The Greg Pass Strategy for getting unstuck.

Issue #275 of the Better Humans Newsletter. Subscribe here for inspiration and knowledge.

This is a business strategy, but I think I can pull off connecting it to life strategy.

One of the first things I did when I joined Medium was to get the team working on fixing a long list of basic issues. As someone who had lived on the platform for years, I was tired of Medium releasing new things when the old things I relied on didn’t work.

Of course, tech folks know a lot about working iteratively thanks to ideas like The Lean Startup. And yet, there is still a lot of room for interpretation on what constitutes an iteration.

Plus, what I had in mind is different from iteration in an important way. Specifically, Medium is a system that breaks down when any component part breaks. So my strategy wasn’t about any single iteration, rather it was about the necessity of a dozen small changes.

I’d never seen anyone give a name to this type of strategy, but I’d heard a story that was similar. That’s where Greg Pass comes in.

In the very early days of Twitter, the service went down constantly and the fail whale was a regular character in people’s lives.

Around that time, Twitter acquired a company called Summize. The Chief Technical Officer (CTO) at Summize became the CTO of Twitter. That’s Greg Pass.

Many things at Twitter were broken to the point that they could bring the entire site to a halt. Greg’s strategy, now distorted through multiple retellings and my own foggy memory, was to focus on short-term triage rather than long-term fixes.

Essentially, he realized that a collection of temporary, duct-taped fixes was the only thing that would give the Twitter team the breathing room to start working on longer-term fixes.

I think of this in school grade terms. Greg went looking for all the Fs and then turned them into Ds. Then he turned all the Ds into Cs and then all the Cs into Bs, etc.

These grades are subjective. But here are some examples of how I grade.

The other day I was involved in fixing a bug in Medium’s response notifications. You’d get a notification that someone had responded to your story, but tapping the notification took you to the responder’s profile rather than the response itself. From there, there was no way to read the response. I’d grade that an F. The notification feature failed to work.

Now, today, there’s a different bug in the same notification system where sometimes you tap on a response notification and get sent to your story page rather than the response. From there, you can tap two times and read the response. I give things like this a grade of D. It works, but very, very badly.

The issue for Medium is that we are known for features you would grade as an A or A+ even, i.e. the editor. But those high-quality features get hidden if they are surrounded by too many Ds and Fs.

That’s about seeing Medium as a system. All the details are linked. For example, nobody wants to write in a beautiful editor if they think nobody will read it.

So I used this Greg Pass Strategy to make the case that we needed to turn all these Ds and Fs into Cs so that our As and Bs would be visible again. I think we’ve done a good job, although I know talking about this invites people to respond with their own grades. Go for it, we’re listening.

OK, that’s a lot of Medium insider stuff. This exact same strategy came up for me at home and I think could work for many of you.

Last year, I converted my garage into an office/gym. But this space is always threatened by other use cases, namely storage and small construction projects. If I’m not diligent about defending the space, it becomes unusable.

I had one of those moments recently. We’d been away and the spiders moved back in. Some wood had been sanded and there was sawdust everywhere. There was a large pile of items meant for giveaway. A heat wave had caused sound panels to peel off the walls. That’s all on top of the standard gym mess and desk clutter.

I don’t have unlimited time to clean and organize. So I’d be stuck if my standard was that my office needed to be perfect. In fact, I had been stuck and was working on my laptop from a different room because I couldn’t figure out how to make the office workable again.

That’s when I pulled out the Greg Pass Strategy. That meant looking around the room for the Ds and Fs.

For me, the sawdust was an F and the clutter from things that don’t belong to my office or gym was a D. The spider webs were also an F. Unsurprisingly, I don’t like them.

Once I fixed those, I could move my work back into the office and could look around at all the Cs and start contemplating how to turn them into Bs and As.

I’d classify this all under the phrase, “perfection is the enemy of good.” This is especially true in complicated systems. So see if giving yourself permission to do mediocre work opens up space for you to then do good and great work.

It also brings up one of my favorite quotes:

The competent programmer is fully aware of the limited size of his own skull. He therefore approaches his task with full humility, and avoids clever tricks like the plague. ~ Edsger Dikstra

This Greg Pass Strategy contains some humility about what you are capable of doing. By moving in manageable chunks, you allow yourself to work toward a bigger goal.

There’s a psychological problem with taking the small, mediocre, good-enough approach. If you aspire to do great things, as I do and as Medium does, then mediocre feels like selling your goals short.

You need to remind yourself that mediocre is a stepping stone. Writers do a good job of this with the phrase, “shitty first draft.” It’s clear to them that additional drafts are required.

This is the reason I wanted to give my Medium strategy a more heroic name. The Greg Pass story isn’t about mediocrity, it’s about persistence. He led that team through from a broken system to a duct-taped system to a functional and stable system. It took the team five years, but eventually, they retired the famous fail whale.

To honor Greg, you can only honestly claim to be using the Greg Pass Strategy if your goal is to move toward greatness.