Holiday Season Timeline: Generating Business During the Holiday Season

Holiday Season Timeline

It is November - which means it is officially the start of the holiday season. If you are US-based, you’re likely intuitively aware of this cycle of business. Here’s a general timeline I use:

• Nov 1 - Thanksgiving: Active
• Nov 25 - Dec 2: INACTIVE [Week of Thanksgiving]
• Dec 2 - Dec 15: Active
• Dec 15 - Jan 15: INACTIVE [All of the Holidays]

During the inactive periods, decision makers are often offline and unreachable. And decisions and work don’t get done.

Bottom Line: Folks spend A LOT of money during this period

There is both opportunity and tact inherent in this period. It’s best to move wisely.

• According to Adobe Analytics, last year shoppers spent $9.8 billion online on Black Friday, up 7.5% from the previous year and U.S. retailers also saw an 9.6% increase in online sales on Cyber Monday to $12.4 billion (RetailDrive)
• For organizations, many companies and government agencies have a “if you don’t use it, you lose it” policy in their budget and are looking to make purchases NOW for work executed in 2025.

If you are a coach or consultant, it is a great time to further the sales/enrollment conversations with individuals and organizations you want to work with.

My Lessons Learned

Here's how to strategically place yourself to generate business and maintain boundaries around the holidays.

1. Build the relationship intentionally NOW. Schedule check-in calls during one of the active periods above. We usually prefer genuine pre-New Years ‘catch-ups’ to Q4 busy work.
2. Don’t force what isn’t there - for your sake and theirs. December 31st is a made-up finish line… don’t rush the sales process or damage the relationship by rushing to close work.
3. Send clients and potential clients a personal holiday gift or thank you note. Send along something authentically you. Bonus points if it’s something that sits near their desk that reminds them of you when they see it.
4. If you haven’t already, schedule your out-of-office responder and block your calendar for the days you plan to spend with friends and family. Protect that time away from work and give yourself something to look forward to.

Final Word

The impersonalization of AI and automation has the world zigging… so instead, zag. Developing deeper, more personal relationships with those who you do business with requires us to be mindful of these relational cycles.

Looking ahead, I believe the premium on trusted relationships and kindness will never be higher.