How to Reframe Failure

Hello and welcome back to Evolve, a weekly newsletter about behavior change.

Before getting into today’s topic, I’d like to try something new. Email me with a recent failure - a behavior or habit you’ve attempted and failed - and I’ll write you back and apply today’s exercise to your challenge. Your example could be anything - a personal habit, a professional objective, whatever.

Drop me a note with your failure and let’s apply this framework together.

Three Things I've Loved This Week

TV Show I’m binging: Billions by Brian Koppelman and David Levin. I came down with COVID this week, and so I’ve spent most of the week sleeping or staring into the middle distance.

Along the way, though, I’ve enjoyed revisiting Billions, which just released the 7th and final season. I’ve long been a fan of Brian Kopleman and his co-creator David Levine and Billions is their commentary of wealth and power. Among other things, the food, music, and historical references throughout the show are very thoughtfully curated.

(I also enjoy Brian’s podcast The Moment.)

Podcast I’m listening to:Hugh Howey: Winning at the Self-Publishing Game” on The Knowledge Project podcast by Shane Parrish.

Long before he became known for Wool and the Silo Saga, Hugh Howey was writing and self-publishing books. In addition to talking about writing routines and the pros and cons of self-publishing, this interview touches on things that I haven’t heard anyone else talk about, like digital ownership rights, deal making, and more.

Hugh also recommends the book The Wayfinders: Why Ancient Wisdom Matters in the Modern World, which I picked up and devoured.

Tool I use every day: Leek pocket knife by Kershaw. While this isn’t the olivewood handled knife I describe in today’s article, I’ve owned a Kershaw Leek since I visited their factory in Portland in 2002. I like everything I’ve used by Kershaw, but the Leek, in particular, is sturdy, elegant, and small enough to be unobtrusive.

How to Reframe Failure - and My Complex Relationship with the Mail

There are a lot of things about being an entrepreneur that I avoid, but one of the silliest is opening physical mail. When I was starting Robin’s Cafe, I got a lot of mail - plans from the San Francisco planning department, legal documents, food permitting, alcohol permitting, pest control notifications, more.

I was so busy figuring out the day-to-day of running the business that I developed the bad habit of just ignoring mail and leaving the pile to build up on my desk for weeks on end.

When I finally got around to dealing with the pile, there was always a notice that I’d ignored for too long - a vendor I was late to pay, an IRS document I’d missed, etc. As we all do when a task is too big, I came to dread opening my mail.

Failure as discouragement

When you fail at a task, the experience is often one of discouragement, and that discouragement leads to a diminished desire to attempt that same task in the future. As I discussed recently, success is usually tied to positive feelings and the release of dopamine. Negative feelings often have the opposite effect and result in a feedback loop of negativity and failure. For me, that meant avoiding the mail until I discovered late bills, which meant I’d continue to dread opening mail and let it pile up further.

Failure is often a sign that the task you are trying to undertake is too big. A trick, then, is to leverage the cue of the negative feelings of “I can’t do this” into action and try again, but make the next attempt different. One way to do this is to break the task down into smaller parts.

Make the next step smaller

When you are overwhelmed by a new behavior, the easiest way to tackle it is by making the next step smaller.

I don’t need to open and respond to all of my mail on the day it arrives. A small step is to open every envelope, even if I don’t take the mail out right away. This small step moves things forward and makes the next steps - removing the contents, reading them, responding - easier.

Take your large goal and just take one small step in the right direction.

Create positive associations

I have a letter opener that I really love - it is a beautiful folding knife with an olivewood handle. I’ve learned, in the years since Robin’s Cafe, that I derive a particular delight in opening mail with this knife.

Look for ways that you can create positive associations around the edges of the habit you’ve been avoiding. Positive feelings equate to feelings of success.

Play more

Play and self-judgment are antithetical. When we are being playful or curious with a habit, it is impossible to regard an outcome as a “failure.”

The best way I know how to play - especially when I’m not feeling playful - is to get profoundly curious about the task I’m trying to accomplish. Another is to make a game of the process. Personally, I get delighted when I see weeks worth of dealt-with mail pile up in my recycling bin!

Look for a step by step breakdown

You can almost always find a step-by-step breakdown of the task you are trying to accomplish. Google “how to do x” or interview someone better at that thing than you are. If you’ve hit a roadblock and aren’t sure how to make a task more manageable, someone else has likely solved this problem before you. In writing this article, I asked a few friends about how they handled their daily deluge of mail and got some interesting ideas I’ll try in the future!

At Zander Media, I receive 10x less physical mail than I did at the cafe. And while there are still remnants of my avoidant behavior, I’m excited to reframe failure as a cue for novel action. These days, I look for areas of my life where I’ve historically failed and replace the cue of failure with the understanding that I haven’t made that behavior small enough, yet.

Now, your turn: what’s something you’ve failed at, recently? Reply back and I’ll respond with one idea for how to turn that failure into a learning opportunity!

Until next time,

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