Breaking Free of a Rut

I love routines.

Routines love me right back.

I love not having to think about what I'm doing next. There's a comfort and a security in doing the same thing day after day. Get up, get dressed, brush teeth, comb hair, pack bag, head off to the coffee shop, work on stuff, head home, have breakfast. It's a simple routine, but I don't have to waste brain power overthinking things. And that makes it easier. No effort. No dithering. Just follow the routine.

And yet... as the years go by... things get... well... boring. We go to the same restaurants. We order the same things (beef dip, please!). We see the same people. Hike the same routes on the same trails. Every day starts to look like the last, and the days blur together and... well... it's boring.

There are days I can almost run the whole thing on autopilot. Same parking spot. Same order. Same table, if it's free. I know what I'm going to say before I even open my mouth. I know what the barista is going to ask. There’s something efficient about it… and something just a little bit numbing. But the idea of doing something different just feels like too much.

I read something the other month that got me thinking. Why is it that when we are young, time seems to crawl by? It takes forever to go from 5 years old to 10 years old. Yet, when we are in our 50s and beyond, five years can pass in the blink of an eye. Not to mention a whole week, or day, or afternoon. "Where does the time go?" we say, perplexed by it all. Has time sped up? Have we slowed down?

And yet... when we go on a two-night getaway to Vancouver, or Cumberland, or Victoria, we come back amazed at how those two days expanded and felt like a week. We were only gone two nights, and yet it felt longer.

And there is the rub... "it felt like"... time is subjective. When every day looks like the one before it—and the one after—time feels like it’s passing quickly. There’s nothing to differentiate the days. But when we go away, even for a day or two, we have new experiences. We stay somewhere different, eat somewhere new, hike new trails, visit new shops. All of those “new” experiences slow time down and make it feel like it’s passing more slowly.

So while the same old, same old is good for conserving brain energy... it also makes time speed up. And new, novel experiences slow it down.

All this leads to... 2026. I had a milestone birthday a few months ago—one that made me stop and think. Do I want to keep doing the same old, same old? Or do I want to try something different?

I had read a book a few years ago called 50 After 50: Reframing the Next Chapter of Your Life. The author, realizing at the age of 50 that she was on the downward slope of life, committed to doing 50 new things—significant, at least to her. That book stuck with me, and I started to think... what would I put on a list like that?

And so when this last birthday came around... I decided to bite the bullet and do 60 new things in 2026. Whatever that might look like for me. Step out of my comfort zone. Go to different places. Hike different trails. Visit new restaurants.

Because while I love routine... I also find it ties me down.

It stifles me.

But I can change that... one small step at a time.

Breaking up with my To-Do List

"I'm breaking up with you!"

That's my biannual scream at my To-Do List. It happens like clockwork. I start sinking under the weight of incomplete tasks and upcoming To-Do's and inevitably think that there's something wrong with my current To-Do List.

If only I had the "right" To-Do List app or method or system or something.

I stomp off in a huff, troll through different to-do list apps and methodologies before I discover a sparkly new one that looks like the answer to my prayers. Harps play, angels hum, lights dazzle and I fall head over heels for my new To-Do List love. I then storm into my current To-Do List and move everything over to the new app/tool/method and slam an invisible door. "I am so DONE with you!" Hmph.

All goes well for a week or two. My new To-Do List and I are in the honeymoon phase after all. I am the energizer bunny of productivity! Things are going swimmingly and then... inevitably... the shiny newness wears off and... I realize that the new app is not cutting it. In fact, it's worse than my old method!

And so I go crawling back to Remember the Milk (my long-term app) and repopulate my To-Do List and swear that I'll always be true. We're good for a few weeks/months and then... it begins again.

This cycle of disillusionment/cheating/switching/reconciliation takes a lot of time and energy and it would be soooo much easier to not have to go through this every few months.

It's not You, It's Me

The thing is... the problem is not with my To-Do List... it's with me. Much as I would love to get rid of my To-Do List... there are way too many moving parts in my life for me to abandon it completely. I need to be able to keep track of upcoming tasks otherwise bills don't get paid, calls don't get made and things don't get done. My To-Do List is my catch-all for everything that I need to remember... in the short-term and long-term.

While I keep coming back to RTM, I've also tried innumerable productivity systems and apps: Kanban, Trello, Todoist, Toodledo, RTM, OneNote, Asana, Bullet Journal (paper-based), Pomodoro, Getting Things Done, Eat the Frog, 1-3-5, the One Thing, Google Keep, Google Tasks, Evernote, Notion, Wunderlist and many, many more. I am a To-Do List junkie.

On top of that, I seem to need to keep a foot in both the analog and digital worlds. A purely digital system doesn't work so well for me. I need something on paper to jot things down, to take notes, whatever. On top of that, my email inbox sometimes functions as a To-Do List. While I aspire to Inbox Zero, sometimes it's easier to leave an email in my Inbox to remind me... "right... need to handle that"... or... "right, waiting for a response on that".

