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.

Kaitlyn Mcmanus

I think I started at the perfect time! I began my cosmetic tattoo apprenticeship in January of 2022 with the owner of The Archery, Jonelle Salzman. Prior to that, I was going to school for art/art education and working in the restaurant industry. After a few semesters, I started second guessing my major choice. I didn’t think that teaching would be a good fit for me long term. While I set school aside and was just working, my sister, who tattoos, mentioned she thought I should get into eyebrows. She had worked with someone at her shop (who I coincidentally work with now) that was in the cosmetic tattoo industry and she thought I’d find great success in that field. I took her advice and sought out my apprenticeship soon after. Read more>>

Michelle Roberts

It’s always been a passion of mine to design wedding invitations as a side hustle, but I was constantly working as a full-time graphic designer until 2024. I am truly grateful for the experience those jobs have given me, but I definitely wish I had officially launched my stationery business much sooner than I did. The turning point came last March when I lost my full-time job. It was tough at first, but it allowed me to reflect on the type of design work that truly makes me happy. Now, I am incredibly excited for the opportunity to focus on crafting custom wedding invitations, paper goods & signage in the Portland, Oregon area. Read more>>

Rani Sanghera

If I could go back in time, I would have put more focus and energy into starting my own business earlier. Like many people my age, I grew up with the belief that pursuing higher education and climbing the corporate ladder was the key to success. I was also told that staying loyal to one company and working my way up would eventually lead to success. However, I’ve learned that the world doesn’t always work that way anymore. Another thing that has shifted from my early adult years to now is my definition of success. It has shifted from material things to connections, love, family and experiences. Read more>>

Alan Garrett

I would definitely start my business a lot sooner than I did. I am thankful I started when I did but just wish it could’ve started my Junior year of college. I went to Kansas State University, and at the time this is 2018. This is my second year having my own, on campus radio show called “Loudkicks Radio” that played Hip Hop and R&B along with request, theme shows, guest from around campus and outside of it. It was a great experience at the time but I remember taking a photography class the summer before leading up to that year, and I feel in love with it instantly if not, quicker than I did with the mic and the ability to make someone day when talking at the radio station. Read more>>

Brianna Henriquez

Looking back, I don’t think I would’ve changed anything about when I started my business. I launched it in the summer of 2020, at a time when I was 22 and a new mom, working hard to get back on my feet.
Starting my business during that period was both challenging and rewarding. The uncertainty of the pandemic motivated me to pursue my passion and create something of my own. If I started sooner, I might not have been as prepared for the demands of entrepreneurship, given my personal circumstances at the time. Conversely, starting later might have meant missing out on valuable opportunities that arose during that unique period. Read more>>

Amanda Keller

It’s easy to say I wish I had started sooner, but I also trust in the universe’s timing.

I left my corporate job in January 2024, after nearly 13 years with the same company. I spent my entire career with this organization and was very attached to it, but in 2019, I started to feel unsettled. And eventually, I admitted to myself that I was ready to move on. Read more>>

Khanh Nguyen, M.a.

If I could go back in time, I would 110% start my resume business MUCH sooner! I launched my LLC in January of 2022 while I was (and still am) pursuing my doctorate in clinical psychology. Ever since high school, I was told that I “have a way with words.” I edited resumes for friends and peers in high school, which helped to get them their first part-time jobs in the food and retail industries. Fast forward to college – they landed internships and their first “big boy/girl jobs” upon graduation after I enhanced their resumes. Then came graduate school – I was in my second year of my five-year doctoral program in clinical and forensic psychology. I was a full-time student while also completing an unpaid externship. Read more>>