By far, the topic that comes up most in our conversations with entrepreneurs and creatives is risk. We’ve had conversations about risks that worked out and risks that did not. We’ve seen eyes light eye sharing about career-trajectory changing risks as well as folks sigh about the risks they wish they had taken. Below, we’ve selected and shared some of those thoughtful conversations.

Megan Starr

Very differently than I have for most of my life.

I am one of those people who struggles with decisions, whether its about what I should be doing financially or which shirt to buy. I think, and overthink, about every detail. Up until the last few years, that meant acting cautiously and conservatively if I had any doubt. And I always had doubt. But sometimes life has plans that are bigger than your risk comfort level. Read More>>

Holly Stocks

If I never took risks I wouldn’t be where I am or who I am today. Every part of who I am always had a risk involved at some point.

It always makes you humble and appreciate life in every aspect, because it’s the journey that makes us not the outcome. Read More>>

Leslie Benson

Being a goth musician in the south – especially during this volatile political climate – is a risk, but the community is growing rapidly thanks to groups like GOTHBATS (for which I’m an event planner), local club and music promoters, and the fans that keep it alive (or shall I say “undead, undead”). I took a risk in 2013 and left the Midwest to move to Nashville and immerse myself in a city where people value songwriters and live music. I haven’t regretted it since. Read More>>