Gordon Charles MacLean on Discipline, Collapse, and the Art of Waking Up

There’s a certain Chicago rhythm to reinvention. It hums beneath the L tracks, flickers in glass towers along Wabash, and lives in the quiet second acts of people who’ve lost everything and decided that wasn’t the end of the story.Gordon Charles MacLean fits neatly into that lineage—though “neatly” might be too polite a word for a life that’s moved through classified Air Force missions, high-stakes commercial real estate, financial collapse, and something like a personal reckoning.In his new book, The Awake Code: 39 Rules for a Fully Engaged Life, MacLean doesn’t offer the usual glossy prescriptions. There’s no sugar coating here, no motivational confetti. Instead, the book reads like a field manual written in the margins of a life under pressure—part philosophy, part survival guide.Before the boardrooms and brokerage deals, MacLean served with the U.S. Air Force’s 9th Reconnaissance Wing, working on electronic warfare and intelligence systems aboard the U-2 aircraft. It’s the kind of work that requires a near-obsessive relationship with awareness. Miss something, and the consequences aren’t theoretical.That mindset followed him into a three-decade career in commercial real estate, where he completed more than 200 transactions across office, retail, multifamily, and industrial sectors. Chicago became a proving ground—where he earned his CCIM designation and built the relationships that would define his trajectory.And then, like so many stories tethered to the late-2000s economy, it cracked.The 2009 financial crisis didn’t just disrupt MacLean’s business. It dismantled it. What remained, by his own account, was a kind of silence—the unsettling realization that the systems he’d trusted no longer applied.“I didn’t write this book to be an author,” MacLean says. “I wrote it because I was trying to survive my own life.”That line sits at the center of The Awake Code, which organizes itself around 39 principles that feel less like advice and more like recalibrations. Strategic rest. Radical awareness. Personal responsibility. The kind of ideas that sound simple until you try to live them consistently.Each chapter blends personal narrative with reflection prompts and action steps, nudging readers toward something more deliberate than autopilot. It’s aimed at professionals, entrepreneurs, veterans—anyone who suspects they’ve been drifting and wants to interrupt the pattern.Chicago, in many ways, is the book’s quiet co-author. MacLean credits the city as a place of both ascent and return—a landscape where ambition meets consequence, and where reinvention isn’t just possible, it’s expected.On Tuesday, July 7, that relationship comes full circle:EVENT: AWAKE CODE BOOK LAUNCH + LIVE PERFORMANCE Set high above the Chicago River, the Grand Salon at Trump International Hotel & Tower will host MacLean’s official book launch—though calling it a “book event” undersells the production.The evening leans more toward a curated convergence: business leaders, real estate professionals, veterans, and curious Chicagoans gathering for a night that folds together ideas, music, and philanthropy.Expect a full sensory lineup:Open bar and cocktail receptionPassed hors d’oeuvresAuthor talk and Q&ABFor more Stories From The 78, follow @tombarnas78 on Instagram and @storiesfromthe78 on TikTok.