Developing my "Big A## Calendar" for 2024

Reflecting on 2023 and setting goals for 2024 to make it my best year yet

At the end of each year, I look back on all that I’ve experienced and accomplished, and I reflect on how I’ve changed and grown. Then I look ahead and set goals for the coming year, to guide my actions for the months ahead.

I’ve been officially doing this since 2020, and it’s served me very well. After all, where focus goes, energy flows.

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Setting directional goals across 10 aspects of my life

In late 2019, for the first time in well over a decade, I started to focus on personal aspects of my life (my interests outside of work, my health and wellness, my friends, and my family) in ways I never used to realize were important, and I love the changes I’m seeing.

I now set annual goals across the ten aspects of my life: health and wellness, mindset, relationships, time, spirituality, finances, work, kids, home, and travel/adventure. Setting these goals has become a great way to make sure I nourish all aspects of my life and don’t neglect any areas that are important to me.

The goals I set aren’t specific accomplishments or milestones that I need to achieve. Rather, they’re direction-oriented. They are targets and focus areas that I carry with me throughout the year. They point me in the direction I want to go. I review the list each week or two to see how I’m doing, and when I look back at the end of each year, I find that I’ve made progress that I’m proud of (whether large or small), in almost all of my focus areas.

There will always be some I don’t achieve, and that’s fine. At the end of the year, I consider whether I will shift each one into the next year, or just make peace with it, decide its not as important as I once thought it was, and let it go.

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Someone who inspired me this year: Jesse Itzler

If you’ve read my posts over the last three years, you’ll know that I draw a lot of inspiration from powerful thinkers, writers, and speakers. One individual who has been particularly inspiring to me this year is Jesse Itzler.

Jesse is a business and life coach, and a successful entrepreneur who’s built and sold five companies, including Marquis Jet, Zico Coconut Water, and 29029 Everesting. He’s written two books, he co-owns the Atlanta Hawks, and, among many other things, he’s married to Spanx founder Sara Blakely. I’ve already been inspired many times over by Sara and how she founded and grew Spanx into a billion-dollar business, and I find Jesse’s content and approach just as inspiring.

Together they are a quirky and hilarious couple—check out this Lewis Howes interview with them on marriage, money and the entrepreneurial mindset. They talk about the misconception that you have to choose either family or career, and how they manage to have a healthy marriage and four kids while both running successful businesses. A big part of it is that they are open and honest with each other, they aren’t afraid to be vulnerable, and they take the time to be intentional in everything that they do.

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The Big A## Calendar: Jesse’s four principles

One of the concepts I’ve taken from Jesse is his “Big A## Calendar.” He advises that we should all plan out our year and use our calendar as a scorecard for an amazing 12 months of mindset change, growth, and success. He explains this concept here: Plan Your Entire Year in 23 Minutes With Jesse Itzler.

Here are Jesse’s principles to keep in mind before planning out your Big A## Calendar:

• Principle #1 – Time is undefeated: Time, as Jesse says, is undefeated; nobody’s figured out how to outlast it. We only get a finite amount of time on this planet, and none of us knows how much we’re going to get. So plan to do the important things now, before someone gets sick or your circumstances change in some other way. There’s no way to know what lies ahead, so don’t wait.
• Principle #2 – Your life resume matters: What matters most is not your professional resume, but your life resume: how you show up, what makes you proud, what you accomplish in your personal life, what adventures you go on, and who you spend your time with.? Schedule these items first before you think about work commitments.
• Principle #3 – More isn’t better; better is better: It’s easy to get overwhelmed with so many goals that we water down our own accomplishments. It’s better to reduce the number of goals you set and focus on the quality of your goals in both your personal and professional realms.
• Principle #4 – Do small things that make you proud: Everybody wants to feel good about themselves. As Jesse says, you don’t have to climb Mount Everest or sell a company to feel proud. You can feel pride in small actions. So rather than focusing on some massive goal, it can be a lot more satisfying to do things you feel proud of every day.
• Principle #5 – Plan a year that you are proud of: You want to be able to look back on your year and feel like you were the person you wanted to be. Circumstances might prevent you from meeting some of your specific goals, but as long as you show up within those circumstances in a way that makes you proud, then you can look back on your year and feel tremendous satisfaction.

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Steps to planning your year

With those principles in mind, Jesse’s system for building a complete calendar year is to focus on these major planning steps:

1.?Identify one year-defining goal (misogi)

This concept is derived from the Japanese term misogi, which is a challenge that pushes you to your limits and forces you to overcome some of your fears, doubts, and weaknesses.

