You're Not Disorganised. You're Running a System You Never Designed

She asked me in the slightly defeated tone of someone who’s been thinking about this for a while: “How do you systemise your life? I can’t figure it out.”

She was creative, energetic, full of ideas - the kind of person who starts several things at the start of the week and is equally excited about them all. She seemed a bit exhausted from the gap between her ideas, to-do lists, and everything else - the tasks that piled up, the things that fell through, the constant feeling that something was probably on fire somewhere or just forgotten to never be remembered again.

I recognised it immediately, and this made me smile. Not because I’m naturally organised (I’m not), but because I’m the same. I simply learned how to make life easier for myself by systemising things.

Sam Carpenter, in his book Work the System, wrote: “unhappy people spend their days coping with the random bad results of their unmanaged systems. Happy people enjoy the intentional good results of managed ones.” Reads a little absolute for sure, but I’ve lived on both sides of that sentence and feel that the difference is real.

The frustrations I remember most clearly involved processes that didn’t make sense, workflows that seemed to go against me, and structures that felt like they’d been built for someone else. But the funny thing is that a lot of them weren’t forced on me. Many of them I’ve built myself without thinking, and then wondered why they kept producing results I didn’t want (or not producing results that I did want).

Thankfully, I later learned to do better. I figured that things are actually manageable and fairly easy to fix most of the time. And I’m not saying that my whole life is now perfectly systemised and running like a “well-oiled machine” or whatever it is that people say. But I have systemised a lot of things for myself, and, most importantly, know how to recognise when the problem is not me, but the process I’m following without much thought, so I can evaluate it and start fixing it.

That’s what this essay is for, and I hope it will help you look at your life in a slightly different light, so you can fix what’s not working, one simple system at a time.

What Even Is a System?

Donella Meadows described a system as a collection of parts that work together toward a purpose.

So your morning routine is a system. So is your hiring process, your client onboarding, and even the way you wind down before bed.

Each one has something flowing in (your time, your energy, your attention). Something that builds up or depletes (your focus, your team, your sleep). And something that’s supposed to tell you whether it’s working.

The part most people miss is the last one - the feedback loop. When it works, the system catches problems early and adjusts. But when it doesn’t, the system just keeps running with the same inputs, outputs, and the same result while you wonder what you’re missing.

So let’s say you set your alarm for 6 a.m. three weeks in a row. You snooze every single day. You are sleepy and not ready to get up that early, so you blame the tiredness. But your tiredness isn’t the problem; it’s just a signal that shows the real problem, which is that you’re going to bed at midnight and give yourself only 6 hours of sleep when you need 8. You don’t adjust your alarm based on the time you go to sleep, so the alarm keeps going off at 6 a.m., and you keep snoozing it. You ignore the actual problem that causes it, and so nothing changes.

Or let’s say at work, your team keeps missing deadlines. Worried and frustrated, you add more check-ins. But these check-ins eat up more time, and the deadlines still slip. This system keeps running because nobody knows why. The system is pointing to the symptom, not the source, and you’re stuck patching the wrong pipe with duct tape.

How to Diagnose a Broken System

The diagnostic is actually pretty simple - just 4 core questions. Every time something feels a little off about how a certain process works, run it past them:

1. What’s going in? This is the actual input. Can be your effort, time, information, money, attention, etc.

2. What’s supposed to come out? The intended result you’d like to see, experience, or have.

3. What’s building up, or draining away, that you didn’t plan for? This is the so-called stock. Think about the things that accumulate, for example, backlogs, resentment, untouched tasks, or drained energy.

4. What’s the feedback telling you? The feedback loop - don’t skip this! How do you know when something is off? What shows or signals it? Does it reach the part of the system that can do something about it?

You’ll notice that the issue is almost always in Q3 or Q4 - either something is piling up that you haven’t noticed before, or there’s a signal that nobody is receiving, or both.

Let’s look at a couple of simple examples.

Work Example: The Onboarding Process

Let’s pretend we work at a startup and we’re hiring fast. Candidates move through the process in under two weeks; offers go out right away; people start the next Monday. Looks great and efficient.

Six months in, three of the last five hires had already left. One wasn’t performing. One felt unsupported. One had, in their exit interview, used the phrase “I didn’t know what I was supposed to be doing for the first two months.”

The leadership team blames the candidates - maybe wrong culture fit, maybe they didn’t understand how startups operate (too “corporate-y”), or were not resilient enough.

But let’s stop and look at this whole situation a little closer:

Input: Fast hiring process, job description, competitive offer, Monday start date.

Intended output: Effective, confident new team member contributing fully within 30 days (preferably sooner, of course).

What was actually building up: Confusion, unasked questions, a new hire performing tasks they weren’t sure were right, never getting clear feedback, expectations or direction.

The feedback loop: Completely broken! Maybe there was no structured check-ins in the first two weeks, maybe what you put in the job description wasn’t an accurate representation of reality, or maybe no one asked: “What do you need from us to do your best job that we haven’t given you?” New hire’s anxiety, slowing output, disengagement, and lack of participation never made it back to the people who could do something about it. By the time it showed up, three months had passed, and now it’s too late to do anything about it.

So basically, every hire that started entered the same broken loop, making it really difficult for them to succeed. The system was working against them. And yet, the exit was attributed to the wrong cause - unsuitable hires.

