On a Living Spree

When you were a kid, you needed permission for everything. Permission from your parents to watch TV, permission from the teacher to go to the bathroom. Raise your hand, get in line, wait your turn. Obviously, that goes away as you get older… but maybe not entirely. 

Because many adults act like they’re still waiting for permission to do what they actually want, especially when what they want isn’t so easy to reach. They tell themselves they can’t, for all kinds of reasons. It’s not the right time, they’re not ready, they’re not good enough, it’s a silly idea, it’s not prudent. No one else around them is doing that kind of thing. It would be selfish or reckless or arrogant to try.

How would you feel if we said right now that you have permission? 

Here it is, in black and white: your permission slip. You have permission to take an acting class, go to Bangkok, paint a mountain landscape, learn to make Ethiopian food. To ask for a promotion. To try something new. To change. Even to fail. 

Time is truly our most valuable natural resource… but we don’t treat it that way. In fact, people tend to be pretty oblivious about where their time goes and why. That’s how they end up “busy” from dawn to dusk and yet somehow not doing anything they actually want to do. When we (mistakenly) act as if there will always be more time, we never get around to achieving our dreams and goals.

“Time” is a paradox. Something that parents of young children say all the time is that “the years are short, but the days are long.” And that’s how life actually is. 

Ever find yourself questioning the true essence of wealth? It's a sentiment many of us share. In a world that often equates prosperity with the thickness of our wallets, let's take a moment to ponder a simple yet profound truth: wealth isn't just about money; it's about the richness of our experiences.

In today’s episode of the Win Monday podcast, we are delighted to introduce two extraordinary individuals, Bridget Hilton and Joe Huff, authors of the book Experiential Billionaire. They have lived a life filled with diverse and adventurous experiences, from training as samurais to dancing with the northern lights, and even standing face-to-face with hungry lions on safari. Today, we delve into their journeys and the lessons they've learned along the way.

In our conversation, Bridget and Joe share their journeys of self-discovery, the importance of experiences over material wealth, and their shift in perspective on life after facing personal challenges. They also provide practical advice on how to start living a life focused on experiences, emphasizing the importance of taking small steps toward achieving one's dreams and goals. They conclude by encouraging listeners to become experiential billionaires by embracing a life filled with meaningful experiences.

Bridget and Joe surveyed over 20,000 people from all walks of life and the result is eye opening. People’s regrets are very similar no matter their age and income status and in our conversation, we talk about why people often put things that matter in the fictional world of ‘someday.’ But more importantly, we talk about the exercises described in their book that can help you have that sense of urgency to start doing the things you love.

If you have a bucket list that you’ve stowed away in that fictional world of ‘someday’ because you think you don’t have the time or resources to do them or they’re simply too big to make them happen, this episode is for you. Our conversation will walk you through the actions you can take to start building a life rich in experiences with no regrets.

Fourteen years ago, I went with four of my friends to get our photo taken with Santa at the Burbank mall. Were we far too old to be doing this? Absolutely. Did we care that we were the only group in line that did not include young children? Nope. Is Santa kinda creepy with five grown women sitting on his lap? Definitely… which makes it even more hilarious. What was meant to be a one-time joke turned out to be so fun that it became an annual tradition, complete with themes and costumes. Even as our own families and lives grow and change, it’s a once-a-year event where we can feel like kids again with each other.

Over time, the things you used to play at become serious endeavors, or to-do list items, or no longer worth doing at all. Running around with your friends outside becomes running on the treadmill at the gym, scheduling coffee dates to see your friends, and attending networking events to make new ones. We think of those activities as good and healthy, but they’re actually remarkably unnatural, not to mention not very fun. Because if you saw a kid doing any of those things, you would feel like you were in an alternate universe. Kids don’t run to stay fit, they run to feel the wind on their face and the grass beneath their feet. Kids don’t network to climb a career ladder, they bond through joyful moments. Kids go for what they want without worrying about why or what for—they just want to have fun. As adults, we deny ourselves that luxury without understanding the incredible benefits we’re missing out on.

Most people bury this knowledge in the back of their brains and heap on distraction upon distraction—anything to avoid seriously reflecting on the fact that our time here is limited. We hide it away in hospitals and retirement homes. We pay lip service with bumper-sticker phrases like “life is short” or “you only live once,” but mostly we just suppress thoughts of our own mortality.

Bringing up this topic is considered bad form. Society operates under a silent agreement to keep any mention of our mortality off-limits. And when it happens—a friend gets in a car accident, a relative passes from a heart attack—you still might think, That's not going to happen to me.

Well, unfortunately, life is not a dress rehearsal, and death is too important to ignore. To embrace and understand what it means to really live, we need to make sure our relationship with and understanding of death is honest and realistic.