Designing a life of freedom, intentionally

My Song 

I just love to talk about myself and when I’m in the spotlight, I feel alive! 

OK, I'm full of shit. 

There’s not many things I like less than making it about me. Yes, there’s probably some underlying insecurity or issue that needs to be resolved. 

On the other hand, helping others is when I really do feel alive. That’s one of the reasons why I pivoted at 50 to taste freedom and start coaching people to pursue a life they were meant to live. It’s also why I launched the Time to Sing Your Song podcast. 

This newsletter is all about sharing the stories of people I've interviewed. Their rock-bottom moment, what they did to pull themselves out, and how they're now singing their song. 

Begrudgingly, I’m starting with me. Not because I’m special, but rather because it's how I got to where I am. And if you plan to go on this journey with me, it probably makes sense to know where I came from, what drives me, and why I do what I do.  

Before I get to it, big thank you to my good friend Jeff Raz for coming up with the idea for the interview, as well as getting the juicy nuggets out of me. Jeff is an amazing person. He's performed around the world, from Cirque du Soleil to Broadway, he's a communications guru, has written 20 plays, directed dozens of shows, and is the author of the three novels that make up The Circus Trilogy. You can find him at www.jeffraz.com.  

I also need to call out my family, the #1 thing in my life. Picture is in Paris over the summer. Freedom has some upside. 

So here goes, my story…

The song I’m now singing was inspired by a series of wake-up calls that made me realize how short life truly is...  

• My mom dying when I was 20 after spending the previous decade drinking herself to death (made for eventful teenage years)

• Near drowning experience with my younger son in Costa Rica (rip tides are no joke)

• Fainting on a flight from Miami to SF because I was pushing myself too hard (very embarrassing)

• Most recently, helping my older son through some challenging times (hardest thing I’ve ever had to work through)

These experiences – and others – made me challenge how I was living my life. If it were to end today, would I have any regrets? Was I living the life I was meant to?  

And then I read a quote from Oliver Wendell Holmes Sr. that set me on a path to freedom.  

The idea of dying with my song trapped inside of me was haunting. I knew I had to do something about it, but what? I had a dream job at a great company, made good money, and had adult responsibilities. 

I quickly realized that I couldn’t just upend my life. I had to explore why I felt this way, how I was going to do it, and when I would take the leap. 

It started with getting very clear on the why. Why was it so important to find space to explore new ideas, go on new adventures, and craft a life focused on helping people? What would I have to give up? Was it worth it? What would people think (upon reflection, this didn't matter)? 

What would I do, both in the grand scheme of life and on a daily basis? A life without constraints and freedom sounds great until you are confronted with nothing to do. That’s misery. 

And then, how could I make this a reality? Remember adult responsibilities. It wasn't overnight. In fact, it was a 10-year journey to get on the same page with my wife (that was easy), prioritize experiences over stuff, save, change how we spend money, shed crap we didn’t need, move to a lower-cost state, and develop new skills. 

If this sounds at all interesting to you, listen to my conversation with Jeff where I share the need to pay attention to signs that you aren't living the life you were supposed to, why the how is 10x more challenging than the why and the what, creating a fulfilling life requires a lot of intentionality, the importance of being ready to take shots when you are doing something different, and why becoming the best version of yourself requires that you treat the hard times as a gift. 

Definitely not as exciting, but I also get into the nuts and bolts of how I created and stayed true to my life plan. 

If you enjoyed, please give the podcast a rating on Apple Podcasts. You can also forward this newsletter to your family and friends. Two simple things to help me get these stories out to more people.  

Speaking of which, if you have a kick-ass story that you want to share or know someone who does, hit me up. I’m at [email protected]. Or call or text me at 415.846.7948. The phone still works! 

Noodle on...

Questions to contemplate if you want to design a life of freedom…

• What are your wake-up call moments and what are they telling you?  

• What are you willing to give up (or not) to live a life on your terms?

• What experiments can you start today to get you closer to freedom?  

• It’s 10 years in future and you didn’t take the leap. What are you thinking? How do you feel?

• How would you show up differently if you looked at the obstacles in your life as a gift?

