Want To Avoid Missing Deadlines? Take the Outside View!

Written by Max Harms

When’s the last time you missed a deadline? Would you be surprised if you missed one in the next month or two? How bad would you feel if you missed the next important deadline?

Well, guess what - most people have a lot of trouble sticking to deadlines! We procrastinate, get tied up in an unexpected delay, or simply forget to do the work. But it doesn't have to be this way if you take the outside view.

Missing deadlines often comes from a failure to predict the future. If you improve your ability to anticipate what's going to happen, imagine how much better off you’ll be! For example, if you realize ahead of time that you’re going to be five minutes late to a lunch meeting with a friend, you could text your friend in advance letting them know that you’ll be ten minutes delayed. That way you can avoid having to rush, skip the anxiety of being late, and pleasantly surprise your friend by being early. The same thing applies to setting aside more time to work on a project, or, if possible, moving the deadline back to give yourself more time. You can level up your ability to plan around and meet deadlines, and it’s a big step toward getting better at predicting the future in all areas.

To give you a taste of how this works, let's start with a story. A long time ago, a teenager was learning how to program computers. He had tried several times to learn because he wanted to make games, and this time he felt like he'd figured it out. Where previously he was stuck, now he felt like he could do anything. Sure, he still had to look up a lot of things, but for the most part he was capable in a way he wasn't before. Compared to the earlier confusion, this newfound ability was like absolute freedom. He was an eagle on the wind with the entire future spread out before him.

You may have had a similar experience, where, after learning a new skill and feeling good about it for the first time, you felt like you were an expert. For many people, this is what learning a new skill feels like from the inside.

Now, what do you think it looked like from the outside? Do you think this teenager who had only just learned to code was an expert programmer? If he said, "I'm ready to code the best game ever!", would you believe him, or would you expect him to struggle and get stuck after a few days or maybe weeks? That teenager was me, and I can tell you from experience that my feeling of expertise was mostly an illusion. I was fooling myself.

The strange thing is that if you had asked that younger version of myself to evaluate a stranger, he probably would've seen that same foolishness in them. Sure, other kids didn't really know what they were doing. But I felt I was different. I was so excited by a future that had no apparent obstacles that I didn’t want to stop and think about whether I actually was as special as I felt.

From the inside you can see and feel all of the ways in which you're capable, but often you don't know about what you're doing wrong. If you know what you're doing wrong, you'll work to fix it, right? But if you don't know what you're doing wrong then the problem will stick around, invisible. This leads to overconfidence and a feeling of capability that doesn't match reality.

What’s your guess about how this is related to making plans and meeting deadlines? Let's say that I have a project which will take five hours of work to finish. I think to myself, "Okay, I'll work on it an hour each day this week and it will be done by Saturday morning." I assume that everything will go according to plan and am just chugging along in my week. Then, on Thursday I go to the grocery store, but by the time I'm done shopping I'm too tired to work. I figure that I'll make up the difference on Friday, but then on Friday I oversleep and just can't finish the project in time.

But what if I had taken the outside view? If I hear about someone who plans to do a project in a week if everything goes perfectly according to plan, I would probably say, "They might get it done by Saturday, but I wouldn't count on it before Monday." By distancing myself from the situation I can become more realistic in my expectations.

When planning for your future (or estimating your skill in anything) it's almost always better to take an outside view and think about the situation as if you were evaluating a stranger. Your internal feelings of being able to accomplish things don't take into account the normal problems and surprises that are part of life. Relying on these internal feelings (like most people do) will lead to missing deadlines, going over-budget, and producing lower-quality work than expected. In other words, your emotional self is too optimistic when predicting the future.

Taking the outside view can also help motivate you! Even if it feels like your deadline is a long way out, imagine two strangers: one of these strangers is working on a similar project right away while the other is procrastinating because they think their deadline is still a ways out. Can the stranger who is goofing off afford to be avoiding their work? Which of these two strangers would you rather be in the long run?

By learning to think about yourself from the outside you can become more reliable and accurate in estimating your capabilities. This skill doesn't just apply to deadlines, either! You can use it to avoid running out of money by predicting how much you'll need, and to be less stressed by accurately predicting how much rest you'll need! For any of these and similar situations, just ask yourself how long a stranger in a similar situation with the same resources would take to finish it. By doing so, you can really improve your planning and avoiding these sorts of typical problems. Imagine how much better off your life would be as a result!

What do you think?

• Have you noticed yourself being late or missing deadlines?
• Are you more realistic when evaluating how long peers will take on projects than yourself?
• What are some other areas besides time where you think taking an outside view would help you?

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