Don't Just Drift into 2026: Design it like a Trip

Thoughtfully plan your year ahead.

December 31, 2025

I bet when you travel, you don't just drive to the airport, board a random plane, and see where you end up. Of course not. A good trip requires intention, a purpose, and lots of planning.

So, why do we treat our lives differently? It always strikes me how much effort we put into a vacation, yet how little we prepare for a new year. We need that 'travel spirit' right now as the new year approaches us. We need to view 2026 as a destination, not just another page turn on the calendar.

Here is how we design that trip.

First: Make a Stopover in 2025

Before we take off for the new year, we need to pause and check our coordinates. We need a layover. For this, I recommend two exercises:

The Wheel of Life

As humans, we have this bad habit of minimizing our victories and exaggerating our defeats. If we evaluate the past year without a helping structure, we fall into the trap of thinking "I didn't do anything notable."

That’s why I love "The Wheel of Life." It guides us to objectively score how we did in eight core dimensions: Physical Health, Mental Health, Love & Family, Professional Growth, Spirituality & Purpose, Friendships, Personal Finances, and Leisure.

Each dimension gets a rating. In the end, we can clearly see our strengths and the areas where we should focus more effort. The Wheel of Life helps because we are often too stingy with our own applause—so look at your wins and clap for yourself! Once you acknowledge the wins, you can identify the areas that deserve more intention in 2026.

The Year in Photos

You've seen those "Spotify Wrapped" lists, right? They’re cool and all, but why let an app have all the fun? Let's do the same thing with the photos we took over the last 12 months.

Go to your phone and scroll through your camera roll. Take your time and pick a handful of photos (say, 12 to 24) that truly define your 2025. Most will be happy memories, but don't ignore the difficult ones if they taught you something and were significant to you.

Then, look at them and ask: Which of these moments are worth repeating? Which ones happened by accident (inertia), and which ones did I intentionally create?

If you have a partner, do this separately and and then compare your findings. Ask each other: Why did this photo make the cut for you? Why was it meaningful? How can we integrate more of this into our lives? This exercise opens the door to incredible conversations about what you value as a team. It is simple, but super powerful.

Second: Forget Resolutions, Start Visualizing

Let's be honest: Resolutions rarely work. I used to do them, and sure, they are better than nothing, but most of them are dead by February.

Why? Because they are often just the product of wishful thinking. Instead, let's try a mental hack: Visualize 2026 as if it has already happened.

Describe a random Tuesday in 2026.

  • Are you still working the same job?
  • Is your relationship dynamic the same, or has it evolved?
  • Who are the people sitting at your table?
  • How does your body and mind feel when you woke up this morning?
  • What is the one specific achievement you are most proud of this year?
  • What old problems have you finally solved?

Ask yourself as many honest questions as you need to build this picture.

Here is the litmus test: Read your description. If it doesn't excite you—if it doesn't give you that spark in your gut—then that is not your true destination. Tear it up and rewrite it until it gives you goosebumps.

Quite a difference, huh?

Third: Design Your "Crown Jewel" & Your 12 Diadems

Ramit Sethi has a provocative proposition: we should all have "at least one exhilarating event every year." I call this The Crown Jewel.

This isn't just a fancy dinner at Olive Garden over the weekend. It must be intentional, it should require serious planning, and it must carry profound emotional weight. This is the memory you will hold onto until your deathbed.

It could be throwing the epic birthday bash you’ve never had, finally finishing that master's degree (or that therapy you’ve postponed), quitting your job to launch your business, or jumping out of a plane.

The Rule is Simple: Ask yourself: "If I only achieved this one thing in 2026, would the year be a success?" If the answer is yes, lock it into a specific month right now.

For me, my Crown Jewel in 2026 is a family trip to Iceland in August. It’s expensive, yes, and it’s a logistical beast to plan—but that’s exactly why it matters.

But listen to me closely: A great year isn't built on just one massive event.

I challenge you to grab your calendar and create Twelve Diadems. Mark a specific highlight for every single month. These are smaller gems—easier to pull off and even free activities, but just as intentional and meaningful.

  • Disconnect to Connect: Schedule a monthly walk in the park where cell phones are banned, just so you can actually hear the wind (or the city) around you.
  • Make it "Team Cooking": Commit to cooking at home once a week, not as a chore for Mom, but as a fun, music-blasting team effort.
  • Reconnect with People: We are drowning in technology but starving for connection. Why not put a date on the calendar to see a different friend every month?

Put these in your calendar before the year starts. Don't wait for life to surprise you. You surprise life.

Stop Living by Accident

We have much more power over the future than we think. We can mold our circumstances if we just take some time to work with intention and purpose.

So, don't just let 2026 happen to you. Don't live by inertia. Live by design.

Let's make this next trip a memorable one.

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