Insights·Training · 777
Training · 777

Winter Is Coming: Training Through the Holiday Gauntlet

*Short days, packed schedules, and family diplomacy, all before the hardest weeks of the training cycle even begin.*

Author
Dena Evans
🇺🇸 United States
Shared
September 17, 2026

For those of us who spend the majority of our time in the northern hemisphere, we are already adjusting our training to shortened daylight hours and maybe dropping temperatures.

By the time of our heaviest volume period leading into this adventure, we will have the shortest days and perhaps the most challenging weather of the entire training cycle. In addition, holiday schedules, family obligations, and potentially other unique logistical challenges are certain to disrupt the well-formed habits we may have established through the fall.

01

A Welcome Challenge in Disguise

We know this challenge will require flexibility and executional calm despite exceptional circumstances, so the holiday period provides us a welcome challenge in that respect. Getting in those extra miles at sub-optimal times of day is a challenge, but it is one that will also prepare us for our upcoming trip.

Instead of viewing this time as a headwind, I hope to regard it as an opportunity for which we can plan.

— Dena Evans
02

The Specific Load of This Specific Time

As we plan meticulously for what we will pack and the trip itself, we also should consider this winter and holiday period. Most of us need a few hours set aside to hit those longer mileage days, and unlike some other years, we'll need to be backing up some of those days with other long days. Daylight hours and favorable weather may be in short supply.

Patience regarding our training schedules among our families and associates may not be as strong as our competitive will to complete this challenge. Diplomacy may be an asset!

03

Plan Ahead, Reduce the Surprises

Good communication, forward thinking, and strategic orchestration of other daily commitments are all possible to maximize with advance notice. Things might not be perfect, but planning ahead for the unique load of this specific time period can allow us to practice making the most of the time we have, and reduce the surprises we face when life intrudes on our plans for lengthy days out on the roads.

  • Communicate early with family and close associates about the training calendar.
  • Map out which days require the biggest time blocks and protect them in advance.
  • Build flexibility into the schedule so that a disrupted day does not derail the week.
  • Use sub-optimal conditions (dark mornings, cold afternoons) as deliberate practice for the trip itself.
  • Treat diplomacy as a training tool, not an afterthought.
Key Takeaways
  • 01The heaviest training volume of this cycle coincides directly with the shortest days and busiest family season of the year.
  • 02Getting miles in at sub-optimal times is not just a necessary inconvenience; it actively prepares you for conditions on the trip.
  • 03Diplomacy with family and associates is a genuine logistical asset, not a soft concern.
  • 04Forward planning and good communication can absorb most of the disruption before it happens.
  • 05Reframe the holiday gauntlet as an opportunity to practice executional calm under exceptional circumstances.
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