The Leadership Hangover
The Leadership Hangover: Unlearning from the Military to Scale as a Civilian
Follow along for the "From Mission to Momentum" Summer Series, running through September. Designed for leaders committed to growth, this series is a structured opportunity to pause, reflect, and recalibrate.
Countless themes of leadership still carry forward. Many military colleagues and partners are now launching businesses, building brands, and investing in new ventures – finally free to chart their own course. And they do it with confidence, because leadership was built, tested, and earned during their military service.
But the reality? It can take years, sometimes decades, to fully adapt. Learning how to hire civilians, build culture, and drive business development without the structure of a chain of command isn’t easy. But for those willing to evolve, the payoff is real.
“From Mission to Momentum”
Week 1: Theme = Reassess
Movie Quote:
"Anything in life worth doing is worth overdoing. Moderation is for cowards."
— Marcus Luttrell, Lone Survivor
That quote hits deep for most of us who came up through the military. We were trained to go hard, lead from the front, and never second-guess a call once it was made. That kind of certainty earns trust in combat. But in entrepreneurship, it can quietly sabotage your team and your growth. When command presence becomes a crutch, it may require us to unlearn certain habits to translate to the business world.
When seen firsthand in coaching Veteran founders, there is a subtle shift to note: their default mode is act first, ask questions never. It works – until it doesn’t.
You end up making every decision, even the small ones.
Your team waits for orders instead of showing initiative.
You pride yourself on command presence… but no one’s growing behind you.
If that sounds familiar, here’s the truth: your instincts aren’t bad. They just need to be rewired for a different kind of mission. Presence matters. But in business, so does patience. So does collaborative problem-solving. So does not being the smartest person in every room.
Humility hits hard for leaders.
Leaders are recognized as the one who makes the hard calls, often the unpopular decisions and owning the responsibility for that one crucial mistake the team made. We all like attention and praise for when things go well, but when it fails? Who is the one to step up?
A poor hiring decision. He looked good for the job. Solid resume, interviewed well, young, hungry. Until he drew strict work hours when he could be available, and refused meetings that would run over his time zone. Turns out he was complaining to HR about the excessive meetings without any honest conversations with leadership. When gaps like this occur, it’s difficult to identify the root problem. Maybe the team could adapt to his time zone and reschedule any and all meetings? Maybe he felt unsupported to have those tough conversations? Maybe the learning curve was too much to handle? After about six months of training and coaching, a “thank you, and goodbye” was the result. And our team is still thriving.
A culture shock. As a young Veteran straight out of a Business Leadership Program, she was promoted to an executive President role at a struggling manufacturing company. “Restore it,” they said. “We got your back,” they said. Long-tenured employees. Unions. 25+ years her senior, close to her father’s age. Dissatisfied, they up and walk out of meetings. They cuss and share crude jokes and fail to show up at all. Scold them? Incentivize with education credits and technology? People are comforted by their old ways. The company came at a crossroads to sell or go bankrupt.
The hardest part of this transition? Realizing that some of the very things that made you successful in uniform – decisiveness, confidence, domination of detail – now need to be unlearned so you can lead with your team instead of at them.
