When we started interviewing people who had completed long adventures — multi-month hikes, solo cycling trips, kayaking expeditions — we expected the biggest obstacle to be money, or fitness, or logistics. It wasn't. Again and again, the thing people were most afraid to do was have a conversation with their boss.
After 20 interviews, a clear pattern emerged. The people who successfully negotiated leave all shared a few key behaviours. The people who struggled — or had to quit — usually skipped one or more of them.
Ask early. Embarrassingly early.
Eva is a civil engineer at a technical consulting firm. She wanted 10 weeks off in the summer to hike Gröna bandet with her friend Frida. She asked her manager in October — eight months before she planned to leave.
"It was very advantageous that I asked so early," Eva told us. "It made it really easy to adjust my project assignments. By the time summer came, all my projects were wrapped up naturally."
Her manager said yes immediately. Eva credits the timing entirely: a project-based business can plan around almost anything if given enough runway. The same request made in April would have been a real problem.
Jessica McGlynn, who hiked 1,300 km with her family, used a similar approach — planting the idea informally with her manager months before making the formal request. "I tried to sell it to my boss gradually. I mentioned it casually before I ever asked officially."
Negotiate it as a condition, not a favour.
Lukas, who walked Norway på langs with his partner Kim, had a different situation — he was changing jobs just before the trip. He used that moment as leverage.
"If I'm going to start here, I need three months off," he told his new employer, before signing anything. His future manager, who happened to love hiking, said yes without hesitation. By making it a condition of employment rather than a request after the fact, Lukas removed the awkwardness entirely.
The lesson: the best time to negotiate leave from a new employer is before you start, not after you've already settled in.
Frame what you're asking for, not how long it is.
Eva shared a tactic that made us laugh — and then realise how smart it was. When she first approached her boss, she didn't lead with "I want 10 weeks off." She said she wanted to hike from Grövelsjön to Treriksröset.
"He said yes. Then I told him it was 10 weeks." She paused. "He still said yes — but I think the order mattered."
Leading with the adventure rather than the duration makes it a human conversation, not an HR negotiation. Most managers respond very differently to "I want to hike the length of Sweden's mountains" than to "I'd like a 10-week unpaid leave."
If the answer is no — wait for a new manager.
Helena had already tried once and been turned down flat. Her previous manager didn't approve leave for big trips. She kept her dream alive, waited, and when she got a new manager, raised the question again. This time she got four months off — combining vacation days and unpaid leave — to hike Sweden, walk the Camino de Santiago, and bike through Switzerland.
"I just knew I needed to wait for the right moment," she told us. "The dream didn't go anywhere. I just needed a different conversation."
And if nothing works: quit.
Kim worked at a paper mill. She wanted unpaid leave. The company policy was clear: no. Her local managers fought for her and offered a compromise — a shorter leave. Upper management overruled them.
"I decided to quit," Kim said simply. "I figured I'd find a new job when I came back. Maybe even a better one." She said it without regret.
Kim completed Gröna bandet solo. Then she walked Norway på langs with Lukas. She found a new job when she returned. "It turned out to be fine. Better than fine."
Quitting is a real option — and for some people, the right one. What Kim's story shows is that the adventure is survivable, and so is the job search on the other side.
The common thread
Across all 20 people we interviewed, the ones who got leave shared one thing above everything else: they asked. They didn't assume the answer was no. They didn't wait until the last moment. They had the conversation — early, clearly, and without apologising for wanting it.
The fear of that conversation is real. But in almost every case, it turned out to be far easier than anticipated.
As Lukas put it: "Now that we've done this twice, we've both realised it's actually easier than it feels. The fear of leaving safety is the biggest obstacle."