Is the glass half empty or half full?

Apparently, your answer indicates whether you’re an optimist or a pessimist. I think that’s silly.

It’s a question of orientation, not optimism. Are you picking it up or putting it down? What’s your motivation in the scene? Are you even thirsty?

Your objective will shape your perspective. So how do we better understand and manage our objectives?

The easiest way to navigate life is by collecting maps. You need to collect data points. Points of reference that help your orient yourself in the world, and heuristics that let you organise the ideas you encounter. We use the ‘maps’ we gather from people around us to figure out where we are in the world, and what goals we should chase after. There’s just one problem.

You may need maps to know what exists, but you need a compass to know how to get there.

When we rely too much on maps and abstracted reference points to identify success, we’re often setting near-impossible targets and robbing ourselves of the wide-eyed joy of exploration.

The Right Measuring Stick

We typically think of success based on outcomes. The trophy, the tangible end product, the smiles on faces, the money in the bank account.

Measuring by outcomes can make us feel stagnant if we fail to achieve the singular goal we earmark as the benchmark of success. Anything short of that absolute goal sounds like failure.

If you had a goal of losing 30 pounds and you lost 28, you may have failed to hit the arbitrary target but clearly, you’ve also achieved something monumental.

The trajectory of your failures is a far better indicator than crossing some imaginary threshold.

I used to participate in a yearly writing competition called NaNoWriMo - the challenge is writing 50,000 words in the month of November (30 days).

In November 2013 I failed, having written 22,758 words.

In November 2014 I failed again, having written 37,569 words.

In November 2015 I won, writing 54,350 words.

In November 2016 I won, writing 50,583 words.

In November 2017 I failed again, writing 29,870 words.

FYI, the year I ruined my potential three-peat, I also averaged 90 hours per week at my day (and night) job in corporate law during the same month. I ended up being sick for a few days. Go figure. This was the trophy on my shelf.

In 7 years of attempts, including numerous failures, I wrote over 220,000 words. With each attempt the quality of my writing improved. My failures dramatically increased my level of output.

I sadly broke my 8-year writing streak in 2021. I was too busy building, launching and teaching the first cohort of my course, Career Hyperdrive. If you'd like to build a career you can be proud of, click here to join us!

Similarly, if you enter the interview process for 5 roles and get 0 offers that might indicate you’re not cut out for the job. But if your first failure was in the initial phone screening where you were describing your background and the last was a final interview delivering a pitch, then your trajectory should tell you that you’re on the right track. Refining your process is more important than counting your wins.

Measure by progress.

Make your benchmark of success the opportunities you garner rather than your outcomes. Outcomes can be deceiving. Legendary poker player Annie Duke talks about the perils of ‘resulting’ in her book, Thinking in Bets.

Annie begins by recounting the story of Seattle Seahawks coach Pete Carroll. In the final moments of Super Bowl 49, Pete made a decision that is widely remembered as one of the most controversial in football history.

If you're not a fan of American Football and have no idea what any of this means, just stick with me!

How to Lose A Super Bowl

The Seahawks had the ball at the 1-yard line. There were 26 seconds left in the fourth quarter against the New England Patriots.  It was second-down, the Seahawks were down by four points, and they had one timeout remaining.

The Seahawks only needed to move the ball one yard forward to score and win the Super Bowl.

Carroll then instructed his quarterback to toss the ball rather than run the ball. The run was the obvious play. It's what everyone was expecting. Carroll called a toss play instead, and the Seahawks lost a Super Bowl game that they were on the verge of winning because the ball was intercepted in the end zone. Insanity.

Did Coach Carroll absolutely just wet the bed? Was this a monumental error? That's what everyone was thinking. The fans wanted his head on a stick. The sports commentators couldn't make head or tail of it.

But here’s the snag - maybe we were all falling for the trap of resulting.

Annie points out that based on 15 years of NFL data, the chance of a short-pass interception is less than 2%. In addition, if the pass is not completed, the clock will automatically stop. The running back can then take the ball and try to score a touchdown without spending a timeout.

What does all of that mean?

On the basis of the information he had, Pete's decision was actually correct. Statistically, despite picking a move that seemed counterintuitive, he was absolutely right. Yet the Seahawks paid a heavy price for an interception that was exceedingly unlikely. They succumbed to an anomaly. And then, as if the interception was inevitable, everyone pointed the finger at Coach Carroll!

Forget about the outcome

According to Duke, when we're judging from a distance, the way we typically measure the quality of a choice is to look at the results. If the outcome is negative, we infer that the decision was also negative, and vice versa. We tend to overlook the importance of luck in the equation.

Self-judgment, on the other hand, tends to be biased in our favour. If the result is fantastic, it's because we're fantastic. We want the blame to be placed somewhere else when anything unpleasant happens. As a result, we tend to place blame on a variety of factors.

So here’s an idea - forget about outcomes.

Ignore the vanity of mimesis and aspirations of accolades; feedback that colludes with ego to quell your ambition. Look for clear, tangible progress. Signal among the noise.

Focus on making the right decision.

Aim to fail on bigger stages. Break new ground with each mistake.

Accepting that failure is a prerequisite for growth is just the first step. Understanding how to intentionally plan for the best possible failures is a next-level skill.

Further Reading

The Now Habit


The Power of Habit

Information Processing Bottlenecks
There is a limit to the amount of knowledge you can access when you first begin studying. Because you’re open and there’s not much to absorb, you’re like a sponge, soaking up everything. Access to information ceases to be a constraint very quickly in primary education. Once you bring home
Swimming vs Thrashing
Life isn’t easy. You’re dropped in a body of water at birth with no instruction manual. Some people have the privilege of extensive training and signposts, but many of us have no idea where to go or how to get there. Nobody will teach you how to swim, and you
Stop pretending broccoli is delicious
One of the most important tools in overcoming inefficient production is the need to be honest with our present selves. Stasis is comfortable. It’s okay to admit that. And often, the things we want to substitute stasis for, lack the inherent goodies to compel immediate action. Cake doesn’t taste
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