Chronic and Acute Stuckness: A Handbook

The feeling of being “stuck” is relatively common to the average knowledge worker, when your work is as much defining the work as it is doing it, and arguably it’s more defining than doing. Various mental conditions contribute to this, ADHD exacerbates the severity of stuckness, depression and PTSD can also make it impossible to see any way forward at all.

I think “being stuck” is a symptom of having too much ambiguity to deal with. There’s things you could be doing, sure, but are they the right things? Are they even good things to be doing at all? If you do them, will you make things worse? Will you be working on something irrelevant, solving the wrong problem? What’s going to make you look good and demonstrate skill and competence? Even if you decided to do something, where to start? Everyone else already has their projects picked out and has momentum, and you have nothing.

All of these questions demand being answered at once, and the end result is that we do nothing, paralysed by choice, ambiguity and doubt.

In specific, I distinguish between two kinds of stuckness, acute and chronic stuckness. Acute stuckness is being caught in limbo for anywhere from an hour to a day, and chronic stuckness is everything past. They require different actions to resolve, and so can’t be treated the same.

Acute Stuckness

This is a list that was first sent to me by a friend, Elly, and I’ve been treasuring and adapting it since. It divides the measures to take by their time expenditure, and the idea is that you try something from the first level, see if it resolved the stuckness, and try a different thing or move up a level if it has not.

First Level

These are all localised interventions, they are there to punt you out of a local slump, rather being able to fix problems.

Second Level

These are more intense context-breakers, in that they involve people, and don’t have an arbitrary end date. For this reason they’re better in getting you out of something that might not be local anymore, but is also still quite temporary.

Third Level

This one’s quite simple, if you’ve done stuff from the first and second level, and you still can’t Do The Thing, then:

Chronic Stuckness

Once the easy, day-localised measures are exhausted, we’re clearly dealing with a larger problem that has to do with either direction and goals, personal health, or environment, and neither of them are resolvable with casual, low-cost interventions.

For context here, I’ve been periodically severely “stuck” all my life, where I was unable to get any work done for weeks at a time. These categories and tricks are originally written for myself, and as such I don’t know how well they will generalise, nor do I make any claim that they will. But if the internet has taught me one unexpected thing, it’s that people work relatively similarly within groups, and so I hope that this will be at least of inspirational use.

Here we need to start splitting by concrete expression of the problem, as the things that need to be addressed start diverging quite heavily.

Lack of Direction and Orientation

This manifests itself primarily in knowing that you should do Something™, but what that may be is anyone’s guess. Maybe you’re afraid to ask, because you already feel like you have been severely underperforming, and that might make it worse.

Like so often, I recommend writing. Mainly for two reasons: It doesn’t require asking/talking to another person, and because paper is not distorted by your head telling you you’re this close to being fired. If you are prone to getting stuck in this manner, I would also recommend that you maintain this structure as an ongoing internal document you can pull up to orient yourself by. In essence, this addresses the direction and orientation by re-doing the work of a project manager, but on smaller/coarser scale.

Ask yourself, and answer, these questions in writing:

Additionally to the answers to the list above, there’s also the aspect of task persistence. A lot of “stuckness” is feeling like there is nothing you could work on, when instead, you don’t remember the things you wanted to do “later”, or noted in the past as “potential improvements” to existing things. Therefore, I recommend you keep a list with:

The nice thing about these categories is that they are usually independent of other people, and they let you visibly do things that others have forgotten, earning you both the recognition of Doing Things and of remembering things.

Knowing what to do, but being unable to do so anyway

This has two sub-flavours: one is Executive Dysfunction, something people with ADHD will often encounter, meaning that things seem too big, or too costly to actually do, and so you’d rather do anything else than start. The other one is that there has come to be significant emotional meaning attached to the Doing Of The Thing that makes it so, so aversive.

Executive Dysfunction, or one of its informal flavours

Here I need to again state that this is my experience, and what worked for me might not work at all for others. Caveat lector:

Get out a text editor of your choice, open a new document. Write down the thing you have been staring at that you should be doing, but have been unable to gain traction on. Then, write out these two things in two lists below. Make sure you absolutely state the obvious, absolutely do state the things that are partially already done. Write a lot, as long as it’s relevant to the thing.

Once you have these, do the same process for each item in each list. What is involved in the doing of the thing, what does it require?

After these two passes you will likely have things you can squint at and do within 2 minutes. Do these first. Then come back to the list, until you encounter more ambiguity on a nested item. Do the process, but again. Write out every single question, every single prerequisite, and do the things that seem feasible. If they still seem bad and too big or aversive and you find yourself not doing anything, apply the process again.

The batch size can’t possibly be too small. I have, in the past, had prerequisites of “outline of message to coworker about the status of the thing written” and “message to coworker about the status of the thing spell-checked” as tasks that I did separately.

This is not being “too slow”. This is moving at all in the face of adversity. The alternative to not splitting up tasks so finely they become feasible is not doing anything at all.

The importance of feedback loops.

Something that is heavily relevant but not discussed enough for knowledge workers is the expedience of feedback loops, most importantly, how fast it is for you to do something, and then learn whether it did what you needed it to, or not. Long feedback loops are terrible for people prone to executive dysfunction. If you find yourself being averse to tasks that take longer than a minute for you to tell you if you were successful or not, find ways to shorten the feedback loops. Automate tests that tell you if you fulfilled your goals, rope in people to do things face to face and quickly. Shortening feedback loops will make a lot of dysfunction go away. The technique of iteratively decomposing tasks above is nothing else than an attempt to bring down feedback cycles to something rewarding.

Emotional significance of the Thing.

After a while, the Doing Of The Thing takes on emotional weight. Often times it’s visible as a form of Writer’s Block, where you know what to do, and you know why you need to do it, but you stare at a blank page. This is different, but related to the executive dysfunction above, and has overlap. The difference comes from the identification with the doing of the thing that is now causing you stress in addition to the non-doing.

Hillary Rettig has written a good, but atrociously-named, book by the name of 7 Secrets Of The Prolific that does this specific flavour of stuckness more justice than I could, and I recommend you read it, if you struggle with stuckness in this variety. It addresses the environmental part of Doing The Thing, and how to set yourself up to be able to Do The Thing as well as possible on your end. It’s specific to book-writing as a profession, but I’ve found that much of the advice within transfers.

Distress at the thought of doing the Thing

Here we start running into uncomfortable territory, namely burn-out syndrome. If you know what to do, where to do it, and how to do it, but the idea fills you with dread and despair, you need to take appropriate, severe action. Burn-out does not go away by itself, nor does it vanish with token intervention like taking a week off.

Burn-out itself is a result of being in a hostile environment that is hard to deal with in some ways, and so the resolution to it can’t come from one-sided action on your end. You will need to change your environment in one way, or another. If you have reached this part, and you don’t know what to do about it, contact your doctor first. Talk to them. Take care of yourself. As a former burn-out myself, it’s very easy to think that it’s your fault, that if you did things better, you wouldn’t need to deal with this problem now. That is both not true, and only serves to tear you deeper into the spot you’re already in.

Even if you do not think you have burn-out, if things are not addressable with any of the prior, it’s likely that it’s worse than you think it is. Take care of yourself, first and foremost.