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.

Jenelle Holmes

Many people might not consider a pastor to be a creative endeavor, but every week my working materials are pen, paper, words, and relationships. I’m helping people sort through their lives and find meaning, wholeness, and community. But I took almost a decade to truly commit to this work. Multiple road bumps got in the way. Read more>>

Steven Haddad

I absolutely wish I had started photography sooner, but it was always something that I never thought I was creative enough to do. I was going back to school on a medical path, and I took a photography class as an elective because I figured I always wanted to try it, and I was gonna need a solid hobby that could take my mind off school stresses…and I instantly fell in love. I have always said that throughout my life I have been passionate about a lot of things, but photography is an obsession. I was working as a professional piercer at the time, and the people that would let me photograph them were my friends and clients…so that’s how I got into photographing tattooed models. Read more>>

Jaimz Dillman

Yes, I absolutley would’ve started earlier than my mid-30’s. I learned a little too late to not care what people think. And everyone’s version of sexy is different. Every single show we have people asking us how they can be a part of what we do. It’s all about confidence, empowerment, and loving the skin you’re in. I think if I’d started earlier, I would have more years of performing. Not that I think there’s an expiration date or an age that will shut things down, but man, I see these 18-year-olds jumping in and taking control of the stage. I just wish I had the same outlet when I was younger. But I guess things happen for a reason and here we are! Read more>>

Jasmine Dix

I always tell myself I wish years ago that this is what I was supposed to be doing. When I started my business I was actually working two jobs to make ends meet. I was working at Pilot travel center and driving for a transportation company. Something had to give. I was missing time with my kids. I was just working trying to survive I wasn’t actually living. I use to just hobby bake around the holidays for extra money until one day I made this strawberry cheesecake that was trending on Facebook an now here I am 4 years later still growing getting better day by day. Read more>>

Luke Lintott

The biggest risk I took, and the thing I’m most proud of, was starting my online coaching business in spite of challenges related to my finances, coming out as a bisexual, and my mindset & anxiety. After losing my job as a yoga teacher when COVID began, I went into panic mode. All five of my private yoga clients canceled their upcoming sessions within a 24 hour period, and on March 15th I was furloughed from my yoga studio. Read more>>

Rebekah Edwards

I was working as the Lead Massage Therapist for a company. I wasn’t worried about finding clients or staying booked. I had an entire book of regulars, a good relationship with the staff, and things were running smoothly. However, my creative side was not fulfilled, and there was so much more I wanted to offer my clients and community. I’m a highly ambitious person, and I wanted to go out on my own, but I was scared. Read more>>

Tiffany Robinson

The Pink Sugar Box was created in July of 2020, shortly after the pandemic was announced. The company was created after I was let go from my 14 year executive position in corporate America. While I do believe everything happens in it timing, I’ve always had an entrepreneurial spirit even as young as 10. Growing up I had started numerous businesses from selling lemonade, clothing, shoes, etc. I always had that business owner IT thing. Read more>>

Alexa Owens-Lustig

I used to often think about how things would be different had I known what I wanted to do with my career sooner. It took me a little while to find this path that I am on now–this was not always what I saw myself doing! I would think “I should have chosen a different major in college” or “Maybe my business would be in a different place had I known what I wanted to do earlier”. Read more>>

Preston Cone

I started my business after getting fired for working my side job. Although my side work was permitted by my current employer, they changed their mind. It’s amazing what some motivation like that can do. Up to that point I had taken a few small marketing jobs for friends and family and referrals. At this point my biggest supporter and fan, and now my business partner, my wife Laura Rebekah gave me the encouragement to start a business and name it Cone Creatives. She took a difficult job to help pay our bills, while I did everything I could to build a business and find new clients… and fast. Read more>>

Monique Robbins

“I am exactly where I need to be for my healing, growth and awakening.” I created this mantra three years ago after challenging myself to define who I was. Not just as an individual or what people thought of me, but who I defined her to be. In 2017, I experienced the loss youngest child as well as my purpose. With the challenge, I dedicated time to find me. Through this journey many things became clearer. The path of Pretty Little Cupcakes was clearer to view. I chose to include this mantra today because it’s been in the forefront for me as my business continues to flourish. Read more>>

Imari Free

I do sometimes wish right after graduating college in 2017 that I would have started the idea of my business. Having a degree in Fashion Design can be a gift and a curse especially being a creative person, sometimes we hold ourselves back from our full potential! It took me almost 3 years after graduating to sit down and think “okay when are you going to stop playing and use your design skills?” So back in 2019, I juggled with the thought of what I ACTUALLY wanted to do with my brand all while developing my skills as being in management in retail. Read more>>

