After 30 years inside corporate travel, the last thing I expected to start was a retreat-planning practice. But the gap between what distributed teams need and what existing platforms deliver is wider than the industry admits — and I'd been preparing to close it for three decades without knowing it.
I spent 30 years inside the corporate travel industry. Most of it on the side of the business that nobody outside it understands — and I include the people who book the trips in that.
I planned executive itineraries that crossed twelve time zones in a single week. I ran meetings & events programmes for Coca-Cola, WWF, and Tyler Perry. I closed framework agreements with annual spend authority bigger than the GDP of small islands. And I learned that none of those clients cared about the spreadsheet — they cared whether the trip worked.
Now I plan team retreats for distributed companies.
That sentence makes more sense if you've watched what's happened to corporate travel over the last five years. So let me show you how I got here, and why your team's next offsite is the trip I most want to plan.
For decades I was the person on the other end of the phone when a CFO's flight got cancelled at 3am Beijing time and his board meeting was at 9am Frankfurt. I was the person who knew which visa office to call on a Sunday. I knew which hotel general manager owed me a favour. I knew which airline's lounge had a working shower and which one didn't.
Those are not skills I went to school for. They're the kind of skills you build only by being in the seat — for years — while real money and real careers depend on the trip happening on schedule. You make mistakes. You fix them at 4am. You learn what actually fails.
What I noticed over those decades wasn't that travel got easier. The tools got better. But the trips got more complex, more international, more stakes-laden. And the people planning them got further from the decision-makers. Travel went from being a strategic function to being something a procurement team tried to optimise on price.
Then COVID hit and the entire corporate travel category broke. Trips dropped to zero. Programmes were paused. Travel managers got laid off. The vendors that survived consolidated.
When trips came back, they came back different. Distributed work meant companies didn't have headquarters anymore. The "annual sales kickoff" wasn't fifty people getting on a flight from Atlanta — it was forty-eight people getting on flights from forty-three cities. The whole logistical operating model needed to change.
What didn't change: most retreat platforms still operate like budget travel agencies — they're optimised for filling rooms, not for designing experiences that actually deliver. The people booking the offsites — founders, People Ops, Chief of Staff — are doing it as a side project on top of their real jobs. And the budget math has shifted so dramatically that nobody knows what a "normal" retreat costs anymore.
I left corporate travel to start Trip Happens originally as a travel-content brand. The idea was simple: I'd been planning trips for the wealthiest, most demanding people on earth for three decades, and almost none of that knowledge was getting through to regular travellers. The blog was the start. The Fora Travel advisor credential came next. And then I started getting a different kind of inquiry.
"We're doing an offsite in October. Can you help?"
That request started coming from founders. From People Ops leads. From Chief of Staff types who'd seen a piece of my content and connected the dots. They didn't want a retreat platform — they wanted someone who'd been on the other side of complex international travel logistics. They wanted someone who could talk to a Four Seasons general manager as a peer, not a customer.
They wanted me. And I realised I'd been preparing for exactly this for thirty years without naming it.
What changed between 2019 and now isn't the kind of travel companies do — it's who plans it. The function moved from professional travel managers to founders and operators who don't have time to learn travel from scratch.
The work is what I've always done — designed for what teams need now.
I work with founders, People Ops leaders, and Chief of Staff types at distributed companies. Specifically:
I'm not a fit if you want a retreat that's 70% structured workshop and 30% laptop time. I'm not a fit if your team is bigger than 100 — at that size you need a corporate-events firm, which is a different category. And I'm not a fit if the only thing that matters to you is per-person price, because the partner programmes that make my work valuable cost the same as booking direct (with more perks layered in).
If this lands and you've got an offsite in the next 6 months, the start is a free 30-minute intake call. We talk through what you're thinking, I tell you whether I'm the right fit, and either way you leave the call with one or two concrete pieces of advice you can use whether you book through me or not.
No commitment. No pressure. No upsell. The whole point of starting this practice was to do work that actually delivers — and that starts with the right fit, not the booking.
Book a free 30-minute intake call. We'll talk through what you're thinking and whether I'm the right fit for your team's offsite.
See How I Plan Retreats → Email Lisa DirectlySome links in this post may earn Trip Happens a small referral commission — at no extra cost to you and never affecting what gets recommended. Full disclosure here.