Some people fear heights, others fear spiders and most fear death.

One of my greatest fears is looking back on my life with regret.

This fear of regret is part of what drives me as an entrepreneur. I want to pave my own way, to make my own choices, to pick how I spend my time and with whom.

It's also why I connect so strongly with Ryan Berman's reasons for starting Sock Problems. Ryan believes that courage is "regret insurance".  And the formula for courage?

Courage = knowledge + faith + action

After a decade of owning marketing agencies, Ryan was in the process of writing a book - and this process caused him to reflect on himself. He wanted something more, something different and something impactful.

Ryan shared, "I justified working in advertising for years. I drove demand, created jobs and kept the economic engine humming - but you can only sell so many sandwiches.  I wanted to use my creativity for a bigger purpose."

As part of his self-reflection, he determined his core values. What did his work need to include so he wouldn't look back with regret?

Ryan came up with the following list:

  1. Playfulness - Ryan wanted to take the work seriously, but not himself.
  2. Creativity - He wanted to do something interesting that tapped into his creative background.
  3. Courage - It needed to take courage and encourage others to be courageous.
  4. Excellence - He aspired to make an impact on a large scale.

Sock Problems, which combines creatively designed socks with 25-50% of every sale going directly to a specific charity partner, checked every item on Ryan's list:

Playfulness: Sock Problems is light hearted, but the causes are heavy.

Creativity: The sock designs and the endless sock puns ("the very fabric of sock problems", "socking a problem", "sock it meter") tap into Ryan's creative background.

Courage: Yes, it takes courage to leave what you know as Ryan has done and start a product-based business, but Sock Problems goes beyond Ryan's need for courage.  The socks themselves are an easy way for people to connect around a cause, to provide someone suffering with a problem a voice or to show support for a friend or family member along their journey.

Excellence:  Ryan shared, "I loved my time as an agency owner, but that does not compare to the mass impact we can potentially create with Sock Problems. What if we built something big enough to actually sock a problem? I'd love for my kids to learn from that."

It doesn't hurt that socks are a big market.  Research shows that each person has at least 20 pairs and they are open to paying a premium, even before you consider the donation to a cause.

Ryan believes "We can make a living in the business of giving."

Regardless of success or failure, Ryan is living his own truth by having the courage to do something bold, to step outside his own comfort zone - he has purchased his own regret insurance.