What Are You Waiting For?

How to actually do the thing that you keep saying you want to do.

Jack Raines
May 26, 2022

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Last Thursday, I wrote about 10 ideas that I had been pondering. Number one, as seen below, covered why you should take more risks. To quote myself:

1) You should probably take more risks.

We live in a society that values margin of safety above everything. Because of this, we tend to delay "risky" activities to some point in the future. We tell ourselves that once we have more money or more experience, we will be in a better position to take a risk.

But that's not how risk works. Responsibilities increase with age, while time decreases. 
The risky idea that could fail when you're 25? It won't ruin you. You have time to make that money back. But when you're 50 and putting your kids through school, you don't have that luxury. While it's uncomfortable to think about this in your 20s, you will get older. And your current opportunities won't be around forever. Peak uncertainty when you are young is the best time to take that shot, because uncertainty = opportunity.

If you fail? Who cares. You gain new stories and new friends, and you have the rest of your life to make more money. And if it works? You won the game.
The risk of not taking any risks only grows exponentially with age. What are you going to do about it?


Turns out that this resonated with a lot of you, so I wanted to dive deeper into this idea of risks.

We romanticize the idea of taking risks, of making changes in our lives. These changes vary from person to person. Maybe it's quitting a job. Maybe it's moving to a new city. Maybe it's ending a relationship. Maybe it's just deciding not to do what society expects you to do for once.

At first, these ideas are exciting. Invigorating. Intoxicating. But the excitement and intoxication always give way to fear and anxiety, and the ideas rarely escape our minds to become realities.

This is a post about making that leap from idea to action.

A few months ago, I came across the idea of fear setting in one of Tim Ferriss's posts.

While I didn't find this piece until recently, I was intrigued by the commonalities shared between my and Tim's thinking. It turns out, I had already been practicing my own form of "fear setting."

Both of our processes boil down to one central point: to overcome decision anxiety, to take those leaps of faith, you have to defeat the fear of the unknown.

I recommend reading Tim's piece in full, as his fear setting exercise is fantastic.

As for my own process? Buckle up, because we're about to dive in.

In the grand scheme of things, there are two seemingly-contradictory truths: everything matters, and nothing matters.

Allow me to explain.

There is only one constant rule in this game of life:

Whether you are a nihilist, pessimist, optimist (my preferred choice), atheist, monotheist, or any other version of -ist, one thing is certain: you are here for a little while, and then you are gone. Alive then dead. Poof!

Even if you cryogenically freeze yourself for 500 years, are somehow resurrected in the future to have your consciousness/brain inserted into a new body, and developments in medical technology have successfully stopped the aging process forever, our sun will still supernova in four billion years before the inevitable heat-death of the universe destroys everything.

Given the endgame here, regardless of your timeline, nothing matters.

Those agonizing decisions that drive your internal turmoil seem pretty insignificant once you zoom out, don't they?

Ironically, these very same circumstances dictate that everything matters more than you can imagine. Within this very finite existence, we are allocated a very finite amount of time. Finite moments. Finite opportunities. We don't know how many of these moments we have, and we can't get them back once they're gone. The opportunity cost of every single thing that we do couldn't be higher.

Our finite amount of time means that every single thing we do is immeasurably important. Everything matters.

If nothing matters, who cares if you quit a job you despise? Who cares if you pick up everything and move? Who cares if you end an unhappy relationship, or ditch toxic friendships?

If everything matters, and every moment carries immense importance, why would you waste a second of your time working a job you dread? Living in a city you hate? Dating someone that isn't a good fit?

The nihilist and the optimist take two different routes to reach the same conclusion.

Nothing like a bit of existential angst to get you to reevaluate your priorities. 

This realization will put your decisions in context, but it isn't always enough to spur you into action. You still have to conquer the fear of the unknown.

My Own Worst Enemy

Our minds are our own worst enemies.

Initially, the idea of change is thrilling, freeing. However, as we move closer to making these ideas realities, we freeze. Our dreams of adventure and new beginnings become clouded with disaster scenarios of "what if?"

"What if I can't find a new job?" "What if I can't make friends?" "What if I don't find love?"

What if what I have right now is as good as it gets, and I give it all away? What if this change ruins my life?

These "what ifs" are suffocating, and they keep us in line. Our fear of the unknown is a feature, not a flaw. Risk aversion is an evolutionary trait that has kept us alive for thousands of years. For most of history, routine meant safety, novelty meant danger.

However, this same propensity for risk aversion entraps us in cycles of monotony today.

Only 34% of American workers are "engaged" in their jobs, which means that two-thirds of workers are at least somewhat disengaged.

