How to Make Bullet-Proof Choices

I tossed a cushy 6-figure tech job into the trash heap to take a shot at Hollywood. I failed.

On paper, people knew that was a garbage decision. On the record, I would do it again and exactly the same way.

In this post, I explore how we misjudge decisions and why most of us have no business wielding that gavel.

Judge By Outcome, Everyone’s Doing It

We hamper our thinking when we judge a choice to be good based on its outcome. And an outcome is good based on its semblance of the intended result.

I moved to Los Angeles to pursue an acting career. So anything short of becoming a famous thespian rendered my choice a poor one, right?

If that is true, then all I had to do to turn my poor past decision  into a wealthy one was to become a famous actor. But my decision could not have been both wise and misguided when I made it. Either I chose well, or I didn’t.

Waiting for an outcome to judge our decision is like waiting for the cops to tell us going 80 in a school zone is a bad idea.

But if we cannot judge our choices by outcomes, then what can we judge them by? The best and only way to judge a choice is by its alignment with your values.

Now before you roll your eyes, I’m not talking about horns vs halos, I’m talking about what matters to you.

And to figure out why judging by value is the best way, you first need to redefine the word ‘decision.’

It’s Just an Idea…

The headline says it all. A decision is an idea you plan to act on, nothing more.

When we judge by outcome, we roll up the idea, the execution, and the results into a case against our choice. I shouldn’t have to point this out, but I will anyway: that’s a recipe for crispy-oven-fried stupid.

To ‘choose’ is to commit to an idea. Bill Burnett so aptly states, “no plan for your life will survive first contact with reality.”

No idea survives reality, full-stop. Your choice is not the butterfly’s wing-flap that causes a typhoon in Maui, it is the idea of lift-off.

My Couch & I: An Unlove Story

A decade ago, I encouraged my then girl-friend to move in with me sooner than she intended. This concluded the ‘long-distance’ segment of our long-distance relationship.

She arrived still a student with courses to finish and her career to begin. I supported us both and promised to do so until she could share the burden.

Two-years later, with my butt pressed against a couch which smelled of dog’s urine, I broke us up.

She had limited income and maximum debt. I let her stay in the apartment, sleep in our bed, and receive my financial support. And for the next 8-months, I slept on that pee-couch.

When I shared details of my situation, I received few Nobel peace prize nominations. According to my parents and closest friends, I had ‘done enough already’ and should have kicked her out.

Despite the constant tongue-lashings, no one could sway my resolve. I knew I had to help her recover both emotionally and financially before we parted ways.

I had to do that because doing anything else would have betrayed my values, what I believed was important. 

I tell this story because it proves my next point. Outcome-based judgments open you to criticism, value-based judgments shield you from them.

Value-Based Choices are Gut Feelings Wrapped in Kevlar

When you make a choice based on desired outcome, failure forces you to judge yourself by how far you fell short.

That rubric exposes you to criticism, regret, imposter-syndrome, anxiety, and depression. But what about a values-based decision?

When you make a choice aligned with your values, that choice remains bullet-proof.

By siding with your values, you reduce your inner-critic’s ability to attack your thinking. You leave no soft spots to stab.

But fail to achieve an outcome enough times and you’ll stop making bold choices altogether.

Make decisions based on value and you can persevere.

Fuel ‘er Up

When you execute a values-based choice, you have more gas in the tank to plow through setbacks.

As reality attacks, you power through naysayers and find new paths forward.

But when you face failure in the pursuit of an outcome, you burn twice. You burn once for failing. Then you burn again when you feel regret for the untold energy you committed to a flawed course of action.

If you’re on board, the last question you might have is: what do I value?

A River Runs Through It

The Chicago river draws water from Lake Michigan through the city and into the Mississippi river. But 120 years ago, it went the other way.

In 1900, the city reversed the flow of the river to avoid water shortfalls. That reversal also secured the city as a crucial trading post by linking the Great Lakes to the Gulf of Mexico.

The city’s managers made a choice: they changed the flow of water. Was that the right thing to do? The managers knew the water would remain as ethical after the reversal as it had been prior.

Which is to say, your values have less to do with right and wrong, and everything to do with which way water must flow.

At my first job, being an eager 20-something, I yearned to help my team work better. I wanted to improve our process and cut the time-wasters.

Management met my attempts with dismay. At my progress review, my manager called me abrasive and tactless. Further, he warned me, “that at any other company, you would have already been fired.”

I stopped trying. I phoned in my work as my passion dried up like a sunbathing prune. What happened next revealed my values: my reviews improved.

I went from getting no bonus to landing thousand-dollar airdrops every 3-months.

The water at work was flowing backwards. A month after my 1-year anniversary, I left.

While it is impossible to know in advance of every juncture, you know water’s going the wrong way when you see it. That knowledge lives in your gut.

Choose Your Gut

When you spot water flowing the wrong way, you have two options. Your first option is to become a salmon. Your second is to ‘go with the flow.’ The former requires boundless effort, the latter boundless compromise.

So when you face a tough choice, mind your values and remember that a person can do the wrong thing for the right reason.

Wrong is a moral or legal judgment, right being a values-judgment.

When you choose your values, you preserve your energy, your dignity, and your access to a good night’s sleep.

Get to it.