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How Do You Tell Whether a Risk is Worth Taking?

Updated: Dec 23, 2021

Note: This is part 2 of series on risk. You can read part 1 here.

“I will not die an unlived life. I will not live in fear of falling or catching fire. I choose to inhabit my days, to allow my living to open me, to make me less afraid, more accessible, to loosen my heart until it becomes a wing, a torch, a promise. I choose to risk my significance; to live so that which comes to me as seed goes to the next as blossom and that which comes to me as blossom, goes on as fruit.” Dawna Markova

Not all risks are created equal. 

Some risks may seem to be daring, but really aren’t. Others may claim to inspire, but are in fact weak and selfish. Others may feel bold, but are actually just foolish.

So how do you tell whether a risk is worth taking?

Beginning with Plato and stretching through many centuries after him, a rich collection of thinkers, philosophers, and theologians have created, debated and modified a brilliant lens for assessing the worthiness of any action we may take. It’s called the Philosophy of the Good, the True, and the Beautiful. It promotes the idea that anything we say or do in life can only be considered truly noble or worthy to the degree that it aligns with these three core guiding principles: 

Is it Good? Is it True? Is it Beautiful?

This test of worthiness overlays nicely with the notion of risk, because it gives us an accessible way of differentiating between risks that are truly meaningful, and those that may be merely diversions, or selfish, or even foolish. 

Let’s explore these three qualities as they might apply to the notion of Risk. As you read the following sections, it might be helpful to bring to mind a risk you are thinking about taking.

1. Is it Good? As it applies to risk, “Good” may be best defined as Noble or Worthy. In other words, is the risk you’re considering in service of something Noble? Will it help or serve others in a meaningful way? Is it for the sake of the planet, or the life on the planet? Will taking this risk serve Beauty in some meaningful way? Will it serve love, or healing, or in some way help set others free? Will it help you become your True Self?

If the answer to any of these questions is a clear yes, then chances are it is a Good Risk.

The contrast, of course, would be any risk taken for the sake of Ego, for selfish gain, or as a way of getting legitimate needs met in illegitimate ways (e.g. porn, shooting up, stealing, reckless behavior). Egocentric risks can be fueled by a desire for others to “look at me, I’m so ______ (cool, popular, brilliant, wealthy, etc.),” or as a means to make up for some self-perceived deficiency—that is, to prove you are worthy of love, respect, status, or belonging. In short, a bad risk is any risk that is ego-driven and lacks a truly noble cause.

2. Is it True? In other words, is it truly a risk, or just an elaborate display of posturing or pretense? It doesn’t take a psychology degree to see how good we humans are at self deception. It can be frighteningly easy for us to convince ourselves we’re leaping off a cliff, when in fact we’re just posing for photos near the edge. Thankfully, there is a litmus test for determining whether a risk is real or fake. Here it is: 

True Risk makes you VULNERABLE—that is, “susceptible to physical or emotional attack or harm.” 

True Risk involves actual fear and discomfort, because something meaningful to you is actually on the line. By contrast, a False Risk has the look of a risk but without any real teeth. Nothing is truly at stake. For instance, when someone declares what they are doing is “risky or daring” when, for them, it’s really not, or it’s really not the deeper risk they need to be taking. 

Here’s a real world example: There’s a fair bit of talk these days about the virtue of “being real” and “speaking your truth.” While this can be admirable, for some it has translated into assuming they have the “right” to be rude and callous and needlessly harsh in the way they speak to other people. “I’m just saying what’s true,” they proclaim. “I’m just telling it like it is.” These individuals often claim to be risk takers. They claim the reason they can be so raw and “real” is because they are braver than other people, and are willing to stick their neck out and say the things that no one else will say. But in fact, many of these people are not actually brave at all. Rather, they grab the spotlight in this abrasive way solely to feed their ego, to make themselves the focus of attention, to be the one who stands out above the rest. Speaking out in this way is not a true risk for them. To the contrary, the real risk for them would be to remain quiet. 

Another example might be when someone engages in daring behavior in extreme sports (as a way of proving he or she is not afraid of risk) but is terrified of taking risks in other arenas of life that would actually be more meaningful. The extreme behavior in the sports arena is a false risk in the sense that it’s a diversion from the actual risk the person needs to take. The whole enterprise is rooted in self deception. 

This True/False dichotomy in Risk can also be more straightforward, as when someone claims to be risking by giving a lot of money away for charity, but in fact they have so much money their choice isn’t really risky for them at all. (See: the biblical story of the widow’s offering.)

3. Is it Beautiful? In other words, is it well-designed? Is the risk well-thought-out, or just thrown together in haste? A Beautiful Risk is one that’s been strategically crafted with wisdom, and clear intention. We like to romanticize the sudden, daring risk taken as a passionate leap of faith, but most truly beautiful risks are not taken impulsively or without forethought. They are designed—with the same quality of artful planning employed by any serious explorer or architect.

Perhaps this is what the Proverb is trying to convey when it says, “The plans of the diligent lead surely to abundance, but everyone who is hasty comes only to poverty.” (Proverbs 21:5)

So here’s another real world example: One of the most common reasons people come to me for coaching is because they hate their job. They want to quit, find something else—something more aligned to who they are and their desire to make a meaningful contribution to the world. This is all awesome, of course. They’re to be commended for seeking out a coach, as that alone is a courageous step in support of a higher vision for their lives. But some of them “come in hot,” as it were—proclaiming in their first coaching call that the best way to break free from their current job is to just quit—to take a leap of faith, with no plan and no forethought about their next steps after that—and blindly trust that something good will come of it. Now let me be the first to say that this is not always the wrong choice. Sometimes, when a job is so toxic you can’t get away from it or even think straight anymore, then quitting immediately may be the best option. But for many, quitting without a well-thought-out strategy for what comes next is really more about impatience than anything else. They don’t like their job. They want to quit now. So they come up with a justification for quitting immediately. While this act may be risky, it is also most often foolish. It’s not that they shouldn’t quit—of course they should! It’s just that they shouldn’t quit without a thoughtful plan for what’s next. 

So what about that risk you’ve been thinking about? Is it Good? Is it True? Is it Beautiful? If it passes the test, what’s stopping you from starting this week? If it doesn’t pass the test, how could you redesign it so it does?

NOTE: This is part 2 of a 3-part series. You can read part 3 here.

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