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.

Melissa Corpuz

I think this may sound trite, but the timing of our business was almost serendipitous. We started the business at a point in time when our children had grown to become slightly less dependent on us and our jobs were a little more steady. We had finished our second renovation and we were almost itching for a creative project. I have one of those minds that needs to multitask and Joe loves a good challenge. So we decided to give it a shot. I think the timing worked for us and certainly our life experience at that point left us wiser and more flexible to take on such a task. Read more>>

Alexia Majors

I think like many people, I was raised to follow a certain path: go to school, get the degree, land a steady job. I value the education I have received but looking back, I think my generation—millennials—wasn’t always given the space to consider something more creative or entrepreneurial. There was a lot of emphasis on degrees as a “golden ticket” and the belief that once you graduated, the perfect job would just fall into place. I can see now how that mindset wasn’t necessarily empowering. Read more>>

Laura Woolsey

I’m Laura Woolsey, founder of Memory Forward, a business dedicated to helping people organize and preserve their most treasured memories. Memory Forward began in 2007 with a focus on printed photo organization, but over the years, it has evolved to address the challenges of both physical and digital photo collections. I started Memory Forward in 2007 as a single woman with no children, living in Austin, TX. At the time, I had spent my career as a computer programmer but was experiencing what I jokingly call a “mid-20s crisis.” I felt unfulfilled in my work and was drawn to professional organizing, which seemed like a way to help people in a tangible and deeply personal way. Read more>>

Antonio Bryant

Great question. I wouldn’t change a thing but I do often wonder what would life be like if I completely ignored what God called me here to do. Read more>>

Tami Jo Urban

I often wish I had started my creative business sooner and dedicated more time to advertising and marketing my work. If I had begun earlier, I could have participated in more art shows, connected with wider audiences, and pursued opportunities like working with an art agent or joining a collective. These steps would have allowed me to grow my artistic presence and explore collaborations that could have taken my career further. While I’m proud of where I am now, I can’t help but wonder how much more I could have accomplished with a head start. That said, it’s never too late. Start now, whatever it is you want to do. Don’t wait for the right time. It’s never the right time, because it’s always the right time! Read more>>

Dariya Repina

Looking back, I wish I had started our “mother-and-daughter creative duo” sooner. Time is precious, and sometimes it takes a while to appreciate certain things in life. My mother, who is my biggest inspiration, has created amazing art, designs, and exhibitions throughout my entire life. But it took me so long to recognize that we could actually create together and blend our creativity.  Read more>>

Abby Nissenbaum

I grew up in Connecticut and started performing in local/regional musical theatre when I was 6 or 7. I took vocal and acting lessons and performed all throughout childhood up to my first year of college, but then pivoted to an academic research route because I thought I wasn’t competitive enough to actually get anywhere in the musical theatre world. Looking back, I think I really internalized others’ negative comments about my body and other aspects of myself, and ended up creating self-limiting beliefs about my talent and capabilities. I put aside all music and acting to become a “serious” academic, and only started writing my own music years later when I was in grad school. Read more>>