Description

On this episode of Destination on the Left, I’m taking you behind the scenes of my own year-end planning process. As we look ahead to 2026, I’ll walk you through how I reflect on the past year, celebrating what worked, identifying lessons learned, and checking in on both team and personal well-being. I share everything from my practical planning frameworks and financial benchmarks to trend forecasting and tips for creating a collaborative culture.

What You Will Learn in This Episode:

• Why intentional reflection and bold, future-oriented questions are essential for setting effective priorities and ensuring organizational growth
• What emerging trends mean for travel, tourism, and hospitality planning in 2026
• How I use practical financial benchmarks and department-level planning to ensure the organization is ready for upcoming challenges and opportunities
• Why operationalizing collaboration by setting clear roles, goals, budgets, and documented processes moves it from a “nice to have” to a real strategic advantage
• What steps you can take to engage your whole team in the visioning and planning process to create greater buy-in and drive results
• How you can use my 2026 planning checklist and reflection questions to set your organization up for long-term success

Begin with Genuine Reflection

Before plotting the future, it’s crucial to anchor your plans in a clear-eyed assessment of the present and recent past. It’s so important to reflect on accomplishments, goal progress, team health, and personal leadership. I ask myself and my team a few probing questions:

1. What did we accomplish this year?
2. Where did we fall short and why?
3. Are our people thriving, or stretched thin?
4. How is my own mental wellbeing impacting my leadership?

These multi-level reflections ground the planning process in reality and provide the learning needed to improve both professionally and personally. Regularly scheduled interviews—such as “stay interviews” with staff—help surface the reasons your team members stay and opportunities for positive change.

Industry Trends and Future Readiness

How well are you anticipating and responding to the shifts in your sector? It’s critical to keep abreast of evolving trends—such as the rise of sustainability and regenerative tourism, persistent workforce challenges, and technological advancements like AI and digital personalization. Simultaneously, there’s a noticeable trend toward travelers seeking meaningful, off-the-beaten-path experiences, as well as a movement to “unplug” and seek present-moment enjoyment.

Empowering Your Team

Planning isn’t a solo exercise. At TAP we use a bottom-up approach: each department creates and presents their strategic plans, which are then built into broader company goals. Our annual team retreats blend strategic planning, culture-building, and a lot of fun ensuring everyone plays a role in shaping the future. We foster a sense of ownership among team members at all levels, after all, when everyone is involved, energy and commitment to the plan dramatically increase.

I want to leave you with this challenge: What role will collaboration play in your 2026 plan, and how will you operationalize it to drive real results—not just good intentions?

Resources:

• Collaboration Research: https://travelalliancepartnership.com/how-we-help/education/research/

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