I am messy. 

Contrary to what folks may think, I do not have a 100% digital setup. Seems a weird thing to say on this blog, but it is what it is. Deal with it.

Nor am I a crazy minimalist pen-and-paper bullet-journalling acolyte. I’m disorganized and my penmanship sucks. I had to type my calculus assignments in college.

My to-do list is spread across two digital tools, a couple notebooks, and way too many tattered sticky notes. I’m a firm believer in having reminders and activity prompts in context. That is, be reminded in the places where I’m actually doing the work.

I use a notebook to manage my woodworking and gardening projects. It’s a mixture of to-dos, dreams, plans and notes. It is appropriate for that kind of work.

I use digital tools for things I use the computer for. One tool is for the work context and another is reserved for my creative pursuits.

My phone is for groceries and a way to capture ideas and tasks when I’m out and about. I don’t work my to-do list from my phone. Or try not to anyway. Okay, sometimes I do. I’m a delightful contradiction.

The upshot here is the idea of having one master to-do list is, in my opinion, kinda dumb. For me anyway.

Yes, write it all down and get it out of your head. Just know that running your life out of a task list is false productivity. 

What do I mean?

These tools will happily capture all your items. Especially the digital ones. Literally every brain fart that runs between your ears can and will hit a digital task list.

It can get so unwieldy that it’s a little more than an artifact to enumerate all your sins of NOT Getting Things Done. Or worse, you spend more time fiddling with your so-called system, that you’re serving your lists instead.

You worry about how many items you can cross off, as if it was some sort of competition.

This kind of scorekeeping of your task list is focussing on the wrong things. 

Put simply: 

Do the work that needs doing.
Do the work that’s important. 

A digital calendar, on the other hand, is where the meat and potatoes hit the plate. Don’t forget the gravy. And the Vegetables of Atonement. Need those too. Got it?

Time is a finite resource. So are energy and attention, but that’s a different conversation that we’ve had before. You only have 168 hours per week and half of those are spent sleeping, eating, chores, and scrolling on your phone in the bathroom. Another 40 hours a week is spent either working or edumacating. That leaves about 4 hours a day to do some cool stuff like reading, working out, learning something new, binging media, or punishing your liver. Hey, I don’t judge. Much.

The point is that the calendar burns up pretty quick if you’re not reasonably intentional with where you place your attention. Which is why a to-do list, by itself, doesn’t work. To do lists don’t give two firetrucks about your time.

Use the calendar to actively decide when you choose to do what. Let it be driven by what’s important, and not what’s urgent.

But here’s the rub: a calendar is really only forward looking. It is a plan for how you intend to get things done. But life happens and it doesn’t always, or even often, go that way. Don’t believe me? How often do you go back and look at the past in Outlook? Be honest.

Plans are worthless,
but planning is everything.

A bunch of people, including Eisenhower and Churchill

That’s where journalling helps. To document what ACTUALLY happened. And show some gratitude while you’re at it. It’s not just woo-woo stuff. Study after study points to gratitude journalling as a key vector in improving mental wellness and happiness. Journalling and reflecting on what really happened is also proven to be the best way to bounce back from mistakes and improve your process along the way. It’s all about harvesting the learnings.

I could list some sources, but you can Google that stuff. Or Bing it. Or have ChatGPT make up some crap.

I’m using Apple Journal for this, because I’m a nerd, but I also sporadically do some reflection in my notebook. The act of reflecting is more important that the artifact. Process over product. Although looking back is helpful. I’m waiting for Apple to implement an “on this day” feature in Journal to make it a little more automagical. Yes, I know DayOne has this, but I’m almost as cheap as I am messy. 

I’m messy and cheap. This makes me giggle a bit. 

Now for some practical advice that you’re free to ignore as you see fit. I’m a big follower of JD Meier’s work. Go ahead and buy his book or take his free 30 day course. 

Here’s some choice habit nuggets that I do that you can do too:

• Schedule your lunch in your calendar and actually take a break. Take care of you. No one else will.
• Schedule 30 minute startup and shutdown routines so you can (1) plan your day and (2) wrap up.
• Schedule a half-hour every day (or twice a day) to deal with your email. Then disable notifications and shutdown Outlook. Seriously. It’ll wait. All of it. Remember, your inbox is where other people’s priorities show up, not yours. Act accordingly.
• Schedule time in your calendar to do focused work. I use Viva Insights for this because it automates some minutia, but it isn’t required. Select which of your to-do items are IMPORTANT to your core work and then get to doing them.

Next level:

• During your Monday startup meeting with yourself, ask yourself, “Self, if today was Friday, what 3 wins would I like to celebrate?” Write them down. On a weekly paper planner. On a sticky note on your monitor. On the whiteboard. Doesn’t matter. So long as it’s within eyesight, you’ll have your compass for the week– low friction like.
• Every day during the startup routine, or the shutdown routine (you choose), jot down the 3 things that would make the coming workday great. Pick them off your to-do list. Sticky that bad-boy to the monitor too. Or, if you prefer, put it in the “all day” part of your Outlook calendar. Works pretty good there as a theme for the day too. Better than string on your finger.
• On the Friday startup, grab all those notes, and reflect on how the week went while there’s still some time to right the ship if you hit the shallows along the way. What worked and what didn’t? What would make next week great? Journal those gems too, but keep it brief so it’ll become a habit you’ll do every week.

I’ve been doing this for more than a decade. It’s low-friction and keeps me on track. Do I have bad weeks? Yup. Sometimes I’m off the rails and don’t heed my own advice. Forgive yourself and eschew perfection. Harvest the learnings. Then try again tomorrow. S’fine. 

Every week and every day is a new opportunity to do something epic. 

Be messy. 

Be awesome.