Michael Ashcroft

June 19, 2021

Being self-directed is its own work

This might be a little self-therapy, but whatever, it’s my notebook and I can do what I want.

I just made a YouTube video on this subject, which is front of mind following a conversation with my friend Salman. I’m going the other way this time and doing some writing after having made the video

In short, the idea is that being self-directed is itself a kind of work, and one that I, at least, am not taking seriously. And by that I don’t mean “I’m not doing it”, although a compelling case could be made for that, but “I keep forgetting that this is a kind of work and as a result of this I’m being unkind to myself.”

For the entire time I was employed I was given some combination of tasks, projects, or objectives. These set the frame of my work and gave me a sense, to some degree of specificity, of what I should be doing with each day, a guide as to what was important and so where I should focus.

The important words there are “I was given”. This, on reflection, is an indication of work that needed to be done that I was not doing.

This becomes immediately clear to anyone who has been a manager (of people, not of projects, because amusingly those things don’t always go together). There are moments when your reports come to you asking what they should be doing or, if you’re a good manager, moments when you anticipate that your reports will at some point relatively soon come to you asking you what they should be doing.

And those moments do not represent easy, casual tasks that can be done with a slight hangover. These moments represent a wide situational awareness, detailed knowledge of what everyone is doing, a quick assessment of this person’s skills and inclinations, and a hundred other things. All of these things, in fact, are the true work of the manager and can easily fill up all of said manager’s time.

So when I quit my job to embark on this self-directed life, and from a management position no less, it’s remarkable that I completely forget this pretty salient piece of wisdom. Each day is now a wide open space of possibility… which is great, but also points to a pretty strong need to fill it in a useful way.

In the absence of a boss, I need to be the manager of my own life. And not only the manager, but every function of the company, too. That’s all on me now. Marketing, strategy, product, HR, finance, that exuberant external motivational speaker who comes in for away days and then is never seen again. All of them.

The point of this post is not for this to be an insightful addition to the world. It’s more like a reminder to myself, and perhaps people like me, that all of these things require focused attention. They are work. It’s not only okay to spend time on them, but vital.

After a career where I spent most of my time as the doer, or the manager of doers, I need to remember that a day reflecting on what I should be doing is probably not a wasted day. Sure, there are better and worse ways of doing this, but the point stands: if I’m tired at the end of the day and all I can point to is “well I wrote a few hundred words of something”, that’s almost certainly neglecting a couple of hours worth of ‘reflecting on the big picture, thinking about what I should be doing, worrying if I’m doing the right thing’ and so on.

And again, there are better and worse ways of doing THAT stuff as well, and I certainly intend to get better at it, because being bad at it is both exhausting and doesn’t get me anywhere.

But the larger point stands: that stuff does exist, it’s valid, and it needs to be brought back into scope of how I treat my days.

This is a stock photo of "Young Successful Manager Looking At Camera While His Colleagues Talking On The Background", which made me laugh