Originally published on Scuttlebutt in 2018. Additional section added with updated learnings.

When I was a teacher I worked with this guy Pete Brailsford, who taught mountaineering. He’d take students up into the snow and build snow caves to sleep in overnight, cross rivers, stuff like that. A major part of the learning in that context was about managing risks. The idea is that you can’t control everything, but you can keep an eye on the probability field you’re standing in.

He talked about it like a slot machine - those ones where you pull the handle and then the options spin and then they lock in like:

🍒 🍋 🍒 🍒 🍏

Normally if you get all cherries or something, it’s a jackpot, but in this story, if you get a row of lemons, that’s bad, like “you got hypothermia and no-one knows where you are” bad.

So you can’t control all the slots, but you can watch where you’re at. Say you set out on our adventure, the slots are spinning, and you know what, someone in our group forgot their jacket BOOM the first slot just came up

🍋 ⬜ ⬜ ⬜ ⬜

Ok it’s a lemon, but no big deal, it’s sunny as. You stop and have lunch, there’s some clouds on the horizon, but it’s so warm. Guess what you just missed a hint, and as you continue to walk it starts to rain and a wind picks up (being a small island in a massive ocean, weather can change very quickly in nz) … now you’ve got 2 lemons

🍋 🍋 ⬜ ⬜ ⬜

Again this is not that big a deal… except you already have that 1 lemon, so now you’ve got someone in your group who’s getting cold. I guess you can see the trend. Any one of these things is no big deal, but a series of little misfortunes have a cumulative effect in terms of the odds you’re playing with. So if you’re in this position

🍋 🍋 🍋 🍋 ⬜

You’re now playing a very high stakes games, where one more little lemon, like a sprained ankle can tip you over into disaster.

How to manage lemons

Lemons aren’t always avoidable, but you can often plan ahead and consider what the odds of lemons are based on different paths. Further, you can reflect as situtations evolve, asking yourself:

How many lemons are we currently at?

Just having this self-reflective question in your toolbelt can change how you think and see. It can be really hard to spot them because they can often be innocuous in the context where they first present … it’s just in concert that the the real trouble manifests. Asking this question out loud to yourself and your questing party can help you spot more of them early, as well as increase the liklihood you’ll keep them in working memory (most humans suck at remembering many small factors).

If you spot yourself crossing 3-4 lemons, you should probably be starting to significantly re-asses your plans. Things like:

• abort: ask yourself if your initial plan is still safe
• simplify: consider cutting non-vital parts of your plan
• alert: increase new-lemon vigilance, prepare to escalate responses faster

But mix, I’m not a mountaineer

This is relevant to anyone on any adventure (solo, or as a team). You could be voyaging into literal mountains, or sailing to Great Barrier Island, or you could be a distributed team building FOSS tools on a limited / no budget.

Some lemons that have fucked up quests I’ve been on:

• having no retrospectives (process for iterating, adaptation)
• just trusting that everyone remembers the agreement we made (contracts, pay, expectations)
• forgetting to ask how people are feeling
• “figuring it out later” for on-boarding / off-boarding / holidays / sick leave
• not telling each other vital quest-changing info (assuming mind-reading or avoiding conflict)
• being unclear on who’s doing what
• using too many different tools for communication / coordination
• being unclear about ownership / responsibility
• saying “this is a flat structure, everyone is equal” (but not actually doing anything to actively distribute power)
• forgetting to account for how disruptive travel can be

Sometimes the course you take has known lemons. Like it’s hard to set up holiday pay processes when you’re a small company and you know everyone and you’re doing it for love and there are so many things to do. You just need to acknowledge (and remember) that you’re carrying a lemon, and if you then try to onboard someone new, you need to adjust your plan by either stopping to build that missing stuff (unloading the lemon), or communicating to the new person clearly about the known lemon.

Lemons in family systems

UPDATE: I’ve added this section because it’s how I’ve most used this personally, and why I reference this pattern so often.

When I say “family system”, I mean any group of people very strongly committed to supporting one another, such that the wellbeing of any one person in the system strongly effects the wellbeing of the system as a whole.

Examples of family systems I’ve seen that this is relevant for:

• parent(s) with kid(s)
• partners where at least one has a disability
• partners where at least one has mental health challenges

You know if you’re in such a family system when e.g. one of you gets sick, and the experience is like the family is sick. The arc of recovery is often slower too, because of the complex interactions involved in one person getting taken out.

Noticing lemons

We don’t track lemons all the time in our family. Lemons in themselves are not bad … unattended compounding lemons tend towards disaster though. Typically we start engaging this pattern when we notice ourselves generally “unreasonably stressed”, “a bit overwhelmed”, or even just “unproductive”.

The next step is to pause and name the lemons we can spot. I’m feeling a bit overwhelmed today, so here’s an example:

• 🍋 work – my work is in transition, lots of uncertainty
• 🍋 community – my school picnic got quagmired, lots of painful learning
• 🍋 health – I’ve had a low level cold for 2 weeks, have had a few nights of bad sleep
• …

Okeee, so we’re at 3 lemons already, and that’s only counting the complexities I’m holding… No wonder I’m feeling a bit overwhelmed!

Compassion

Even noticing that you’ve carrying a bunch of lemons can be transformative. My first step is usually to laugh a little, and feel a little bit of relief – I’m not useless, we have a lot on! 😅

Having some compassion for ourselves can immediately unload shame / guilt / pressure, which is very strategic, because:

• you just cut a meta-lemon (wasting brain cycles beating yourself up)
• you likely have less of a white-knuckle death-grip on your initial plans, making it easier to adapt to your actual reality

Complexity capacity 🍋 🥄

Another pattern we use in our family is Spoon Theory. The core idea is that if you’re living with some disability you may have very limited capacity, and that we could model how much capacity people have with units of capacity, spoons 🥄 say. A person with very limited capacity might start the day with 8 spoons, and then have to ration their spoons over the day e.g. shower costs 1 spoon, commute to work costs 2 spoons etc). If you run out of spoons… maybe you cannot get home, maybe you can but end up in massive spoon-debt (goodbye tmrw).

Expanding spoons from the individual (to collective capacity) and blending in the lemons pattern, we can start to say things like “today we only have capacity for 2 lemons”. Lemons here represent complexity which will incur spoons (capacity) cost.

This feels kind because it acknowledges our current capacity, and helps us bound expectations of how much complexity we can perhaps carry.

Concretely, while going to a kids birthday in the morning followed by a friends bbq in the afternoon may seem easy, if we only have 4 spoons, and this plan takes us to 0 spoon exactly… that leaves no capacity for unforeseen lemons, which world put us in spoon deficit. Better to plan one just the one activity and have spare capacity for curveballs and still be within safe operating bounds.

This concept is also useful in the context of startups. Startups are typically operating with very limited resources (spoons). Basic operations cost capacity (spoons), and innovation tends to cost in unforeseen complexity (lemons). To that end it’s important not to innovate on too many fronts simultaneously. Examples of things which incur complexity cost:

• 🍋 “fancy” legal structures - e.g. coop, foundation + for-profit symbiosis, ….
• 🍋 novel technologies - e.g. encrypted replicatable database
• 🍋 ethical investment mechanisms - e.g. non-voting shares, redeemable preference shares, …
• 🍋 world-spanning teams - e.g. NZ, EU, USA