Jesse uses this idea to mean choosing one major goal for the year to focus on—a goal so big, so all-consuming, that it defines your year. So when you look back on your life, you can pinpoint the year by that activity: “2024 was the year I ran my first marathon,” or “2024 was the year I wrote my first novel,” or “2024 was the year I hiked to Everest basecamp.”

Imagine if you started doing this in your 20s or 30s? You’d have dozens of major accomplishments to look back on and put on your “life resume.” So Jesse’s advice is to start with that one big goal and put that on your calendar first, along with all the activities that go along with achieving it.?

2.?Kevin’s Rule

Kevin is a friend of Jesse’s. His rule is to take one day every other month to do something you normally wouldn’t do. It might be going to a museum or taking a cooking class or running a 5K—anything that is outside of your norm. This guarantees that you will have six mini adventures that expand your horizons and expose you to new ideas. That’s dozens or hundreds of mini adventures over a lifetime—just think about how you’ll look back on all those adventures and be proud of everything you squeezed out of life.

3. Introduce one winning habit a quarter

Jesse’s next principle is to introduce one winning habit every quarter. These don’t have to be big; in fact a lot of us have habits we want to introduce that are quite small. Maybe it’s drink lots of water every day, or be on time for meetings, or do Wim Hof breathing (those were on Jesse’s list for 2023). By the end of the year, you’ll have incorporated four new habits into your life.

I can confirm that this approach works.? I went to the Dimensions cannabis retreat Ontario’s Haliburton Highlands in July (you can read about that here), and when I got back I was inspired to introduce a daily habit of meditation, which I’ve kept up every day. Then in October, a quarter later, I started working out every day. By giving each habit three months to get ingrained, they have become critical parts of who I am. I’m reaping the benefits of both—I am more focused, I have more energy, and I feel great.

4.?Make a list of your “vitamins”

The concept of vitamins here is not your old Flintstones chewables or your daily Omega-3 supplement. Jesse’s advice is to make a list of all the small, regular things that make you happy. Those are your vitamins. He encourages you to make a list of ten of them, and commit—by putting them on your calendar—to taking two or three of those vitamins every day.

For me, my list of daily vitamins now includes working out, spending 15 minutes in a sauna, meditating, and connecting with at least one friend or family member. Committing to doing a few of these activities each day will ensure that I get a regular dose of peace, joy, and satisfaction.

Just imagine. By the end of 2024, by following these four principles, you can accomplish one huge goal, have six mini adventures, adopt four great new habits, and feel a daily sense of peace, joy and satisfaction. These four simple ideas add up to a truly incredible year. I’m working now on mapping mine out for 2024, and I encourage you to join me.

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My year-defining goals (misogi)

I hadn’t heard of the concept of misogi until this year. But when I look back, I realize that I’ve actually been doing this since 2017. I’ve done some pretty major things that in retrospect pushed me to my limits and in many cases forced me to confront my fears, doubts and weaknesses, and they do define my last seven years.

• 2017 & 2018 – Attended Harvard Business School: In each of these two years, I did a YPO executive education course at Harvard Business School with leaders from around the world. It had been 16 years since I finished my MBA at Ivey Business School, and at first I was a little intimidated about being back in school, at Harvard no less! But I fit in perfectly, I contributed in ways that made me proud, I was completely reenergized and enriched by these programs, and I made friends from around the world.
• 2019 – Travelled to the Yeotown Health Retreat: In 2019 I took a new tack and focused on my health and wellness. This retreat, in Devon, England, started me down a path of understanding how food can make me healthy or sick, and how exercise can help me maintain lifelong wellness. It was one of the first times since having kids that I focused on my own health and wellbeing, and it both challenged me and changed my life in many ways. I wrote about the experience in this article.
• 2020 – Bought and renovated a home after my divorce: This six-month project was a labour of love that I poured my heart and soul into. I worked hard to create a home that my kids and I could all love. When I step into our home, it’s like a warm hug every time. Completing that project is one of the most beautiful, fulfilling things I’ve ever done. In this article series, I talk about the whole process, along with some of the other personal improvements I was making along the way.
• 2021 – Climbed a mountain and conquered my fear of heights: This was much more of a mental challenge than I’d ever taken on before, and I would never have thought it possible until I did it. I’d always been terribly afraid of heights, so I did a lot of work to prepare myself mentally to climb the via ferrata course on Mt. Nimbus in BC. I went deep within myself, knowing that the only way to overcome a fear is to go through it. And I did! The moment I put my hand and foot on the first rungs of the climb, my nerves dissipated—and nothing will ever compare to the thrill of summiting that mountain. I wrote about that life-changing adventure in this four-part article series. (And to inspire anyone who might be tempted by this adventure, here’s a Rick Mercer video that shows what the climb was like.)
• 2022 – Attended an ayahuasca psychedelic retreat: In 2022, I went even deeper into myself. So many of us are conditioned to just be inside our own heads, but where you really grow as a person is when you can get in touch with your heart. Rythmia was my first experience with psychedelics—specifically ayahuasca—and I can confirm that I experienced incredible, metaphysical visions and felt a tremendous sense of healing and joy. I wrote about the entire retreat, including the incredible setting, food, wellness treatments, and people, in this article series. ?
• 2023 – Attended a cannabis psychedelic retreat, and started to date: I enjoyed my time at Rythmia so much that I went on another psychedelic retreat, this time using cannabis in Ontario’s Haliburton Highlands, as I mentioned earlier. But 2023 was also defined by something entirely new: I decided to start dating again.

