Systems and Routines for Consistent Progress

Life is chaotic. Things change. Kids get sick. Parents get old. Friends need help. Companies change priorities without warning.

So how do you maintain productivity and effectiveness in the face of all that chaos?

I had a friend ask me this question recently, asserting that I'm good at it. My first reaction was to deny that I'm good at it. And in some ways that's true - I'm not natively good at it.

My brain is a sieve, I am easily distracted, often have strong emotional reactions that disrupt my days, and a tendency to overcommit and get too busy. But upon reflection I realized that over the years I've put together a pretty big toolchest of systems and routines to keep me consistently moving forward.

This post is an attempt to outline those systems and routines, in case they might be useful for anyone else.

Set aside time for retrospective and planning

This forms the foundation on which most of the rest of my routines sit. I specifically set aside time both to look back at what I've done and to look forward at what I need to do. And I try to write it all down and think of how/when I'm going to make it happen, and put it into systems that will help make me follow through.

I set aside this time a weekly, monthly, and annual basis.

Every Monday, I have an hour long block on my calendar for weekly planning. If I get to it before that block, fine (sometimes I'm already thinking about my week on Sunday and if the kids are busy and I don't have a conflict I can do some planning), but if it doesn't happen before that block it happens then.

Once a month, that block is half an hour longer and includes monthly planning.

Once a year (usually either around my birthday in November or at the end of the year) I do a yearly version. This usually is long and spread out over several days

Typically these planning sessions involve a bit of a retrospective (Looking back at the last [week/month/year], what happened that was good, what happened that was bad, and what do I want to learn/take away from this. And then they involve looking forward to the next [week/month/year], identifying what am I trying to accomplish.

The fidelity of the forward looking plan varies based on the time frame, but usually it's around 2-3 high level themes or goals I'm trying to accomplish, and a rough outline of when I think I might do those things.

Todo lists

I keep lists of todo items mostly in my universal notes application. Which I have. It used to be a paper notebook (well, many notebooks over time), but now I use a web and mobile application called RoamResearch for this. Notes aren't honestly the best tool for a todo list, but they work all right and I already have a habit of looking at them regularly.

When I do my weekly plan, I'm often filling out todos for each day of the week (though I hold this pretty lightly - todos can move around, or sometimes I decide I'm not doing something after all).

Also when something comes up that I want to handle, I add it to a TODO list, either for today or for a future day if I know when it is.


I use my calendar(s) HEAVILY, to block time for myself, to give myself reminders, and of course for scheduling meetings & the like.

I use calendly to let people schedule with me. It has some very nice features around not only letting me set available time, but also looking across my multiple (personal, work, shared) calendars to determine availability even if it is only adding to a single calendar.

Phone reminders

Similar to calendaring, if I need to remember something during the day, sometimes I reach for my phone and set an alarm. Especially if I'm not going to be at my computer much that day, because I find the alarm gets me more reliably than the phone calendar notification.

Habit chains

I try to build habits on top of each other. I don't have massive numbers of habits, but when possible I try to link them together to make sure they happen. For example, during allergy season in order to remember to take my allergy pill regularly, I linked that to my morning habit of shower+toothbrush. I always do dishwasher unloading & related work when I make breakfast in the morning.


Calendaring, phone reminders, and habit chains are forms of "prompting", which is basically, "When X happens, do Y". There isn't always a good habit or specific time/day calendar thing to hook into, so instead sometimes I'll just think ahead about what will be a good prompt for something that needs to happen. An example here is any time I have a day without a lot of meetings, I check to see if I need to run laundry. Why? Because if I don't have a lot of meetings it will be reasonable for me to be taking random times to move laundry around, fold things, etc.

Recurring commitments

The last trick I can think of is just committing to other people about something happening, and particularly happening on a regular basis. My newsletter goes out on Tuesdays (a previous one I ran went Fridays). I commit to that, and then am motivated to make it happen. Sometimes it isn't ready until the last minute. But I've committed to when it's going out, so it goes out that day. The deadline/commitment makes a difference.

Similarly I wanted to be doing research on LLMs, so I set up a weekly study group with some other interested people. We review 1 paper together each week on Wednesdays at noon. If I didn't have that, I'd have a lot more trouble getting myself continually making progress in that area.

Creating your own systems

I've cobbled these various tools together over the course of years, but my pace of creating and adopting systems for myself (and coincidentally also my overall happiness and sense of effectiveness) shifted dramatically around 2017-2018. This happened due to the coincidence of three factors:

  1. I was running my own business, so nobody was setting my schedules and expectations for me.
  2. I had two kids and my parents were having health issues, so the level of chaos in my life had ramped way up
  3. I worked with a coach for the first time. She was incredible at prompting me to think about and think through what was holding me back and how I could set up systems to move forward.

Perhaps unsurprisingly, that experience was also part of what set me on the path to becoming a coach myself.

I dunno what your factors might be, or what chaos your life is throwing at you, but if this resonates with you and you'd be interested in working with a coach to help you set up your own systems, that is something I do now. You can learn more about my services here or sign up directly for a free exploratory session here.