Simple Isn’t Easy…Yet Why Hard Things Get Easier (and How to Make That Happen)

Introduction

Some things (2×2 tables for example) trigger an instant “old man shouts at clouds” reaction from my teenage daughter.
I can be halfway into what I think is an insightful rant, cue the eyeroll.

However, there is an inverse relationship between the rotational force vector of teenage eye-rolling and the quality of a middle-aged dad blog post, so we’ll risk it.

If you’ve been around my blog for a while, you know I like simple mental models. The Eisenhower Matrix? Classic. Urgency vs. importance, immortalized by Steven Covey — a neat 2×2 that can reframe your to-do list in minutes.

Today’s rant is another 2×2, but one I’ve found even more useful for personal growth, performance, and untangling the excuses we make for ourselves: Simple vs. Complex on one axis, Easy vs. Difficult on the other.

And if you read my In Praise of Doing Hard Things (badly) post, you’ll recognize the DNA regarding the “how” of growing through challenge. It also happens to line up perfectly with something my collaborator said recently:

“Everything becomes easier the moment you stop wanting it to be easy.”

Here’s why that matters: The most important work you’ll ever do often lands in a quadrant that’s simple and difficult — and the only way out isn’t a secret trick, it’s time, practice, and persistence.

Before we dive into the mechanics, it’s worth making sure we’re all speaking the same language — because how we define these terms determines how we use the framework.

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Definitions

One of our rules around here is “words mean things.” So, before we get ahead of ourselves, let’s define our terms.

• Simple: Few clear steps, logical order, easy to understand, some flexibility in sequence.
• Complex: Many steps, some simultaneous, strict sequence, not obvious without experience.
• Easy: Low effort, low focus, minimal skill or resilience required.
• Difficult: High effort, sustained focus, developed skill and resilience required.

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The 2×2 Effort Map

Now that we have our terms, picture a grid. Across the top: Simple on the left, Complex on the right.
Down the side: Easy at the top, Difficult at the bottom.

That gives us four quadrants:

1. Simple + Easy – Walking, eating, watching TV. Things you can do without much thought or effort.
2. Complex + Easy – Driving a car after years of experience, or solving a short chess puzzle where the moves are obvious once you see them.
3. Simple + Difficult – Meditation, training for a 5K, having a hard conversation with someone you love.
4. Complex + Difficult – Space travel, musical improvisation, pitching in the World Series.

These quadrants aren’t about immutable truths — they’re just where a task sits for you at a given point in time.

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Where We Get Lost

Simple ≠ Easy

Knowing the steps doesn’t mean you can pull them off without effort. Running a marathon is simple: train regularly, pace yourself, don’t stop. It’s also 26.2 miles of your legs filing HR complaints and your brain offering 47 different reasons to quit.

Star Wars fans: I just saw a terrific meme about Anakin Skywalker in Revenge of the Sith. The “simple” choice was to leave the Jedi, keep his powers and lightsaber, and hang out with his rich, gorgeous senator wife. Simple choice, right? It’s so simple that the meme makes you laugh out loud and wonder why you believed the character’s angst through three movies. Except for the small matters of a galaxy-wide war, unresolved trauma, impossible expectations, and a raging inner critic whispering in his ear. Easy? Not even close.

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Complex ≠ Difficult

We also tend to assume something is hard because it’s complex. Sometimes, it’s just unfamiliar. That belief can keep us stuck “researching” or “learning the secret” instead of practicing.

This mix-up is probably the single biggest barrier to my progress as a musician. I have so many different books, methods, online communities, and lesson plans — the progress I’ve managed to make is when I pick one, and work it regularly, intentionally, and consistently over time. There’s no real secret in any of them — the method you actually use is the effective one.

The same pattern shows up in sports. I frequently see it with the boys on the baseball team I coach: they’ll happily watch Trevor Bauer explain the perfect changeup on YouTube for 45 minutes. Then they’ll announce they “know how to throw it” despite never picking up a ball. I tell them the secret is called the bullpen, and for some reason they don’t seem impressed.

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The Role of Time and Practice

Here’s the good news: Quadrants are not permanent.

• Complex → Simple: With experience, you start to “chunk” steps together.
• Difficult → Easy: Through stress adaptation — mental or physical — the same workload feels lighter.

Examples:

• Cooking an egg so it’s edible vs. cooking one for the head chef at a Michelin star restaurant.
• Fielding a ground ball in the backyard vs. as a Yankee shortstop in Fenway with 35,000 people yelling at you.
• Running an ICU checklist in a calm training lab vs. during a real code at 3 a.m.

Each of these has a gradient in the stakes, the arbiter of success, the pressure/stress, or the aspect of unknowns. But it’s plain that starting with the first step makes more sense than starting with the latter step. Each successful practitioner of the latter stage (expert chef, Derek Jeter, me in the ICU) started out in their own kitchen, the backyard, or the simulation lab.

My positive psychology professional group shared a practical definition of hope:
Hope is optimism with a plan — believing effort now will make things easier later, and showing up until it does.

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The Diagonal Path: Progressive Goal Setting

Once you’ve moved something from Complex + Difficult toward Simple + Easy, you can use that diagonal path to choose new goals — ones that are just hard enough to stretch you without burning you out.

This ties back to Challenge as a Feature: the best goals live in the growth zone, where they demand focus without crushing you.

Self-Determination Theory:

• Autonomy – You pick the challenge.
• Competence – You feel yourself improving.
• Relatedness – You share the struggle with others.

This is the path I’ve taken on the guitar. I jumped back into music more seriously after I retired from the Army. I didn’t start with unrehearsed public performance with other musicians — that would have been a disaster. I started with improvisation to backing tracks, recordings for my teacher to critique, and performing for my Labrador (very forgiving, he is). These were still challenging, but by reducing the stakes I made it easier, and reducing the complexity made it simpler.

Since then I’ve progressed to a group blues jam at a wonderfully supportive workshop I attended. Gradually, public playing will move into “simple/easy.” Then I’ll head out for a blues jam and make it more complex by playing with strangers, in front of other strangers. Once that’s conquered, I’ll add singing. Getting my voice up to snuff will be a process, and then integrating it with playing an instrument at the same time will be another process.

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Practical Self-Check

What are some practical tactics to put all this into practice? When you are struggling to make progress or even get started, ask yourself:

1. Is this actually complex, or just difficult?
2. Am I wishing it were easy instead of accepting it’s hard?
3. Have I given it enough time and reps to let the quadrant shift?
4. Is my next goal in the growth zone, or the comfort zone?

Red flags:

• “It’s so simple — why can’t I do this?”
• “There must be a secret I’m missing.”
• “I just need the right method.”

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Closing

Hard things get easier. Complex things get simpler. But only if you give them time, attention, and repetition.

The 2×2 isn’t a label — it’s a map. Where you are now doesn’t dictate where you’ll be a year from now, but the only way to shift quadrants is to start moving.

Pick something in your Simple + Difficult or Complex + Difficult quadrant today. Commit to the reps. Your future self will thank you — and maybe even admit you were right.

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