Why Spreading Yourself Thin Feels Like Winning.
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Why Spreading Yourself Thin Feels Like Winning.<br>Every commitment you take on is another border you have to defend
Steve Huynh<br>Jun 17, 2026
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Photo by Dave Photoz on Unsplash<br>If you’ve ever played Risk, you will know the feeling.<br>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.<br>Then come the counter-attacks.<br>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.<br>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.<br>And, just like that, the board has flipped, and you don’t feel so good.<br>That’s the seduction of Risk.<br>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.<br>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.<br>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.<br>That scenario plays out the same way off the board.<br>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.<br>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.<br>If we plan our lives on the days we feel powerful, we open ourselves to a major flaw.<br>The problem is simple.<br>If the powerful versions of us make commitments, our ordinary selves are left with the task of trying to live up to them.<br>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.<br>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.<br>So you keep saying “yes.”<br>Because every “yes” is one more country on the board.<br>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.<br>To me, more on my plate meant that I was winning.<br>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.<br>In the middle of it, I distinctly remember thinking to myself, More on my plate means I’m losing.<br>It took me years to see what was wrong with using the plate to determine winning or losing.<br>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<br>The quality of work on one’s plate always beats the quantity.<br>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.<br>2. “An empty hour is a wasted hour”
You’ve tried to start out doing this right. You’ve picked your one thing,...