Last week, I posted my annual calendar on Instagram stories. A few friends were interested in it, so here it goes.
One of the most important aspects of my business costs about $12 on Amazon. It’s a cheap plastic 12-month calendar that I stick on a wall.
Ever notice how the calendars on your devices keep your focus small? You can’t put a 12-month calendar on a screen, at least not one using. On a phone, you can basically only look at one month at a time.
(I swear, all these tech companies want us to think small and short-sighted.)
This cheap, physical 12-month calendar helps me see the big picture. It shows me where the big rocks are (more on this in a bit), where my white space is, where there are seasons for opportunities, and where I’m overcommitted.
What My Life Was Like Before This $12 Calendar
Let’s go back to 2021 as an example. For context, my first book, You Are the Brand, had just come out a few months earlier, and I was in insanity mode:
Look at that: nearly every single day jammed: coaching calls, workshops, travel, recording sessions.
Granted, this schedule was appropriate for the time. I was in expansion mode: my book hit two bestseller lists and I launched a coaching program around that book to the tune of $150,000. This was what it took to make that happen.
I had insane young guy energy back then, but even so – there’s no way that pace was sustainable. When you’re in seasons like this, it’s hard to see the end of the tunnel, especially if you’re only looking at life one month at a time.
Eventually, I went back to my typical planning which starts with:
Trimesters, Not Quarters
Quarters are too frequent for my business, so I plan in trimesters:
- January–April
- May–August
- September–December
Life is going to throw you curveballs. If you cram every moment of your calendar, curveballs will be much more disruptive.
When my Dad passed last year in May, it threw off my plans to launch my AI Summit in June. Because I’d planned in trimesters instead of quarters, I punted to late August without blowing up my whole year.
Life happens. You need margin.
Schedule Big Rocks First, Once a Trimester
I love this physics demonstration. If you put the pebbles and sand in first, the rocks won’t fit. If you put the big rocks in first, everything else finds its place. It’s all the same amount of material, it’s the order that counts.
I define Big Rocks as things in your business that have natural deadlines, urgency, or scarcity:
- Webinars
- Summits
- Launches
- Live events
- Book releases
A secondary benefit to Big Rocks: they are publicity stunts exactly because they have deadlines. Webinars end. Launches close. Books get released.
Because of this, Big Rocks allow you to self-generate momentum. If ten years of running my own business has taught me anything about success, it’s that you need to be able to self-generate your own momentum.
One caveat: when you’re launching something for the first time, say a podcast or a new YouTube channel – I consider that a Big Rock. But after you launch it, it becomes a smaller pebble because you’ll be publishing consistently and there’s no scarcity to it.
For the time being, my big rocks for each trimester in 2026 are webinars. I have no book releases, live events, or anything else planned so I’ll just host webinars in February, May, and September.
I prefer hosting webinars on Thursdays because I usually launch programs the following Tuesday or Wednesday. This gives my prospects enough time to consider the offer and allows them to watch a webinar replay over the weekend.
Then they still have the following Monday to decide. My programs typically start Tuesday or Wednesday, so I have a natural deadline and do not feel like a sleazy internet marketer who pounds the cart close date harder than a $2 steak.
I’ve done Tuesdays or Wednesdays before if I want longer cart open periods. If I host a webinar on Tuesday, I can close the cart that Friday.
If I do Wednesday, I can close the cart Sunday. I’ve been successful at both, but personally I don’t like answering cart close emails over a weekend, so I stick with Thursdays for now.
***
Another thing: in ten years of my work I’ve never not made money on a webinar. That is not to brag, it’s just an objective truth.
Like you, I have an inner critic who always runs his mouth about how I’m going to fail in life forever. I call him “Tar” because he likes to slog me down. Sometimes he sends his Imps, the little Fraggle Rock sh*tbirds who never stop yapping. I’d very much like to kill them all with fire and watch them die a slow death.
When these idiots run their mouths, I look at my calendar and say, “Burn in hell, fools. See all these webinars I have scheduled? Looks like I’ll continue to be able to eat and live indoors in 2026. GTFO.”
You can’t be nice to the Tar and Imps in your life.
Give Each Big Rock a Two-Week Runway and Off-Ramp
A webinar, launch, or book release doesn’t just happen the day you go live. If you host a webinar, you need at least two weeks prior to the date to set up the marketing and prepare the presentation.
(You’re not going to prep the webinar the day of the presentation and expect to get great results, are you?)
Then, you need to plan for the launch, and then the actual delivery of your offer. In total, I view a webinar period to be nearly six to eight weeks. This is why I plan in trimesters instead of quarters.
Let’s say I do a January 15th webinar that leads into a four-week program:
- Jan. 1-14 = promotion
- Jan. 15 = webinar
- Jan. 20 = cart close
- Jan. 20 – Feb. 28 = deliver the program
- Rest and recover
If I’m done in February and not doing my next webinar until May, that leaves me two months of time to do other things: attending conferences, speaking, VIP days, writing, or my own events.
This year, I’m speaking at SXSW in March. Maybe I’ll host an in-person mastermind or a 1:1 VIP Day in Austin that week, who knows. But if I do, I won’t be overwhelmed because my schedule is paced out.
