Plan Your Escape! Part 1: Why Bother?

Welcome back to Plan Your Escape, a New Escapologist blog series by New Escapologist’s Chief Leisure Officer, Lentus Ambulandus.


In Part 0 to this series, I said we’d be exploring a simple, logical planning framework.

The method I’ll describe here is loosely based on The Combat Estimate, which I learned about during my military service. The Estimate is comprised of four steps:

1) Aim.

2) Factors.

3) Courses.

4) Plan.

In the military context, this method is useful for solving all sorts of problems: applying a limited budget, organizing a training event, engaging one’s enemy.

Here at New Escapologist, however, we’re interested in a project that’s so much more appealing than mortal combat: life, and how to live it well.

1) Aim. What does it mean (for you) to live well? Are you sure about that?

2) Factors. What aspects about your own character and your situation do you need to consider, and how do they inform and shape your solution?

3) Courses. What avenues are realistically available to you?

4) Plan. Among the options available, which path grants you the greatest probability of achieving the good life?

In truth, there’s nothing really remarkable about this method, and it’s not strictly a military tool. You’ve likely seen elements of the process in your workplace, because operational planning is at the heart of all organizations: where are we? where do we want to go? how do we get there?

And if you think about it, we inherently go through this line of questioning at the individual level, in a continuous, subconscious decision-making loop: where am I? where would I rather be? what’s the best way?

So. Why Bother?

Right now you’re probably feeling a little ripped-off.

If there’s nothing remarkable about the process, and we already do it, what’s the point of this blog series?

Because most of us don’t do it very well. We don’t do it deliberately, or holistically, or consistently. At best, our lives are a process of trial and error–we’re like paramecia, bumping into the same obstacles over and over, hoping for different results each time. Through equal parts luck and pain, we finally figure things out after X iterations…by which point we’re in our 40s. That’s the most likely scenario. The worst case scenario is that we make a complete hash of things, but don’t realize it until it’s too late.

Wouldn’t it be better to strive for the best case scenario? To cut the crap, avoid the hassle, identify early on what it means to live well, and make a beeline for it? That’s really what this is all about: efficiency, economy of effort, focused action.

Because personally, I’d rather come up with something like this:

My mission is to live well through self-sufficiency and community involvement, which I’ve determined to be the true drivers of my happiness.

After considering all the relevant factors, I’ve concluded that I need to break this mission down into three phases. Phase 1: I’ll optimize my finances by maintaining my current job, by embracing scorched-earth minimalism, and by focusing only on core leisure activities. Phase 2: I’ll quit my job, I’ll move to a place conducive to my long-term goal of self-sufficiency, and I’ll find interim work that pays the bills. No later than July 1, 2017 I’ll purchase a small parcel of land. Phase 3: I’ll develop an organic farm and I’ll turn my attention to being a productive member of my local community. Common to all phases is the maintenance of my fitness and my close relationships, because without those things, I am nothing.

My main effort–what I’ll focus on when I have to prioritize–is the accumulation of savings for the purpose of buying land.

My desired end state–the performance metric by which I’ll judge my success–is to produce 50% of my family’s food consumption on my farm, and to be a positive force within my circle of influence.

My immediate tasks for Phase 1 are: [insert list]

Especially if every single phrase in that statement was the result of careful contemplation and analysis.

By contrast, I’d like to avoid saying something like this:

You know, I always wanted a farm. I guess it was just a silly dream, and in any case, life got in the way. Marriage, house, dog, kids…then I got a promotion and a transfer at work, and my responsibilities piled up. Life just happened, and before I knew it…blah blah BLAH!

Life doesn’t just happen. We make it happen. For the record, I don’t want to be an organic farmer, because I’m very lazy (my laziness is a key factor that I must consider when formulating plans)…it was just an example. But regardless of what your personal version of the good life is, a statement like the one in the example is what you want to aim for by the end of this series. We’ll work on that together.

Of course, the skeptics will say that planning is futile. That plans are almost always overcome by events. “No plan survives first contact with the enemy”, someone once said. To which I’m tempted to respond, “Okay, don’t plan…go shopping instead…best of luck with your tiresome, cookie-cutter, unplanned, unfulfilling life of sheer bullshit.”

Thankfully, I’m above that sort of response.

Instead, I’ll argue that planning has benefits beyond your basic probability of success. Even if things don’t go exactly according to plan, you’ll have gained crucial insight. You’ll have a much greater appreciation of yourself, your situation, and the underlying factors that constrain or enable your success. This understanding will grant you strength and flexibility in the face of adversity. Your plan will be a stable, thoroughly-reasoned starting point from which you can make informed adaptations.

A Word Of Caution

I’m going to show you a process, but nobody can do the work for you. Because it’s your life, and it’s a personal voyage. The more you’re willing to put aspects of your situation (your character, your relationships, your work, where you live, your preconceived notions of success, etc) into play, onto the table, and up for debate, the more you’ll get out of it.

Ideally, this series will make you think, engage your imagination, and ask yourself some awkward questions. The good news is that it will be both fun and rewarding. Most of the hard bits can be accomplished while lying on the floor staring up at the ceiling, and by doodling on blank sheets of paper.


In Part 2: Good Intentions, we’re going to discuss the importance of establishing a long-term, overarching intent. To prepare you for that, I have a question:

What do you think it means to live well?

See you next week.

As always, we invite your comments and participation.

★ Help fund the forthcoming Escapology book. Order a copy today.


Lentus Ambulandus is New Escapologist's Chief Leisure Officer. He advocates doing the things worth doing (hiking, cycling, sipping coffee, reading books), and proudly accomplishes less in a month than most people do in a week. His creed is simple: Death Before Employment.

3 Responses to “Plan Your Escape! Part 1: Why Bother?”

  1. Sisyphus says:

    I like this kind of approach! I think it might go a long way towards getting my wife on board…

  2. Drew Gagne says:

    Dear Sisyphus:
    Just so I’m clear, you want your wife to get on board and help roll that giant boulder up the hill? Gutsy move. Good luck.

    In all seriousness, thanks for stopping by and commenting. Indeed, if you’re in a relationship, planning (and Escapology in general) is necessarily a team effort. And so it should be: nobody has a monopoly on good ideas, and to plan in isolation would be to forego another valuable perspective.

    In my posts I frequently use “I” and “me”, but in reality my wife is right here with me. We often bounce ideas back and forth, and while I’m a good “ideas guy”, she’s very good at the practicalities of execution. Because she’s irritatingly rational, she often provides a healthy reality check to my exuberance, standing at the ready with a cup of ice water to throw in my face. You’ll see what I mean in Part 3. And Part 4, come to think of it.

  3. bikevcar says:

    I agree with your sentiments – I think this might be described as ‘conscious living’, being aware of the life you are trying to lead. And hoping that you actually walk the talk. It’s very difficult, and like you say sometimes your plans don’t work out. In fact, they never really work out like you imagine. But you need to have some kind of goal you are working towards and then the short and medium term plans can be adjusted as you go along.

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