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The Wisdom of Risk

I couldn’t help but stop and take notice. I’d just written a sentence in my journal that didn’t sound like me. I wasn’t even sure what I thought about it.

“Wisdom is sometimes overrated.”

I was seeking to capture some of my turbulent thoughts and emotions surrounding a decision we were considering; a big decision to put a deposit on a lot to build a small cabin on a small lake in Michigan.

Even considering this decision was uncharacteristic of us. We don’t typically take financial risks. We’re conservative when it comes to our lifestyle choices. This opportunity which came our way unexpectedly felt big, scary, and risky. And that was it.

Risk in my mind is in opposition to wisdom, especially at our stage of life. Taking money from our retirement funds when we don’t know how much we will need or how long we will need it seems irresponsible. And yet we can’t deny the persistent ache and attraction for “a place” to get away to, a place to replenish our souls. And this place checked all the boxes!

We’ve dreamed about this kind of place for most of our married life. But we also know that we don’t want another place to take care of. When we vacationed at this property in June, we discovered a beautifully maintained community of small cabins, with tons of amenities, and where the property managers take care of the exterior of the cabins and all the grounds. Unexpectedly, the main concern we had about caring for another place was resolved. Could this work?

This ignited an ongoing conversation between David and me, one that has had many highs and lows, “what if’s” and “buts,” and has culminated in the decision to move ahead. What’s become clear in the process is that living wisely doesn’t eliminate all risk.

I have had a bias, at least in my thinking, that wisdom is a virtue and risk is a vice. Yet, as I survey my life, I see clear evidence that this simply isn’t true. Wisdom has guided me toward thoughtful risk. And taking risks has helped me align with an interior wisdom, a way-finding wisdom, which has led me toward the life God has called me to live.

I now concede that risk is not an adversary to wisdom after all. Some of the most important decisions I’ve ever made involved risk. Take for instance the enormous risk David and I took when we left our roles at a mega church almost 20 years ago. We resigned simultaneously with no exit strategy or jobs in queue. We simply knew that we couldn’t continue without destroying our souls.

Ten years later, we sold our house in the suburbs, took out the largest mortgage for the biggest house we’ve ever owned, and moved to the city and founded Fall Creek Abbey. At the time, many of our friends were talking about downsizing as we “upsized” in order to fulfil a God-given dream.

Both instances call into question conventional wisdom, the generally accepted way of thinking about and doing things. Leaving a job without having a job and upsizing at a life stage that calls for downsizing is risky! And both decisions have proven to be undeniably positive ones.

So, when is it wise to take a risk? As I reflect on my life, risky-yet-wise decisions share several common themes. Here are some questions that capture these themes for me:

  1. Have I entertained the consequences if the decision doesn’t pan out? If so, am I able to say, “I’ll be okay and those I love with be okay, too.” This is called taking a “calculated risk.” In other words, I’m not engaged in magical thinking, avoiding the facts or minimizing the potential for loss. I see it. And I see a way to recover.

  2. As I consider the outcome of the decision, does it provide obvious benefit to myself and others? Does it multiply goodness, provision, and opportunities? Does it lead to life? Is the risk worth the good it has the potential to achieve?

  3. Is not taking the risk a matter of life and death, not merely physical but spiritual, emotional, and/or relational? If I don’t take the risk, what will it cost me? What will I be sacrificing?

  4. Is the desire that motivates this decision coming from my true heart, or from superficial, compulsive energy that is simply seeking a quick fix?

  5. Can I slow down the decision-making process, let go and surrender this desire to God? Am I able to be indifferent, holding the outcome of this decision loosely?

The wisdom of risk is not always apparent. That’s why we need questions like these, along with conversation partners and unhurried time to help us work through the complicated process. Wisdom is sometimes overrated. And that confession no longer feels like blasphemy to me.


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