May 5, 2022

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In 2020 I wrote a book about executive assessments, which came out in late 2021. I've always wanted to write a book. Honestly though, I always expected to write a short bad novel about college or something and then move on to a more interesting topic.

So, it has been a curious experience to see my first book take the form of an academic-adjacent primer aimed at a rather specific professional audience.

Since the book came out, a couple of things have been rattling around in my mind about it. How did I come to write that book and not another book? Will I write another book? And oddly, because the book had a good bit to do with interviewing people, a lot of questions about questions themselves:

• What makes a good question?
• What does a good question do?
• How do you ask a good question?
• Are there times when there is a "right question" and a "wrong question"?

In general, questions help us gather information, unlock insight, and shape how we think about solutions/answers. As Thomas Pynchon put it, "if they can get you asking the wrong questions, they don't have to worry about answers."

To that end, asking the "right question" can be a prerequisite for making a "good decision."

In the course of thinking about this, I did what I frequently do, I bought a few books about it. I'm working my way through them now, but the first I read was The Coaching Habit by Michael Bungay Stanier. It's a quick read with some useful points, but the line that's been ringing in my ears since I finished is actually a quote in the book by Tim Ferriss:

Oof. I don't usually think of myself as a particularly busy person, and frequently take some effort to ensure that busyness doesn't overtake me. However, the aftermath of a recent daycare shutdown has created a run of back-to-back zoom days that has me feeling pretty fried. And more than that, has me wondering if this rise in my busyness has me focused on the right things.

​Busyness has long been an odd sort of status symbol among a certain class of people, but it's that same busyness that can lead us astray professionally, cause us to burnout (even in jobs we like), and can generally decrease creativity and compassion (among other negative impacts).

The aforementioned Tim Ferriss quote is in a part of the Coaching Habit called "The Strategic Question," which is:

Or, to paraphrase my friend Jon Yarian, doing something is, if nothing else, the final decision on what you won't do.

Indeed the root word of 'decide' is decidere, which means "to cut off." When we decide to do one thing, we're cutting off other options. Which is why deciding can be so agonizing at times (for me at least). I find this to be an incredibly clarifying logic. So clarifying in fact that I find it hard to consider in its fullness, like staring into the sun.

Because "saying yes" frequently happens quite passively, feels good, and doesn't exactly feel like making a decision, we don't always consider the implicit no's that are coming along with it.

If I say yes to writing a book about executive assessments, am I also saying no to writing a short bad book about college? At least for a time. If I'm saying yes to this meeting (zoom), project, job, trip, move, etc., what am I saying no to? What am I not doing with that same time? And am I thinking critically about these things - making decisions about what I'm prioritizing - or am I just letting lazy thinking and indiscriminate action wash over me?

To be clear - I tend to be terrible at all this. Perhaps that's why I find it interesting? I'm an anxious decider. I can't help but think about all the precious possibilities that fall by the wayside each time I make a decision or say no to some kind of work that interests me. It has taken some time to learn that making a definitive (read: hard) choice definitely does 'cut off' opportunities, but it is also clarifying in its own right, leads to insight and growth, and leads to a host new opportunities.

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There is an element of this perspective that assumes one has the autonomy and/or economic stability to realistically ponder these types of questions and make changes.

The cultural/societal issues with work that shape what some people must do just to get by is a bit outside the scope of what I'm aiming at in this newsletter, though I don't think it's irrelevant. Jonathan Malesic (fellow Wahoo), has some great writing on that subject, and burnout, and work in general if it's of interest.