Re-entering the dating world

This year, I finally decided to set up an online dating profile. This was a big thing for me, as I’m sure it is for anyone who’s been divorced. It had been three years, and I was finally ready. Not just because enough time had passed, but because I’d put in so much effort “doing the work” to better understand myself and to unravel both the conscious and subconscious patterns that were influencing my life.

The most powerful advice I received came from my therapist who said, “Go dating, not to meet someone else, but to meet yourself. What if you could be yourself entirely without hiding parts of you?” And by parts, she meant the Internal Family Systems therapy parts that I learned about at Dimensions in July and describe in this article. I’m embracing this concept, and it’s been truly liberating.?

With that in mind, I dove in, and I have to say the dating landscape has definitely changed in twenty years! I’ve experienced all the ups and downs you’d expect. I’ve met some interesting, kind and accomplished people. And I’ve experienced emotions and feelings I haven’t in many, many years. All in all, the word I’m left with is delightful. It’s been so much more fun than I expected.

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Valuable relationship resources

Not only have I done a lot of work on myself, but I’m also spending a lot of time learning about how I can be the best possible partner, which is not something that gets discussed very much. Compared to when I was dating in my twenties and early thirties, today we have so many incredible resources at our fingertips, exploring topics that weren’t discussed in any depth back then or that hadn’t even been defined until recently.

I’ve come across some incredible podcasts and websites that are extremely valuable for people of any relationship status, even those in long-term or unfulfilled relationships. They are educational, enlightening and quite fascinating. I feel like I’m getting a degree in concepts that are rarely talked about, definitely not taught, and yet are some of the most important and impactful areas of our lives.

Here are some of my favourites, recommended to me by a good friend who’s a few years ahead of me on this journey. Follow these experts on Instagram, listen to the podcasts, search for them on other podcasts, or take a course—you won’t regret it.

• Jillian on Love: Jillian Turecki is a relationship coach, teacher and writer, and her goal is to teach people to “completely transform their love life.” Whether you want to strengthen an existing relationship, heal from a breakup or choose better partners, Jillian is filled with incredible advice and information based on 20 years of coaching experience.
• Where Should We Begin? With Esther Perel: Recognized as one of today’s most insightful voices on modern relationships, Esther’s podcast features real couples in therapy sessions as they share the details of their relationships, from breakups and open relationships to workplace conflicts and fractures in the family. You can learn a lot about your own world by listening to others.
• Gottman Institute: Drs. John and Julie Gottman are highly respected psychologists with extensive experience in an incredibly wide range of areas related to relationship and family counselling. Together they founded the Gottman Institute, which helps families “create and maintain greater love and health in relationships.”
• SelfHealers Soundboard: This podcast, hosted by Dr. Nicole LePera and Jenna Weakland at the Holistic Psychologist, helps people address a wide range of relationship topics including triggers, habits, traumas and inherent wisdom to help us become our best selves.

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What I’m planning for 2024

While I don’t have a firm plan yet, I’ll be working on it over the next week. But I can tell you that at least part of my plan will be to build on the habits and progress I’ve made in the last several years. I’ve found that one habit builds on the next, and it starts to create a domino effect: once I started meditating every day and realizing how great it felt, then I started eating healthier, which felt even better. From there I started working out every day, which led me to pick up my gratitude journal again after a several-months lapse. That put me in the frame of mind to tackle a few other important things in my life that I’d been neglecting. And once I realized how good it felt to accomplish all of that, I was finally ready to start dating.

2023 was a great year. I’m thrilled with the habits I’ve built, the adventures I’ve gone on, large and small, and the new people I’ve met along the way. I can’t wait to see what 2024 will bring—and you can bet that I’ll bring you up to speed just as soon as my new adventures are underway.