The Thirteen Habits of Highly Effective Risk Takers
...and what this means for career advice
Although I don’t have to line manage any more (and haven’t for some time), I’m still in the habit of trying to distill key points here and there from books that I’ve read. Partly (as I’m sure others will sympathise with) this is so that I don’t forget them, or can refer to them later, and partly it’s because I still do a little bit of mentoring and career advice and these notes can be useful in those cases.
One of the most interesting chapters in Nate Silver’s 2024 book On The Edge is the middle chapter on risk-taking behaviours. Something that I’ve observed a lot when looking at the careers of others is that they don’t take enough risks. I’ve never particularly thought of myself as a risk-taker, but with the benefit of fifteen years of hindsight, it appears that, compared to the average, my perception might not be correct.
While reading the book, in fact, I realised that on some level, much of my advice to folks (particularly those at the start of their careers) could be summarised as, “take on more risk,” with a side of “but make sure that it’s calculated.”
To make sure that you’re making a good calculation here, a good rule of thumb is to figure out what the upside of a given choice is—the terms I tend to think of here are simple: money or learning—and optimise for what matters to you most at the time.
I’ve taken jobs that were more about the money, some that were more about the learning,1 and some, like my second engineering job at the data consultancy Swirrl,2 which rather fortunately offered both.
As Erik Deitrich points out, when you take a job, you tend to get more benefit than the company that hired you, especially if you’ve chosen a new workplace where you will upskill, but that over time, this learning levels out, and the relationship becomes that your employer benefits more than you do. This is why it’s important to have clear success and exit criteria in mind to govern when you will move on to your next challenge, a mentality he describes as “Always Be Leaving.”
I’ve always encouraged folks to have a rough five year plan3 and to have some kind of heuristic for making decisions. In Scott Hanselman’s Scaling Yourself talk, he references a quote from a banker (name forgotten, apologies), “if it isn’t making me money, I drop it.” He then flips that to put his own primary goal in its place, “if it isn’t helping me spend more time with my family, I drop it.”
This kind of heuristic is continually useful, for evaluating both decisions in the large (do I take this job) and the small (do I take a meeting in person rather than online).
But anyway, back to risk. Silver’s 13 habits aren’t all strictly relevant to thinking about risk in your career, but some of them are (I’d say 1-3, 5, 8-10, 12, and 7 is crucial—these are all in bold):
Successful risk-takers are cool under pressure.
Successful risk-takers have courage.
Successful risk-takers have strategic empathy.
Successful risk-takers are process oriented, not results oriented.4
Successful risk-takers take shots.5
Successful risk-takers take a raise-or-fold attitude toward life.6
Successful risk-takers are prepared.7
Successful risk-takers have selectively high attention to detail.
Successful risk-takers are adaptable.
Successful risk-takers are good estimators.
Successful risk-takers try to stand out, not fit in.
Successful risk-takers are conscientiously contrarian.8
Successful risk-takers are not driven by money.
If you want to read his full reasoning, pick up the book—obviously this is just a tiny summary for the purposes of this article. I’d also note—although this is a subject covered elsewhere in my review of the book—that many of these behaviours are also present in non-clinical psychopaths. Oh well.
Including, after all, starting a PhD, which involves a large amount of learning and which nets you negative money.
I will be forever grateful to Ric and Rick for mentoring me, as well as introducing me to functional programming, lisp and emacs.
Even though, obviously, nothing ever goes to plan, and even when it does, the plan changes.
Silver describes this is “playing the long game”—while this is good advice for certain situations, such as the high-stakes poker that concerns the first half of the book, it is not strictly good advice for careers, without some tweaking. You should care about systematizing processes, so yes, being process-oriented matters—however, the outcome is what counts in business. Tersely, are you making money, or are you saving money?
Be “comfortable with failure” Silver advises, so long as you are “explicitly aware of the risks [you are] taking”—this is great advice.
Or, back to Dietrich, Always Be Leaving; “they know when to quit.”
This is both on the conscious level and the intuitive level. Building an intuitive grasp of systems, patterns et cetera is something that I’ve written about elsewhere in the context of Apprenticeship Patterns (the book and the mindset) in software engineering.
“There is an oft-neglected distinction between independence and contrarianism,” Silver writes; he notes that effective risk-takers “have theories about why and when the conventional wisdom is wrong.”