The Sunday Planning Session
My #1 productivity enhancer
👋Hello, my friend. I’ve got a tactical one for you today — an overview of my weekly scheduling practice, very unimaginably called “The Sunday Planning Session” — which is the absolute #1 productivity enhancer that I’ve found to-date. I’m going to walk you through exactly what I do every Sunday and why I think it’s so effective. Stick around to the end for a few content recommendations, including a controversial parenting podcast. 👀
Let’s do it!
📅Losing the battle with my calendar
A few years back, I found myself running into a problem. I was so busy — especially at work — that I could not fit all that I needed to do into a given week.
It got to the point where I was literally saying “Since I have to do all of these meetings and respond to all of these emails all day long, I can’t do my ACTUAL WORK until the weekend.” So that’s what I ended up doing. Spending my weekends working. Ugh.
Not only was that not fun, but it wasn’t fair to my family. And since I was spending literally all of my time just trying to keep my head above water at work, I most certainly was not focusing on things like: my relationships, my fitness, or having any fun.
I realized that this problem wasn’t anyone’s fault but my own. An endless number of people — many of them in my own life — had more on their plates than I did; they had bigger jobs, more kids, more roles in the community, but somehow they weren’t drowning.
I realized I had a scheduling problem. And a prioritization problem.
💻The Sunday Planning Session
Enter The Sunday Planning Session, aka the productivity system that finally got me organized, less stressed, and able to get done what I needed to get done.
Well, maybe “productivity system” is a little over-the-top. Prepare to be underwhelmed because what I’m about to explain is much simpler than that.
So here’s what it is: Every Sunday, I sit down for about 15 minutes in front of my computer, fire up my calendar and start scheduling the week ahead (all 7 days of it).
What gets scheduled? In short, everything that I want to make sure actually gets done. In other words, my priorities.
And how do I know my priorities? Well, if you read my 2025 planning newsletter, you’ll know that I slotted my priorities into 4 main categories this year with some specific goals under each one. Here’s the visual if you need a reminder of what I’m trying to accomplish this year. (I have separate goals for my day job which I’ve intentionally left off this list).
So here’s what I do. You see those health goals above? Those are not going to happen on their own. They only have a shot of happening if they are scheduled. I don’t want to have to “decide” every day if I’m working out or not, or which workout I’m going to do. Those decisions for the week happen on Sunday. Then I just execute.
So for instance, I think to achieve my VO2 Max and bodyfat % goals, I need to workout ~6 days/week including ~3 weightlifting sessions + at a minimum of 150 minutes of cardio (in the form of lots of walking or Z2 rides/runs + 1 HIIT session).
So workouts get scheduled first. This aligns with my broader view of “putting your own oxygen mask on first” or making sure the foundation of everything else (health) is prioritized.
Now the workouts, or at least the walking part, overlap with relationships for me as I have a standing Monday walk with my wife that we try hard not to cancel. So that’s in both of our calendars as a recurring meeting.
Then I want to make sure I’ve got 15 minutes scheduled to meditate. This is an easy one to skip if it’s not scheduled. I mentioned I’m using this app called The Way this year. I’m enjoying it so far so I’m keeping this as a priority.
Then I want to make sure I’ve got time to write this newsletter. It takes a few hours typically and if I don’t schedule it in advance, it either a) doesn’t get done, or b) is a source of stress in the background for the week. So it gets scheduled.
Finally, I want to make sure I’ve got some “fun” scheduled into my calendar. Sounds weird because you don’t really need to “schedule” this earlier in life but at a certain point you realize that if it’s not scheduled, that time will inevitably be eaten up by kids, work or any number of other random time sucks that pop up at the last minute. For me, fun is hitting golf balls or playing pickleball. So those get scheduled.
If I take out all of the work tasks/meetings, kids sports, doctors appointments, etc., below is what the calendar looks like based on everything I’ve just described above.
Of course, every week is different. So if I can’t walk (usually 45 mins, incline on a treadmill) during lunch on Tuesday and I know that in advance, I’ll try to schedule that at another time. Similarly, if I know my son has baseball games all day Saturday, I’ll look for other times where I can possibly schedule my writing or my “fun.”
