opening my own salon suite at such a young age was extremely risky, but I think I chose the perfect timing. I firmly believe in following your intuition, and I did just that. Honestly, there were multiple opportunities presented sooner, but something always felt off. For example, I was working outside of the city and had already built a strong reputation and clientele. I was about 2 years out of school and felt very confident in my skills at the time. Read more>>

Joey Mancuso-Ellis

If I could go back in time the only thing I would change about the timing of my business opening is not to do it the same month I was getting married and buying a house! To say I was completely stressed out would be an understatement! Not to mention I also am the mother of 2 small children so it was a lot! With that being said though I am grateful I didn’t try to open my own business right after graduating school and being so young. Read more>>

Katie Nassiff

I think that if I could tell a younger version of myself anything, it would be to stop waiting. There’s no perfect time to decide to change your life, so the sooner you take action, the sooner you’ll find out whether it works (or if it doesn’t, which happens, too!) Read more>>

Camille Campbell

I absolutely wish I had started my business earlier, but I let fear hold me back for years. My initial business that i started was a Nutrition Coaching business and I literally had had the idea for it about 5 years prior, but I talked myself out of it. “Who on earth would pay me for Nutrition Coaching advice? I’m not qualified for that and it will take far too much time to GET qualified for it, so I won’t even bother to start.” All total nonsense. Read more>>

Jacinda Brown

Honestly, I wish I would have started my business sooner. I was always a very driven young woman, who inspired to be everything God had set out for me, and own my own business. I had this fear for years though. Life felt sort of like a big ball and chain that I was dragging for so long until I finally took a leap of faith and went for my dreams. I was at a bad place in my life when I decided to start my business, at the time I was preparing for a divorce that I didn’t know would be so messy, and it was something I never anticipated. Read more>>

Yennifer Lopez

This is a double edge sword response. I never wanted to be a photographer. I always said that what was the point of me taking pictures if people will just store it somewhere in an album in a moldy attic or worse, end up in frames in a near by GoodWill. (I was purchasing frames and saw a ton of pictures of a kid from a few months to him as a teen) Read more>>

Gene Fryer

When I first started my photography I had dropped out of college with no thought of my future let alone starting a business with my photography. I was wanting to use my photography as an outlet for myself to feel unrestricted as an individual and to have a way to let my mind roam free. As I went along this free spirited journey I met many like minded people and those like me, who felt like a drifter in life. Read more>>

Angelica Olguin

If I could change when I started, I would have started later. Although I don’t have any regrets, I feel I could have approached some things differently. First, I pride myself in my aesthetic and I felt I rushed to open my salon even though it was not what I envisioned. I started working and remodeling at the same time. Looking back it makes more sense to have done it before I started to ensure that I didn’t face the stress of balancing both at the same time. Read more>>

Christena Berry

If I could go back in time, I would have started my business sooner. I was so excited to start a career doing something that I was passionate about. I found studio space at the end of 2019 and started renovating it to my liking. The previous occupants had the walls painted gray trimmed in red and outdoor black carpet and I wanted the space to feel warm, welcoming, and royal. Read more>>

Jessica Scott Santo

I opened up my business “Jessica Scott Hair“in May of 2019. A few years prior to opening up my salon, I was at a salon, where it was not bringing me joy anymore. I was a mom of 3 kids, wasn’t making the income I wanted, and others around me just had a negative outlook on life. I’m the type of person where I’m always thinking to myself. What else is out there or what else can I achieve? So I worked with a company and I started educating. Read more>>

Cole & Morgan Earles

Looking back at everything that has happened to lead us to where we are today, we firmly believe that God has been writing our story all along and His timing is perfect. We are so grateful for the experience and knowledge that has shaped us into the design and build team we are today. Read more>>

Sydney Williams

If I could go back in time I would have started my business sooner. I officially launched Adamma for Mama LLC in 2019, but had I started sooner I could have reached some young girls & women who are lost in the mainstream standards of beauty. If I could change anything about my experience I would have been more outspoken about why it is that I do what I do. Read more>>

Jessica Gemma

Since I was a child, I have always LOVED all things beauty and fashion which included getting scolded in grade school for playing with my friends hair during class. Immediately after high school, I went to cosmetology school and graduated with my license in 2003. Over the course of the past 20 years, I hadn’t always been full time in my bridal hairstyling career. I am incredibly grateful for working various positions at a number of companies over the years because I have learned not only priceless life lessons but invaluable business skills that I feel extremely proud of. Read more>>