Why Spreading Yourself Thin Feels Like Winning.
Every commitment you take on is another border you have to defend
If you’ve ever played Risk, you will know the feeling.
Early on in the game, expansion feels incredible. First you take one country off an opponent, then another, then another. Eventually, you capture a whole continent. Every territory you hold earns you more new armies when your turn comes around again, and it feels good to see the map of the world filling up with your color. It looks like you’re winning.
Then come the counter-attacks.
And because you had to spread your armies thin to grab all that land, you’ve left some territories guarded only by single pieces. The moment your opponent breaks through into one, they can then bulldoze their way through a whole swath of your territory in a single turn.
With only a single die to defend against your opponent, you watch helplessly, a mere spectator, as, one by one, your understrength armies succumb to the onslaught.
And, just like that, the board has flipped, and you don’t feel so good.
That’s the seduction of Risk.
Spreading yourself thin feels great while it’s working. While you’re winning, it doesn’t feel like you’re risking anything. Or if you’re aware of the risk, it feels worth it.
The board fills up with your armies. Every turn, your position looks better than the last, and your momentum convinces you that you’re winning.
That feeling holds right up until the tables turn. And when they turn, the same sprawl that felt like progress is what makes your fall so total.
That scenario plays out the same way off the board.
In college, our advisors told us to take fifteen credits a quarter, eighteen at the most. Me, I thought, Why stop there? If I could handle eighteen, surely I could handle twenty. Maybe even twenty-five. I felt sharp and ambitious, and that cap looked less like good advice and more like a challenge.
I didn’t end up taking the twenty-five. It was luck more than wisdom since the classes I wanted were full, but it spared me a lesson those advisors had clearly watched plenty of ambitious students learn the hard way. Doing well enough with fifteen proved to be difficult enough.
If we plan our lives on the days we feel powerful, we open ourselves to a major flaw.
The problem is simple.
If the powerful versions of us make commitments, our ordinary selves are left with the task of trying to live up to them.
Every “yes” is a check written against the future that has to be cleared. And clearing checks written by “powerful Us” is especially tough. Why? Because, by definition, we are only average most of the time.
This article provides a guide to recognizing overextension in ourselves, so that, before we commit to things, we can be sure that we are only taking on what we can hold.
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1. “More on my plate means I’m winning”
When your work piles up and your calendar is crammed with activity, you may feel that this is proof that you matter. The more you’re holding, the more important you must be.
So you keep saying “yes.”
Because every “yes” is one more country on the board.
When I first entered corporate life, I felt left out because my calendar was empty. I wanted to be in all of the meetings. I thought that would mean that I was important enough to be essential.
To me, more on my plate meant that I was winning.
Contrast this to the years right before I left Amazon. Every hour of the day was double-, triple-, or quadruple-booked. I had essentially declared time bankruptcy. And I longed for those days when my calendar was completely empty.
In the middle of it, I distinctly remember thinking to myself, More on my plate means I’m losing.
It took me years to see what was wrong with using the plate to determine winning or losing.
The number of appointments on my calendar was never the score. Treating either calendar as the problem meant I was counting the work instead of weighing it
The quality of work on one’s plate always beats the quantity.
Actionable advice: Ask yourself what would be the most worthwhile use of the time in front of you. What would make today worth it? What would make this year worth it? Whatever your answer is, it’s more likely to be one big thing, a single win, that would overshadow everything else you might otherwise spend time on. It will rarely look like a long to-do list. Find that one thing. Make it your main quest, and let the rest be side missions that you can drop without losing the game.
2. “An empty hour is a wasted hour”
You’ve tried to start out doing this right. You’ve picked your one thing, you’re guarding the time for it, but now you’ve hit a natural pause, and you’re waiting. It could be for an approval, or maybe there are major dependencies that aren’t ready, or a decision is stuck one level above you.
There’s slack in your week. And slack feels like failure.
So you do the responsible-looking thing and fill the empty space. You pack the open hours with new commitments, because you think that an empty calendar shows you’re not doing enough.