Now, let’s not be naive. We all know that “life happens.” So, despite best laid plans, inevitably one of my kids will get sick. Or something will blow up at work. Or any other number of things can pop up to displace a workout or a writing session.
And that happens. I’d say that for me, on average, at least one day per week does not get executed as planned. Even so, if 6 out of 7 days I actually get done what I scheduled, that’s 85% or “a solid B” as my thirteen-year-old would point out. That’s not too bad.
And it’s WAY better than the alternative: Having no plan or only a very vaguely defined set of priorities like “I want to workout a decent bit this week” because I can assure you, from personal experience, that absolutely does not work.
So that’s pretty much it. I told you that you might be a little bit underwhelmed. It really is not rocket science. It just involves two things: 1. Setting priorities, and 2. Scheduling them.
Finally, for those of you with day jobs who get pummeled with calendar invites from colleagues non-stop, I’ll leave you with this one little tip:
Schedule time for yourself in your own calendar.
This is kind of the whole philosophy of The Sunday Planning Session anyhow, but somehow I went like 20 years without doing this and it now seems insane to me. It’s why I found myself having to do my “actual work” on weekends.
In my day job, I need to do a decent bit of writing or editing or thinking… thinking about hard problems, or how to come up with a new approach to something, or how to get a new initiative “socialized”… anyhow, that stuff takes time if you want to do it right.
So here’s what I do. I schedule time for that in my own calendar and I mark it as tentative. That signals to my colleagues that: The time is not blocked (so if a meeting absolutely has to occur then, it can) but that my preference is for it to be another time.
Whether or not the signal is interpreted as I’m intending it to be probably doesn’t matter. What does matter is that 9 times out of 10, no one will try to schedule a meeting at those times with me. So I get to do my “actual work” and end up a much happier person.
If you’re not doing that, try it now, and thank me later. 😎
Okay, that was kind of a long way to explain that I recommend scheduling out your week every Sunday for 15 minutes but here we are.
I hope there’s at least a little bit of value in there for you somewhere.
Like I said above, check out the content recommendations below - (oh by the way, I actually think ahead on Sundays about that, too… what podcasts do I want to listen to this week? And I queue those up so I’m as intentional as I can be there, too… but now maybe I’m just over-optimizing).
Enjoy your week.
Greg
Content Diet
🎙️Podcast: Tim Ferriss, Naval Ravikant & Aaron Stupple — How to Raise a Sovereign Child, A Freedom-Maximizing Approach to Parenting
This is the “controversial” parenting podcast I referenced upfront. Doctor, teacher and father of five, Aaron Stupple has just published a book, The Sovereign Child, which touts a parenting philosophy known as Taking Children Seriously (TCS). In this episode, which is in some ways a debate, Stupple and Ravikant dive into this method of parenting, which essentially involves raising kids without rules. Think: no enforced bed times, no forced teeth-brushing, no limits on screen-time, etc. It’s obviously quite the unconventional approach. I’m still getting my head around what parts I completely disagree with and where I see value. On the one hand, I definitely can’t see myself giving unfettered Diet Coke and Oreos access to my 4-year-old; on the other hand, I do see value both in terms of the parent-child relationship and the child’s ultimate creativity and agency in life, of having fewer absolute, enforced rules in the household. Take a listen and let me know where you land.
I shared this tweet with the author, who gave it a “Ha!”
🎙️Podcast: Dr. Andrew Huberman & Dr. Jeffrey Goldberg: How to Improve Your Eye Health & Offset Vision Loss
🚨Old guy podcast recommendation alert: Okay, this is a super random one but I’ve been struggling with “dry eye” recently — probably something to do with age, dry air, and too many screens (I *think*), so I went looking to educate myself about all things eye health. Anyhow, if that’s a topic of interest, this conversation is quite comprehensive, including overviews of the biggest issues people run into with their eyes (especially with age) and strategies for offsetting those. And if you have any cures for dry eyes that you swear by, I’m all ears (maybe quite literally if this eye problem persists).
Okay, we’re getting into pun territory. Time to wrap it up.
Have a great week.
Greg
