There Are Two Kinds of Fine

As I write this, the sun sets at 6:49.

That's fine. Right now, it actually is. But I know what's coming. On November 1st the clocks fall back, and just like that it's dark before dinner. By December the sun's gone before 4:30, and from October to June the air out here is some version of wet. Not raining, exactly. Just... moist. Cold enough to get into your bones, not cold enough to snow in the city. And nobody carries an umbrella, because in the Pacific Northwest that's the code. You get wet and you act like you didn't notice.

I'm not even in it yet. I'm dreading it from here.

I love it here when the sun's out. My house is great. Most people would love it. When it's sunny, this place is heaven.

But every year around now, I hear myself say it.

It's fine. It's not that bad.

It's not fine. I hate it. From October to June, I fucking hate it.

So why am I still here?

My kids.

That's the whole answer. They're here, so I'm here. It's fine. It's not that bad. I love my kids. Hahaha.

Yeah. I heard it too.

In my book, the second framework is the trap: every "fine" tightens the stocks. Nobody locks you in. You surrender your way in, one "fine" at a time. I wrote that the only way out is to stop saying fine, and I still believe it. (How "fine" built a whole decade of my life is chapter 2, and I'm not retelling it here.)

But I'd be lying if I told you I never say it anymore. I do. Mostly at work. And they're not all the same kind.

Some fines you pick. Some fines pick you.

The fine I picked

The rain is one I picked. I know it's a fine I chose for one reason: I can tell you exactly what it costs and exactly what it buys.

It costs me nine gray months. It buys me my kids.

And I don't just sit in the dark and take it. I've got a 4WD, and when the city is gray and wet, I drive up into the mountains, because the same weather that's making everyone downtown miserable is dumping snow up there. I ski. And when the gray gets to be too much, I leave. California. Hawaii. Portugal. Anywhere with sun.

That's the difference. I'm not pretending the rain doesn't cost anything. I know the price, and I'm doing something about it.

The fine that cost two years

Now the other kind.

2018. Microsoft. The platform I worked on ran its user group program through a third-party company. I thought it was a bad call. Honestly, a shit call. I wanted us to run our own program. Hire in-house. Build it on our own platform.

So I said it. Out loud, to the room. I don't remember my exact words. I remember being sure. I told them what I thought would happen if we handed our user groups to somebody else.

A marketing leader shut it down. Decision made.

And I said it.

Ok. Fine.

I KNEW it was wrong. I'd already said so. There was nothing left to argue, and somebody had to keep the peace, so I said "fine" and went back to work.

It took about two years. I was there when it all fell apart. That company jacked up its prices and hijacked the relationship, and we didn't want to pay the new price. So they kept the user groups. All of them. The community org at Microsoft had to rebuild the program and restart every group from scratch.

I was right. Being right didn't save a single user group.

Here's the part that bugs me. I did the thing everybody tells you to do. I spoke up. When researchers Frances Milliken, Elizabeth Morrison and Patricia Hewlin interviewed 40 people about speaking up at work, 34 of them had stayed quiet with their boss at least once about something they thought was important. That's 85%. I wasn't one of the quiet ones that day.

And it still ended in "fine."

The no you're scared of is cheaper than you think

Outside of work, I barely say "fine" anymore. I say no. A lot. I get to define my own life now, and I'm way better at it than I used to be.

And the no costs way less than it feels like it will.

In a 2024 study, Julian Givi and Colleen Kirk found that 77% of people had said yes to a social invitation they didn't want, because they were scared of what saying no would cost them. Then they tested it. The people doing the inviting were way less hurt, angry or offended than the people saying no expected.

Read that again. At least when it comes to saying no to the party, the fallout you're dreading mostly isn't coming.

Work is harder. Sometimes you lose the argument, and going along is the right call. Jeff Bezos has a name for the good version. In his 2016 letter to Amazon shareholders, he called it "disagree and commit": say your piece, then actually commit.

On paper, that's what I did in 2018. I disagreed out loud. Then I went along.

But I didn't commit. I complied. My "fine" meant "fine, I'll do it, and I'll be right eventually."

How to tell which one you just said

You can say the price out loud

"It costs me nine months of rain and it buys me my kids." If you can't finish that sentence about your fine, you didn't make a trade. You made a surrender.

You said it to make the conversation stop

Not to decide anything. Just to end it. You'll know this one by the relief when the other person finally stops talking.

You're complying, not committing

You said your piece and lost. Fine. Now be honest about what your "fine" means. If it means "I'm in," that's commitment. If it means "I'll go along and wait to be right," that's the trap. Either get in for real, or put a date on the calendar to look at it again, out loud, with the people who decided. I spoke up once and never reopened it. Don't make that mistake.

Where to start

Don't try to kill every fine in your life this week. You can't, and some of them are worth keeping.

Find the one you already know is a lie. You don't have to hunt for it. It's the one that showed up in your head the second you read the title of this essay.

Here's the exercise from the end of chapter 2, word for word.

"Fine" kept the peace for me for a lot of years. It got me through rooms I couldn't win. I'm not going to pretend it never helped.

But a fine you didn't pick isn't peace. It's a no you're still paying for.

Tonight the sun still sets at 6:49. In a month it won't, and I'll be saying "it's fine" about the dark again. At least I'll know which kind I'm saying.

So which one is yours? The one you picked for a reason? Or the meeting where you already knew?

Write it down. Say the price out loud.

And quit acting like you're not wet.