A dear family member has an annoying tendency to lose things – sometimes causing a delaying “But where did I put the keys?” situation when leaving home, sometimes brief panics when wallets go missing, and sometimes causing losses of valuable gadgets. I rarely lose things. This got me thinking about the difference in our approaches. Here are some strategies I seem to follow to avoid losing things.

This is intended more as an exploration of the practical philosophy and logistics of everyday life than an ultimate manual for never losing anything ever.

Since we spend so much of our time in everyday life, the returns of some time spent considering and improving it are large, even if the improvement is about small things.

Concentric layers

I think one of my core principles is to keep important stuff on me. I always keep my phone in my breast pocket, my glasses on my nose, my wallet and keys in my pocket. On travel, my passport is there too. My laptop, travel/backup drive, business cards, umbrella, USB connectors etc. are in the backpack I carry around or have in the same room. If I had a car, I would have tools, outdoor equipment and some non-perishable snacks in the trunk. Books I care about are in my own bookshelf, other books distributed across my office or social environment.

The principle is to ensure that the most important, irreplaceable things are under your direct personal control. The probability of losing stuff goes up as it moves away from our body.

Someone once said: “You do not own the stuff you cannot carry at a dead run.” I think there is a great deal of truth to that. If things turn pear-shaped I should in principle be able to bail out with what I got on me.

A corollary is that one should reduce the number of essential things one has to carry around. Fewer things to keep track of. I was delighted when my clock and camera merged with my phone. The more I travel, the less I pack. Fewer but more essential things also increases the cost of losing them: there is a balance to be made between resilience and efficiency.

Layering also applies to our software possessions. Having files in the cloud is nice as long as the cloud is up, the owner of the service behaves nicely to you, and you can access it. Having local copies on a hard drive means that you have access regardless. This is extra important for those core software possessions like passwords, one time pads, legal documents or proofs of identity – ideally they should be on a USB drive or other offline medium we carry at all times, making access hard for outsiders.

For information redundant remote backup copies also works great (a friend lost 20 years of files to a burglar – and her backup hard drives were next to the computer, so they were stolen too). But backups are very rarely accessed: they form a very remote layer. Make sure the backup system actually does work before trusting it: as a general rule you want to have ways to notice when you have lost something, but remote possessions can often quietly slip away.

Minimax

Another useful principle, foreshadowed above, is minimax: minimize the max loss. Important stuff should be less likely to be lost than less important stuff. The amount of effort I put into thinking up what could go wrong and what to do about it should be proportional to the importance of the thing.

Hence, think about what the worst possible consequence of a loss. A lost pen: annoying if there isn’t another nearby. A lost book: even more annoying. A lost key: lost time, frustration and quite possibly locksmith costs. Lost credit card: hassle to get it blocked and replaced, loss of chance to buy things. Identity theft: major hassle, long term problems. Lost master passwords: loss of online identity and perhaps reputation. Loss of my picture archive: loss of part of my memory.

The rational level of concern should be below the probability of loss times the consequences. We can convert consequences into time: consider how long it would take to get a new copy of a book, get a new credit card, or handle somebody hijacking your Facebook account (plus lost time due to worry and annoyance). The prior probability of loosing books may be about 1%, while identity theft has an incidence of 0.2% per year. So if identity theft would cause a month of work to you, it is probably worth spending a dedicated hour each year to minimize the risk.

Remember XKCDs nice analysis of how long it is rational to optimize daily tasks.

Things you have experience of losing a few times obviously require more thought. Are there better ways of carrying them, could you purchase suitable fasteners – or is their loss actually acceptable? Conversely, can the damage from the loss be mitigated? Spare keys or email accounts are useful to have.

There is of course a fuzzy border between conscientiousness, rationality and worry.

Scenarios

I have the habit of running through scenarios about possible futures whenever I do things. “If I leave this thing here, will I find it again?” “When I come to the airport security check, how do I minimize the number of actions I will need to take to put my stuff in the trays?” The trick is to use these scenarios to detect possible mistakes or risks before they happen, especially in the light of the minimax principle.

Sometimes they lead to interesting realizations: a bank ID device was stored right next to a card with a bank ID code in my wallet: while not enough to give a thief access to my bank account they would pass by two of the three steps (the remaining was a not too strong password). I decided to move the device to another location near my person, making a loss of both the code and the device significantly less probable in a robbery or lost wallet.

