How I Help Freelancers Grow Into High-Achieving Travel Managers
Building Skills That Drive Results
Building Skills That Drive Results
Hi, I’m Hamish – and my advisor journey didn’t begin with a badge of honour or a corner office. It started in the Nesting Advisor phase, a role where I trained fresh freelancer travel managers who had just completed their pre-live training on e-learning platform. Imagine a classroom mixed with an airport, mixed with a call center, mixed with a motivational seminar – that was my daily scene.
Back then, the nesting period lasted three full weeks. After completing these three weeks, the freelancers were supposed to move to the advanced team. Simple plan. Train them, guide them, build their confidence, and send them off to start earning. But the reality? Let’s just say the plan looked great on paper.
Since this is a pure performance-based position, success depends entirely on communication, convincing skills, and the confidence to speak with customers like you’ve been doing it for years. And these skills don’t magically appear after watching a few training videos. Many managers needed time – and lots of it. Even after three weeks of nesting, we would struggle to get enough graduates ready for the advanced team and ready to take the marketing calls.
And honestly, there were two main reasons.
Reason number one:
When most freelancers joined Dreamport, they came with the expectation that earnings would start immediately – like Day 1, or maximum Day 3. They thought they’d be printing money while sipping chai. But this role doesn’t run on imagination; it runs on skill. During this journey, you’re asking a customer to take money out of their pocket and trust you with booking their airline tickets. To do that confidently, managers need knowledge, workflow understanding, and consistent practice. And that naturally takes time.
Reason number two:
Many freelancers joined with the mindset of doing this limited hours. But the truth is, shaping communication skills, learning airline fare rules, understanding quotations, handling reservations, and managing payment processing – all of this requires full-time focus. We deal with real customers, real money, and real airline systems. This isn’t a “do it for two hours and disappear” kind of opportunity. It needs patience, discipline, and a lot of practice (with a little stress sprinkled in for flavor).
Despite these challenges, my goal as a Nesting Advisor remained the same:
To shape the travel managers’ skills, build their confidence, and prepare them for the advanced team so they could start earning well.