The Questions I Keep for Bad Days & Seasons

Early in my career, a manager decided I should go. Not fired — pushed. Pressured to back down or get out.

Around the same period of my life, joint ventures with a couple of friends flipped over, a few times. A business stint went sour. None of it gradual — the kind of news that arrives in one conversation and rearranges your week, your year, your sense of yourself.

Here’s what I learned in those rooms, and it’s not the lesson I expected: when shock hits, normally your thinking is the first thing to go.

Everyone assumes that in a crisis they’ll rise to the occasion and think clearly.

Most of the time, honestly, you won’t.

At least, I speak for myself. I clearly didn’t. In shock, pain, or denial, the mind doesn’t generate good questions — it generates loops.

Why me.

What did I do.

How could they.

Those loops feel like thinking. They’re not. They’re the mental equivalent of pacing.

You can’t build the tool while drowning

The fix I stumbled into then, and have deliberately built on since, is this: the questions that save you in a crisis have to be written before the crisis. You don’t fight a flooded mind with willpower, the same way you don’t fight any default in the moment. You pre-commit — and a pre-committed question is just a pre-committed rule for your attention.

It tells your mind where to go when your mind has stopped taking suggestions.

Back then my set was crude — questions I’d picked up from the personal-development books everyone read. They were borrowed, and they were better than nothing, because any prepared question beats the loop. But over twenty years of decisions — clinics, property, partnerships, family — the borrowed set got replaced, piece by piece, with questions earned from my own failures.

This is the set I actually run now.

The set

1. What’s the stated reason — and what’s the reason actually operating?

The fear-check. When I’m avoiding a call, delaying a decision, or suddenly very busy with something else, the explanation I give is usually respectable and usually not the real one. Fear and ego wear logic as a costume. Naming the operating reason, even just to myself, collapses half the problem on its own.

2. What here can I actually control, what do I merely influence, and what do I touch neither?

Then ruthlessly: all energy off the third bucket. In the firm episode, I controlled none of my manager’s politics — but I controlled whether I stayed. The moment the question sorted those buckets, the decision stopped being about them and their drama, culture or politicking..

3. Will this matter in five or ten years…or longer?

Not rhetorically — actually answer it.

Most of what shock inflates to life-size is invisible at five years. The few things that do still matter at five years are where the real decision lives. This one question separates the urgent from the important faster than anything else I know.

4. What’s the downside, fully priced?

Not “what’s the worst case” as a comfort exercise — the actual cost in money, time, and relationships if this goes completely wrong, written down. Shock makes everything feel fatal. Pricing it usually reveals it’s expensive but survivable. And on the rare occasion it really is fatal, better to know that sober.

5. What can I do about it that’s really mine to do?

The last question, and the one that ends the loop. Not what’s unfair, not what they should do, not what God should fix. Of everything on the table — what is the one piece with my name on it? Then do that piece.

Proof under fire

The questions look easy on a page. They are brutally hard to run when you’re in shock — which is exactly why they’re written down before you need them.

When I ran the early version of this against the firm situation, the answer came out clean: leave. It felt like loss at the time. It turned out to be one of the best decisions of my life — it’s the fork that led to everything I’ve built since.

When the joint ventures failed, the questions stopped me looping on the friends involved and put the lesson where it belonged: I had invested on trust without structure, taken things for granted that should have been written down. That lesson got expensive once. It has paid for itself many times since — it’s why everything I do now leaves a paper trail and I no longer partner with anyone, even if anyone brings money to me or the table.

Money, I can earn myself.

But HOW we work together, the synergy and how fulfilling it is, is 10000X more important than any dollars anyone can bring.

I had also learnt, that when some people have some money or have invested some money, they may become pre-committed and also either have certain expectations, to which, it doesnt justify having them or whatnot kind of batshit bad behaviors that I dont want to see or be even close to.

Build yours before you need it

You will have a day this year — maybe this month — when the news arrives in one conversation. On that day you will not think your way to good questions. You’ll run whatever is already installed.

So install something.

Steal mine, adapt them, or write your own from your own scar tissue — the source matters less than the timing. The only rule is the rule of every default: decide in advance, because in the moment you won’t be deciding at all.

Leave a Comment