Career Reinvention After Government Service: What a Multi-Year NATO Base Negotiation Taught Me About Patience in Business
The Portugal negotiation that took longer than most marriages
Career reinvention after government service usually gets sold as a leap — one resignation letter, one clean break. Mine is taking longer than most marriages.
From 2016 to 2018 I was the political advisor to the four-star general running U.S. Air Forces in Europe and Africa. 104 countries - all with different priorities and competing interests to keep straight.Sounds glamorous. Mostly it was motorcades and then hours of paperwork in rooms with bad coffee.
The file that ate two years of my life was an air base called Lajes — a Cold War leftover Portugal and the U.S. had been half-heartedly arguing about since before I was born. I inherited a folder with a decade of history in it and stacked two more years on top before it finally closed.
First move, obviously: push harder. More meetings, sharper asks, the full playbook. Didn't budge it an inch. It moved because I got boring. I showed up so many times that people stopped explaining the history to me and started just — talking. The deal, when it landed, wasn't a plot twist. It was a Tuesday where everyone had already agreed and nobody wanted to say it out loud first.
Same stretch had louder wins — $3 billion in NATO investment, F-35 lobbying with the Norwegian and Dutch Air Chiefs, the kind of thing that reads well in a bio. Same engine underneath, though. Stay long enough and specific enough, and eventually people stop treating you like a guest.
I left the Foreign Service for reasons that had nothing to do with Lajes. The part that caught me off guard: I already knew how to build slowly, I just hadn't done it for myself yet. My winemaker in Sonoma didn't save us the good barrel in year one. The villa in Tuscany that lets us into rooms other companies never see — nobody emails their way into that. You just show up for years.
Someone asked me recently what surprised me most about starting over. Nothing, honestly. Same instinct, new client. I spent twenty years being patient for the United States government. Now I'm patient for something I actually get to keep.
If you're sitting on your own Lajes file right now — the slow, unglamorous middle of reinventing something — I write about this stuff most Mondays. Follow along on Field Notes, or find the rest at sojournandsoiree.com.