Are you leaving behind an easily found trail of accomplishment?

Few people are interested in your resume any more. Plenty are interested in what you've done.

The second thing you'll need to do is regularly note what you produce in a log or find some other way to keep track.

The first thing is more difficult: If the work you do isn't worth collating and highlighting, you probably need to be doing better work.

SOLD OUT. Thanks.

The bestselling ShipIt journal has surprised me in how much impact it has had on the teams that have used it. I ended up selling tens of thousands of them.

I have about 600 left and rather than pay warehousing fees, I lowered the price a whole bunch and will leave it that way until they are sold out. (The rest of the inventory is here). I don't expect to reprint them, sorry.

Also, Jess Bachman's Death and Taxes poster is available at a great bulk price for the next 28 hours at an already funded Kickstarter. I think every classroom and office ought to have one.

Sooner or later, you'll ask for something or read something or expect something and you won't like what you get. You'll feel like I wasted your time, wasted your money or didn't meet your expectations.

Not just me, of course. Everyone. Even you. You will disappoint someone, and the organizations you depend on will disappoint you. Expectations keep rising, and promises keep being made. We keep bringing more magic into the world, but rising expectations mean that there's more disappointment as well.

That's part of the deal of being in the world.

The alternative, I'm afraid, isn't to choose a path where we make everyone happy and always exceed their expectations. Nope. The alternative is to hide, to fail to engage and to produce nothing.

A pretty easy choice.

Lightning rarely strikes. Instead, achievement is often the result of stepwise progress, of doing something increasingly difficult until you get the result you seek.

For a comedian to get on the Tonight Show in 1980 was a triumph. How to get there? A series of steps… open mike nights, sleeping in vans, gigging, polishing, working up the ladder until the booker both saw you and liked you.

Same thing goes for the CEO job, the TED talk on the main stage, the line outside the restaurant after a great review in the local paper.

Repeating easy tasks again and again gets you not very far. Attacking only steep cliffs where no progress is made isn’t particularly effective either. No, the best path is an endless series of difficult (but achievable) hills.

Just about all of the stuck projects and failed endeavors I see are the result of poor hill choices. I still remember meeting a guy 30 years ago with a new kind of controller for the Atari game system. He told me that he had raised $500,000 and was going to spend it all (every penny) on a single ad during the Cosby show. His exact words, "my product will be on fire, like a thresher through a wheat field, like a hot knife through butter!" He was praying for lightning, and of course, it didn't strike.

There are plenty of obvious reasons why we avoid picking the right interim steps, why we either settle for too little or foolishly shoot for too much. Mostly it comes down to fear and impatience.

The craft of your career comes in picking the right hills. Hills just challenging enough that you can barely make it over. A series of hills becomes a mountain, and a series of mountains is a career.

One way for a candidate to change the conversation around her candidacy: have her followers pelt the opposition with waffles at every public appearance. Eggos in particular are lightweight and their shape makes them easy to toss.

Particularly in primaries, simplicity and certainty are rewarded. The waffling candidate, the one who hesitates to give a clear yes or no answer to every question is seen as weak.

(Worth noting that the word "waffling" didn't start appearing in books much until after the 1960 elections).

Of course, this post isn't about politics at all. Customers and employees and vendors and regulators almost always prefer simplicity and certainty.

There are two ways to begin an answer to most questions we face in organizations:

"It's simple" and

"It's complicated."

Both are usually true. At 10,000 feet, most challenges are simple. But actually making something work is quite complicated.

Nuance is the sign of an intelligent observer. Nuance shows restaint and maturity and an understanding of the underlying mechanics of whatever problem we're wrestling with. After all, if the solution was simple, we would have solved it already.

On the other hand, resorting to nuance early and often can also be a sign of fear, of an unwillingness to go out on a limb and make a difference. Hence the reactions of boards hiring consultants and CEOs, or of passionate primary voters. "Don't tell me it's complicated. Just show me the guts to make something happen."

My vote: your goals and your strategy must be simple. You must have passion and certainty in order to make a difference as a leader. Your tactics, on the other hand, should be layered, multi-dimensional and reflect the patience of someone who cares about reaching a goal.

When Howard Schultz talks about coffee or Jill Greenberg talks about lighting or Cory Booker talks about education, they can impatiently demand clear and simple results. At the same time, successful leaders see the nuance they'll need in executing to get there.

The paradox is that the simplicity we often seek in search of solutions rarely leads to the patient leadership we need to get them.

The irony is not lost on me... the decision on when to be bold is a nuanced one.