The Art of Letting Go

How to Overcome Obstacles and Move Forward With Confidence

The Hidden Trap of Expectations

Slack, the well-known corporate messaging platform, was initially created for video games. It failed. We can only assume that the founders, Stewart Butterfield and his team, were quite upset at the time. Their initial use case didn't work out.

This anecdote highlights an important principle, a common expectation that we usually take for granted. We don’t just make plans—we become attached to the order we expect them to unfold in. The disappointment comes when reality doesn’t match the imagined sequence. This seems like an obvious response, right? Things aren't going our way, and our initial plan doesn't seem to be working.

We assume this is bad news. How did it work out for Slack?

The False Beliefs That Hold Us Back

We'd all like to believe that we're completely rational when it comes to analyzing our circumstances. Examination of our core assumptions suggests otherwise. Even though we may not state the following out loud, when we look at our past reactions to hardship, it becomes clear that we often harbor several unhelpful core beliefs:

• “If I can’t see how it will work out, then it probably won’t.”

• "Success requires that events unfold as I expect them to "

• "Unexpected points of resistance are bad—proof of failure."

These assumptions raise an important, and fairly obvious, question:

Why do we treat unexpected events as “bad”, when history shows we couldn’t have predicted most of our successes in advance?

Why Our Minds Resist Change

If you hadn't previously considered this, don't feel bad. There are several common psychological drivers that lead to these erroneous assumptions:

• Affective forecasting errors: we’re bad at predicting what will make us happy or successful.

• Catastrophizing bias: we interpret resistance as doom.

• Linear planning bias: we prefer the predictability of well ordered processes and outcomes, whereas reality is nonlinear and emergent.

All this considered, is there a better way—a more helpful framework with which to approach life's unfolding, both professionally and personally? As with anything, your expectations determine your experience. Simply enhancing your level of awareness on this topic can result in asymmetric gains.

Success Emerges Through Iteration

So how do you keep confidence alive when negative developments occur?

The simple answer: expect them.

The probability of your plan working exactly as expected is zero.

This is not a problem, and it's not a weakness—it’s by design. It can be no other way, and it doesn't need to be. Success is emergent, not predictable.

You don’t need to control the unfolding. You only need to respond honestly to what arises.

In fact, you've been doing this all along. You're just in denial about how often it occurs. There is no need to quote any science here, as the truth is self-evident. Think back on all of the big accomplishments in your life, personal and professional: your top achievements and most important relationships. How many of them came about because you had planned them out perfectly, in advance? Conversely, how many of them involved chance encounters and unpredictable developments? If you look carefully and honestly, the answer is so obvious that it's not even debatable.

The Slack Example: When Failure Creates Opportunity

So how did it work out for Slack?

The video game failed. Glitch never caught on, despite years of effort from Stewart Butterfield and his team. But the story didn’t end there. In the process of building the game, they had created an internal communication tool to keep their distributed team aligned. What began as a side utility—almost an afterthought—would become the foundation for Slack.

They shut down the game and turned their focus to the tool. Within a few years, Slack wasn’t just a useful product—it had redefined workplace communication, scaling to millions of users and a valuation north of $20 billion at its peak.

The lesson isn’t that failure is good. It’s that failure contains information. The obstacle wasn’t a dead end; it was data. The end of one plan provided the raw material for a better one.

And here’s the paradox: if Glitch had succeeded, Slack would never have existed. The very outcome that looked like disaster was the condition that made the greater success possible. The “wrong turn” was the way forward all along.

The initial “failure” became raw material for a new trajectory. This is always the case if you're willing to be open and adaptable. If you're able to maintain conviction in the face of uncertainty.

It's an inconvenient truth for those of us that insist on total control: if the original plan had worked as imagined, the larger success would never have emerged.

Practicing the Art of Letting Go

Use the following exercise often to further integrate the approach:

Step 1: Name the setback. Write down a current or recent obstacle—something that feels like it blocks your progress.

Step 2: Capture your first story. What’s your immediate interpretation? (“This is bad because…”) Let the raw, unfiltered version spill onto the page.

Step 3: Invert the meaning. Ask: If this were secretly an opportunity in disguise, how might it redirect me? Don’t aim for certainty, just possibility.

Step 4: Generate three new paths. List at least three ways this setback could be useful:

• A skill it forces you to develop.

• A blind spot it exposes.

• A door it closes so you can notice another.

Step 5: Choose a next step. From the list, pick one possibility and take a small action that moves in that direction.

This isn’t about positive thinking. It’s about training your mind to see data where it wants to see doom. Over time, this metacognitive habit—questioning the meaning you assign to events—shifts how you meet reality itself.

Moving Forward With Confidence

The reason people give up early isn’t lack of talent, or because the setback itself is devastating beyond repair. It’s over-attachment to their imagined version of success—and the inaccurate conclusions they draw when reality doesn't conform to their initial expectations. Most people are unaware that they harbor unhelpful and inaccurate core assumptions. This prevents them from working with reality, and as a result they fight against it. They miss opportunities and erode their confidence and conviction in the process.

Success doesn’t come from controlling the map, but from walking the terrain as it arises—adjusting with each step and, most importantly, realizing that this is the most efficient way forward. Iteration isn’t compromise; it’s the only way forward.