Bonus: Create your Freedom Fight Blueprint 

Interested in charting your path to freedom? Here's the approach I’ve been working on to help my clients live a life on their terms. I call it the Freedom Fight Blueprint. 

Before I get going, here’s my take on freedom: Freedom is the ability to act or change without constraint, to possess the power and resources to fulfill one's purpose, unhindered, and to have an abundance of options.

1. Dream an impossible future 

A life of freedom likely feels impossible, but that doesn’t have to be the case. Sit back, take a deep breath, and brainstorm exactly what your future could look like. What are you doing? How does it make you come alive? What does a typical day look like? Where are you living? Who are you doing it with? 

Reality check. You’ve likely applied the constraints of your life to the brainstorm. Now ask, what’s impossible? Write it down. 

2. Pen your Freedom Manifesto

There’s nothing like looking up on your wall to see a beautifully written declaration of your impossible future. Something that gets you fired up each and everyday to do the work that is necessary to achieve freedom. To stay focused when motivation is low or when life gets in the way. 

Not a writer. Don’t fret. Just take what you wrote down when outlining your dream and start crafting your story. Don’t let perfection get in the way. You can iterate as much as you like. You can also get help from a friend who knows how to write.  

3. Go in with eyes wide open 

Pursuing a life of freedom has a cost. Life is about trade-offs. You'll have the ability to do things you can’t today. But you may have to adjust your lifestyle. Your decision may also impact relationships. Your ego may take a hit as well.

It is important to understand the costs and benefits. Write them down and ensure that you are going in with your eyes wide open. Before moving on, ask yourself if freedom is worth the inevitable pain. 

4. Pick a date

Super tactical, but a dream is often just that. Something that is exciting but not real. If you're going to take the leap, you must commit to a date. It doesn't have to be tomorrow or even next month. But you have to put a stake in the ground. My date was when I turned 50. 

5. Get your finances in order and start living below your means 

Let’s be honest, money is what holds most people back from pursuing freedom. Totally makes sense. You have responsibilities. But if you're truly committed to living a life of freedom, you have to figure out how to fund it. This may require that you save for a period of time. It may also force you to change how you spend money, which in my experience is most important. Not to get on my minimalist soapbox, but the average person buys a lot of crap they don’t need or value. Figure out what that is and cut it from your life.  

6. Stop giving a shit about what others think (beyond family)

There are a lot of people who will think you are a nutball. Why would you give up an incredible, well-paying job? Why would you create a situation that could negatively impact your family? How could you give up that country-club membership or second home? Or for crying out loud that new car!

Accept the fact that there will be a lot of people who will criticize you, directly and behind your back. But don’t worry, they’re not thinking about you. Secretly they’re jealous. 

7. Design your fight strategy 

Being intentional is such a cliche nowadays but your odds of failure are pretty damn high if you don't have a kick-ass plan. Key will be working back from your date, setting milestones, and putting into place the right actions to get you there. Once you put your plan together, think about who can help you on your journey. Maybe friends, family, mentors, advisors, basically people you trust. 

8. Know what you’ll do when you get knocked on your ass 

You will have setbacks; you may even get knocked on your ass. Life doesn't turn out like it should, it turns out like it does. Think through the different scenarios where your plan could go sideways and come up with actions that you'll take in the moment. You won’t come up with all of the scenarios but you'll cultivate a mindset where you're ready to pivot when shit comes at you. 

9. Join the freedom gym and go daily 

Now that you have your Freedom Manifesto, your plan, and a mindset that your impossible future isn't that impossible, it's time to join the fight. Everyday. Build the habits to execute on your goals; make it a core element of your life.

Have bad habits or need better ones? There's lots of good books and podcasts that you can check out. Atomic Habits, anybody?

10. Celebrate like a rock star 

Your journey may be a long one, which is why it’s so important to come up with key milestones. A milestone can be anything. Saving a certain amount of money, being hired on the side to do some work, finishing your Freedom Manifesto, anything. When you hit these milestones, celebrate with family and friends, maybe even by yourself. Honoring your progress may be the most important thing to keep you in the fight.