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Difficult People: Deals, Frogs, Expectations & Your Superpower | Risk Management, Loss Prevention/Safety, Trending

by: Jake Dickman | March 10th, 2026

Disclaimer:
The term “difficult persons” in this work is used descriptively to discuss challenging interpersonal dynamics and is not intended to refer to or characterize any specific individual, group, or affiliation. Perceptions of interpersonal difficulty are situational and subjective and should not be interpreted as judgments of a person’s character or inherent qualities. Individuals described in this context are better understood as people navigating challenging circumstances or relational dynamics.

Let’s make a deal. You and I. I’ll be the author and you’ll be the reader. I’ll trade you my time and creativity for your time and attention. Good deal, right? Especially considering it’ll take you significantly less time to read this as it has taken me to complete its writing. So, we can likely state without too much argument that: a ‘good deal’ means I got enough out of it without having to give up too much. It then follows, a ‘bad deal’ means I lost more than I received. This is often how we are left feeling when dealing with difficult people. As a public servant, I’m sure you can relate.

To uphold my end of the deal - that is - making your time worthwhile, let’s talk next about ‘the frog’. Specifically, the one attributed to Samuel Clemmens, aka, Mark Twain. Twain is thought to have posited the question to all of us: “If you had to eat a whole frog every day – How would you do it?” It’s as provocative as it is disgusting once you realize that nobody is asking you to eat a frog every day. Enough thought on the subject should leave you understanding, whether it is hypothetical or not, this doesn’t sound like a good deal. Twain, like many others, thought it would be best to eat it whole, and first thing when you wake up. The goal being that if you must do it every day, your day can’t get worse once you put that behind you.

I often see the frog used to illustrate why it’s best to do your worst task or hardest portion of your day first. While this is a fine productivity hack, that’s not how I prefer to think of the frog. I like to think that eating the frog each morning is me making a deal with myself about the world and the way I expect it to be that day. Which is, much the way it was yesterday, the week before, and month before – full of people that at times, can be quite difficult.

All too often I believe we trick ourselves into believing that the world is going to somehow ‘come around.’ Yesterday, the week before, and the month before that – flukes. Today is the day New-Yorkers apologize for bumping into each other, the barista gets my order right, and the person on the freeway uses their depth perception well enough to merge safely behind me instead of cutting me off. Yeah…. Right.

Today is not that day, it’s not coming next week, and you can rest assured, it’s not next month. So, what’s the deal Jake? Must I simply give up my hope that people are good and then the world will be livable? Hardly. The deal I’m recommending is one where every morning you acknowledge reality. Make peace with the turmoil that you haven’t experienced yet. Learn it deep in your being that: if you work with people – today is a day that you might interact with a difficult one.

When we flip our expectations, we grant ourselves a real-life superpower. The ability to predict the future – more accurately that is. I say ‘more accurately’ because human nature is predictive. We wouldn’t have gotten this far without the ability to recognize patterns and operate on those observations. Think of a coastal people that never learned about the tide – sounds ridiculous, doesn’t it? Watching the water recede, believing it will never return to the line of seaweed left by high tide. Accurate predictions allow us to plan effectively. Ex: let’s gather clams at low tide. How similar are people to the tide? Do people ebb and flow predictably? Or are we often like to the sea in a storm, bound to churn and thrash against the rocks? To be sure, it’s both column A & B but because B exists, we must plan for it.

Here’s how you activate your superpower when storms interrupt the predictable ebb and flow; keep in mind it assumes that you woke up and ate the frog as described before.

  1. As soon as you interact with the first difficult person of your day, be it in traffic, at the workplace, or elsewhere – utter these words, or something like it (in your head): 
  • “I’ve been waiting for you”
  • “There you are”
  • “Ah, we meet again”

Or… my personal favorite

  • “Mr. Livingston, I Presume"

         2. As soon as you interact with the second difficult person of your day: Repeat step 1.

Why does this work for me? Oftentimes, we are caught reacting to difficult people or situations - and not on our terms. To bring our analogy back from earlier – we get put in a ‘bad deal’. They surprise us and often trigger some of our offensive or defensive instincts. We might be more prone to raise our voice, clench our fists, or worse. Not anymore!

By acknowledging quickly that you’re engaged in something difficult, you are given your presence back. It provides choices when before there was only reaction to stimulus.

I can’t tell you how to handle each situation. Nobody truly can. But I can make you a ‘good deal.’ Or rather, you can make this deal yourself: expect that difficulty will arise during the day. When it does, you’re not surprised—you’re prepared. That preparation keeps you from reacting on someone else’s terms and lets you decide how much of your energy the moment deserves. By accepting the difficult person or interaction as expected, you protect your peace and leave more room to appreciate the good.