When are you going to tackle your bucket list?

My guest today is Alan Worden, a serial entrepreneur focused on leisure-seeking Baby Boomers who founded Scout Real Estate Capital.

For Alan, there came a time when he realized it may be now or never if he wanted to chase his dreams.

In 1999, Alan asked 10 trusted friends and advisors for advice. He asked each if it was a good idea to drop prosperous careers and go sailing from the U.S. to New Zealand with his wife.

Independently, each of them said “If you can do it, do it now. It’s never going to get any easier.”

That was in 1999. Soon after that, Worden spent exactly 365 days sailing to New Zealand in an Everest-sized adventure you’ll love to hear about. (Including a brush with death I won’t spoil for you.)

He spent all that time and most of his money to make it happen.

For him, it was as much about conquering fear as it was about a bucket list item to cross off. See, Alan’s biggest fear is the ocean.

And he crossed 18,000 miles of it in his “do it now” year.

The lessons he learned on that sailboat have carried him to new heights in life and in this episode you’ll learn just what they are.

If you think you could make your dreams happen and something is holding you back, this episode is for you.

If you have trouble facing your fears but want to get better at it, listen to this conversation with Alan.

And if you just want to hear about a real-life adventure that changed one life for the better, click play in the player above to get started.

In this episode, hear from Alan Worden how to ‘do it now’ and more:

• Why the most influential family members aren’t who you think.
• The critical difference between research and “need-search”
• A stunning piece of advice that came from an unlikely source.
• What will make the world care about your business.
• The paradigm shift that put Alan’s life in high gear.
• Why you should be OK with sucking at some things.
• Meditation for cynics.
• The thing you might think that constitutes “the height of arrogance.”
• How to make your “worry quotient” go down—and fast.
• Why 95 percent of what you fear shouldn’t scare you.
• Giving yourself a superpower.

Books and resources mentioned in this episode:

• “The Power of Habit: Why We Do What We Do in Life and Business,” by Charles Duhigg
• “Essentialism: The Disciplined Pursuit of Less,” by Greg McKeown
• “10% Happier: How I Tamed the Voice in My Head, Reduced Stress Without Losing My Edge, and Found Self-Help That Actually Works--A True Story,” by Dan Harris (And the app.)
• “The Big Leap: Conquer Your Hidden Fear and Take Life to the Next Level,” by Gay Hendricks
• “The Slight Edge: Turning Simple Disciplines into Massive Success and Happiness,” by Jeff Olson and John David Mann

How to contact Alan Worden:

• Email