'Tis the Season! (For Strategic Planning, That Is)

By Lybbi Hebel, Creative Marketing Strategist

It’s that magical time of year when time blindness is upon us. Halloween just ended, and we’re slowly starting to pull out the holiday decorations and get a headcount for who can make it to Thanksgiving dinner. Though we're currently reveling in all the space between now and the end of the year, the holidays will be upon us in the blink of an eye. The panic will set in, and we’ll frantically finish our shopping, cookie baking, card writing, and so on, just in the nick of time.

The same thing tends to happen with our businesses. Right now, 2027 still feels far enough away that planning for it can wait. Then the holidays arrive, and between family obligations, last-minute client requests, and the usual end-of-year tasks, there’s no room left to think about anything beyond the next deadline. The strategic planning never happens, January comes around, and the new year unfolds without implementing any of the “I’ve been meaning to…” items on the list.

The problem with big-picture planning is that, while it’s important, it’s never really urgent, so it loses out to everything that is. To stop the cycle and start the new year on the right foot, let’s take steps to make 2027 planning a priority as soon as possible.

Make the time before it disappears

Put a planning session on your calendar for a specific date and time in the next two to three weeks and treat it like a client appointment, meaning you will take it seriously and won’t bump or cancel it when something else comes up. Even if all you can promise yourself is a focused half-day, that’s an excellent place to start.

To truly focus on the big picture and pull yourself out of your day-to-day, it helps to literally pull yourself out. Get away from your usual workspace, where your pile of to-dos will be calling to you, and instead head to a coffee shop, the library, or even a different room in your house. Set an out-of-office message for those few hours, close your email, and silence your phone. For bonus points, pull your reports ahead of time so you can spend the session thinking instead of digging for numbers.

Look back before you look ahead

Before you set any goals for 2027, take a good look at how 2026 went. Once you get out of the weeds and look at the past year from a bird’s-eye view, you’ll likely find some surprises and things to pay more attention to.

Review your revenue and commission by client, supplier, and trip type. Notice which clients were the most profitable relative to the time they took, which ones you loved working with, and which type of client you’d like more of. Look at where your new leads came from, and weigh the costs of your various marketing efforts against the results they produced. Think about which supplier partners you leaned on most and where you’d like to build stronger relationships. Look at where your time went and which tasks you could streamline, systematize, or hand off.

Decide what 2027 is for and map it out

Once you have a clear picture of your business, narrow down your long list of hopes and dreams into a short list of clear priorities for the year, and set three to five goals with measurable targets.

From there, map your calendar around those goals. Add touchpoints throughout the year so you know whether you’re on track to hit your targets. Build a marketing calendar around when your clients book, not just when they travel, so you can proactively reach out and catch them at the right time. Put your own vacations, professional development events like conferences and FAM trips, and dedicated working hours on the calendar now, before the year fills in around them.

Keep it flexible

Your plan doesn’t need to be perfect, and some of it will change by spring, which is completely normal. Revisit it every quarter and adjust as you go. The point isn’t to predict the year perfectly, but to start it with a clear direction and move forward with a strategy in place.

The holidays will sneak up on us the way they always do, but your 2027 plan doesn’t have to be one more thing you finish in the nick of time.

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