Sometimes You Need to Lose to Make Space for What You’ll Gain

I’m not joking when I say what I’m most proud of is not killing myself.

I lost everything in my life that mattered to me over the course of about 18 months. Just one piece of that was the 1,500 square foot home I owned in Oregon. Following some bad advice, I sold it at a loss, and rented a 1,000 square foot townhouse. Then I went through an excruciating divorce and moved alone into a 500 square foot remodeled garage. Oh, and that was when my cat died suddenly. I didn’t realize I had any tears left. My dreams shattered, my net worth 15% of what it was, alienated by most of my loved ones, I heard a voice that said, “Go to Maui for a few months, you’ve been through a lot!”

I listened. It was the best decision I’d made in a decade. But two weeks after I arrived to the island, my best friend told me he was dating my ex-wife. Wow, the dominoes that were my life structures kept on falling. 

The beauty and tropical weather aside, the first couple years on Maui were crushingly lonely, but it’s what I needed to learn to trust and care for myself. I spent a lot of time alone with my guitar at the beach, sometimes in joy, often in depression.

Eventually, I started to heal. After having lost nearly all of my friends, I have an entirely new tribe of wonderful people. I did a lot of difficult work with myself, and now the depression appears to be gone.

My increasing strength and self-reliance automatically made my work more focused and powerful. In two years, I made back all the money I had lost in the divorce—and then some. Then a friend let me buy her house on the north shore, off the market. It’s over 2,000 square feet on over two acres with an ocean view. It’s literally a dream come true. My net worth is now 40% above where it was before the disaster.

I went through hell, and I’m so glad I did, because it got me to heaven. Nearly every aspect of my life fell apart and I lived in the empty abyss that remained for about two years before a new life began to form.

I share this with you because this is what I see happen in the most successful businesses, but you’ll rarely hear about it. We love the idea of steady, linear growth. We love the idea of comfortable, joyous expansion that happens exactly according to plan.

The problem is those are just ideas. It almost never works that way.

Because we learn the most from painful experiences, growth is almost always on the far side of difficulty or even catastrophe. [Click to Tweet]

I wouldn’t trade my rock bottom for the world, because it taught me so much. Do you relate the same way to the worst experiences of your life? The things that “happened” to you?

If the worst times of your life still make you cringe, it could be you haven’t yet learned your lesson. Learn those lessons now, or life may give you another opportunity to get it. [Click to Tweet]

I’ve worked with over a thousand businesses over seventeen years, and here’s what I see. I’ve had two kinds of clients: those who are willing to dismantle what truly isn’t working and allow for temporary losses so they can rebuild the right way, and those who grip the status quo for dear life.

I’ve helped my clients close beloved locations, terminate treasured product lines, and even fire employees who are family members. This is the work of undoing, and it’s far more difficult than doing. Most people don’t seek this kind of sacred, deconstructive work. It requires fortitude, courage, and a commitment to truth, all dying values in our society of exaggerated promises via quick-fixes.

When you realize the “X Easy Ways to Blah Blah Blah” method won’t serve you, and you’re ready to the do the real, hard, but effective work, Clear and Open will be here. In the meantime, I wish you all the best with those lists of tips and tricks.

By industry standards, I’m a wildly “successful” coach. I could look back over my career and pick out a few things that “made” me that. That’s what authors do. I could write a book about my “radical curiosity,” or how to make financial management so simple a 5th grader could do it, or how to help people write great visions and plans, how to sell, how to manage, etc. I have many talents and cooked up a lot of content; and while the book might help many people, it would be a lie.

I owe my success to Life and the fierce grace it bestowed upon me, destroying everything that wasn’t true. All I did was listen. How to do that is a book I could get behind. In fact, I’m considering have it be the topic of my April live course. “Surrender to Life as Your Manager: How to Listen Before it Kicks Your Butt” or something like that.

It’s not a color-by-numbers, but there is a method. Is that interesting to you? Hit reply and let me know what you think.

Real work is not about strategizing your way through life with predictable, safe outcomes that don’t challenge your comfort zone. Real work is about making hard decisions based on true principles and actual facts, and trusting that the outcome, however daunting, will work out.

Have you noticed that Life doesn’t seem to care how successful you are? It only cares about you waking up. When you are aligned, things eventually go your way. This is a leap of faith, yes. Surrender or suffer. Accountability often means an undoing—a letting go.

Clear and Open is a community of people learning and embodying these rare but powerful values. Grab your FREE trial here.

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