I once heard a story about the dying wish of a man of God. Despite his godliness, he had a soft spot for his possessions and prayed repeatedly that God would let him bring his things with him until God allowed him one suitcase.

His final day comes and he shows up to the Gates of Heaven where he is stopped by St. Peter who is overcome with curiosity:

“I have to ask,” Peter says, “what did you choose to bring?”

The man slowly opens his suitcase and Peter’s eyes open wide to see a suitcase filled with the most brilliant gold bricks man had ever beheld. Peter’s reaction explains everything:

“Paving Stones!?! You brought Paving Stones!”

In our lives, deciding between right and wrong is rarely a difficult thing. The hard decisions are selecting which of two right options is the right-er? Life is particularly difficult when we are trying to hold on to something good for fear of finding nothing better.

This is something I discussed in my recently released 2nd TEDx talk about the impact of fear and the way it holds us back from our greatest desires. This talk was inspired by a question that has plagued me for years:

How do I know the difference between finding contentment with a good thing vs settling for less than I deserve?

This is one of the heaviest questions that keeps coming up in my life and in the lives of my clients and the people I care about. Answering it incorrectly can result in divorce and ending of relationships. Sometimes it means leaving a job we shouldn’t or chasing a side hustle that will only cost us a fortune.

Working in management, I’ve done a lot of reading, speaking and writing about the impact of millennials entering the workforce. One of their defining characteristics is being risk averse. In their short time in the workforce, they’ve seen recessions and economic meltdowns so most aren’t afraid to live on their mother’s couches or walk away from jobs when they don’t have another job lined up.

In other words, they aren’t afraid to lose everything and start from scratch. This is something we can learn from and sometimes avoid.

Today, I’m going to talk to you about more than weight loss. I want to talk about losing everything you have.

In my life, there have been many times when I felt like I had lost everything.

  • I lost everything when my wife left me two weeks before my daughter’s first Christmas and returning to a stripped house and crying in the middle of her bedroom until I passed out, exhausted.
  • I lost everything when I got the memo that my company was laying off a majority of its California workforce in the middle of the Economic Meltdown and finding myself unemployed with zero savings, no degree and no hope.
  • I lost everything when I received a call from a terrified resident of my Dad’s apartment building. He had fallen and could not be awakened. He would never recover.

My favorite line from my TEDx talk was actually improvised. It was towards the end and I slowed down to see that I had 90 seconds left on the board and knew the time had come to make a final point or two before sitting down. I made eye contact with a stranger in the third row and felt inspired to say:

“If you trace back the series of events that led to the greatest thing that ever happened to you, I’m willing to bet that the path that led there started with something that you labeled a failure at the time. And I congratulate you on that failure.”

I’ve learned that the only things that separate the worst thing that ever happened to you from the best thing that ever happens to you is the passage of time and perspective.

The Rock, after being cut from football referred to that cut as:

“The best thing that NEVER happened.”

It led to him becoming an incredible star, far more than he would have been as a third string pro football player. The same has been true for me:

I gained everything after my wife left and I was forced to learn how to love someone properly.
I gained everything after I lost my job and found the time to lose weight and become my best self.
I gained everything after my father passed and I realized what really mattered in the world.

Unlike the man entering the gates of heaven, when you lose everything, you don’t get to bring a bag. Whether you believe in the Christian traditions of a judgment day or some other form of hereafter, there are very few things we get to take with us no matter what and where we go. These things are eternal. They cannot be stolen or seized by creditors. When all else goes, they remain. These forever items are of eternal consequence:

  • Knowledge
  • Wisdom
  • Character

Things like bank accounts and even relationships may come and go but principles are eternal and worthy of our attention. When we learn to focus on what manner of man or woman we want to become, we can maintain focus and build resilience. Items that used to be tragedies in our lives are mere turbulence en route to our personal paradise.

What if you’ve lost everything?


Growing up, I always dreamt of finding a fairy tale love story. I married at 20 and prepared to live my legendary love.

But my fairy tale was written in the wrong order: “The End” came before “Happily Ever After”. After trying everything including counseling and losing 225 pounds, The End came and I felt so broken, perplexed, confused, beset on all sides by soul crushing loss.

The years before The End produced life’s greatest silver lining in my two gorgeous daughters. They became new story: they were the ones I’d slay dragons for and adventure with.

Seeing them, I thought I’d finally arrived at “Happily Ever After” only to find that there were more chapters in the story. It had been a few years. Dating as a single father has meant finding a woman who would fall in love with three of us and finding someone all three of us would love back.

In all great fairy tales, there is an obstacle to overcome and while the hero may reject the call to face it at first, the story cannot progress until he or she does. I never planned on my marriage failing. But isn’t that how love stories go anyway? Prince Philip was just passing through the forest when he heard Sleeping Beauty sing. Romeo was just going to a party with friends.

My divorce and then being cheated on felt like great tragedies in the moment but I could not recognize my “happily ever after” until I’d gotten to “miserable right now”. Sometimes losing everything we want frees us to find everything we’ve ever wanted.

I don’t want to give the impression that getting through these periods of grieving has not been easy. But as Winston Churchill once said, sometimes the only way out is through. For me, I had the best tools available.

If you’ve been through a terrible breakup, I want to take a minute and put in a recommendation for my dear friend Traver Boehm’s incredible work:

This workbook is an incredible resource for regaining perspective and footing after a difficult breakup. I’ve used it personally after my fiance cheated on me with my neighbor (after I’d paid for our future wedding and we’d appeared on national television). The book has daily readings to get you through that all important first few months of recovery.

If it wasn’t for Traver’s book and counseling, i don’t know how I could have made it past this problem. But like every other

problem in my life, it has led me to incredible blessings and my life has never been better.

I’ve walked away with some scars and rough spots. I struggle to trust people to this day and sometimes feel unloved when I have no business feeling that way. But maintaining an eternal perspective, focusing on principles and surrounding myself with incredible mentors has made all the difference.

Once I became myself again, I was freed up to find my happily ever after in a woman who loves me better than I ever imagined being loved and has taken me to a higher level of happiness than I ever knew was possible.

What are you going through and what is it going to take you to? The decision is yours.