The Disappointment Sabotage: How Avoiding Disappointment is Disappointing You

It happens a lot. I meet someone who is interested in hiring an executive coach and I ask, in different ways, about their vision for their work, life, and legacy.

What do they want that they don’t have now? What is the “big dream” that induces passion in their voice and body? If nothing stood in the way, what would they do with their remaining time on the planet?

“I don’t know,” they initially respond, “those are big questions.”

They are big questions. “I don’t know” is a telling answer.

I relate. Not long ago, I felt stuck in my legal career. I was achieving and comfortable as an attorney, but simultaneously stressed and bored. This job wasn’t “it,” but I didn’t make a move because I didn’t know what “it” was and I was afraid “it” did not exist. One day a friend asked me, “What’s your hope for your future?” I froze as an unsettling fear swept through me. What was the answer?

Most of us struggle to answer these "big" questions for one of two reasons: (1) we don’t know and avoid knowing by offering a vague response like “I want more happiness” and “greater freedom” or (2) we know the vision, but we are afraid to reveal it “out loud.” Just beneath the surface of these reasons, the common source of our hesitation (to know or to answer) eventually reveals itself in a predictable refrain: “I just don’t want to be disappointed.”

At the core, we struggle to describe a “vision” for our future because we fear that talking about what we want most, out loud to another human, will make us unacceptably vulnerable to crushing disappointment if those things do not happen.

On the other hand, if we downplay what we want from our careers, finances, relationships, or our impact on the world, maybe we’ll feel accomplished or pleased when we trick ourselves or others into believing we’ve exceeded our purposefully-sandbagged expectations. Does any of this sound familiar?

I call this mind-maze “The Disappointment Sabotage" because the very actions we take to avoid disappointment only serve to guarantee its presence in our lives. We aren’t avoiding disappointment, we are living in it.

We all want beautiful, thrilling, and meaningful stories for our lives whether we dare to utter those desires aloud or not. Our fear of disappointment only validates our longing for something we do not currently have.

Resisting a big vision to avoid disappointment is like standing in the rain at the edge of the ocean refusing to swim because we don’t want to get wet.

We are soaked to the bone and we don’t have the benefit of exploring the vast power, depth, beauty, challenge, and adventure that await us if we dive in.

Will a big vision create opportunities for disappointment? Yes. Will you be disappointed if you avoid the vision? Yes.

So how do we avoid disappointment? We don’t.

But we can ensure the vision we’re after is worth the disappointments we suffer on the way.

What vision for your future is worth the risk of failure?

What are the costs of staying on the shore?

If you see in yourself a belief that you are “avoiding” disappointment, I encourage you to get curious about the questions above.

The shore isn’t going anywhere, let’s see what the ocean has to offer.