It’s more than a Carly Simon song.

It’s more than a great Heinz ketchup commercial.

Anticipation plays a surprisingly important role in our lives—at home, at work, and in all the places we tend to get ourselves into trouble.

Unfortunately, it gets a bad reputation.

We usually treat anticipation as anxiety’s cousin—the one who shows up uninvited, pours a drink, and spends the evening worrying about things that haven’t happened yet and probably never will.

But that’s only one version of anticipation.

There’s another kind.

A useful kind.

The kind that doesn’t keep you up at night—but quietly makes you better at almost everything during the day.

It took me an embarrassingly long time to figure that out. And like many lessons that stick, I first learned it somewhere completely unrelated to where I use it now.

College football was harder than high school football. I know—stunning revelation.

The difference wasn’t just size or speed. It was complexity.

In high school, you lined up and tried to hit people harder than they hit you. In college, you had to actually think.

Every week, we spent hours in the film room studying our next opponent. Not highlights. Not motivational montages set to questionable music. Just tape. Lots of boring tape.

If they lined up this way, with that personnel group, they ran one of three plays.

If the safety cheated left, this happened.

If the linebacker stepped forward before the snap, that happened.

By Saturday, we weren’t guessing. We were recognizing patterns we’d already seen dozens of times.

Sometimes their athletes were just better and beat us anyway. That happens. Life enjoys reminding you who’s in charge.

But we were rarely surprised.

And it turns out that matters more than I understood at the time.

Eventually, it clicked that this wasn’t a football lesson at all.

It showed up in academics first. The students who struggled weren’t always the ones who didn’t know the material—they were the ones who hadn’t anticipated the questions. The strongest performers weren’t necessarily smarter; they had simply spent time asking, “If I were writing this exam, what would I ask?”

Later, as a speaker, the same pattern appeared. The talks that landed best weren’t improvised brilliance. They were structured around anticipating audience questions and objections—and answering them before hands went up.

The best presentations feel conversational not because they’re spontaneous, but because the conversation has already been rehearsed.

Years later, deep into real estate, I noticed it again.

Some negotiations felt smooth. Others felt like full-contact sports.

The difference wasn’t confidence or charisma.

It was anticipation.

Here’s the distinction that finally clarified everything for me:

Preparation is gathering information. Anticipation is deciding how you’ll use it.

We weren’t memorizing plays to recite them on command. We were rehearsing responses so thoroughly that recognition became instinct.

Preparation is the key.

But anticipation is the key cutter—the thing that shapes raw preparation into something useful under pressure.

Or, as the old military aphorism puts it: “Plans are useless, but planning is indispensable.”

The value isn’t in the script—it’s in the thinking that produced it.

There’s a natural progression here. It isn’t complicated—it just requires intention.

Picture what’s likely to happen before it happens. Not worst-case spiraling—realistic scenario mapping.

If I’m negotiating this inherited property, what objections usually surface?

If I’m meeting this contractor, what concerns are almost guaranteed?

That’s not fortune-telling. That’s experience applied forward.

The longer you do something, the more familiar it becomes.

Sellers in distress ask remarkably similar questions.

Contractors raise predictable concerns.

Lenders want the same documents—just arranged differently.

Familiarity isn’t boredom. It’s competence.

Practice responses before you need them. Not rigid scripts—flexible frameworks.

If they say this, I’ll respond that way.

If the conversation pivots here, I’ll redirect there.

I do this before difficult calls. Then I make myself do the hardest ones first each day.

Now, when the real conversation unfolds, you’re not scrambling. You’re recognizing something you’ve already prepared for and responding with something you’ve already practiced.

Most “thinking on your feet” moments are really just thinking you did earlier that finally got its moment.

This is where anticipation stops being a tactic and starts becoming wisdom.

After every meaningful project—a property disposition, a business initiative, anything that mattered—we do a review.

Not a blame session. A learning one.

Wins get acknowledged. (Briefly.)

Challenges get examined—not to assign fault, but to extract signal.

Lessons get documented: what worked, what didn’t, what we’d do differently next time.

This is how experience turns into wisdom instead of just becoming memory.

Life, helpfully, keeps offering similar situations in slightly different disguises.

If you review the tape, the next version feels familiar instead of chaotic.

Most Sunday evenings, I spend a few minutes anticipating the week ahead. Sometimes I do the same in the morning.

Not worrying. Anticipating.

What conversations are coming?

What decisions might be required?

What objections are likely?

Then I rehearse a few responses. Nothing elaborate.

Before an important call, thirty seconds to think through my opening usually does the trick.

Does this eliminate surprises? Of course not.

But it dramatically reduces how often I’m caught flat-footed, inventing responses in real time and hoping no one notices.

Most people prepare reactively. They think about the negotiation in the parking lot. They rehearse the difficult conversation while it’s already happening—about as effective as changing a tire at highway speed.

Effective people prepare proactively. They anticipate scenarios before they arrive and rehearse responses before they’re needed.

Preparation is the key.

Anticipation—practiced intentionally and refined through reflection—is what turns that key into something that actually opens doors instead of sitting in your pocket looking important.

Try it this week. A few minutes. One cup of coffee.

Anticipate what’s likely. Rehearse a response or two.

Then, after your next win—or loss—review the tape.

That’s how you build your own film room. And eventually, your own wisdom.

And if nothing else? You spent a few minutes thinking intentionally instead of doom-scrolling.

Which feels like a win either way.

Confusing, jargon-packed, and time-consuming. Or quick, direct, and actually enjoyable.

Easy choice.

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