[51] A Fork in the Road

Jan 09, 2023

GM Readers,

As we are rounding the corner toward Life in Color’s one year anniversary later this month, we are spending January writing more reflective / philosophical / musings type essays.

This also gives us a chance to take a break from the deeper Web3 and technology pieces we’ve been writing for the better part of last year.

We’ll end January with our 1-year reflection. Stay tuned!!

Today’s Essay: Recently I’ve had different people reach out to me for advice (which I always consider an honor that people want to hear what I have to say). Particularly in light of the current market conditions (tech market correction, Web3 implosions, Crypto Winter, etc.), people are worried about their careers, companies and the broader industry they are in. In a bull market, when times are good, the answer is easy. When times are tough, which path to take at the fork in the road feels higher stakes.

Today we unpack this through some musings in a short essay.

Hope you enjoy!

📈 Life in Color Tip:

In times of chaos (pandemics, bear markets, crypto winter), we often want things to return to normal. We want the world to go back to where it was, to simpler times… to better times.

But deep down inside, we know that the world has changed, and we cannot simply just go back to the way things were.

The tension and angst we often feel comes from two places: the first is knowing the world has changed, the second is accepting that the world has changed.

The former is easy, but the latter is challenging.

We know we have to accept this new reality, but most of us don’t want to accept it.

But why don’t we want to?

Because if we accept the reality of this new unstable world we are in today, we have to let go of the stable world of yesterday we are used to.

There is a fear of loss involved, so we constantly ask ourselves: will we ever get back to where we were? Will things ever go back to normal?

This happens whenever we enter new realities. We find it hard to accept a new reality because we haven’t figured out how life will work in this new reality. We struggle with this because the certainty we get from our old life gives us some sort of peace.

A Fork in the Road

After a crazy 2022, it feels like the world has only gotten more chaotic. We’ve now entered a full-on crypto winter. More broadly, the technology sector is going through a huge correction (i.e. layoffs, etc.). The party of the bull market has come to a full stop.

And all of this feels like just the tip of the iceberg. 🥶 🧊

Everyone is facing high amounts of uncertainty and in light of the unknown, we are all presented with our own forks in the road. There are big decisions to be made across many areas of our lives:

On a personal level, some of us are thinking, should I go back to a stable job and/or industry or do I continue down the risky path of working in Web3 / startups / emerging industries?
At the company level, some founders are thinking: should I pivot to profitability now that VC funding has dried up or do I continue to focus on growth at all costs?
From a sector level, as an industry we are thinking: should we reign in our experiments and play it safe or do we continue pushing the envelope on innovation?

Usually when the fork in the road metaphor is presented, it highlights a high stakes situation where once an important decision is made, the course cannot reverse.

False Precision

The precision that most education systems teach us is largely false in the real world.

For example, in math class, once you solve a particular problem, you’ve completed that specific task and are rewarded for it. Whatever happens in literature class or science class doesn’t influence the math class problem. Further, in the math class example, you either got the math problem right or you got it wrong. There is no middle ground.

In the real world, things don’t really work like this (or they rarely work like this)!!

There isn’t a clear concept of right or wrong.

It’s not definitive.

Decisions are interconnected and influence each other in a never-ending web of complexity. Understanding this is a hard thing even for adults.

In reality, looking at decisions as a spectrum (which way do you lean, where do you overweight or underweight) is more useful because it takes the binary out of the equation.

The world is chaotic. The sooner we see the world for what it really is, the better.

So what choice do I have?

Going back to all the forks in the road that we might be facing, there are a few considerations that I’ve seen to be effective in helping us get some clarity:

Regret Minimization: Which decision would you regret less?

Clear Optimization Function: Are you optimizing for downside protection (and capped upside) or are you optimizing for risk taking (and uncapped upside)?

Assume either path leads to failure: What if both paths lead to failure, which failure would you prefer to have?

Can you do a bit of both: Does your decision have to be binary? Can you be overweight in one versus underweight in another? Is it a true fork in the road?

What are your tradeoffs: Either path has tradeoffs. Which tradeoffs are you more content with?

Ultimately this is about being deliberate.

Yes, this is common sense. And almost a stupidly simple answer to “which fork in the road do I take?”

But common sense is often not common practice.

Simple is not easy, simple is often hard.

Where I’ve seen people fumble with big decisions is that they don't know what they want out of the decision.

So absent being deliberate, many of us (whether we want to admit it or not) reason from a “should” framework. I.e. I should do this because of some arbitrary framework for life that’s been prescribed to me by some system or person.

The problem with operating from “should” is that it removes the world’s complexity from a decision. It assumes that if few variables about you, your situation and your problem are true, then there is an obvious / “right” answer. For smaller decisions or more deterministic ones, a “should” framework might work.

But for big, hairy, uncertain, fork in the road type decisions… operating from “should” completely misses the point.

Our world is filled with conventional wisdom that tries to take the complexity from your decision and (over) simplify down to some “obvious” answer.

Conventional wisdom has said when faced with a fork in the road, take the road less traveled. But either path you choose at the fork in the road has not been traveled by you… so either path, to you, is a road less traveled (or has not been traveled).

Whatever decision you make won't be right. But it won’t be wrong either.

“Right or wrong” is the wrong framework. The right decision is the one you make deliberately.

This essay can only tell you to be deliberate.

But it cannot tell you how to be deliberate. Because if it did, it would be prescribing yet another “should” framework.

We all need to stop “should’ing” ourselves. 💩