WIIAWO Issue #6: What if I make the wrong decision?

When it comes to making decisions, I get paralyzed by all of the different variables and potential outcomes, and feel compelled to map out every possible scenario. This is true for everyday choices (What should we eat for dinner? Which space heater should I buy?), business decisions (Should I take on this project? How much product should I order?), and big life changes (Should I sign this lease? Should I change jobs?). And it still feels like I never have enough information or certainty to take action.

Here's a business decision that I've regretted for years:

I shipped out two large boxes of inventory to myself from New York to Boston for holiday markets, which were my primary revenue stream for the season. Each box contained hundreds of cards, stickers, and art prints, which represents many hours of labor and thousands of dollars. I shipped the first box with added insurance, and it was delivered the next day without a hitch. Insurance is costly, and so I opted not to add insurance to the second box because it was going the same short distance to the same address. This second box, however, was delivered to the wrong address. Despite urgent, desperate calls (and tweets) and combing through the neighborhood for stray boxes, it was gone. And because I didn't insure it, I had to absorb the cost of the lost merchandise and sell at the holiday markets with only half of my inventory. I felt so stupid and regretful: I should have added insurance. I should have used another carrier. Why did I make such a careless, terrible decision? Years later, I still remember how harshly I berated myself. 

I actually make decisions all the time that seem like the wrong ones, which in turn makes me even more hesitant to make decisions. 

My old, sad tweets to FedEx, hoping to spur them into action to find my package, but with no avail. 


I've been thinking more about what makes a decision "good" or "bad" and also a productive way to evaluate my decisions when the outcome is not what I wanted or expected.

1. Every outcome is shaped by some degree of uncertainty and luck

Past experience, statistical odds, or logical reasoning can help predict or improve the probability that we get the outcome we want. But luck is an input to even the most researched, thought-out decisions, because we don't live in a lab or a computer model; our decisions play out in the complex, chaotic world.

Everything that happens is shaped by some degree of uncertainty or luck.

In the case of the lost package, I reasoned that since the carrier was experienced and reputable, and had successfully delivered to this same address the day before, the second box would very likely also be delivered.

But there are countless factors at play. Maybe the delivery person misread the address or scanned the wrong box. Maybe the usual delivery person was sick that day and their substitute was less familiar with the addresses on the route. Maybe someone happened to walk by and steal the package off the wrong porch.

The future is unknowable and unpredictable. We never know at the time we're making a decision if it will lead to the outcome we want.

2. Judge decisions based on the reasoning, not the outcome

More recently, I've been trying to judge decisions based on the soundness of my reasoning in the face of imperfect information, not the outcome. If I'm doing what seems best given what I know at the time, that's the most I can do. Even if it doesn't pan out, I can feel good about my decision-making process.

In other words, don't judge your decisions based on the outcome; judge them on the soundness of your reasoning:

 The quality of decisions are only based on the soundness of reasoning, not the ultimate outcome

Looking back, while I did have a reason to not add insurance given my experience with the first box, I didn't account for luck in my plans or expectations. Going forward, I'm learning to factor in the unexpected, and also to hold myself accountable only to making thoughtful decisions and not their outcomes.

3. Most things will turn out OK anyway

While it's good to think through decisions and to have a plan, at some point you have to just take a leap of faith. And if things go wrong, trust that you have what it takes to navigate whatever comes next.

Most decisions aren't all good or all bad, or complete and total disasters. Even though I lost money and sleep over the missing inventory, I did make it through the holiday season and many more after that. It is also a reminder that I am part of a community that shows up when things go wrong. For example, a maker friend saw my public plea and volunteered to drive around the neighborhood to look for my missing package.

Worst case scenario (which I tend to think about), an outcome of our decision is irreversible and disastrous. But, it's done. Sometimes we make mistakes and poor decisions, because we're human. And we move forward, the best we can.

Do you have your own story, experience, or advice about making decisions? I'd love to hear it! Just comment below.




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