Earn Your Leisure Podcast

Episode: "Who Deserves a Holiday Tip? Best Year-End Tipping Practices"

Date: December 22, 2025
Hosts: Rashad Bilal, Troy Millings (with Maite Gomez Rejon and Co-host)

Episode Overview

This episode delves into the topic of holiday tipping: who should receive a tip or year-end gift, how much is appropriate, and how tipping practices can nurture important relationships in daily life and business. The hosts share personal practices, offer practical advice, and touch on the cultural and etiquette aspects of tipping, especially within their community.

Main Discussion Points and Insights

1. Who Should Receive Holiday Tips?

• The hosts list and debate the types of service workers and professionals to consider:
  • Valet parkers and doormen, especially if you live in a building with such services.
  • Teachers (with discussion about which grade levels and types).
  • Cleaning staff or housekeepers ("cleaning ladies").
  • Sanitation workers (garbage collectors) – particularly if you live in a private home.
  • Mail carriers and package delivery workers.
  • Barbers and personal care providers (manicurists).
  • School bus drivers.
  • Building concierges and house managers.

Quote:
"Valet for sure. Shout out to the guys doorman for sure because they, they keep a lot of chaos away teachers if they are a good teacher." — Co-host, [04:49]

Host note: Teachers are especially highlighted from preschool to elementary, with additional gifts when there's a significant positive relationship.

2. Factors Influencing Who and How Much to Tip

• Living Situation Affects Tipping:
  If you live in an apartment vs. a private home, your roster of service workers will differ.
  "If you live in an apartment, you don't see a sanitation worker. So that's not even a thought. If you live in a home... that's a more personable thing." — Maite Gomez Rejon, [05:48]

• Relationship Quality and Service Level:
  They agree that only those who offer good service and positive attitude throughout the year should receive tips.
  "Are you not tipping anybody that does a bad job just because you do something?" — Maite Gomez Rejon, [12:07]

• Consistency:
  Workers relied on regularly (daily or weekly) should be especially considered.

3. Etiquette and Cultural Awareness

• There is an acknowledgment that some people, especially within their community, may simply not be aware of holiday tipping etiquette, rather than being stingy: "A lot of people don't fully understand etiquette when it comes to year end gifts. Tipping holiday tips. They don't even know you have to do that." — Maite Gomez Rejon, [12:37]

• The conversation connects tipping to general business practice: "Even in business. You should be sending gifts out in the year for the people that's taking care of you." — Co-host, [13:13]

4. Benefits of Tipping: Reciprocity and Service

• Hosts candidly discuss the pragmatic benefits of tipping beyond gratitude—better treatment and preferential service: "You're also having some level of, let's be honest, preferential treatment going forward." — Maite Gomez Rejon, [14:13]

  "They're going to treat you better... Pay it in advance." — Co-host, [14:33]

• Real-life examples are shared about hotel staff and restaurant servers offering perks, room upgrades, and improved experiences when tipped upfront.

• There’s humor and candid advice: "If you don't treat [your cleaning people and drivers] well, your information may end up on the dark web. So be careful. Take care of them, please." — Co-host, [16:02]

5. How Much to Tip?

• There’s no fixed answer; it depends on the relationship and the role the worker plays in your life.
• Thoughtfulness, frequency, and acknowledgment of the value they provide all matter.

6. Memorable/Notable Quotes with Timestamps

• "Anybody that you're relying on either on a daily or weekly basis that has a high level of customer service throughout the year should be getting a tip." — Maite Gomez Rejon, [13:38]
• "One way to get great service is to tip as soon as you get there... before dinner." — Co-host, [14:49]
• "Jabril... broke it down. Passport heavy. Shout out to him. He said what he does is he started tipping the hotel, checking people... and miraculously, he just starts getting room upgrades, fruit baskets sent to the room." — Maite Gomez Rejon, [15:10–15:29]
• "Take care of them, please." — Co-host, [16:08]

Noteworthy Segment Timestamps

• [04:01] – Introduction to the main topic: Who deserves a holiday tip?
• [04:16–05:48] – Listing of professions/service providers usually tipped.
• [05:48–06:39] – How living situation and personal relationships affect who you tip.
• [11:39–12:19] – Additional service providers (barbers, bus drivers); only tipping those who do a good job.
• [12:37–14:13] – Tipping etiquette, community awareness, and who should always receive a tip.
• [14:13–15:29] – The “pay it forward” mentality and how tips earn better experiences.
• [16:02–16:08] – The vital importance of caring for people in key roles.

Tone and Language

Conversational, candid, practical, and informative, sprinkled with humor and personal anecdotes. The hosts emphasize real-world practicality, mutual respect, and goodwill, while keeping it relatable for their core audience.

Summary Takeaways

• Tip those who provide valuable, consistent service to your life or family.
• Relationship quality and frequency are key to deciding who deserves a tip.
• Tipping is not only about gratitude but building goodwill and better service.
• Educate yourself and those in your community about year-end tipping etiquette.
• There’s no hard rule for amounts; be thoughtful and acknowledge those who make your life better.

For anyone wondering who deserves a tip during the holidays and why it matters, this episode offers a lively, nuanced “business class meets real life” breakdown—just in time for the season.