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Ending it gracefully

Just about every business, every initiative and every intervention fails sooner or later.

Since that’s demonstrably true, it’s worth considering how you intend to fail when the time comes.

You can pull out every stop, fight every step of the way, mortgage your house and your reputation–and still fail. Or, perhaps, you can quit in a huff at the first feeling of frustration.

The best path is clearly somewhere between the two. And yet, too often, we leave this choice unexamined. Deciding how and when to quit before you begin is far easier and more effective than making ad hoc decisions under pressure.

The discard pile

Walking away from something that we’re used to, even if it’s unjust or inefficient or ineffective–it usually takes far too long. Fear, momentum and the status quo combine to keep us stuck.

And so it builds up. The cruft calcifies and it gets in our way, making our world smaller, our interactions less human. What used to be normal is rejected and obsolete. It turns out that the status quo is the status quo because it’s good at sticking around.

But brave people stand up and speak up and take action. And far too slowly, the system starts to change.

Sunk costs are real, but we must ignore them. Culture changes, our standards evolve, opportunities arise.

Better is possible… if we care enough to walk away from what was and brave enough to build something new.

The map is not the territory

And that’s a feature, the reason the map exists.

The phrase reminds us not confuse the diagram or model or overview of the situation with the situation itself. Because they’re not the same.

We make a map so we can leave things out.

By leaving things out, we can help people focus on the core concepts we’re trying to get across. And so, the map of the London subway is not actually the London subway. In fact, it’s not even geographically accurate. That’s okay. The job of the map isn’t to show us precisely where each station is, the job is to make it easier to get around London by showing us a theory of the subway.

And the words someone uses don’t accurately convey everything they’re feeling and thinking. They simply stake out some of that in a way that the speaker hopes will express the point they’re trying to make.

When we decide what to leave out, we’ve made a series of decisions about the story we’re trying to tell with the parts we leave in.


When we do our work without regard for a third party, simply to serve the reader, the customer or the story, we’re creating something that’s unsponsored.

The third party shows up when we’re encouraged (by payment or other means) to have multiple objectives. And those usually bring compromise.

When our goals are aligned with those that we serve, we have a rare chance to maximize both. It’s worth seeking out. We’re not unsponsored. We’re sponsored by the very people we’re engaging with.

Backward about coming forward

If your comment is helpful to anyone else, then it’s generous indeed.

Holding back is selfish, because it deprives the group of your insight at the same time that it normalizes non-participation.

If you’re wondering, so is someone else.

Investments and expenses

One goes up in value, the other doesn’t. One creates value over time, the other doesn’t.

It’s fun to imagine that our expenses are investments, but if they were, we’d call them investments.

Our tools can be re-used, and our assets have value to us and to others. Skills can be an investment, compounding as they grow. Expenses, on the other hand, fade away.

Everyone is rational

But if that’s true, then why don’t we all agree on the right next step?

It could be because everyone has a different experience, different data and different goals.

Or, it could be that you are the only one who’s rational.

And it could be that we all like to tell ourselves we’re doing the right thing, but ultimately, all we can do is make choices based on how we see the world.

The way we see things drives our choices, and, of course, our choices change the way we see things.

Bad Company

The arc of institutions, including governments and corporations, particularly public ones, bends toward short-term thinking, bullying, anti-competitive behavior and laziness.

The antidote is persistent vigilance and heroic leadership.

The organizational math is compelling. When a toxic employee shows up, it might be easier to simply work around him. When competitors engage in graft or corruption, the easy path is to compete in the same way. It’s only fair.

And when employees are rewarded for short-term actions that lead to short-term stock gains, the bad behavior compounds.

Some theorized that cutthroat competitive markets were the antidote to the corroding organization. After all, if your team is losing the game, you’ll get your act together–it works in baseball, they say.

The problem is that short-term competitive markets reward short-term competitive thinking, which, while it might diminish sloth, does little to help in the long run.

The entropy of organizations means that difficult conversations and a positive ratchet of culture change are unlikely to occur on their own.

But there’s an alternative. The alternative is the leader (regardless of her title–authority isn’t the point) who says, “not on my watch.” This is the person who realizes that today at work never happens again, and this opportunity to make things better won’t present itself another time.

Of course, it’s exhausting, because you have to do it every day.

But that’s why it’s such an extraordinary opportunity. Not simply as a competitor, but as a human.

To make things better.

Can you see it?

Do you notice that you’re dressed dramatically differently than everyone else at the event?

That you’re driving at a different pace than everyone else?

That your question at the end of the talk lasted four times longer than anyone else’s?

That your band’s new single is half the volume of everything else that’s being pitched to this program director?

That your code isn’t commented and everyone else’s is?

There’s absolutely nothing wrong with being different from the crowd. In fact, it might be the ideal path forward. The problem begins when you don’t see what’s not matching up.

The best way to transform the path is to see the path first.

History doesn’t always repeat itself, but it usually rhymes.

“You’re not that good”

These are the three problems with creative work.

The first is that when we begin, we’re not that good. This is a fact. The breakthrough for anyone on this journey is adding the word “yet.”

It doesn’t pay to pretend that we’ve figured it out before we have. It’s counterproductive to adopt a brittle attitude in the face of criticism. In fact, during this stage, “you’re not that good,” is precisely what we need to hear, because it might be followed with insight on how to get better.

The second is that once we start to build skills and offer something of value, some people are going to persist in believing that we’re not that good. Fine. They’ve told us something about themselves and what they want and need. This is a clue to offer our leadership and contribution to someone else, someone who gets what we’re doing and wants it. The smallest viable audience isn’t a compromise, it’s a path forward. Find the folks who are enrolled and open and eager. Serve them instead.

The danger is that when you hear rejection during this stage, you might come to believe that you’ve accomplished nothing, as opposed to realizing that you might simply be talking to the wrong people.

And the third comes full circle. Because it’s possible that in fact, we’re not that good yet, and there aren’t enough people who want what we’ve got. We’re simply not good enough for this part of the market. So we embrace that truth and begin at the beginning. We’re not good enough yet. We haven’t practiced enough, found enough empathy, understood the genre well enough and figured out how to contribute. Yet. At least for this audience.

And then we get better.

Sooner or later, these three problems become three milestones on the road to making a difference and doing work we’re proud of.

PS today’s the best day to sign up for the Freelancer’s Workshop offered by Akimbo. I hope you’ll join in…

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