How Do You Transform Obsession into Your Greatest Ally?

How Do You Transform Obsession into Your Greatest Ally?

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At a dinner last night with a group of women sharing similar political views, I asked one who was particularly vocal, “When did you become obsessed with your specific political beliefs?”

Silence fell over the small dinner table of six, the air thick with unspoken tension.

For a moment, I thought I must have crossed over some invisible line. Did I say something uncalled for, or worse, rude?

After all, isn't it apparent to everyone when obsession is evident? Moreover, I intended to offer a compliment.

I was relieved when the awkward silence was disrupted by collective laughter and a light-hearted acknowledgment of the truth of my statement.



You see, I think obsession is not only a positive quality but also a required one for anyone who wants to accomplish a worthy goal or a challenging mission.

My definition of obsession is a laser-focused quality of undivided attention and deep conviction. To be obsessed with a mission is to wake up, live with, and go to bed with that goal. Obsession doesn’t guarantee success and linear improvement toward the goal, but it means that we get back on the saddle no matter how many times we fall off the horse.

Obsession has gotten a bad rap mainly because of Hollywood; think Basic Instinct. But the truth is that it’s a powerful forcing function for directing our attention.

Twenty years ago, we didn't require as many tools and skills to safeguard and guide our attention because external sources weren't as adept at diverting our focus. Smartphones and social media have massively diminished our capacity to concentrate. 

In today's world, committing to reclaiming our most precious resource—our attention—is essential to achieving significant accomplishments. Because in the absence of a total reclamation of our attention—and this takes WORK—we are checking off boxes on a page instead of adding bricks to the house of our worthy goals.

Bronnie Ware, whose book, The Top Five Regrets of the Dying, is one I recommend to all my clients, learned through her long-time work as a palliative nurse that, surprisingly, almost all people have one of these five regrets on their deathbed:

  1.  I wish I'd had the courage to live a life true to myself, not the life others expected of me.
  2. I wish I hadn't worked so hard.
  3. I wish I'd had the courage to express my feelings.
  4. I wish I had stayed in touch with my friends.
  5. I wish I had let myself be happier.

I want you to pause and pull out today’s to-do list. If you’re in my community and interested in this work, I’m betting you have one or even multiple lists that decide and direct your limited and precious attention.

Take an honest look at each task. Does that task bring you closer or further to one or more of the regrets above?

My guess is that very few, if any, of those tasks, even when completed perfectly, contribute to reducing your end-of-life regrets.

My suggestion is to utilize obsession on purpose to focus your attention in a way that will lead to a life without regrets.

If you were obsessed with ensuring you don’t have one or more of these five regrets (before it’s too late to do anything about them), what would you add to your to-do list that’s presently missing? 

What would you subtract? For example, if you choose to be obsessed with being free of regret number 3, what actions might you take today and for the next three months to express your feelings?

What emotions will you make space for even though you don’t want to acknowledge them? 

How will you cultivate the courage to have difficult conversations that honor your emotions? 

Who can help you develop the skills to handle this situation with grace and care for yourself and others?

Where in your day will you make time for this work? 

How can you turn this behavior into a lifelong practice rather than just a three-month experiment?


I once heard David Wolpe share an old joke about a rich man who dies and stands before God. God asks, “I made you so wealthy, why did you give nothing to charity?” The man answers, “I will, I have many assets on earth, just let me give now!” The response from God thunders, “Up here we only accept receipts!”

Our time is limited for gathering receipts. Let’s get started. 

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