How to Plan

As humans, we’re bad at estimating the length of time it usually takes to do anything. There is even a word for this common phenomenon — it’s called the “planning fallacy”, coined by psychologists Daniel Kahneman and Amos Tversky in 1979. I wrote about it briefly in my piece on creating buffer.

Here’s an example: I was late for a recent workshop. I had it all planned and figured out the day before. I even knew the location of the workshop (more on this later). I found and saved the location in my maps a couple of days prior and booked my taxi ride in advance. Needless to say, I had more than enough time to make it to the workshop (or so I thought). The taxi showed up a tad late. The traffic was more congested than usual at certain points. Still, I was confident I would get to the workshop on time. When we got to the location of the workshop in the map, it turned out that the location was incorrect. The workshop was nowhere near the location marked in the map. I called the workshop organizer and found the correct location to be a few miles away. In the end, I ended up arriving a few minutes late to the workshop.

Looking back, my first thoughts were: I should have left a bit early; I should not have assumed the location on the map to be correct; I should have coordinated with the workshop organizer to get the exact location and added buffer time to plan for unexpectancies. Of course, hindsight is 20/20.

The real lesson to be learned here is that things might not always go as planned, even when you have “figured it all out”. The best we can do is hedge ourselves against it; in this case, it would have helped to have some buffer time (50% more time than it would take normally) because things typically take longer than expected. Just because things may not always go as planned doesn’t mean that we don’t plan for things to happen.

Other times, we might arrive late to a meeting because we end up doing things until the last minute (making that phone call, sending that email, or squeezing in one more thing), thereby not leaving enough time to make it to the event. In other words, we think we can do it all, but we can’t. In our rush to check items off our list, we forget basic things like the value of showing up on time.

Then, there are times when we forget to pack something for a trip — I know I often do, despite having a checklist. Using checklists can help, but we use them as if they are static and make-it-once-and-forget-it-later kind of things when they are not. They need to be dynamic and updated all the time (to a point where it’s so refined that you don’t have to update it anymore). Despite what I wrote earlier about creating a checklist to pack only what is needed (for instance), I think the purpose is not to pack everything you need, but to make sure you’re not forgetting anything. There is a difference. You might not need all the items from your checklist, but the items in the list serve as a reminder for you to check if those items are needed.

Another example. I don’t know about you, but I rarely do things unless I plan for them. I might have an endless list of things in my list manager that I want to do, but unless I have scheduled time for doing things, I’ve found they almost never happen. For instance, to-dos will continue to pile up in my “Anytime” list (list of things I can do anytime without any deadline). This is the list that typically gets ignored. I suspect it’s because of the way I’ve structured my work in terms of how I get work done.

Building on that example, I know that if/when I don’t take some time every week to plan my week, I feel a bit off; I feel things are a bit out of control, and I find myself lacking perspective.

By the way, I don’t mean to suggest that you schedule every minute of your day so that everything fits perfectly. That would be ridiculous and would likely burn you out. The point is to have just enough structure (using some idea or process) in your work so it enables you to work better. I wrote about this in Order and Chaos.

At any given time, we are doing one of these types of work: doing work that we have thought and planned about in advance, doing work as it shows up (ad hoc), and lastly, planning our work. The problem is that we don’t spend enough time in the last category. We live reactively on a daily basis doing things as a response to something versus being in control of things and doing them proactively.

In fact, most of the time, we do so much work ad hoc that we don’t give the attention required for doing the work that matters most. The thing is that there will always be some ad hoc work that shows up at any moment, which is fine as long as you can keep it to a minimum and by taking sufficient time to plan your work. We have to spend some time planning every day, and we have to know the outcome/result of our projects.

The whole point of planning is to get a desired result in the future. Of course, market conditions may change (as they do all the time), but that doesn’t mean we don’t plan for things to happen. When you don’t have a plan, you’ll end up wasting time.

Focus more on the planning process and less on the resulting plan. The whole idea behind planning is not to come up with a plan as much as it is about having some understanding of what is likely to happen in the future and to do your best to prepare for it.

Think of a plan as a guide. It is not set in stone. It is also not supposed to be a set-it-and-forget-it thing. It is supposed to be dynamic and updated all the time. For instance, you’re planning on a weekly basis while adjusting daily (more below). Things might not always go according to plan; nevertheless, we hope for the best and plan (or prepare) for the worst.