The point is not to plan for everything, but over time as you notice them patch holes in your everyday habits. Again, there is a fine line between forethought and worrying. I think the defining feature is emotional valence: if the thought makes you upset rather than “OK, let’s not do that” then you are worrying and should stop. The same for scenarios you cannot actually do anything about.

When something did go wrong, we should think through how to not end up like that again. But it also helps to notice when something nearly went wrong, and treat that as seriously as if it had gone wrong – there are many more teachable instances of that kind than actual mistakes, although they often are less visible.

Poka-yoke

I love the idea of mistake-proofing my life. The trick is to set things up so my behaviour will be shaped to avoid the mistake: the standard example is putting your keys in your shoes or on the door handle, so that it is nearly impossible to leave home without them.

Often a bit of forethought can help construct poka-yokes. When washing clothes, the sound of the machine reminds me that it is ongoing, but when it ends there is no longer a reminder that I should hang the clothes – so I place coat hangers on the front door handle (for a morning wash) or in my bed (for an evening wash) to make it impossible to leave/go to bed without noticing the extra task.

Another mini-strategy is gestalt: put things together on a tray, so that they all get picked up or there will be an easier noticeable lack of a key item. Here the tray acts as a frame forcing grouping of the objects. Seeing it can also act as a trigger (see below). For travel, I have ziploc bags with currency, travel plugs, and bus cards relevant for different destinations.

Habits

One of the main causes of loss is attention/working memory lapses: you put the thing there for a moment, intending to put it back where it belongs, but something interferes and you forget where you placed it.

The solution is not really to try to pay more attention since it is very hard to do all the time (although training mindfulness and actually noticing what you do is perhaps healthy for other reasons). The trick is to ensure that other unconscious processes – habits – help fix the situation. If you always put stuff where it should be by habit, it does not matter that your attention lapses.

The basic approach is to have a proper spot where one habitually puts the particular thing. First decide on the spot, and start putting it there. Then continue doing this. Occasional misses are OK, the point is to make this an automatic habit.

Many things have two natural homes: their active home when you bring them with you, and  a passive home when they are not on you. Glasses on your nose or on your nightstand, cellphone in your pocket or in the charger. As long as you have a habit of putting them in the right home when you arrive at it there is no problem. Even if you miss doing that, you have a smaller search space to go through when trying to find them.

One can also use triggers, a concrete cue, to start the action. When going to be, put the wedding ring on the bed stand. When leaving the car, when you are one pace beyond it turn and lock the door. The trick here is that the cue can be visualized beforehand as leading to the action: imagine it vividly, ensuring that they are linked. Every time you follow the trigger with the action they get strengthened.

Another cause of lost items is variability: habits are all about doing the same thing again and again, typically at the same time and place. But I have a fairly variable life where I travel, change my sleep times and do new things at a fairly high rate. Trigger habits can still handle this, if the trigger is tied to some reliable action like waking up in the morning, shaving or going to bed – look out for habits that only make sense when you are at home or doing your normal routine.

One interesting option is negative habits: things you never do. The superstition that it is bad luck to put the keys on the table serves as a useful reminder not to leave them in a spot where they are more likely to be forgotten. It might be worth culturing a few similar personal superstitions to inhibit actions like leaving wallets on restaurant counters (visualize how the money will flee to the proprietor).

Checklists might be overkill, but they can be very powerful. They can be habits, or literal rituals with prescribed steps. The habit could just be a check that the list of everyday objects are with you, triggered whenever you leave a location. I am reminded of the old joke about the man who always made the sign of the cross when leaving a brothel. A curious neighbour eventually asks him why he, such an obviously religious man, regularly visited such a place. The man responds: “Just checking: glasses, testicles, wallet and watch.”

Personality

I suspect a lot just hinges on personality. I typically do run scenarios of every big and small possibility through my head, I like minimizing the number of things I need to carry, and as I age I become more conscientious (a common change in personality, perhaps due to learning, perhaps due to biological changes). Others have other priorities with their brainpower.

But we should be aware of who we are and what our quirks are, and take steps based on this knowledge.

The goal is to maximize utility and minimize hassle, not to be perfect. If losing things actually doesn’t bother you or prevent you from living a good life this essay is fairly irrelevant. If you spend too much time and effort preventing possible disasters, then a better time investment is to recognize this and start living a bit more.