Stacee Lilly

I always wanted to model when I was younger that was even the persecptive growing up to be “young & beautiful”. However, the ideal model was not plussize and because of that me becoming a model at a young age did not happen for me. My insecurities and fears really got the best of me and hindered me from at least trying. My weight has always been an issue, since the age of 4 I have had asthma and most medications I took had steroids in them. I was always a heavy girl even when I participated in sports, band or JROTC, me being plus-sized I had to get use to. Read more>>

Jessica Nicole Brown

There have been many times when I wished that I had started my creative career sooner. I honestly feel like I’m just getting started, and to me, that means I’m late. I think I see it that way because I see other people doing big things in their careers at younger ages. I know everyone has their own paths, but it can be hard not to compare at times. Then, I started to reflect. If things would have taken off when I wanted them to, I don’t think I would’ve been ready in any way. Read more>>

Kristan Howard-Cooper

As a stay-at-home mother and wife with 3 children at the time, I had completely lost myself in the world of just going with the motions. I was a cook, an in home maid, chauffeur, doctor, counselor, mediator, etc. Let’s just say I filled many rolls but wasn’t doing good at taking care of myself. I decided to turn our extra bedroom into my own little area to decompress and started buying canvases and paint to relax. Read more>>

Veronica H. Speck

Hindsight is always 20/20 so as much as I would like to say I wish I had started my business earlier, I actually think it happened organically and at the right time in my personal and professional life. Entrepreneurship runs in my family and I had always planned to start my own business, but I am glad I waited and gathered as much experience as possible. As of early 2020, I was working with Chef Daniel Boulud, spearheading the communications and marketing strategy for his global hospitality group, and a member of his Executive Team. Read more>>

Leurisa Watson

I fell in love with cooking as a freshman in high school. I wanted to venture into the culinary world post graduation. However, it didn’t appear to be a profitable decision at the time. Instead, I went to a 4-year college and pursued a career in Corporate Accounting. Similar to everyone else, I moved through life. I got married and had children. I always felt unhappy and unfulfilled in my career. In 2016, I suffered a traumatic loss and began to view life differently. While on maternity leave in 2018, Read more>>

Jamaree Woods

I feel like I did start my career sooner. I took it seriously in 2018 as I entered my second semester at Morehouse College. At that time, I was struggling on trying to fit in on campus, so I thought me getting a camera for Christmas would solve that problem. Instead, I fell in love with how different I was from others after I got my first camera. I gave myself the “campus photographer” title when I started shooting. There were other media outlets on campus, but the only difference was that I was the only photographer providing content for the school and myself without having to be fully committed to any on-campus clubs. Read more>>

Tom Lyles

Looking back i would have definitely started sooner than i did. Most of my hold backs were not having the right confidence n myself r my gift i was always looking 4someone 2b there 4me so i would wait on others instead of my doing all that i knew i was more than able of doing myself! I was an professional athlete at the tyme but always knew my art was my true destiny and here we r 2day! Read more>>

Autumn Angel

I sometimes wish that I had started my journey earlier, but than I realize that I was suppose to have started it when I did. Things happen for a reason and I am just going with the flow. Read more>>

Alonzo Lee

This is a Great Question I do wish I could have started earlier than I did. I moved to Houston from Dallas as a technology major at the University of Houston but then as I started to develop relationships with people in Houston with many different backgrounds I began to discover new interests that were better suited for my skill set. After almost 2 years of taking Tech classes, I quickly realized I had no desire to do this for the rest of my life, I was having way more fun helping friends create business designs and planning ways to implement them. Read more>>

Christina Prudenti

Yes, I do wish I started my artistic career sooner. I began making art at a young age but I began making shirts around age 31.
At the time I was working front desk at a hair salon. On one of my off days, I was walking in the lower east side of nyc and stumbled upon a small Thai art gallery displaying mini canvas work of different animals. I fell in love with the idea of mini canvases. Read more>>

DAVID STEWART

From my high school days till my early 20’s I played in a country southern rock band. Went to work in the construction industry then married and dropped the music career. Divorced and remarried and had two wonderful daughters. Divorced again and married a true music lover!! Was laid off in 2008. While unemployed I started to study songwriting. With encouragement from my wife, I started writing more songs. Playing open mics and kept writing. I ended up with enough songs to record my first CB, The Backwoods and have been writing and recording ever since. I would not change any of the past decisions because they got me where I am today. Read more>>

Jessica Mákàńjú González Martínez

Life can be an onion sometimes. Yea, an onion. It’s not what you expect a story to start off with, but the reality is layer by layer the impact of the onion can uncover something deeper inside you that never was wanted but can be very rewarding…well if you like onions; which I do. Deep down inside I always felt I was an artist. I saw the world through a giant, creative lens and applied it to how I tackled problems and implement actions in my career. Over ten years ago, I took a step into becoming a designer of strategies in the field of economic development. I built programs that helped people get into good paying jobs, I designed incubator spaces to connect entrepreneurs to realize their business dreams; Read more>>