When there’s a complex situation that feels foreboding, you might need a manual, a coach and even a system to move forward.

Or, it’s possible you simply need someone to tell you, “you’ll figure it out.”

“Will it work?”

Along the way, we’ve been pushed to load our decisions with a need for certainty. It’s easier, it seems, to not try than it is to fail.

But the question, “is it worth trying?” unlocks possibility.

A surgeon in the middle of an operation should probably not experiment with an untested technique. But a writer, a leader or a musician can make that question part of their craft.

It’s the only way we learn.

Where do con men come from?

There are three conditions that need to be met:

First, there needs to be rising societal pressure to get ahead, cut the line and find a win.

Second, there needs to be people willing to set aside their ethical principles to take advantage of others in their community.

And third, we need to be lulled into a state of unjustified credulity, eager to believe that seeds might be magical or that motion might be perpetual.

While all three of these conditions are present throughout time, they go in cycles.

And we’re having one right now.

We’re far too tolerant of ridiculous promises, particularly around tech, money and leadership. And instead of quickly learning to become a bit more skeptical, we get caught in a cycle of letting the con man (person, actually) off the hook.

Inevitably, when it ends badly, we overreact and become too risk averse, costing us nearly as much with our skepticism.

If someone tells you that they forgot to put the word ‘gullible’ in the new edition of the dictionary, don’t dismiss them out of hand, but yes, check first.

But connection is where the value lies.

Connected, resilient communities create possibility and forward motion.

Division is satisfying in the short run, and it might even draw a crowd. But the only useful reason to disconnect is if it opens up the chance to increase connection somewhere else.

Really?

Which self?

The self you were when you were two years old, almost out of diapers?

The self you were when you were screaming with the fans at the big game?

The self you were after a long night?

How about this: Become the self you’d be proud to be. Hang out with people and ideas that help you become that self. Act like that self every chance you get.

We might not seek it out often enough in our work. It’s a musical term, but we can use it too.

The light touch. A way to make a sound without making a commotion. Delicate and graceful.

Showing up with care and with just enough extra, but not more than that.

see also: sprezzatura

“Obvious” closes the door to inquiry.

“Perhaps” opens it.

Busy people in important organizations waste a lot of time naming things.

It could be that once a name is good enough, you’re done. That’s certainly true for the logo.

Nike is hard to pronounce. Starbucks is named after an obscure character in a mostly unreadable book. Apple is named after a fruit, Google is spelled wrong.

These are good names, not perfect ones.

It’s worth noting that when asked to name a great logo or a great brand name, almost everyone picks a brand they like and trust. The name is simply a symptom of that, not a cause.

I know why you’re so focused on the name. It’s your brand’s personality. It’s under your control. It is something everyone on the committee is an expert on, because no one is.

Once it does the job, you’re done.

Pick a good one and get back to work.

[My take is that ChatGPT is a terrible name. It has too many syllables, it has needless requirements for capitalization, and most of all, it’s not an empty vessel ready to contain our story about the brand. Claude is better. Not perfect, but good.]

“Nobody wants this” is unlikely.

“Somebody will like this” is almost certainly true.

“Everyone needs this” is a trap.

The work begins with finding the right somebodies, while ignoring the imaginary everyone.

Scale is rarely the first signal of important work.

Since the days of Atari and Apple, the culture of Silicon Valley has been based on the idea of programmers and early employees owning equity in the startups they took a chance on.

The media is always happy to write about folks who took a shot on stock options and did very well indeed.

Too often, though, people who deserve an upside and need an upside the most are left out, because they don’t have the standing or resources to insist.

And more frequently than we notice, the stock options people trade salaries and effort for fail to become valuable.

The financiers and investment banks are sure to profit the most, with individual contributors often left in the dark. The closer you are to controlling the cap table, the better you do.

Being in alignment with the people around us is really valuable. And ownership is a powerful concept.

But there are ways to simulate the promised benefits of stock ownership with simpler and more direct tools. Instead of offering a magic ticket that has no real connection with the efforts of an employee, why not tie significant bonuses to relevant outcomes? If we actually want alignment, perhaps we could write down precisely what success looks like.

Often, equity isn’t based on equity.