Say you are part of the 66% of Americans who aren't engaged in their jobs, and you want to quit. Your thought process goes something like this:

First, you imagine putting in your two weeks notice. You think of your newfound freedom. With the corporate shackles removed, you can do whatever you want! The sky is the limit!

Yet as you come closer to pulling the trigger, doubt begins to cloud your mind.

What if I run out of money? What if I can't land another job? What if my friends go on to achieve great success while I derailed my career? What if everyone thinks I'm a loser, and this decision permanently ruins my life?

My finest art. You can zoom in to read the text.

Suddenly, the idea of quitting the job that we hate seems like a guaranteed train wreck. 

Because of the anxiety associated with change, most people would rather live in the misery that they know than deal with the discomfort of the unknown.

You won't be surprised by your current situation. It might suck, but at least you know what's coming tomorrow morning... and the next day... and the next day...

At least you know the reality of your current suck. An unknown future represents infinite possibilities of suck that you can't imagine!

The unknown represents risk, so you have to make the unknown known. And how do you do that?

Writing everything down. 

Writing produces clarity of thought, because half-processed thoughts cannot create coherent writing. Writing out your fears turns possible "what ifs" into realistic outcomes.

Tim Ferriss refers to this exercise as "fear-setting."

Back to our previous example: say you are unengaged with your career, and you want to make a sharp pivot. You make $100k, but you are miserable, and you want to quit to travel and pursue other interests.

Write down the worst-case, realistic scenario that could occur if you do this.

You run out of money.

Okay, that sucks. What do you do next? Get a new job. Do you have skills that would make you employable? Well, yes. Obviously. You wouldn't have your current job if you lacked the skills needed to do your current job in the first place. Maybe it takes you a few months to land a new full-time job, so you have to drive for Uber or bartend in the meantime. Whatever it takes to pay the bills. But you will eventually land a new full-time job.

What if you don't like your new job?

That wouldn't be great. However, we're only doing this exercise in the first place because you are afraid to quit your current job, which you hate.

So your worst-case, rock bottom scenario is that you run out of money, have to get a new job, and hate your new job.

Well considering that you hate your current job, your worst-case scenario results in you ending up right where you started.

The only difference is you will have more fun in the meantime.

Suddenly, the unknown is known. When you realize that your worst possible outcome is your current reality, that leap becomes less intimidating. In fact, not making the change begins to look outrageous.

Now, let's write out the best-case scenario. You are going to make countless memories, and forge new friendships. You can travel to places that you've never been to, and you don't have to answer to anyone. You have time to pursue other interests.

You might figure out how to make a living through one of your new interests. Maybe an irresistible employment opportunity emerges from your ventures. At the very least, you will better understand your life priorities, and you can reenter the job market with renewed focus.

Your worst-case scenario is your current existence. Everything else is potential upside.

Once you make the unknown known, you can make decisions with increased clarity.

You can apply this to anything. Scared to ask out the girl? You're already not dating her. What, are you going to do, "not date her" harder? 

Scared to ask for a promotion? You're already not promoted. What's the worst-case scenario? You don't get promoted? You are already "not promoted."

How we think about change is quite different from the reality of change.

Once you make your unknowns known, you will see that nine times out of ten, you are already living your worst-case scenario. Making that change is an asymmetrical bet on improving your life.

Real alpha is achieved by leaning into your fears. 

There's Only One Question Left:

What are you waiting for?

Every single person reading this, myself included, has a change they want to make or a risk they want to take, but they're dreading it. They're terrified of the unknown. Maybe it's a job, a relationship, or a tough conversation. Maybe the fear of embarrassment is keeping you on the sidelines, or maybe it's the fear of the unknown, but we all have something.

And we have these little lies that we tell ourselves. Maybe you have convinced yourself that life will improve on its own, or maybe you have become resigned to accepting life as it is.

"Oh, well once I get this raise, everything will be better!"


"This is just how adulthood works."

Life isn't going to improve itself, but it can get better. The independent variable is you. This game isn't a spectator sport; you have to be the one to initiate that change.

Ferriss put it best, "Are you better off than you were one year ago, one month ago, or one week ago? If not, things will not improve by themselves."

Inertia is tough. Breaking routine is tough. Difficult conversations are tough. Change is tough. But resigning yourself to a life of indecisive settling is tough too.

If nothing matters, then what are you waiting for? Who cares? Throw caution to the wind and take that shot.

If everything matters, then why the hell are you wasting your time with people, places, and things that you dread?

What are you waiting for?

- Jack

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