(2/26/21) how to get unstuck, an overthinker's guide

because i keep getting stuck in new and unpredictable ways

Hey everyone,

This one is a bit longer than usual! I think you’ll enjoy parts I and V if you want to skim.

Come back later for the rest. There are references at the end.



Table of Contents

I. We Are Stuck
II. Visualizing Stuckness
III. Discovering Control
IV. Ways of Losing Control
V. Getting Unstuck
VI. What Should We Control?
VII. What We Cannot Control
VIII. References

I. We Are Stuck

I haven’t sent you an email in over a month. But prior to taking this break, I sent you an email for 20+ consecutive weeks. Sending them has been excruciatingly difficult. I haven’t been satisfied with anything I’ve written during this time.

Many weeks I just wanted to phone it in and retire from the small-stakes game of sending essay-length rants to my friends.

If you’ve tried doing anything new with any consistency, this should be a familiar feeling. The first week or so, you’re inspired and motivated. You’ve got everything organized, maybe a strict schedule, and plenty of ideas of how to put things into action.

And then … things … get hard.

You slip a few times, you fall off the wagon a few more times. You look at the quality of your output and notice it’s not perfect. Something else catches your attention.

You get stuck.

Open and shut case. You weren’t cut out for this.

You quit.

I’ve done this so many times for so many different things. It’s really unbelievable. My mind has the ability to persevere in some areas and completely give up and shut down in other areas.

Many of you probably feel the same way. I’ve been reviewing the past year of your replies and feedback to things I’ve written, and the following themes appear over and over:

  • I’m often distracted by ____

  • Where do you even start with ____

  • How do you decide ____

  • How do you create time to ____

  • ugh the pressures of modern life, overdosing on screens, the patriarchy, capitalism, broken institutions, etc, etc

We’ve never been more materially well off. But our wellbeing is out of wack. Why?

In The Psychology of Money, investor Morgan Housel cites the work of mid-century American psychologist Angus Campbell. According to Campbell, our wellbeing comes down to having a sense of control:

Having a strong sense of controlling one’s life is a more dependable predictor of positive feelings of wellbeing than any of the objective conditions of life we have considered.

A sense of control is the first thing modern life snatches from you.

If you’re not swept up by social media scrolls or TV binges, you’re caught in the storm of corporate career maneuvering and tyrannical bosses.

If not that, you’re fretting over personal finances or whether you’ll ever be able to afford a house or find a partner.

And all of this assumes you have a steady paycheck, live in a safe zip code, and aren’t crippled by student debt or car loans.

The default configuration of modern life is that we’re trying to escape something about it. But when we try, we get stuck.

When you don’t have a sense of control, you get stuck. If you don’t know how to snatch control back, your stuckness will deepen and you’ll wake up one day wondering what the fuck happened.

I wish there were a playbook for getting unstuck. Something like “Getting Unstuck: A Manual for Overthinkers”.

So for the remainder of this email, I will be cobbling together the rough beginnings of such a manual. (I’ve been working through this for a few years, here’s some prior thought on ruts if you’re interested)

II. Visualizing Stuckness

How dare you settle for mediocre just because you’re busy coping with too many things on your agenda, racing against the clock to get it all done.”

The Dip, Seth Godin

Being “stuck” goes a little like this:

  • You know that there’s somewhere else you’d rather be.

  • You’ve tried making moves before but you see limited, unconvincing progress.

  • You have no idea how to make more effective progress.

To reiterate, to be stuck is to lack a sense of control. Feel the anguish of the stickman below. Where should he go? How?

The Dip is a compelling visual. Just by looking at it, you recognize the fundamental struggle:

To improve and get anywhere worth going, we have to pass through circumstances that feel an awful lot like getting worse.

The dip is where we get stuck.

How we navigate this dip determines our sense of control over our lives.

How we navigate the dip depends on discovering how we discover what we can control.

III. Discovering Control

I first heard the Serenity Prayer from a former mentor Mrs. Gay. During my failed stint as a math teacher, a series of very challenging events reduced me to tears.

I sat in my classroom explaining the situation through sobs. Mrs. Gay sighed, gave me a big hug, and said:

God grant me the serenity to accept the things I cannot change,
the courage to change the things I can,
and the wisdom to know the difference.

These words cut deep. I can choose to feel hopeless about the external conditions that trap me. But I can also choose to act on my locus of control.

What can I change? How do I claim control over these aspects?

Since that moment almost ten years ago, I’ve viewed my life as a laboratory for answering these questions. Through a lot of trial and error and study, I’ve learned that control follows a process.

The degree of control you have or don’t have depends on your mind’s relationship with a particular flow of behavior:

You “see something.”

Prior to sensing that something, it is undifferentiated and conceptless. Your mind conceives “something” and turns into a recognizable set of symbols.

“A room with a couch, a rug, and a coffee table.”

“A man wearing a swastika tee shirt.”

This initial activity breathes life into your field of experience:

  1. Discriminate: the mind conceptualizes. It subdivides, recombines, sequences, merges, attacks, weakens, and organizes objects to make sense of them.

  2. Motivate: the mind imagines and fantasizes. It merges concepts with memories, desires, and fears to create inspired simulations, beautiful visions to aspire towards, nightmare scenarios to avoid.

  3. Decide: the mind makes conclusions. It takes strong motivations and translates them into convictions and attempted actions. We could also call a decision an intention.

  4. Act: the mind realizes intentions into action. But only if confidence — or the expected emotional outcome (EEO*) — of taking action is sufficiently high. Otherwise, no action will be taken.

*EEO: From Luca Dellanna’s The Control Heuristic.

An important note about this flow:

It doesn’t always happen linearly. You may cycle back and forth between different parts of the process.

