...and Anticipate Joy

This was actually the first article idea I had in our little duology on planning for all eventualities. (Read part 1 here if you missed last week's newsletter.) I got Gayle the book Disney Adults for Christmas. Something in the book sparked a conversation about anticipatory nostalgia. My note about the article idea it spawned was that I wanted to try to create that in as many ways as possible.

And then, as I started writing this article, I realized that anticipatory nostalgia is NOT what I want to build. Instead, it's anticipatory joy. Let's look at both terms.

• anticipatory nostalgia - being nostalgic about the present moment before it has actually come to an end
• anticipatory joy - taking pleasure in thinking about positive/happy upcoming events or outcomes

Let's look at an example of each one.

Say you're at your family's holiday gathering. As you sit and watch everyone chat and interact, you feel a tug that you're going to miss this when a beloved family member - maybe one who is older - is gone. That's anticipatory nostalgia. It can be positive as it can instill in you a desire to make the most of the present moment. However, it can also be negative as it takes you out of the present moment and may make you sad.

Now, consider an event that's coming up. Let the joy and happiness you anticipate for that event wash over you. That is anticipatory joy. Even though the event hasn't happened yet, you're already feeling joy from what you expect to happen. While this takes you out of "being in the present", it is also a joy-filled activity. Some people might say that it can set too high of a bar for the actual experience, leading to the experience itself being a let down. I've never found this to be the case.

When we went to London and Amsterdam last year, I got incredible joy from creating our 82 page personalized travel guide. And, to that point about anticipatory joy perhaps raising the bar too high, I'll say that no bar could have been higher than the one we set for that trip and it delivered in every possible way.

As I prepare to head to Australia with my sister and nephew later this year, I take joy from every conversation we have about the trip and from working on the travel guide for that trip (although my sister Susie has done nearly all of that travel guide so I need to move beyond reading and add some more details myself!)

In addition to building travel guides for myself, here are a few of my tried and true activities for building anticipatory joy:

• Focus on events, not things - One of the biggest lessons I've learned in life is that the experience is the valuable commodity - not the thing. I used to fill my bags with souvenirs and trinkets on trips. And, while I still enjoy a small gift to commemorate a trip or event, the experience itself is so much more important. I've written before about trying to take a 1, 2, 3 approach to events and experiences which helps me make sure I'm not turning into a hermit - and instead getting out and enjoying life.
• Put yourself in the moment - whether I'm looking at the menu for an upcoming lunch with a friend, looking for a local bookstore or library I want to visit in a town I'm visiting for work, or making a travel guide for a big trip, the act of putting myself in the moment before I get there always helps me build anticipatory joy.
• Vision Boards - In 2026, I'm bringing back my practice of creating monthly vision boards. This is a monthly planning practice that has served me well in the past and I'm excited to spend a few minutes thinking about all the things I’m looking forward to doing - and hoping to do - in that month in this exercise.
• Gratitude Journal for the Future - Gratitude Journaling and other forms of intentionally noticing what you're grateful for are incredible mood and happiness boosters. Take a few minutes and journal about what you're most looking forward to about an upcoming experience.

As I mentioned, we're on a cruise this week - exploring Disney's new ship - the Disney Destiny. This is a "work trip" for Gayle (and I try to do my best as photography assistant). We're exploring the ship so she can build anticipatory joy for her travel clients by telling them all about the ship from her first-hand experience. I enjoy trying new foods and meeting new people. And, we're both excited to reconnect with a cast member we've seen many times before on previous sailings. And, given my yearly theme of Sail the Ship, I also have a few photo ideas I want to try to make happen on this cruise.

How do you build anticipatory joy? Is this a practice you've thought about intentionally in the past? What ideas from this newsletter sparked anticipatory joy or maybe even happy nostalgia for you? Hit reply on this email or click the Let's Chat button to go to the Circle Community where you can chat.

Some Other Things You Might Find Interesting

What I Published This Week

This week's what I published is a little different. And, it's part of how I'm going to keep newsletters going all year. I won't be able to provide direct links to things because they are publishing while I'm traveling - and after I've scheduled this to release. That said, there will still be info on how to find what was released. If anything beyond what's listed below gets published this week, I'll recap that after I'm back.

• If all goes as planned, the fourth installment in the Tasks Mini Series, which is all about using creating task queries, will go live on my YouTube channel this week. If you're a member of my Circle Community, you'll be able to find that in the Obsidian space as well.
• I'm finishing up my yearly planning articles with a look at my 26 in 2026 list. I've done these each year, but I think this is the first time I've specifically written an article on the list itself. You'll find this in the Resources section of the Circle Community.

What's Coming Up?

February 2026 Financial Date - Budget With Me & YNAB Office Hours

February 16, 2026 06:00 (Pacific Time (US & Canada))

Do you want to get a better handle on your finances? If so, join me for a free one hour workshop to talk all things money. This is a great time to hold your own financial date with yourself (which I talk about in the Facts of Life Book Course). Get financial questions answered, see software tools like YNAB in action, or just chat about money. This is a judgment free zone so come with your questions. 

February 9, 2026 Obsidian Office Hours

February 09, 2026 13:00 (Pacific Time (US & Canada))

Join us for the bi-weekly Obsidian Office Hours Session. Office Hours are a time to ask questions about Obsidian. If you have a question, reply to the event with your questions - or attend live and you can get your question answered in the session.  When appropriate, office hours sessions will be recorded and the recording posted here. 

Knives Out 3: Wake Up Dead Man

Over the holiday break, we watched the third film in the Knives Out franchise. As a recap, the first was excellent, the second was not so great, and the third...it was the best one so far. If you're not familiar with this franchise, the films take a look at social issues in a creative way. Knives Out 1 explored privilege, classism, immigration and xenophobia, wealth, and greed - just to name a few. The second film also looked at wealth and greed, specifically from the perspective of influencer culture. There was a healthy dose of the corrosiveness of social media in that one as well.

This third installment takes aim at how hypocrisy has devalued the moral influence of the church, abuse of power in institutions, Christian nationalism, and the clash between faith and other worldly concerns. While it might not sound like a good time to you, this is a film I will absolutely watch multiple times. The cast of characters includes Glenn Close, Kerry Washington, Daniel Craig, and Josh Brolin - and the acting from everyone is phenomenal. I love a film that both entertains me and makes me think. Knives Out 3 did both better than most!

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