Everything I learned in the last two years was about failure. And I’m finally okay with that.
This week I went through an exercise designed to generate writing topics quickly. It begins by having you list what you’ve learned in the last two years. Hmmm. I stared at a blank page, then finally began. When I’d run out of ideas, I took a look at what I’d written. There were no new productivity solutions, technical skills, or marketing techniques. Almost every item was about what hadn’t worked for me. The fails. The dead ends. The hard lessons. Sigh. Such a list wasn’t exactly going to generate viral writing.
If you’ve taken inventory of your recent learnings—perhaps for a job interview or just personal reflection—and have felt disheartened by the lack of tangible gains, don’t despair. I am someone who values learning, is almost always involved in some kind of class, and thinks of herself as a lifelong learner, and yet….my list was almost anti-learning. What not to do. After reflection, however, I realized what I have learned in the last two years is actually quite deep stuff. And I suspect you will find the same.
Learning changes over a career
To gain some perspective on my list of failures, I thought about the creator of the exercise, a very successful and well-respected (including by me) person who teaches online writing. He is 25. He works as an investment analyst but as a side-gig offers a course and ebook, and writes Twitter threads, all about writing. To be clear, I think he’s very good. But he’s at a completely different career stage than I.
If you’re over 50, think about what you were learning 25 years ago. It was no doubt quite different. This exercise showed me that what works for some, doesn’t work for others—and sometimes that is based on age or stage.
Skills, hard and soft
People in their twenties are learning highly specific skills. These are valuable and quantifiable. Twenty-five-olds write excellent threads like, “I grew my followers from 100 to 100,000 in 30 days. Here’s how I did it.” Or “Founders, here’s how to hire your first five employees.”
By the time you’re over 50, those skills you learned at 25 no longer even feel like skills. They are part of who you are, woven into the fabric of so many disciplines. It becomes harder to quantify what you’re doing or rationally assess its value. Plus, chances are, in your role you are called to something less tangible: to manage, to lead, to cultivate a culture.
Fully internalizing the hard stuff
It can take decades to actually learn the stuff conventional wisdom explains in a single, obvious sentence. For example, a mainstream concept these days is that working on improving weaknesses is a waste of time and energy—instead, focus on strengths. I have believed this for a long time. Yet, it wasn’t until this year that I actually began making decisions based on it.
One of my weaknesses is phone calls. I have despised initiating phone calls since my college days. Unfortunately, for a traditional journalist, phone interviews are a necessity. Only in the last year, did I stop “powering through” and decided to do a different kind of writing. It was an easy concept, but a hard lesson.
I’ve also learned to get okay with pivoting. Not the sunshiney, “an incredible opportunity came my way” pivot, but more like, “this isn’t working, so now what?” pivot. There are plenty of books and articles on knowing when to ditch a project (one that comes to mind is Seth Godin’s, The Dip: A Little Book That Teaches You When to Quit). But the truth is, the real learning is in actually coming to grips with yourself. Again, an easy concept, but a hard lesson.
The lessons that don’t work in “threads”
These are lessons that cannot be taught. They must be experienced, lived. And rarely in a straight line. I suppose one could write a Twitter thread on, “How I learned to accept my weaknesses, and you can too.” But I suspect it wouldn’t get much traction—it’s not a headline that halts a scroll.
We are drawn to the shiny objects that are easily broken down, able to be dashed off in a thread or a listicle. But those of us in wisdom-accumulation-mode know that the really valuable stuff doesn’t come that way. It’s a lot of trial and error. A lot of failings. And we’ve been doing that for a lifetime. That’s what success looks like.
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