Rebuilt to Rise: What Chicago's Skyline Teaches Us About the Travel Industry's Comebacks

Image: Skyline view over Chicago, Illinois. (Photo Credit: Adobe Stock/Iuliia Sokolovska)
Image: Skyline view over Chicago, Illinois. (Photo Credit: Adobe Stock/Iuliia Sokolovska)

A few weeks ago, I took the Chicago Architecture Center's river cruise just expecting to admire the buildings. Instead, I spent ninety minutes thinking about our industry, because that skyline exists largely because the city once burned.

In October 1871, the Great Chicago Fire destroyed more than three square miles and left roughly 100,000 people homeless. Chicago didn't just replace what burned. It rebuilt with new rules: stricter fire codes, then steel frames that let buildings climb higher than ever. The Home Insurance Building, often called the first skyscraper, rose in the rebuilt Loop in 1885. In 1909, Daniel Burnham's Plan of Chicago reimagined the entire city.

The fire didn't make Chicago. It forced a decision: rebuild the way it was, or build for what's next.

Travel has faced that decision repeatedly. When airlines eliminated base commissions, the advisors who thrived added fees and specialized. After 9/11 and SARS, clients wanted someone who understood risk. After 2008, value and loyalty mattered most. COVID was our Great Fire, and it reminded travelers why a trusted advisor matters when plans fall apart.

Meanwhile, we've heard endless warnings about the fire that would finally burn us down: the internet, then the OTAs, now AI. Each time, we built for what's next.

Your Fire Codes: The Rules You Run On

Chicago's fire codes weren't written for one fire; they were written for any fire. Your business rules should work the same way, because the next disruption won't look like the last.

  • Do you apply a written fee policy consistently?
  • Is travel protection discussed on every booking?
  • Can you reach clients who are mid-trip when a disruption hits, and can they reach you?

Your Steel Frame: The Structure That Lets You Grow

Steel let Chicago build higher without collapsing. Your frame is the set of systems that lets you take on more without breaking.

  • Is client data (passports, payment details, personal information) stored securely, rather than sitting in email threads and screenshots?
  • Do your after-hours policies protect you, your employees and your clients?
  • Does your client information live in a CRM, or is it scattered across your inbox?

Your Burnham Plan: Where You're Deliberately Heading

Burnham didn't plan the next block; he planned the whole city. Too many of us plan only the next booking and neglect the systems that build long-term success.

  • Can you describe your ideal client in one sentence? Are you ready to fire the clients who don't fit and who start brushfires of their own?
  • Do you know which product lines drive your revenue, and is that the right mix for the effort each one demands?
  • What should your business look like in three years, and what are you doing this quarter to get there?

The Pattern Underneath the Pattern

Every time travel has been knocked down, the advisors who came back stronger didn't simply rebuild what they'd lost. They asked what the moment was telling them to build instead. That's the lens I keep coming back to at MAST. We're here not just to help members recover from the last disruption, but to help them build something that can take the next one and come out taller.

The next fire is already smoldering somewhere. You can't choose when it starts, only what it finds when it arrives. So don't wait for the smoke. This week, answer one question from each section above, then act on it. Write the policy. Move the data. Draft the client profile. That's three small builds, done before anything burns.

Next time you're in Chicago, take the boat tour. Look up. Every building on that river proves that rebuilding with intention beats rebuilding out of habit.


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Laurence Pinckney

Laurence Pinckney

CEO of Zenbiz Travel, LLC

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Agent At Home

Helping leisure selling travel agents successfully manage their at-home business.

Subscribe For Free

Agent Specialization: Group Travel

Laurence Pinckney

Laurence Pinckney

CEO of Zenbiz Travel, LLC

About Me