But then the thing you were waiting on clears, and now you’re supposed to get back to the main quest, but you can’t. You’ve spent the slack on the obligations that you picked up to avoid the discomfort of waiting.
The problem is magnified on a team. I have seen managers lose their minds when they’ve seen blocked developers sitting idle. To them, a waiting engineer was wasted money, so the reflex was to hand them another thing, anything, to fill the gap. But when the blocker cleared, the engineer was buried in filler work, and the high-priority thing they were supposed to finish had to sit untouched for another week.
In the AI era, we’ve built a faster version of the same trap. When an AI sits idle, we feel the same itch to keep it working, so we feed it busywork. Hand it work that doesn’t matter, and all we’re doing is burning tokens to feel productive.
I did this to myself once on a cross-functional project I was leading. The senior engineer I needed sat on another team. He went out for a week, and I was blocked until he returned. Instead of protecting that gap, I told a few recruiters that I could take more interviews. But because of the scheduling, those extra interviews took place during the weeks after the senior engineer got back. Also, while he was away, I had grabbed a “small” task that was simple to build but also happened to be critical. By the time he had returned and the main quest needed me again, I was buried. I spent the next three weeks digging my way out of the hole I’d dug for myself.
Actionable advice: When slack appears, treat it as a reserve that you’ve earned, not a hole to be plugged. If you do decide to fill it, take on only things that you can drop the instant the main quest comes back online. Before you pick anything up, ask one question: When the blocker clears, can I walk away from this cleanly? Anything that fails that test will be a commitment you’ll regret taking on, no matter how small it may look.
3. “The busier I am, the more valuable I am”
This one feels true. Being in demand looks like a measure of value. If everyone needs a piece of you, you must be important. So you spread yourself thinner, you take that extra meeting, or you own the additional thing, and you justify it by saying that you are indispensable.
I’ve sat on the other side of that, across the table at a lot of interviews and promotion conversations. The people who moved up were never the ones who did a little of everything. Instead, they owned something so deeply that the org or team couldn’t route around them.
In contrast, a person who is spread across ten different things is easy to replace, ten times over.
Depth is what makes you hard to replace.
In Risk, the player with a concentrated position is more likely to succeed. They can absorb the hits that would wipe out thinly spread players.
The cruel thing about “The busier I am…” lie is the timing of its appearance. It feels most true exactly when it’s costing you the most.
The week you find yourself in every meeting, copied in on every thread, and pulled into every decision is the week you feel the most valuable. Yet it is also the week that you are quietly becoming the most replaceable.
The feeling of winning and the fact of losing both grow in parallel, which is why almost no one catches it when it’s happening.
Actionable advice: Think of a few people you admire for what they’ve achieved. Look closely at how they got there. Are they impressive because they do a staggering number of things at once, or because they do a small number of things at a high level? It’s almost always the second. The people we tend to remember are those who have gone deep on something. We rarely remember people who spread themselves thin across the board.
Hold What You Can Defend
In Risk, the player whose armies have spread across almost every territory may look like they’re winning. But more often than not, in my experience, that euphoria lasts only until they realize they can’t hold their ground. An opponent attacks a poorly defended territory, and then they all fall like dominoes in one turn.
The player who usually takes the game is stacked deep, with a reserve still in hand. That’s who you need to look out for.
Your commitments work the same way. Don’t be overly ambitious on day one and create a pile of work for yourself.
You can want a lot and still come out ahead. The best way to get there is by never holding more ground than you can defend.
So before you decide to take on a new “territory”, look hard at the ones you already have. Ask yourself if they’d survive a bad week.
Above all, remember that if you spread yourself thin, you may feel like you’re winning, right up until it all comes apart.
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Love the take. A little too risk heavy analogy tho. A little explanation of the game would be a very important hook for someone who hasn't played the game.
Oof. A timely reminder. Thanks. Great analogy. It’s been quite a while since I played Risk or Axis & Allies or Dungeons & Dragons—tabletop games were sacrificed on the altar of productivity years ago. Might be time to play again. Incidentally, my morning pages were about constraining my capacity for new clients and the relationship of that number to the price I need to set on my time to hold that line.