3 Hard Lessons I Learned From My Greatest Failure

My marriage failed.

It failed me, and it failed my partner.

That’s how I wanted to see it.

But the truth is, I failed my marriage. We both did.

A marriage doesn’t just succeed or fail on it’s own — it’s the culmination of every step each partner takes in the relationship. Some steps move you closer towards your partner, and other steps move you away.

It’s much easier to blame the marriage than ourselves .. to try to create some sort of distance or detachment from all the moments that led to the failure.

People say, “it was a bad marriage” or “they have a great marriage” as though it’s an object they bought on Amazon or found on the beach. But the marriage is co-created by two human beings.

Human beings are infinitely complicated creatures. Each partner carries into the relationship their own set of expectations, beliefs, fears and complexities. Unwittingly, they pull their past wounds and traumas in behind them, like a wagon.

Each partner falls in love with the perception of what they see as the other person, but often don’t or can’t see the deeper or darker elements of themselves that will eventually surface to create tension, friction and resentment.

Hindsight is a cruel teacher, because it makes it much easier to look back and see where you made mistakes, and what different decisions you should have made. They can only be seen after the fact, which is frustrating of course — but gives you the benefit of that perspective for the future.

Thrust into a space of uncertainty and turbulence over the past couple of years — driven not only by my marriage breakdown but also selling my primary business — I decided that I needed to do a lot of personal and painful internal work. I had ignored that little voice deep inside for so long that I didn’t want to hear. I decided it was about to time, because maybe it had something helpful to say.

(HINT: it always does, even though you probably don’t want to hear what it is).

Instead of starting a new business and getting crazy busy again — to avoid the pain and hard work — I decided to slow everything down and focus internally.

This post is about me and some of what I learned and have taken away from the heartbreak of a failed marriage. I have a very long list of lessons that I am grateful to have been given through this very difficult and sad experience.

It’s written through the lens of what I contributed to where things ended up, and what I needed to learn from the experience. Among the many lessons, here are the three biggest ones that have made a substantial impact on how I relate now to myself and to others.


Nobody can fix you and your problems, and you certainly can’t fix those of another person, no matter how much you love them. Creating the environment to encourage, support and inspire someone you love to make changes, to grow and to seek help with whatever challenge they might have is important — but it’s futile if the person is unable or unwilling to take a step towards help and healing.

In a relationship, it’s easy to become self-righteous and think that you’re doing everything you can to make things work, and it’s the partner that isn’t pulling their weight. Human beings have an extraordinary blind spot that hides their own weaknesses and failings. Before long, you start to believe that your partner needs to change, and you begin to believe it’s your partner that is at fault.

Having another human being point out a blind spot you are unaware of is very difficult to accept. If your partnership is not grounded on respect and trust where both partners feel that the other has their best interest at heart, it’s easy for your heart to start closing down.

If you don’t do the work on yourself to recognize and resolve your own shadows, you’ll never find enough light in others to overcome your darkness.


I look back and can recall so many times where I just said the easy thing or took the easy way out of a conversation. I didn’t bring up how I was truly feeling or step out onto the thin branch and become fully vulnerable. I tolerated things that I shouldn’t have, and the result was a slow buildup of resentment and frustration. My naive intent to avoid creating turbulence or awkward conversation was the by-product of cowardice.

(Side note: In case you think this insight applies only to marriage, it doesn’t. You could take anything of the things in this article and apply them to any important relationship in your life. That’s what I’ve done, and I have some of the most amazing friends who know me and love me better today than ever in my life as a result.)

If I were to choose the single trait that likely lacks in most unsuccessful relationships — and it certainly did in mine — it would be courage. Brene Brown uses the phrase, “Courage over Comfort” and this perfectly describes the choice that everyone makes in their relationship, every day.

One option is to remain comfortable, safe, unthreatened .. you don’t want to hurt the other person’s feelings or create upset. You don’t want things to change. You settle. You tolerate. You accept. You choose comfort as a default.

The other path — which is much less traveled but infinitely more rewarding — is to choose courage. Choosing to be brave and vulnerable, and to say what you truly feel and open your heart to your partner.

As Brown says, “we can measure how brave you are by how vulnerable you’re willing to be.” When you can’t be fully vulnerable and honest with your partner — no matter what justification you use — you betray your partner the gift of vulnerability.

That crack in the foundation of your relationship begins to allow a slow decaying of connection, intimacy and trust. The gap between you widens ever so slowly, and is often unnoticeable — until one day, you look and realize there’s a huge chasm separating you and your partner.

If you’re not being courageous with your partner, you can’t be honest. You can’t be vulnerable. You don’t deepen your trust, and don’t have these things reflected back. And without honesty, trust and vulnerability, good luck building a truly loving and healthy relationship with anyone.


This is perhaps the greatest lesson that I’ve learned over the past couple of years. As much as I wanted to believe I had it all figured out and that I was happy with who I am, it turns out that was just a story I was telling myself.

Through a variety of different modalities, I’ve done a lot of work to peel back the onion of who I am, and where I stand with myself. Perhaps the hardest question to hear an honest answer to was the question — do I truly love myself?

When I sat in moments of truth, I found that the answered revealed itself as ‘no’. When you don’t love yourself, it’s impossible to fully accept love from another human being. You never feel worthy, and you create a whole universe of coping mechanisms to try and hide from the truth.

Whether it’s alcohol, porn, food, shopping, work or whatever other distraction you choose, it’s an effort to distract yourself from the fundamental fact that you don’t love yourself.

It’s an attempt to escape the pain that your little internal voice continues to quietly sob about. You can hear the sadness internally, but you try to numb and drown it out with whatever escape you can find.

Admitting to myself that I did not truly and fully love myself was difficult. I mean the reality of admitting you don’t love yourself feels like a huge failure — if you don’t even love yourself, then you must be completely unlovable.

“What a loser!” screams your internal voice.

You’re supposed to be your greatest fan .. so what does it mean about whether anyone else should love or admire you if you can’t even do it for yourself?

This was perhaps the greatest gift that I was given through the failure of my relationship — the Universe knocking on my door and telling me I had work to do on myself (and a lot of it, at that). Work that was necessary before I could show up fully in a relationship with another.

None of this has been easy, but it’s been tremendously rewarding.

Today, while it is a work in progress (and I think it will always be), I feel grounded and at peace in the thought that I do love myself. And I’ve come to realize that it is this single thread that runs through almost everybody .. a struggle to love ourselves deeply and authentically.

Ultimately, having such an important relationship fail is not the way that I would have chosen to receive the unexpected gifts that I have.

It has taken a lot of work to move through the pain, devastation, embarrassment and anger that inevitably flows through you in such a difficult experience.

Life isn’t meant to be easy.

If it were, you wouldn’t have any appreciation of the amazing moments and people that come through your life. Life is sometimes hard and isn’t designed to allow you to avoid pain. But it’s through having the courage to face that pain and adversity where you learn about yourself. It’s moving through the difficult times that forge who you are and give you the opportunity to learn from them.

When you choose to walk directly through that fire instead of trying to find a short cut around it, the pain is real — but it becomes a healing part of you that allows you to never have to bear that fire again.

Yet when you consistently avoid the fire, it burns slowly inside you, and creates a low-grade ache that won’t go away until you deal with it.

Today, I’m grateful for my life, and for who I am. Most of. all, I’m deeply grateful for the gift of my son Cooper, who will always help remind me of all the beautiful parts of my marriage and all the good that came from it.

Life is beautiful. It’s messy, extraordinary, challenging and rewarding.

And I wouldn’t have it any other way.