February 11, 2018.
Recently I read The Dip: A Little Book That Teaches You When to Quit by Seth Godin. It's something like sixty pages, short enough that you can read it in one sitting, but the ideas are interesting enough that I've brought them up quite a bit during conversation lately.
The premise is that there are three different kinds of scenarios, that it's often obvious which of them you're in, and that with a bit of courage you can use this awareness to focus your energy and time.
The first is the dip, which is when something starts out rewarding then gets very frustrating, but later gets rewarding again.
This is often the transition from talented amateur to professional, when you stop doing what feels natural–and has worked well for you thus far–and start to use the most optimal approaches, which can feel very unnatural and which you'll initially be much worse at than your previous approach. Folks often describe this experience shortly before they break through to higher proficiency in a second language.
The second is the cul-de-sac, which is when things never get terrible, but also never get particularly good. You can work indefinitely at the task, pouring in energy, and never make much progress.
This is probably something that you've never been particularly good at and are unlikely to ever exceed at. This was my experience at some of my earliest jobs, where I had incompatible beliefs and values, which I struggled to reconcile but never made much progress on.
Finally, the cliff, a cul-de-sac that ends badly.
I think this one is often the result of external forces, like working hard to deliver a project for a client, but having them get fed up with you and leave. The most interesting, and perhaps distressing, part is that it's hard to tell the difference between a Cliff and a Cul-de-sac until things go quite badly, which is a good argument for being careful of staying in either!
The next time you're trying to make a difficult decision, try thinking about which of these charts applies, and maybe it'll help you see something that you've been trying to ignore.