The Return

The check-in text arrives and the planning starts. Not packing. Not logistics. The other kind of planning, the kind that has nothing to do with getting there and everything to do with what happens after you land.

Chicago is the fifth city in my consulting rotation, about a year and a half into doing this full time. The framework was still forming then, though I wasn’t aware of it at the time. Thirteen years and eight to ten stints later, Chicago operates differently than anywhere else. The difference isn’t the city. It’s what repetition builds when you pay attention to it.

The check-in text lands and within an hour I know which week works for dinner with my college friend. I’ve checked whether the Cubs or Sox have an evening game on a Tuesday or Wednesday. I’ve already considered whether this is the week for a steakhouse, Eataly, or a Rick Bayless reservation. The plan doesn’t get built on arrival. It starts before the bag is packed.

That’s the pre-arrival ritual in its most developed form. By the time the wheels touch down at Midway, the city isn’t unfamiliar territory. It’s a place with a standing dinner, a game on Wednesday, and a reservation I may or may not use. The pool is already warm before I get in.

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Midway versus O’Hare is a decision that got made early and has remained consistent. Most travelers default to O’Hare. It’s larger, serves more airlines, sits closer to the city’s nicer neighborhoods. Most of my Chicago assignments fall south of that. Midway made the geographic sense from the start. Rental car pickup is faster. You’re not deposited directly into heavy traffic the moment you have a car. Thirteen years in, I don’t reconsider it.

This is what the framework produces over time. Not just a list of preferred restaurants and reliable third spaces, but a set of resolved decisions that don’t require revisiting. Attention that used to go toward figuring out the airport now goes somewhere else.

The pre-arrival ritual runs on that same logic. Dinner with the college friend is a standing conversation that picks up where it left off regardless of how many months separate visits. The Cubs or Sox game is a Tuesday evening that would otherwise blur into the rotation. The three restaurants aren’t reservations I’ve necessarily made. They’re history I’ve built. If the evening opens up and supports a longer meal and a drive into the city, I already know where I’m going. None of these take long to arrange. They take longer to develop: the relationships, the familiarity, the confidence that the option will be there. That development happens across years, not weeks.

The pool metaphor from Less Away applies here with one addition. In a city you’ve worked long enough, the pool isn’t cold when you arrive. The college friend. The reservation if the evening supports it. The game on Wednesday. You get in and it’s already there.

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Every repeat traveler builds some version of this. The details differ. The logic is the same.

What does yours look like in the cities you keep returning to?

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The pre-arrival ritual is the visible part of the framework. The part that gets built first and refined most consciously. But there’s a layer underneath it that develops more quietly and matters just as much: the human infrastructure.

I’ve learned to look for who I might know within range of wherever I’m working. Facebook is useful for this in ways that have nothing to do with what Facebook was designed for. A high school friend I hadn’t seen in nearly forty years showed up in a search before a stint in a city I’d never worked before. A grade school friend I cross paths with every two or three years. A team member within an hour’s drive who I’d otherwise only know through a screen.

A dinner with someone who already knows you works differently than recognition you’ve built through repetition at a bar or a Sky Club. The bartender earned that familiarity across visits. The college friend already had it. One is constructed carefully over time. The other was already there, waiting for the calendar to align.

I lead a team of about ten other travelers. If two of us are close enough to meet in the middle during the same week, I try to make that happen. A convergence dinner with a team member produces something a solo dinner at the rotation restaurant can’t. Shared context, shared vocabulary, the specific relief of talking to someone who already understands what the week looked like without needing it explained. That’s not a hospitality outcome. That’s something the hospitality system can support but not replicate.

The Facebook search has become part of the pre-arrival ritual for cities I haven’t worked before. Not an expectation. Most searches produce nothing useful. But the ones that do produce something are disproportionately valuable. A two-hour dinner with a high school friend you haven’t seen in forty years is not a small thing. It’s a reminder that the human network built over a lifetime is geographically distributed in ways that occasionally align with a consulting rotation. When they align, the week looks different.

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None of this is available in Springfield, Ohio or Salina, Kansas in the same way. Smaller cities, single contracts, fewer stints. The rotation restaurant and the convergence dinner and the college friend don’t always exist within range. The pre-arrival ritual is shorter. The resolved decisions are fewer. The pool takes longer to warm because there are fewer visits to warm it across.

The intent is still there. I’m still looking for whatever version of the cycle is possible in a smaller field. The framework scales down without disappearing. What changes is the timeline and the depth, not the underlying logic.

The endzone is the same. The field is just shorter.

What the smaller cities have taught me is that the framework isn’t dependent on scale. It’s dependent on attention. A single reliable restaurant in a town with three options produces the same return on investment as a full rotation in Houston or Chicago. You stop making that decision every night, and the attention goes somewhere else. The math is the same. The accumulation is just slower.

Less away isn’t a destination city outcome. It’s a repetition outcome. You get there by showing up more than once and paying attention each time. The city doesn’t have to be Chicago. It just has to be somewhere you’re coming back to.