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Tipping used to be simple but now it’s a full-blown holiday headache.

In Season 6 Episode 7 (Ep 129) of What Dewey Do?, the pressure to tip is everywhere, from coffee counters to self-checkouts. Just in time for the season of giving, here’s a no-BS guide to tipping with confidence, generosity, and a clear conscience. Tipping takes center stage from its origin story to the post-COVID spike in expectations, including the tech-fueled “tip creep” phenomenon.

You’ll learn when to tip, what to tip, and when it’s totally fine to skip it. Holiday tipping guidelines, auto-gratuity red flags, guilt-driven screens, and personalized service rules are all part of this tipping playbook that’s just as useful for 2026 as it is right now.

Skip the awkward pause at the tablet and stop tipping out of guilt. Watch the full episode and head into the holidays with your wallet in balance.

Quotes:

- Dewey Steffen: "The general rule: tip when someone provides personalized service and relies heavily on your gratuity."

- Dewey Steffen: "Holiday tipping is different. You’re giving a bonus to people who support you all year long.”

- Dewey Steffen: "In self‑service situations, there’s no need to tip. Don’t let a tablet screen guilt trip you."

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Thanks for watching! What Dewey Do? is a podcast by Great Lakes Wealth (www.greatlakeswealth.us) and executively produced by Evry Media (https://www.evry.media.com) and Broadcast Your Authority (https://www.BroadcastYourAuthority.com). Great Lakes Wealth, LLC is a registered investment advisor. The information provided is solely for informational purposes. Advisory services are only offered to clients or prospective clients where Great Lakes Wealth and its representatives are properly licensed or exempt from licensure. No advice may be rendered without a service agreement in place. Securities offered through Purshe Kaplan Sterling Investments, Member FINRA/SIPC Headquartered at 80 State Street, Albany, NY 12207.

Purshe Kaplan Sterling Investments and Great Lakes Wealth are not affiliated companies. The views reflected in the commentary are subject to change at any time without notice. Nothing herein constitutes investment advice or a recommendation that any particular security, portfolio of securities, transaction, or investment strategy is suitable for any specific person. Any mention of a particular security and related performance data is not a recommendation to buy or sell that security or a depiction of past investments made by Great Lakes Wealth, LLC.

The Psychology of Tipping (Holiday Edition)