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The world’s worst boss

That would be you.

Even if you’re not self-employed, your boss is you. You manage your career, your day, your responses. You manage how you sell your services and your education and the way you talk to yourself.

Odds are, you’re doing it poorly.

If you had a manager that talked to you the way you talked to you, you’d quit. If you had a boss that wasted as much of your time as you do, they’d fire her. If an organization developed its employees as poorly as you are developing yourself, it would soon go under.

I’m amazed at how often people choose to fail when they go out on their own or when they end up in one of those rare jobs that encourages one to set an agenda and manage themselves. Faced with the freedom to excel, they falter and hesitate and stall and ultimately punt.

We are surprised when someone self-directed arrives on the scene. Someone who figures out a way to work from home and then turns that into a two-year journey, laptop in hand, as they explore the world while doing their job. We are shocked that someone uses evenings and weekends to get a second education or start a useful new side business. And we’re envious when we encounter someone who has managed to bootstrap themselves into happiness, as if that’s rare or even uncalled for.

There are few good books on being a good manager. Fewer still on managing yourself. It’s hard to think of a more essential thing to learn.

Cliches

When you launch a new idea or project into the world, you'll probably use connections to what has come before as a way to tell your story.

Caribou Coffee, for example, uses all sorts of metaphors and cues and even verbal tropes that we learned from Starbucks. These signals help us understand that the place we're about to enter isn't a steakhouse, isn't a shoeshine stand and isn't a massage parlor. It's a place to get a latte.

Books that want to be bestsellers work hard to look like previous bestsellers, from the store where they are sold to how many pages long they are to how much they cost. These signals help us determine that this object is something worth buying and reading.

Cable TV does this, politicans do this, computer resellers do this.

Here's the thing: you can't stand out if you fit in all the way, and thus the act of deciding which part isn't going to match is the important innovation.

Matching an element almost looks like failure. Matching not-at-all, on the other hand, is the refreshing whack on the side of the head that causes attention to be paid.

When your car looks like a car but the doors are gullwing, we notice them. When your suit looks like a suit but the lining is orange, we notice it. When you apply for a job and you don't have a resume, we notice it.

This was the secret of the golden age of comic books. 90% of every hero was on key, professionally done, easy to understand… which allowed the remarkable parts to stand out.

You can't be offbeat in all ways, because then we won't understand you and we'll reject you. Some of the elements you use should be perfectly aligned with what we're used to.

The others… Not a little off. A lot off.

The inevitable decline due to clutter

Digital media expands. It's not like paper, it can get bigger.

As digital marketers seek to increase profits, they almost always make the same mistake. They continue to add more clutter, messaging and offers, because, hey, it's free.

One more link, one more banner, one more side deal on the Groupon page.

Economics tells us that the right thing to do is run the factory until the last item produced is being sold at marginal cost. In other words, keep adding until it doesn't work any more.

In fact, human behavior tells us that this is a more permanent effect than we realize. Once you overload the user, you train them not to pay attention. More clutter isn't free. In fact, more clutter is a permanent shift, a desensitization to all the information, not just the last bit.

And it's hard to go backward.

More is not always better. In fact, more is almost never better.

Who owns Wikipedia?

You have probably noticed the big banner ads with Jimbo Wales' smiling face on them… they show up whenever you visit Wikipedia, the single most useful destination online.

The question: why are they there?

After all, if Wikipedia ran Google ads in the sidebar just three days a year, they'd pay for all of their operating expenses.

I haven't talked to Jimmy about this, but here's my guess, one that applies to other community-funded efforts: If the user supports it, she owns it. If support comes from anonymous government money, or some corporate sponsorship, then the interactions don't matter so much, and it's more distant from you.

I would bet that any charity or cause that gets involvement from its supporters (and I believe that volunteer support is worth more than cash) outperforms equally well-funded organizations that don't have as deep a connection.

In other words, you own Wikipedia.