The calendar shows you the openings, but only if you see the whole year.
Calendar Your Small Pebbles: Standing Commitments
After big rocks come the Small Pebbles: your recurring commitments.
One reason I don’t do webinars on Tuesdays is because I meet with my mastermind groups then, every two weeks.
On Wednesdays, I need to be available every two weeks for calls for a side business, and on Thursdays I have teaching calls for my membership, You Are the Brand Academy.
For several years, I’ve scheduled all these calls to be on the same week when possible. That way I have a “teaching week” and a “BLOCK” week. I also almost never take calls of any kind on Mondays or Fridays – I use those days for content creation.
I literally put BLOCK on my calendar on non-teaching weeks, and Mondays and Fridays aren’t available on my Calendly scheduler.
This may look like a lot of free time, but I always have other things that come up: events, communities I want to join (I still need to grow, after all), or time to work on my business instead of in it.
I can also take that time to read, learn a new skill (last year was basic editing for YouTube and some AI).
Block Your Content Creation Days
After wandering around my content creation efforts last year, I locked in at the gentle behest of Ryan Levesque to write a weekly newsletter.
I figure if I want my newsletter to be really good, then I need actual time to research, think, and write. I write on Fridays and Mondays, and I publish Tuesdays.
Those days also include recording the newsletter for YouTube, syndicate the audio to my podcast, and format the newsletter for email. This takes more work than you think, and it’s one of the things I’m hiring for in 2026.
AI slop is everywhere. I just don’t think “average” is going to cut it, so I’m giving more of my own effort and intention to putting my best stuff out there. (I hope you can feel the home-cooking in my newsletters these past three months.)
Schedule Your Time Off
I might be the worst boss I’ve ever had. Boss Kim always expects me to work long nights and never gives me a vacation. To overrule him, I schedule my time off ahead of time. This year:
- Spring Break: April (why should only college kids get this?)
- Birthday Month: All of June (cheat calendar to get July 4th off, too)
- Fall Break: Labor Day week (cheat again, get the long weekend)
- Winter Break: The liminal period between Christmas and the New Year
If you don’t schedule time off, it usually won’t happen.
My Five Principles for 2026
Everything in my calendar flows from these five principles:
- Fewer commitments
- Stronger yeses
- Slower starts
- Deeper fulfillment
- Cleaner endings
I didn’t get here overnight. None of this would be possible without the crazy seasons from years past, when I paid the price to lay strong foundations. Don’t expect this kind of flow when you’re in Start Up or Build Up seasons.
For those who have laid strong foundations, let me unpack these principles:
Fewer commitments: I don’t want 2021 Mike in 2026. I’m done with that pace.
Stronger yeses: I’m willing to give bigger yeses to clients: 1:1 VIP days, smaller intensives, retreats. But these also require stronger yeses from clients: travel, investment, and willingness to work deeply. If we both commit to bigger yeses, better things will happen.
Slower starts: My morning routine (save the cold showers) go at a turtle’s pace. But I’ve also been building waiting lists for my offers so I’m not always guns blazing when heading into a launch. I’m giving things room to breathe.
Deeper fulfillment: I love VIP days, intensives, and retreats. I think I’m good at them, too – so again, Stronger Yeses. I also love writing these newsletters, and while they aren’t always easy, I am so fulfilled when I wake up on Tuesday knowing they are out into the world. So, more of that kind of feeling.
Cleaner endings: Every commitment I have right now ends in June. I’ve always prided myself on offering clean off ramps. I do not expect anyone to work with me until kingdom come, and neither do I want anyone to stay out of obligation. It’s okay to be excited about something without it having to last forever.
***
About two years ago, I read Learning to Love Midlife by Chip Conley. I met Chip at a retreat in Santa Fe years earlier where he shared thoughts on ego, soul, and legacy. I was excited when this book came out. One of my favorite concepts:
Take one gap year for every decade you live.
I’m thinking of doing that starting in June. Predictably, Tar and the Imps tell me I’m insane. But I at least need to have the notion on the table, and I’m running out of years before I’m no longer in my 40s.
Maybe I’ll keep going past June, revitalized with new passion for taking what I’ve built to it’s next evolution.
Maybe I’ll sunset everything and move to Tibet to become a monk.
Maybe I’ll vagabond life with some cameras, interview all my global friends, and start a YouTube channel where I just “Anthony Bourdain” it with them.
I do not know. But it’s nice to use my imagination again. That space only exists because I can see the whole year on my wall.
An annual calendar can help you plan a year, but it can also help you plan to live days that are worth repeating.
So, a quick recap:
- Get a 12-month calendar for your wall.
- Divide into trimesters.
- Plan one Big Rock per trimester.
- Calendar your Small Pebbles.
- Schedule time off.
This isn’t prescriptive, it’s just how I do it. I hope some of these concepts help you think differently and you can apply something to your own life.
I mentioned in the last issue that I try to make each of these newsletters worth $500 of insight. I know that if you plan your year with intention, however you do it, you’ll reap that many, many times over.