A Shift in Attitude
A few weeks ago, I could feel the frustration/overwhelm/disillusionment building within me. There was soooo much to get done! Every day, I would review my modified BuJo To-Do List at the end of the day and push forward a bunch of incomplete tasks. I'd review my Remember the Milk app and see so many snowplowed To-Dos... And yes, I have tried the Eisenhower Matrix of urgency/importance... doesn't work for me. At this point, everything is Urgent AND Important! Or at least... it feels that way.

I get to the point where I want someone else to just say: "OK, here's your next to-do... and when you're done with that... I'll give you the next one." I don't want to have to make the decisions... to scan a list with dozens of items and try and figure out what is next. Argh!!

A few weeks ago, I could feel a To-Do List break-up coming and thought... "this is ridiculous - there must be a better way". Right now, I'm staying with Remember the Milk for my overall catch-all of information that I can review on a weekly basis. For my day-to-day and week-ahead planning, however, I'm considering several tweaks.

1. Make each task an actual "task", not a project! I have this annoying tendency to write "redo garden beds" on my To-Do List. It is not an actionable task and so my goal is to break each project down into small, actionable items. One of my big issues is that I overestimate how long something will take. But breaking down a task/project into sub-tasks, the entropy hurdle is less. Or so thinks my rational brain.
   
   This would require a shift in attitude and execution on my part. To recognize that I am a bit of an over-achiever and approach my To-Do list with some compassion for myself. I don't have to climb the mountain... I just have to take the next step.
2. Write the reason for a to-do list item - not just what it is. For a slightly ridiculous example: Normally I would write "windshield wipers" on my to-do list, knowing that the current ones are leaving horrible streaks. But that might sit on my to-do list for weeks for any number or reasons. My new strategy, beyond breaking the task down into sub-tasks (buy windshield wipers, install windshield wipers) is to write it thusly: "install new windshield wipers so we can drive to Victoria safely tomorrow".
   
   I came across the idea of writing the To-Do List as if I were writing it for someone else. It made sense and it adds a certain clarity around priority and urgency. Again, this requires a shift in both attitude and execution. At first glance, I'm thinking this might help me prioritize things better... rather than seeing everything as Urgent AND Important.
3. Write a DONE list in my notebook. I used to have a running To-Do List in Remember the Milk and out of that would write a daily To-Do List into my notebook. The same To-Do List that was only half-done at the end of the day. Shifting away from that... and instead writing a Done List in my notebook, because there are a lot of things that I get done that never even make it on to the To-Do List.
   
   I've always been a person who looks ahead. I don't rest on my laurels, but am always jumping ahead, looking at what is still to come. The DONE list is a way for me to appreciate what I have done in a day and focus on the complete rather than the incomplete.
4. Schedule tasks into my day. Apparently, many millionaires (and probably billionaires) do NOT have a To-Do List... they just have a calendar. Huh. I have tried blocking time before but... actually scheduling things... in a realistic way? Not so much.
   
   I think part of my reluctance to look at a calendar-based system is a left-over twitch effect from when I was care-giving for my Dad. All of my careful time-block schedules went out the window during a very unpredictable time. My life is slightly more predictable now... perhaps it is time to try calendars again.

A Balancing Act
Part of my fixation with time and to-do lists right now is this... I have noticed that I will go for a walk with my partner when she is home. But when she is not home, I won't go for a walk. I know that a walk is good for me. I know this... and yet... when I am home alone, there is always something "more important" to do. This is perplexing to me...

I've tried adding "walk" to my to-do list. I can't tell you how often it gets postponed or ignored. Apparently I have no trouble prioritizing others... just myself.

Right now, I am trying to rejig by life by scheduling tasks into my calendar. And the first things to go on the calendar are self-care activities - like walks, reading and eating healthy meals (which always takes longer so my temptation is to take short-cuts and skip the healthy bits). Once my self-care items are blocked into my day, I have a better sense of how much time I actually have for other tasks. And it then becomes easier to prioritize what absolutely needs to get done today and in the coming days.

I've known about the rocks and the mason jar for a while now and have tried various ways of implementing it. Important things first... then smaller things. When I look at the picture here though... I can see how the left mason jar would result in my current sense of overwhelm... "OMG!!! I don't have enough time for these things!!" Tis very true... So this time, I'm putting my intentionality behind creating the right mason jar...

I'm planning a week ahead and I really have to watch myself or this little over-achiever will try and schedule too much into a day. I am trying to build in some white/flex/blank/down/transition time. If I find that I have some flex time in the day because things went quicker than anticipated, I can regroup, see where I'm at and maybe tackle a few of the smaller tasks that always need to be done - cleaning the toilet, doing dishes, flipping a load of laundry into the dryer, etc. It always amazes me what I can get done in 15 minutes, if I just put my head down and do it.

The idea is that my self-care activities are inviolable. If my schedule said "Walk with friend", I would make that appointment. I would never blow off my friend and not show up for the walk, barring a legitimate emergency. But if my schedule says "Walk [for me]", I somehow see that as optional and an appointment that I can keep... or not.

Sooo... my Small Step this week is to keep my appointments with myself. Treat myself with the same courtesty that I treat others. Wish me luck.