Mind The Gap Between Expectations and Reality

During the last Breakthrough Weekend, I was in a room full of successful entrepreneurs—people who had achieved the kind of success most only dream of. Their businesses were thriving, their influence was growing, and they’d hit major milestones in their lives. But as we talked, there was this unmistakable feeling in the room, something you could sense just below the surface. It wasn’t something anyone said directly, but you could feel it—a quiet sense that, despite all the success, something was missing.

I am not a stranger to this feeling – especially amongst people who have tasted success but are dealing with a kind of restlessness, an unease. On the outside, everything looks great, but on the inside, there is a lingering sense of is this it? It is as if no matter how much they achieve, it doesn’t bring the joy they thought it would.

As we dug deeper, it became clear what was going on. The group wasn’t stuck because they lacked success or ambition. They were stuck in what I call “The Gap.”

Will Smith, in his memoir, captures the Gap perfectly:

Becoming famous is amazing.
Being famous is a mixed bag.
Losing fame is miserable.

This same emotional arc applies to becoming wealthy:

Becoming wealthy is amazing.
Being wealthy is a mixed bag.
Losing wealth is miserable.

In both cases, it’s not the actual amount of fame or wealth that matters. The issue lies in the expectations we build. As we rise, our expectations rise with us, and if reality doesn’t meet those ever-shifting ideals, we feel a sense of loss, even amidst abundance.

Imagine living a life where everything improves, but your appreciation never catches up because your expectations keep rising as fast as your circumstances. This, my friends, is the trap of The Gap.

Pause & Reflect

Where in your life do you feel the pull of The Gap? Are there areas where your expectations might be preventing you from recognizing your achievements and growth?

How much of your current “ideal” is influenced by your own values versus the standards set by others?

Coaching Tool of the Week

Mind the Gap Exercise

One of my favourite tools to break out of the gap is Entrepreneur Coach Dan Sullivan’s Mind the Gap exercise.

Here’s how to apply it:

Look Backward, Not Forward: Instead of measuring yourself against an ideal future that always moves further out of reach, reflect on where you started. Think about where you were three months, six months, or even a year ago.

Identify the Gains: Write down the tangible and intangible gains you’ve made since then—skills developed, relationships strengthened, goals achieved. Focus on what has improved rather than what is still missing.

Appreciate the Progress: Spend a few moments appreciating how far you’ve come, not just in business, but in life. Realizing that you’ve already achieved growth gives you confidence and satisfaction.

Repeat Regularly: Make this exercise a habit. Every time you feel yourself slipping into The Gap, take a moment to shift your focus to what you’ve gained rather than the distance to an ever-moving goalpost.

By consistently reflecting on your gains, you rewire your mindset from lack to abundance, from dissatisfaction to fulfillment.

Final Thought

The gap between expectation and reality can either motivate us or trap us in a cycle of dissatisfaction. As you move through this week, remember that success is not defined by how far you are from an ideal, but by how you embrace the reality you’ve built. Close that gap with gratitude and see how much richer life feels.

Keep playing your Infinite Game,
Coach Sid

P.S. If today’s insights resonated with you, share this with someone who might be struggling with their own expectations. Forward this post to a friend who could use some extra clarity.