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Type 2 Fun

The best experiences I've had didn't feel good while they were happening. That's the point.

May 22, 20267 min read
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The weather app says rain. I'm doing it anyway.

Sunday I'm running 20K through the Niagara Escarpment at the Sulphur Springs Trail Race. Mud, roots, 500 metres of climbing. The forecast says 100% chance of rain. None of that changes the plan.

That's the thing about decisions made in advance: conditions don't get a vote.

What Type 2 Fun Actually Is

The term comes from outdoor climbing culture, credited most often to alpinist and writer Kelly Cordes, though it has been passed around mountain huts long enough that nobody really owns it. The framework is simple.

Type 1 fun is fun while it's happening. A good meal. A flat trail on a clear day. A sales call where the client already wants what you're selling. Easy, enjoyable, no real friction.

Type 2 fun is not fun while it's happening. It might be uncomfortable, scary, or genuinely hard. But in retrospect, it becomes the story you tell. The thing you're proud of. The thing that changed you.

Type 3 fun is not fun during, and still not fun after. This one is a signal that you got the risk calculus wrong.

The distinction matters because most people conflate Type 1 and Type 2. They wait for things to feel good before they begin. They want the commitment to feel right, the weather to cooperate, the timing to line up. What they're actually doing is waiting for Type 2 to become Type 1.

It rarely does.

Type 2 requires choosing discomfort in advance, before you know exactly what it will cost you. That's not stubbornness. That's the whole point.

Up the Chief with Kallem

A couple weeks ago I was in Squamish, British Columbia with my son Kal. He competes in the Pro division of the Canadian Ninja League and was there for the National Finals.

While we were out there, we climbed the first peak of Stawamus Chief.

If you don't know it: the Chief is one of BC's largest granite monoliths, rising straight out of Howe Sound on the Sea-to-Sky corridor. The trail up is not a walk. It starts with hundreds of steep wooden and stone stairs, then shifts to chains, ladders, and rope assists on open granite slabs. At some point you stop hiking and start making decisions.

Near the top there's a section where you're pulling yourself up by a chain bolted into the rock, looking down at the boats in the water far below. No railing. No net. The granite is worn smooth by thousands of hands before yours. Your feet are on a grade that would slide you off if you let go.

That moment is unnerving. My brain is very clearly trying to convince the rest of me to just sit down for a minute and reassess.

We didn't sit down.

Standing on top, clouds moving through at eye level, Squamish spread out below: that's what the whole thing was for.

Kal trains for moments like that. The obstacles on a Ninja Warrior course are designed to test exactly what that chain tests: the ability to commit when backing off feels easier. He has built an entire practice around choosing hard things. Watching him compete, and doing this climb together, made something obvious.

The people who show up for Type 2 moments are the same people, doing it again and again. That's not a personality trait. It's a practice.

What This Looks Like at Work

I'm a Solutions Architect. Most of my job involves being in rooms where the answer isn't clear and the stakes are real.

Hard things at work wear a different shape than a chain on a granite wall, but they have the same quality: you can see exactly why you'd back off, and backing off would be completely reasonable.

This pattern shows up everywhere in professional life. The cold approach at a networking event when you could just check your phone. The hand raised to present to a room you've never addressed. The certification exam you've been deferring for two years. I know it best through the lens of the work I do, so that's where I'll go.

The project with unclear scope and an aggressive timeline that nobody wants to own. You can already see three ways it fails from where you're standing. You can also see that if you walk away, it will absolutely fail. So you raise your hand anyway and start building the plan.

The delivery conversation where you have to tell a client something they don't want to hear. You've built a good relationship over months. This will test it. The easier path is to soften the message enough that it doesn't land, buy yourself a few more comfortable weeks. But that's not actually easier. It just moves the problem forward with compounding interest.

The competitive bid where you're not the incumbent, the competitor has a cheaper number, and you're not sure the client fully sees the difference yet. You could shade the proposal to match price and hope. Or you can write the honest case, show the total cost of the cheaper option, and let the work stand on its own.

In all of these, what separates outcomes is not talent or experience. It's the willingness to grip the chain and commit to the move.

The best outcomes I've been part of came from someone, often the least senior person in the room, saying "let's do it anyway" at the exact moment when doing nothing would have been completely defensible.

How to Tell Which Hard Things Are Worth It

Not all hard things deserve a yes. There's a version of this mindset that curdles into self-punishment. Type 3 fun is real and it costs you more than you think.

The filter I've found useful is two questions: is the difficulty voluntary, and does it point somewhere?

Voluntary hard things build capacity. Running in the rain when you could sleep in is voluntary. Taking on the difficult client engagement when you could pass is voluntary. The difficulty is the point; it's the resistance that creates the adaptation. You chose the weight, which means you get to put it down.

Involuntary hard things just drain you. Grinding through a broken process you can't change, working for a manager who actively undermines the team, staying in a situation with no path forward: none of that is Type 2 fun. That's just suffering without the retrospective payoff.

The second question, "does it point somewhere," is what separates productive discomfort from punishment. Sulphur Springs points to finishing. The Chief points to the view. The difficult bid points to the relationship and the work that comes after. If you can name what the hard thing is pointing toward, it's probably worth doing.

If you can't name it, that's worth sitting with before you grip the chain.

Don't Wait for the Rain to Stop

The race is Sunday. The forecast is not improving.

I'll be on trail in the Dundas Valley on the Niagara Escarpment, running 20K through mud and roots in the rain, with 500 metres of climbing. It will most likely not be fun while it's happening. I'll be cold and wet through by kilometre five. At some point I'll be doing the math on how far I still am from the finish.

But I already know what it feels like to stand at the top of something hard.

That's what I'll think about at kilometre fifteen.

The conditions don't improve until you stop waiting for them to improve. The rain is not a reason to wait. It's the whole point.

See you on the other side.