Know When To Fold 'Em

I'm not very good at giving up on things.

Somewhere in the dark and twisted pile of memes and pop culture references that is my personality lies a machine that is really good at feeling obligated to do things, relentlessly and obsessively chasing them to a meaningful conclusion.

It sits right next to the machine that helps me to procrastinate, and the two often work together, with the procrastination machine using data from the obligation machine to make a case for why I shouldn't start doing a thing.

With that mental image firmly in mind, it should be quite obvious that this is a stream of consciousness blog post, so strap in if that's the sort of ride you feel like going on.

Now, being bad at giving up, otherwise known as being tenacious, is different from being stubborn.

Being stubborn means that you don't adjust your view or path when prompted with new information, you just keep plodding along without adapting, like a moron.

Being tenacious isn't the same. If you are tenacious, you are free to change your approach or the target that you're aiming at or anything really. You're more focused on achieving an outcome of some sort, and simply refuse to give up.

Being tenacious can be beneficial.

It means that you can be relied upon to do a thing that you need to do, without just getting part way through and deciding to give up because it's too hard.

But tenacity can be debilitating.

If you feel obligated to run everything through to a meaningful conclusion, you can easily get overwhelmed and exhausted, because there are always more things to do than you have time to do them in. Also, the better you get at doing things, the more people expect you to do things.

The reward for a job well done is generally another job.

It's a vicious cycle.

So, the real trick is to know when to be tenacious. To be able to clearly identify the cases when latching on to something and ensuring that it gets done will be worth the effort, and to be willing to give up on stuff that doesn't fall into that bucket.

That's where I fail.

Someone asks me to review a document that they've written? That goes in the backlog, and I'll make damn sure that I do it, even if it means that I don't spend time on something else that is probably more valuable, but harder to reason about.

Basically, I have a hard time saying no, and also a hard time really understanding the difference between things that are important and should be tenaciously chased and things that don't really matter in the grand scheme of things.

I should probably lean more heavily on the Eisenhower Matrix, which I have included below because otherwise that would be a weird throwaway statement that a bunch of people wouldn't understand.

Judicious classification of things according to the method above seems like it would help me to at least use my tenacity more effectively, instead of just applying it to everything that crosses my line of sight, like an overly aggressive bulldog.

I need to get better at knowing when to give up.

But I'm not the only one.

In every company I've ever worked at, the overarching entity known as the business has shown that it is terrible at giving up on things, at least consciously.

The people in the company identify the things that need to be delivered, they make plans, they align those plans across teams, and they get to executing with a feverish dedication that borders on fanaticism.

But then things change, new priorities arise and get added to the big old list of things that need to be done, and no-one ever takes things out of the existing list.

I think the expectation is that it's okay if the lower-priority things fail naturally, and the business is hedging its bets on the off chance that through some great act of sorcery everything does actually get done and they can have their cake, eat it, sell another cake and also have an additional cake that's in the oven.

I think that's stupid.

Surely the most common outcome is that everything will be half-assed and eventually everything will grind to a half because it's all built on a foundation of sand, duct tape, hope and prayers.

It requires strong leadership to know when to give up on something, to be willing and able to say that it's okay if we don't achieve this outcome, as long as we get this other outcome instead.

I've seen hints of that sort of leadership, but it just isn't very common.

This sort of consistent inability to give up on stuff is incredibly frustrating for someone like me, because I'm a meaningful part of the delivery machine. That means I'm constantly having to add new things into my list of stuff, which I will dutifully chase tenaciously, which leads to me feeling exhausted and burnt out when I inevitably can't make enough progress on everything to satisfy all of my stakeholders.

Being able to know when to give up on something as an individual seems like a skill that can be taught. It's a prioritisation exercise, picking and choosing your battles and applying your limited pool of effort where it will create the most benefit.

Surely that's no different for a company.

But whereas I, as an individual, can improve myself, I have no idea how to stop the amorphous entity that is the business from making the same mistakes. There are too many individuals in the melting pot who all have different goals and preferences and willingness to throw others under the bus in order to get what they want.

And that makes me sad.