However, each step is a gate to the next step. Only qualifying members of one step get to move on to the next step.

  • You’re not gonna be very motivated by something if you can’t make sense of it.

  • You’re not gonna decide on something if you aren’t motivated by it.

  • You’re not gonna take action on something if you don’t have sufficient confidence about it.

Gates are very important for us to function. Imagine if every single sensory input and discursive thought was treated exactly the same, all the time. You wouldn’t be able to discern your mouth from the air it sucks in.

But our personal successes and tragedies (and our genetics to a degree) color how we gate. They protect us and keep us alive by pushing us towards what feels good and away from what feels bad. Hence why in some areas we persist and other areas we quit early.

We can take control of our lives piece by piece by thoughtfully observing each of these gates, then making subtle tweaks.

But before we get into how we can gain control, it’s useful to look into how we lose control.

IV. Ways of Losing Control

When we feel stuck, we lose control of the things we once probably did control successfully.

You can identify how you’ve lost control by asking yourself a few questions — these are some of the same ones listed out in Part I.

  • Discrimination: What the hell am I doing?

  • Motivation: Why am I so unmotivated?

  • Decision: How do I decide what to do?

  • Action: Why can’t I stick to anything?

Usually, one of these questions stands out. It might even hurt to see on the screen. That question’s corresponding gate is probably the primary bottleneck that’s keeping you stuck.

Recognizing that you have a problem is key. You can’t get unstuck if you can’t acknowledge you are stuck.

After that, identifying the bottleneck is crucial. If you’ve got an action problem, stop thinking it’s a discrimination problem.

I’ve lost track of the number of times I’ve tried getting unstuck by focusing on the wrong thing. Or pretending I don’t have a problem at all.

V. Getting Unstuck

Once you’ve identified the bottleneck of your stuckness, you have to flex your intellect, creativity, and emotional resilience to get unstuck. You’ll have to use your full being to gain control back.

I like to visualize control as breathing life into a wad of concepts you have in your head. (Represented by the humble sticky note).

This wad of concepts dances with your desires and your instincts, hurling you into motion. Changing your relationship with it in the right ways will allow you to steer it, rather than it steer you. And each bottleneck has different tactics you can deploy to create this change.

Your Bottleneck: Motivation

If you’re having a tough time staying motivated, go on a sense-making expedition. Go find experts. Coffee chats, phone calls, conferences, books, podcasts, whatever it takes. Understand things better.

Your “wad” of concepts will begin to take a more dynamic, relational shape:

When you start connecting the dots and making sense of things, your ability to dream will improve. And so will your motivation.

Example: Considering searching for a new job or career change

Your Bottleneck: Decision

If you’re having a tough time making decisions, go on a motivational journey. Find a community working together on some of the same challenges you’re struggling with. Look for testimonials, firsthand accounts, and anecdotes. Get inspired.

By doing so, you will allow your memories and desires to interact more freely with the concepts you have in your head. Some of your cherished memories and desires will naturally fancy some of these concepts more than others, making them loom larger and more pressing in your mind.

Working on memories and desires can help resize concepts, making some more relevant and some less so. This resizing process allows the most compelling ideas to become no-brainer decisions. It also might point out big holes in your understanding, kicking you back to another sense-making expedition.

Example: Deciding on where to go for school

Your Bottleneck: Action

If you’re having a tough time taking action, go on a decision-making retreat. Figure out why it doesn’t feel good to act on certain decisions (even though you know you want to act on them).

Rearrange your immediate environment to attach positive emotions to the action you wish to take. Replace all snacks in your pantry with nuts and blueberries. Hire a trainer so that you get excited for your workouts. Produce a weekly newsletter and focus on stirring conversation (aha!).

By making it feel better when you do take action, you’re more likely to do it again and again. This process might also take you back to the drawing board. Maybe the actions you want to take are way too hard to produce a strong EEO (expected emotional outcome) for.

Example: Sticking to a workout or diet plan

VI. Conclusion: What Should We Control?

There are things we can control, and there are things we cannot control. When we get stuck, it is usually because we’re not making use of our own minds and bodies to get unstuck.

Here’s the thing about control, though … the control desire can go rogue.

Let’s take the example of an office that is too cold.

Reactive — You could turn up the thermostat, making the room itself warmer. #globalism

Responsive — You could put on a sweater, making your immediate environment warmer. #localism

Adaptive — You could use your mind to grow accustomed to the cold office. #solipsism

Each of these approaches to gaining control can be successful or disastrous, depending on the context. The Serenity Prayer acknowledges this tension: “…and the wisdom to know the difference.”

Thus the pursuit of control needs to be very patient, honest, and open to learning. Otherwise you may end up addicted to control and tear up the entire earth so that it bows to your needs. Or so scared of control that you tear yourself up to bow to the world’s needs.

VII. Bonus: What We Cannot Control

There is also the realm of why we think we have any control at all. But that gets us to a place where written language cannot go. For those curious about this realm, I highly recommend Wisdom Eccentrics by Ngakpa Chogyam.

VIII. References

  1. Ngakpa Chogyam’s Wisdom Eccentrics

  2. Luca Dellanna’s The Control Heuristic

  3. Morgan Housel’s The Psychology of Money

  4. Seth Godin’s The Dip

  5. Countless conversations with people reading this email. Shoutout namely to my younger brother for years of exploring (and still exploring) these concepts together.

Thanks for reading! It’s a bit raw and unrefined, but I hope some of you find it helpful.

Spring is right around the corner, and I’m feeling good. There’s a side project I’m shooting to launch in the next couple months. I’ve been posting early explorations of it to my Instagram Stories, so give me a follow if you wanna check it out.