Teach everything you know

When I was a lieutenant in the Air Force I had the privilege of serving as an Executive Officer to Major (now Colonel) Heather Blackwell while she commanded the 87th Communications Squadron at McGuire Air Force Base, New Jersey.

One of my many takeaways from the experience stems from a conversation we had about her taking leave and who would take over her various responsibilities while she was away. She said “One of the measures of how effective I am as a leader is not how poorly the unit performs while I am away, but how well it performs.

It’s counterintuitive at first because you might think that if someone who plays an important role within an organization suddenly leaves, that the organization would suffer as a result. But her point was that if things fall apart, that means she hasn’t done an effective job teaching us about what she does and how to do it. That’s not only important if she goes on vacation, but also because by teaching us she’s helping us become more effective leaders and preparing us for commands of our own one day.

I’ve been thinking about this a lot lately because I realized that in my role at Automattic, there are several things that I work on where I’m basically the only one who knows how those things work. For example, I built a system for tracking visitors who click on our ads so that we can measure our return on ad spend, but haven’t done a good job making sure other developers on the team understand how it works. Similarly, I work a lot on building email marketing lists for WordPress.com users who meet certain criteria, but never took time to document how to do it until recently.

Teaching others has so many advantages:

  • It ensures you’re not a bottleneck for the work that you do
  • If you go on vacation, change roles, or leave the organization, it ensures your team will continue operating smoothly because someone else will be able to carry out the tasks that you previously performed
  • It helps you learn from others because they’ll likely have feedback that will help you improve the way you do things
  • It helps you clarify your own thinking and processes
  • It will help others develop their skills and grow professionally

Also, if you’re an entrepreneur, teaching everything you know also has huge advantages which Nathan Barry has written about at length (there’s even a t-shirt!).

If you find yourself in a position where you’re the only one who knows how certain things work, find ways to involve your coworkers or hold a learn-up or just write documentation – whatever you do, don’t let yourself continue being the only one who knows how to do those things. Good things will follow.

The WordPress.com Desktop Apps Will Make You Want to Blog More Often

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Just before Thanksgiving Automattic opened sourced Calypso and released the beautiful WordPress.com Mac App. The Mac app and the Calypso post editor within it are the main reasons why I’ve been able to keep up this blogging streak for as long as I have (this post will the last in the streak at day #30).

For me the editor makes all the difference in the world. If the UI is bloated or slow or contains frustrating bugs, it really distracts me from the writing experience. Fortunately the new Calypso editor is none of these things. It’s clean and fast and makes me want to write more often, not less.

We also released a Windows and Linux version this month giving you no excuse not to try one of them out for your WordPress.com or Jetpack-enabled site.

Thank you to everyone at Automattic who made them possible.

What we can learn from the math behind small probabilities

In high school stats class we had a homework assignment during our section on probabilities that went something like this:

A rock climber estimates his odds of dying on an individual climb are 1 in 1,000. What is the probability that he’ll die before his 1,000th climb?

Kind of morbid, but I’ve always remembered it because it has a non-intuitive answer for reasons that we can apply to a lot of real-world situations.

Many people will answer that the climber’s odds of dying after 1,000 climbs are 1 in 1,000, but that’s incorrect. It’s true that his odds of dying on an individual climb are 1 in 1,000, but we have to account for the fact that he’s doing those individual climbs 1,000 times.

The math works out like this:

His odds of dying on an individual climb are 1 in 1,000 (0.001) meaning his odds of surviving are 999 in 1,000 (0.999). His odds of surviving 2 climbs is 0.999 * 0.999, his odds of surviving 3 climbs is 0.999 * 0.999 * 0.999, his odds of surviving n climbs is 0.999^n. For 1,000 climbs, his probability of surviving is 0.999^1000 or 0.368, meaning he’ll die 63.2% of the time before he reaches his 1,000th climb. Ouch.

How can we us this to our advantage? Consider a more uplifting example:

You’re a junior developer and estimate there’s only a 1 in 50 chance of getting hired by a large Silicon Valley software company. What are your odds of getting hired after 10 interviews? 1 – 0.98^10 = 18%. After 25 interviews it’s 40%, after 50 interviews it’s 64%. For each individual interview there’s a 1 in 50 chance of getting hired, but because you keep interviewing, that 1 in 50 will likely eventually happen [1].

To sum it up:

Unlikely risks will likely eventually occur if you’re exposed to them often. Similarly, unlikely opportunities will also likely eventually occur if you’re exposed to them often.

Use the latter to your advantage by pursuing big opportunities even if you don’t think it’s likely they’ll ever happen because if you keep at it, chances are one eventually will.

[1] The reality in both situations is a little bit more complicated because the odds aren’t static. A rock climber that begins climbing with 1 in 1,000 odds of dying will improve his skills as he climbs which decreases his odds of dying. But he or she will also likely be increasing the difficulty of the climbs, possibly negating the decreased odds of dying due to the improved skill. Similarly, the junior developer will hopefully be improving his interviewing skills along the way, making his odds of getting hired better than 1 in 50 the more he interviews.

Tracking Blog Post Ideas

My friend Adam asked me how I’ve been keeping track of ideas for blog posts. For that and pretty much anything else that involves lists or notes, I use Workflowy:

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When I started this little daily blogging challenge I would have laughed at the idea that I could write every day for more than a few days. I just didn’t feel like I had that much to write about.

But when you force yourself to do a daily blogging challenge, you have to set the bar much lower in your mind for what’s worthy of writing about. If you restrict yourself to only one or two topics or only publish long, insightful posts then you probably won’t be able to blog daily for very long.

When I committed mentally to doing this, I suddenly had a lot of ideas for things that I could write about. They’re kind of scattered and some posts won’t be interesting to many people (and some to none at all), but that’s fine. It gives me enough to write about to keep it up and that’s what the challenge is all about.

On that note, I’ll hit a 30 day streak on Christmas Eve at which point I’ll take a break and start up again in January. I probably won’t try to do it daily again, but will try to keep posting once or twice a week going forward.

Thanks all for reading.