The fix here isn’t to “hire better people.” It could be a 30-minute check-in at day 3, day 10, and day 30 (or more, if needed). You can ask: “What do you need that you haven’t been given?” and listen eagerly to what they have to say. Give them space. Maybe you need to realign what the expectations are and what success looks like, and that’s fine. Give them clarity, tools, and space, without pressure. Make it your mission to ensure new hires work out, not test them, whether they can handle it.

Find the cause, close the loop, give people a real chance to succeed.

Personal Life Example: The Exercise Habit

It’s the 1st of January, and you feel motivated. You’ve booked the gym, laid out the kit, and set the alarm for 6:45am. By 12th January, you realised that you had gone to the gym twice and left your gym kit somewhere in the deep corner of your closet. You tell yourself that you’ll go back as soon as your workload decreases and the weather improves, but by March or April, you feel like giving up for real.

Your willpower might be at fault here, but the real problem is the system.

Let’s look at this in more detail:

Input: Motivation, gym membership, good intentions, alarm set.

Intended output: Consistent exercise, energy, the good feeling of having done the thing, feeling healthier, looking stronger, etc.

What was actually building up: A gap between the version of you who signed up (fresh, optimistic, free of other commitments) and the version who shows up at 6:44 a.m., having stayed up too late, already behind on emails, feeling tired before work and also after work. You’re weighing the gym against other things that are just as urgent and important, and they’re winning.

The feedback loop: You only tracked whether you went to the gym or didn’t. The feedback meant that missing one session felt like failing the whole system, and so you decided that there was no point in continuing.

Instead of getting fixed, the system broke down entirely, and you’ve little desire to figure out how to make it work.

The fix could be changing the feedback, not the effort. Instead of tracking your trips to the gym, track movement minutes. Instead of only counting 1-hour gym sessions, start counting any 20-minute movements. Because the feedback loop is gentler and more realistic, it’s less likely to crash and keep running. Three months later, you may view it as imperfect, but you’ll see that it’s still going. Then you can decide to make it a little better with small, gentle changes. The system stays alive long enough to eventually work.

Another few:

Planning your day but not following it

Input: A to-do list, good intentions, maybe a time-blocked calendar.

Intended output: A realistic, mostly ticked-off list by the end of the day and a sense that you moved the right things forward.

What’s building up: Tasks that keep moving to tomorrow, a list that grows faster than it shrinks, and a deep feeling that you can’t do it.

Broken feedback loop: You plan in the morning but never review what actually happened by the end of the day, so you never notice that you consistently overestimate what’s possible in eight hours (usually significantly less than you’d assume).

Fix: A two-minute end-of-day check - what actually got done, and was the plan realistic, knowing what you know about your day now? Maybe you need to protect certain time windows and slot fewer, higher-priority tasks at a time. Adjust tomorrow accordingly.

Your meal prep situation (cooking/having food go bad)

Input: A trip to the grocery shop, meal ideas.

Intended output: A fridge full of products that get used, no waste.

What’s building up: Forgotten vegetables slowly dying in the bottom drawer, three open jars of the same sauce, things you bought that you didn’t need in the end or things you needed but didn’t buy and had to go to the store again to grab.

Broken feedback loop: You shop based on inspiration, not a plan. You never check what’s already there before buying more.

Fix: Check what’s already in the fridge and your kitchen cupboards. Decide what you want to eat this week - then decide what you’ll need to cook the meals and go buy that.

Meetings interrupt your flow

Input: A workday, a calendar, and a genuine intention to get things done.

Intended output: A workday that has both collaboration and deep work in it.

What’s building up: Half-finished work, a brain that never gets into gear, end-of-day frustration that you were “busy all day” with stuff but produced nothing you’re proud of.

Broken feedback loop: You accepted every meeting invite without asking what it costs you in focus time. Or if you haven’t purposely accepted, you had no choice but to show up.

Fix: Block your two best focus hours before anyone else can, mark them as “don’t disturb”, and ask your team to view them as sacred so they don’t use them for meetings. Have meetings outside these blocks.

So, What Actually Needs Fixed?

Usually not what you think.

When something keeps going wrong, the instinct is to add more of something. Maybe more effort, more tools, more rules, more meetings about the thing that isn’t working. Instead, try picking one system you keep thinking about, observe it, simplify it, and make it kinder or more concrete for yourself - whatever you actually need. Remember, you’re not a robot, and you’ll most likely appreciate some flexibility, whatever you decide the system should look like, so work toward that.

Run the four questions. Name the inputs and find where the stock is building up. Find where the feedback loop is broken, delayed or pointed at the wrong thing. Then make the smallest change that closes the gap. And then iterate. It doesn’t need to be perfect right away. Adjust as you learn more about what works and what doesn’t for you and how you operate.

If you feel disorganised and that your life is a mess, then you might be running on systems that were never designed to work for you, leading to random results, piling up the wrong things, and failing to tell you about it in time.

So the next time something goes or feels wrong repeatedly at work, don’t just ask who failed. Ask where the feedback loop is broken.

And the next time a personal habit you really want to be a part of your life collapses, don’t blame your lack of motivation. Look at what’s building up in the background that makes the system work against you.

In short, the simplest system health check is this: Is the result I’m getting what I intended? If not - what’s accumulating that I didn’t plan for, and what have I been ignoring?