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Life's a Game (Plan):
How to make the most of 2026

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Every year I sit down and plan out my year ahead. Jesse Itzler is known for doing this with his “big a## calendar” but I just use a small a## google sheet.

Today I’m giving you free access to my planning 2026 template that goes along with the below exercise. Simply click here and make a copy for yourself!​

♟️ MY TURN:

The past 10 years of my life have included......

• A reality tv show
• 2 startups, 1 exit
• 4 marathons
• 3 babies
• Launching a newsletter, course and community
• Publishing a USA Today Bestselling book
• Becoming the host of Ambition 2.0 podcast
• Finding love again and getting married
• And so much more.

Planning each year in advance has allowed me to do three things:

#1: Slow down time

Many people like to joke that I get more done in a month than most do in a year.

Planning my calendar ensures I inject my life with novelty which has been proven to slow down the feeling of time.

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​#2: Not waste time

Time is relative.

A week to a newborn is an entire lifetime. A week to a 1 year old is 1/52 of their life. A week to a 10 year old is 1/520 of their life.

Let’s look at Urban's chart of the "life of the typical American."

• Each row is a year.
• Each dot in each row is a week.
• The colors show the basic periods in the typical life.

If I live an average life span for my gender (83), I only have another 2,340 weeks left!

So there’s no way I’m going to waste any.
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#3: The Year Of.....

I always have a big hairy goal for the year ahead.

Finish this sentence: 2026 will be the year of _________.

2023 was the year of "leaving corporate America" and I will always look back and remember 2023 as the year I stepped out on my own.

2024 was the year of "finding my person" and I will always look back and remember knowing that I knew I wanted to grow old with Dan.

2025 was the year of "becoming a published author" and I'm so grateful for all the support in getting that to *bestselling author*

2026 is the year of "Building a startup". I'm rejoining the world as a CMO of a new brand that launches later this year. It's also the year "Building our family" as I get married and explore the pathways of potentially growing our family.

Some "Year of" statements have been personal goals (like running a marathon before each baby turned 1) and some have been professional (launching a company, newsletter or promotion).

So how will you finish the sentence?

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​#4: Maintain relationships

As I get older it becomes harder and harder to get quality time with friends. People are busy, kids' schedules take over.
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By planning ahead, I can make sure months don't go by without seeing people who are important to me.

Ready to level up and get the most out of 2026? 👇
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♟️ YOUR TURN:

I approach my yearly planning the same way I approach building a marketing calendar as a CMO. I slice the calendar in 4 ways:

• Annual tentpoles & events
• Quarterly launches
• Monthly beats
• Weekly non-negotiables

Reminder: Use this link to get your 🧩 Life's a Game Planning calendar.​

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Annual: First look at the year as 1 year

Step 1. Identify your tentpole moments

Start by planning your tentpole moments in the full calendar year. Things that require you to step away from your life and do something new, exciting and different.

• Vacations
• Competitions
• Conferences / Trainings
• Sporting events

My tentpoles in 2026 include:

• Wedding + Honeymoon
• Solo long weekend at the start of summer
• Family trip during summer
• October Birthday Trip with friends (this year is my 40th!)
• One physical challenge (I'm thinking a hyrox in the fall)

Step 2. Add your annual celebration moments

• Birthdays
• Anniversaries
• Holiday gatherings

I also add in preventative health at this stage of planning: it’s important to me and also a pain to stay on top of so I just pull them over from year to year. Feel free to steal my calendar below.

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Quarterly: Now look at the year as 4 quarters

Step 3: Add your quarterly launches / goals

What do you hope to launch personally and professionally in the upcoming year? Let's break those now into quarterly launches and goals.

By putting that goal on a calendar you now have something to plan toward and hold you accountable instead of punting it into the obscure “in 2026 I want to do this” verbiage.

Things like:

• The quarter I launch a newsletter
• The quarter I run a half marathon
• The quarter I get serious about Instagram
• The quarter I move to a new apartment / home

I also have a few things that I want to happen every single quarter to ensure I'm staying connected to myself and my family:

• Overnight staycation with my partner
• 1:1 dates with each kid
• Quarterly solo staycation retreat

Monthly: Now look at the year as 12 months

Step 4: Add your monthly to-dos & non-negotiables

Every month it's important to create the things you want to complete and then schedule them into your calendar.

Here are my monthly staples:

• Community: Every month I want to have at least one dinner with friends
• Parenting: Every month I want one planned, fun outing with my kids
• Relationship: Deep dive check in with my partner
• Me day: One day to get a massage & facial & do whatever I want to do

Weekly: Now look at the year as 52 Weeks

Step 5: Add your weekly goals you want to maintain

Every week has a rhythm. Without planning ahead it can become easy to let it just slip by. Here are my non-negotiables in a week.

• Kids: at least 2 family dinners together
• Partner: 1 date night
• Body: 3 workouts
• Content creation: 1 day for thinking / writing
• Finance Fridays: every Friday I review my P&L

By completing this planning exercise you've now got a HUGE head start on everyone else as you head into 2026. ​
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♟️ Let's Win Together.

PS If you are ready to take your game to the next level this year, here are 4 ways I can support you in 2026.

• My 35 Hard challenges tackle one big goal over the course of 35 days. These are pre-recorded so you can go at your own pace! They are each $43.
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  Want to grow a personal brand in 2026? Click here.
  Want to launch a newsletter in 2026? Click here.
  Want to build a digital course in 2026? Click here. ​
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• Life's a Game: The Masterclass is my 10 module productivity and focus course teaching all the frameworks I use to juggle 3 kids and 5 income streams. Click here to get the course for just $143.​
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