BEFORE YOU HIRE ANYONE FOR YOUR TRAVEL BUSINESS, READ THIS
You're drowning. You know you need help. But the first hire you're thinking about making? Probably the wrong one.
There's a retreat founder I know who came to me with a very clear diagnosis.
"We just need to hire a social media manager."
She wasn't getting enough bookings. Her Instagram felt neglected. She was exhausted and behind on basically everything. A social media manager felt like the answer — someone who could just handle the online presence while she focused on running the actual retreats.
Makes sense, right?
Except when we dug in, here's what the "social media manager" would have walked into on day one:
No social media strategy
No brand voice document
No content bank
No collateral — not a single on-brand photo set, no copy templates, nothing
A founder with zero bandwidth to brief them, review their work, or give feedback
Basically a blank whiteboard and a vibe.
Here's the thing nobody tells you when you're drowning in the day-to-day of running a travel or retreat business: hiring an executor before you have a strategy doesn't solve your problem. It just gives your problem a salary.
The Pattern I See in Nearly Every Travel Business
You built something real. Guests are coming back. Word is spreading. You're doing a lot of things — answering inquiries, managing logistics, running the actual experience, handling the finances, trying to keep up with marketing.
And somewhere in the middle of all that doing, you hit a wall.
Not because you're lazy. Not because you're bad at this. But because the same scrappy, figure-it-out-as-you-go energy that built the business is now the thing standing between you and a business that actually runs well.
You're not short on execution. You're short on architecture.
The instinct when you hit that wall is totally logical: get help. Hire someone. Delegate. But here's where most travel founders make a very expensive mistake — they hire for execution when what they actually need first is strategy.
Why Execution Without Strategy Always Fails
A social media manager can schedule posts. A VA can handle your inbox. A marketing coordinator can build a content calendar.
What none of them can do is pull your strategy out of thin air and hope it matches the one that was living in your head.
When you hire an executor without giving them a strategy to execute from, one of two things happens:
Option A: They produce a lot of activity that goes nowhere. Lots of posts. Okay engagement. Zero bookings. You're frustrated. They're confused. Nobody wins.
Option B: The whole thing implodes in 90 days. They leave (or you let them go), and you're back to square one — except now you've spent money, time, and energy you didn't have on a hire that didn't work.
Both outcomes tend to end with the founder concluding that "hiring just doesn't work for my business." That's not the lesson. The lesson is that the sequence was wrong.
What Needs to Come Before the Hire
This is the part that feels unsexy, but it's the whole game.
Before you bring in anyone to help with marketing, operations, admin — anything — you need to be able to answer these questions:
What is the actual goal? Not "more bookings" (too vague). What does a successful next six months look like in concrete terms? What's the revenue target? What's the booking conversion rate you're aiming for? What does success actually mean?
What is the strategy for getting there? Your social media manager shouldn't be inventing your marketing strategy. That's not their job. Who is your ideal guest? What makes your retreat or tour different from the 47 others that look similar on the surface? What does your booking journey look like, and where does it break down? These are strategy questions. They need answers before anyone starts posting.
What infrastructure needs to exist for execution to work? A social media manager needs a brand voice guide, a content direction, visual assets, and some sense of what has worked before. A VA needs SOPs, clear boundaries, and a communication system. An ops hire needs to understand the financial picture. None of these people can create this infrastructure — they need it to already exist, or they need someone with the strategic authority to build it alongside them.
What does this person need from you to succeed? Because here's the uncomfortable truth: even a great hire will fail without founder input and direction. Not daily hand-holding, but clear strategic guidance, regular check-ins, and the ability to escalate decisions. If you're too underwater to manage a hire, a hire will not get you above water. It'll just give you one more thing to manage.
The Right Order of Operations for a Travel Business That's Drowning
If I were sitting across from you on a discovery call right now, here's what I'd tell you:
Step 1: Get clear on what's actually broken. Not what feels broken (everything). What is the specific thing, if fixed, that would move the needle most? Is it that inquiries aren't converting to bookings? That you can't market consistently because you have no system? That you're hemorrhaging money on expenses that aren't tied to outcomes? Start there.
Step 2: Build the strategy before you build the team. Who is your guest? What do they need to see, hear, and feel before they book? What's your content direction? What's your pricing strategy? What's your revenue mix? These are strategy questions, and they need to be answered by someone who thinks in strategy — which, honestly, most travel founders don't. (That's not a knock. Your brain built a remarkable experience. Strategy is just a different skill set.)
Step 3: Then hire the executor. Once you know where you're going and how you're planning to get there, bring in someone to help you do the doing. Now they have something to work from. Now they can actually succeed.
A Note on the "I'll Figure Out Strategy as We Go" Approach
I know. You've been figuring it out as you go since day one, and it's gotten you here.
Here's the difference: in the early days, figuring it out as you go was the strategy. You were experimenting. Learning what worked. Building something from nothing. Speed and adaptability were the whole point.
But once you have a real business — real guests, real revenue, real team members depending on you — the "let's just see what happens" approach stops being scrappy and starts being expensive. Every hire made without a strategy is money spent on activity that may or may not connect to anything that matters.
The business you built by running fast? Now needs you to pause and think.
FAQ: Hiring Help for Your Travel or Retreat Business
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It depends entirely on where the biggest gap is, but in most cases, the first hire a travel founder needs isn't an executor — it's strategic support. Someone who can help you understand where your business is actually losing money, where your booking conversion is breaking down, and what a coherent marketing and operations strategy looks like. Execution hires come after that foundation exists.
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Usually because the hire was brought in without a clear strategy, brand voice, or content direction. Marketing coordinators and social media managers are trained to execute on a plan — not to create one from scratch. Without strategic infrastructure, even skilled marketers spin their wheels
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Ask yourself: do I know exactly what I want this hire to do, why it will work, and how I'll measure success? If the answer is no — if you're hiring because something feels broken but you're not sure what — you need strategy first.
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Operations strategy is the work of connecting your day-to-day activity to your actual business outcomes. It means knowing what it costs to acquire a guest, which of your offerings is actually profitable, where your team's time is going, and whether all of that effort is moving you toward the business you want to run. It's the layer most travel founders skip — and the one that makes everything else work.
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Before you hire, you need clarity on what you're asking marketing to accomplish. What's your conversion rate on inquiries? Where are guests finding you? What does your booking journey look like? If you can't answer those questions, hiring a marketing person is premature. Fix the strategy gap first, then invest in execution.
The Bottom Line
You don't need to hire more. You need to hire smarter — and in the right order.
The travel founders I work with who scale successfully aren't the ones who hire fastest. They're the ones who take the time to understand what's actually broken, get clear on where they're going, and build the scaffolding before they bring in people to execute on it.
If you're drowning right now and trying to figure out what help you actually need, let's talk. That's exactly the kind of conversation I have on discovery calls — and usually, 45 minutes of honest diagnosis is more useful than any hire you could make today.
Related reading: Why Your Small Business Feels Stuck | The Biggest Mistake Founders Make When Hiring for Operations | Your Small Business Is Growing — So Why Aren't You Profitable?
