Why You Can't Admit Personal Mistakes on the Internet

My uncle is an entrepreneur-turned-corporate executive and has achieved considerable career success in his life, which is just to say that he's imposing and has a track record of getting what he wants.

One summer between my junior and senior years of college he hired me to help landscape his lawn. Several weeks after I had started, I made a small mistake.

"Oh, sorry about that, I'll just --"

"George, never say you're sorry" he said.

"Sure, I just meant that --"

"I know what you meant, but never say sorry, it makes you appear weak. Instead of saying you're sorry, fix the problem." He paused for a moment, looking at me, and then went back inside.

His advice ran so counter to what I had been taught that it stuck in my memory. I had always been taught to admit mistakes and correct them, but here he was suggesting I skip the first step. I'm still not sure I agree with it completely, but like every good over-generalization it has a nugget of truth: admitting a personal blunder to someone who has no empathy for you is ill-advised. That summer was all about me becoming employable, so I'm pretty sure my uncle meant that I would appear weak to a boss or employer, but the rule holds doubly-true for internet readers.

In the past, I have been tempted to write blogs about my goof-ups. I have almost always decided not to write such posts, not for want of subject material, but because they don't have any upside for me or my company. In the best case, people will think I'm humble, in the worst case they will think I'm incompetent. Simply put, I'm not willing to risk being labeled the latter for the former. And neither should you.

Self-aware people admit failure to get constructive criticism and seek catharsis. You aren't likely to get either if you bare your soul to the anonymous masses on the internet by first saying "I'm sorry."

Now You Are a Geek: Saying Goodbye to Wave

This was originally published on 2/2/2012.

Google Wave closed write access several days ago. This had been on my radar for some time, but as a heavy user and advocate of the service, it's difficult to see it go.

Seeing a pet project die is a right of passage for a career technologist. It's not just that it's a coming of age event, it's an important part of becoming better at building and improving ideas.

When I was young, I didn't think about technology or specific projects as transitory. I had such a short period of reference that everything was effectively permanent. I used Altavista for search because that was the only search engine that had ever existed and I played Descent 2 because it was the best game. I spent a lot of time playing games, trying operating systems, and installing utilities without thinking much about the people behind those monoliths of time and effort.

When you don't have an ownership stake in what you consume, it's easy to remain agnostic about games, operating systems, programming languages, server platforms, SDKs, editors, project management styles, deployment techniques,  and a hundred other topics about which technologists care deeply.  As I transitioned from being a consumer of web technology to a producer, I began forming opinions about the tech that surrounded me.

I love Google App Engine, dislike AWS, love Python, hate Java, dislike Windows, but think Mac OSX is for snobs, snub Firefox for Chrome, love Winamp, hate iTunes, loath antivirus software, prefer Google hangouts to Skype, and a hundred other subjective preferences. For having so many pet technologies, I have seen remarkably few get abandoned. Among those that I have lost, Wave has been the most important.

I was enamored with Wave because of the ideals and dreams of the people who invented it. I don't know much about the creators of Winamp [1] but I could put a face to the Wave development team and I wanted them to dethrone email, destroy chat programs, and better organize all web communication.

The fact that it failed makes me more of a real geek. I invested heavily in Wave and will now pay the price [2]. But in going away, Wave has also taught me some valuable lessons. I've learned that even well-funded projects die, technology doesn't often win out against established behaviors, and evangelism can only go so far.

The pace of innovation in web technology is accelerating and there is a tendency to avoid investing in any platform, but I think that it is the mark of a mature and invested hacker to have a small cemetery of pet technologies to grieve for. Don't hang on and be that backwards guy who wants to implement everything in Pascal, but remember what you've lost and use it to build better products in the future.

[1] This is because I wasn't old enough when Winamp was disruptive and being talked about, I have heard anecdotes that suggest it is quite an interesting story.

[2] Endless exporting and unsorted data migrations await. There is a strong temptation to accept the data loss and start over on another platform, but there is data in Wave that I simply cannot afford to lose.