Ep. 18: On Planning

Caspian Almerud
6 min readFeb 23, 2020

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This is a transcription of episode 18 of “Caspian with a riff on:”. To listen to the episode, klick one of the links below.

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When Christopher Columbus headed out on the big Expedition that we all know him for, he had a plan. He was going to find India. As we all know, he didn’t. But he didn’t know that. He had a plan and it failed horribly. Although, he didn’t know, so he proceeded with the plan as intended. He handled his failure as if it wasn’t one, because it didn’t know it was one.

That’s one way to handle failure in your plan. And that’s what we’re going to talk about today.

Weekly planning can go wrong as well.

Every Sunday I sit down to plan my week. I go through all of the projects that I’m currently involved in, I make action plans for them, make to-dos and then I plan those into the week, and I set a schedule for myself. Sometimes that schedule includes lots of open space for me to work by myself. Other times I need to plan in sleep and exercise in order to actually do it.

Last week I planned my Wednesday and my Friday to be working alone days. And so I put a lot of To-Dos into both Wednesday and Friday because I knew that I would have the time to do them. Wednesday came around and I’d one meeting booked, so I went down to the library. I sat down to work. I went to my meeting and then I went back to the library.

It went according to plan. When Friday came around, all of a sudden I’d planned six phone meetings and one lunch with a friend. All of the phone meetings were supposed to be about half an hour long and they were an hour apart from one another, meaning I wouldn’t have the time to actually get into the work that I needed to do between each meeting.

What I want to say with this is that I’ve come to realise that predicting is impossible.

The two things you can control in planning

There are two things that you can control when it comes to planning. The first one is that you actually plan. That you set off the time needed to plan and you’re reasonable with your planning.

The second one is how would you react when things go wrong. Or more precisely: when things don’t go according to your plan.

Christopher Columbus as I said had one method of this. He didn’t know he failed his plan and so he just went on with his expedition. When you know you’ve failed a plan, it’s even more important. Not you change your attitude and that you either regroup to the plan, or make a decision to not go for the plan at all.

What I needed to do last Friday was to just let go. I realised that I wouldn’t have the time nor the energy to do all the work that I needed to do. I made the most of my time between my meetings, but I also had to replan.

The stock market and life is quite similar in this regard

I’ve actually been talking a lot about this with one of my employers. He’s deeply involved with the stock market, personal finance and in savings. In each podcast episode that he makes he has to say that past tendencies or past things that have happened on the stock market aren’t predictions for what’s going to happen in the future. He’s working a lot with Statistics and with science within the field of finance and economics. Yet he says this, because what happens at the stock market cannot be used as a tool to predict what’s going to happen in the future.

I think the same goes with life. If you would have all of your past activities or your weeks or even your whole life put into calendar. Each and everything in your calendar could have been planned.

Try making predictions based on past events

Yet, you’d also realise that most of those things didn’t go according to plan. Now looking ahead, you could presume that things aren’t going to go according to plan. That’s the only constant when we’re planning.

I want to talk a little bit about attitudes when it comes to how you handle changes in plans. I’ve had a really rough time with his. When things changed in my schedule in back in school I used to just lock down. If I had a class canceled or if a teacher didn’t show up and we had a substitute. I’d go on lockdown. If I could I would go home to play video games. If I couldn’t, I would play something on my computer in school, because I had a very tough time readjusting my focus to something else other than what was planned.That’s something I still struggle with, and I think it lies in the attitude.

Become immensely comfortable with your plan

See when you blindly trust your plan, you become so comfortable with that plan and you become focused on whatever it is you’re planning to do. If you’re preparing for a job interview and you have some expectations of who’s going to interview you and all of a sudden that changes, it’s going to throw you off. Especially if you put a lot of time and effort into preparing.

Now I’m not saying that you shouldn’t plan or shouldn’t prepare. I think when we’re planning and when we’re preparing, there needs to be a part of preparing for that element of “what if”.

We need to become so comfortable with our plan, that we could just say screw it, let’s wing it. The same goes for anything that you plan.

I’ve spoken publicly a couple of times. None of those times I said the exact words that I’d written down or the exact words that planned on beforehand. What I’ve done is that I’ve exercised my material, rehearsed it so many times. I’ve become comfortable with picking up at any specific point in my speech. I’ve become comfortable with going off track or comfortable with picking up something that happens in the room.

You should become so comfortable with your week, your day, the next coming hour or meeting you’re going into that you’re be able to say “Let’s wing it!”.

Plan your attitude for when things go wrong

I want you to picture this. The next time you sit down to plan something. The next time you sit down to plan your week, plan a meeting or write a text that you’re going to present to someone. I want you to make a list of all the things that could go wrong and corresponding attitudes towards it. Attitudes that you’d like to have if these things happen. Because in that case you’re planning for failure as well. Planning for yourself to be thrown off your planning, for things to go wrong, for things to change or for people to fall ill, for people not to show up.

That’s what you want. In that case you have backlog of scenarios and corresponding attitudes that you can just default into. Just as your plan. In that list you could list all of the things that could go wrong or just some of the most probable. What I also want you to include in that list is a “What if: Whatever.” as well as a corresponding attitude to that, or an action.

In that case you have a default whatever happens not just to the bad scenarios, not just to the worst case scenario, not just to the most probable things that could go wrong, but to whatever.

I want to conclude this episode with saying something that a friend told me that that her friend in turn told her: planning is easy, prediction is impossible. And that’s what we need to keep in mind when we’re planning.

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