Although planning is required at the outset of a project, it’s possible to go overboard. The problem occurs when we get too fixated on the planning and pay less attention to execution or doing things.

Here are some ideas for planning in our everyday lives:

Separate your thinking (or planning time) from your doing time. There is a time to think (or plan) about your work and there is a time to do the work. Keep them separate. Do them at different times. Use the morning and evening to plan your work and use the day time to do your work. Figure out times that work best for you. Setting aside a time for doing weekly planning and review is also an example of everyday planning.

When you’re about to do something, stop questioning yourself on what you decided to do earlier and, instead, do it.

There is a difference between hoping and planning. When you hope to do something, it will likely not happen. There is a difference between hoping you’ll get the work done, which is uncertain at best, and planning your work; the latter improves your chances of getting the work done. The idea is to go from hoping you’ll do something to trusting that you’ll get it done. Having a trusted system can help you capture those things and make sense of them later.

For recurring projects (such as planning your travels), use dynamic checklists. A personal or a business trip is a good example. For instance, having a list of things you need to pack for a two-day business trip helps so that you don’t have to keep thinking about what to pack every time you travel for that duration.

Always give yourself more buffer time than it takes (about 30-50% more) for you to do something or get somewhere, as we are all susceptible to the planning fallacy. I don’t know who said it, but I paraphrase that an hour early is better than a minute late. I think that quote exaggerates the point I want to make, which is to show up on time and doing whatever is needed to make that happen without giving any excuses. For instance, if you have a meeting that lasts 45 minutes, schedule an hour for it in your calendar. That way, you’ll have some time to “breathe” and to make it to your next event. Having back-to-back meetings is never a good idea for a variety of reasons.

A common fallacy is we often wait until we know everything is available. Oftentimes, we might not have the complete information to make decisions. Not knowing the entire plan at the outset is fine as long as we are not using that as an excuse to procrastinate. In that case, figure out only the next thing you need to do to move that project forward.

We might not always know the outcome/result of our project, but that should not be reason enough to not get started with it. The least we can do is start the process of thinking about our project, and maybe that will get us somewhere. Not doing anything will get you nowhere. Sometimes, we need to explore things before we can figure out the outcome for our project.

As an extension of the previous example, any time we get a project with a deadline far out in the future, we can start small and early. We don’t have to do everything at one go, but taking some time early on in the process will help you define and structure your project. Also, it doesn’t have to be fully fleshed out at the outset. Having a head start will improve your chances of finishing the project on time.

Schedule time for things that matter to you. It’s the only way you’ll ensure they get done; otherwise, you’re deluding yourself. For instance, it is only by planning (and doing) that I have been able to put out my writing each week every week for the last three years.

This might seem counterintuitive — plan your time for everything, but don’t schedule every minute of your day. Plan your recurring to-dos in your list manager. For instance, you might want to review your monthly subscriptions toward the end of each month or pay all your bills on a certain date. Or, you might call friends and family every few weeks to ensure that you keep in touch with them because they matter to you.

Project planning is something we all naturally do. The point is to make it explicit even for our personal projects (beyond work) such as planning a party. You have to make a list of guests you want to invite, guests who have RSVPed, arrange food and drinks via catering, set up the venue and music, etc. Without planning for things, you won’t be satisfied with the result.

Doing regular weekly reviews helps us course-correct and figure out next steps for our projects. That is how we stay on top of things.

When others are involved in a project, bring the key people early on in the process as part of planning, not at the end. Make it clear that those who don’t come now can’t have any say in the process later on when it’s time to ship.

Planning does not equate to doing things. We could plan perpetually, but until we do what we set out to do, it’s all just empty words. We know that we are defined by our actions, not our words, and planning is not an action. For the most part, some might even say it’s guessing. But, (some) planning is required so you have enough structure to your process, whatever that may be for you. Planning is what brings a method to the chaos.

Planning alone won’t help you do your work, but it greatly improves the chances that you’ll do the work. More importantly, it puts you in a proactive position where you focus on getting started rather than trying to figure it all out at the start. It gives you enough structure to do the things you want. You need planning in some form or fashion, no matter how basic or rudimentary to begin with, so you know where you are and where you need to go. You can always course-correct later. Plan your work and work your plan.

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