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On Planners and Habit Tracking

As I stood on a subway platform one late February evening, I suddenly understood why people wanted to jump. I was in Jackson Heights, on my way home from work. That job -- the reason I had moved to New York in the first place -- had slowly absorbed my entire identity. Now it was gone. With my entire self worth suddenly wiped out, I felt devastated. No. Worse than that, I felt numb.

A year earlier, my dream job had called everyone back to the office. As one hundred people crammed into two conference rooms, the owners excitedly announced we'd been sold. That was the day I became angry.

I would become so angry, I would physically feel a vein tight in my chest. Little things would set me off, and I would go on long walks after work to get out the anxiety because I physically had to move. I began to snap at people. I started taking it out on my girlfriend. It would be months before I realized I needed a gym membership, and three years before I would get a therapist. Only then would I realize just how deep this went.

I wasn't really here because of my job. I wasn't here because of my girlfriend. I was here because of myself. I was here because of neglect.

It was so easy to pour myself into a job. After all, why wouldn't I wrap my identity in my daily labors? I worked hard at them, and I took pride in delivering for the bosses I respected. I never equated this behavior with the trope "betting it all on red," which is why learning that the "only constant in New York is change," was such a hard lesson for me.

The Crisis

As we go through life, we all know about the crisis. The midlife crisis, the quarter life crisis. At some point, we’ve been on autopilot for a little too long, only to wake up one day and realize we drove here, but we don’t remember how. After waking up in the middle of a figurative winter, I began to mourn my own life. Then one day, I knew I wanted to be happy again, and there was no one else here but me.

I started looking inward.

I had been using a planner for a few years, and in the margin, I wrote myself a note: “You have friends” Under this, I listed several names. I needed a reminder: I wanted to see these people, and just… hadn’t.

A month later, I would start working with a shrink for the first time. We started working on building habits by being prepared. I told him about my list of friends, and working together, we started to plan ahead. We made lists to remind me of my friends, things to do, etc. We also set an intention, and a quota for each week -- some sort of weekly target to remind myself what to do.

Flash forward another eighteen months, and I would be in a much brighter place. Life was not solved, but I was making progress. I had good habits in place, I had achieved goals like running marathons and consistent friendships. I felt good again. I couldn’t have gotten here without my planner. It took me from a reactive person, waiting for the world to fall into my lap, to someone who made a plan, went out and did it.

Step One: Start with a Plan

My journal/planner has evolved a lot over the years, but it’s always come down to two pages. On the left, the play-by-play of daily events. On the right, the blueprint for the week.

Plan A: The Day-to-Day (Left Page)

My journaling began as planning. My default was to “go-with-the-flow,” which drove my forward-planning ex crazy. As my friends got jobs, serious relationships, and kids, calling up and asking “Wanna hang out in 2 hours?” just stops working. So I started here.

On this page, I focus on a few things: Log notable achievements (Think of this as the “win” column) Biked 40 miles to Inwood Meditated today Baked sourdough for the first time Track daily things here: Number of cups of water / coffee / tea (make them icons!) What was my commute like today? Meal or Mood tracking, etc Log plans and events: (traditional planner) Article Draft Due Today See Mike at 6pm Moth Story Slam at Housing Works @7p.

Plan B: The Week Ahead (Right Page)

What started as a single to-do list for the week, became my weekly dashboard. This evolved as I realized “pick up some eggs” and “run 3 times this week” were not the same thing. I kept the to-do list, but added a weekly habit tracker, broader goals (I call these “Epics”), and various reference lists. I also started a weekly quote.

A few things to consider here:

When possible, set a goal or target quota. Keep repeating things separate from one-time things. (Keeping lists small makes them easier to complete. Crossing things off is where a list gets its power.) Add one thing here that is purely for fun. I like weekly quotes, and I’ve seen others do weekly definitions (word of the week). Reference Lists help you keep track of things you already know. (more on that below)

Reference Lists

Remember that first note I made myself? “You have friends.” This is the origin story of my reference lists. If I’m writing it here, I already know it. But maybe I don’t know it when the mood strikes.

Three I repeat are:

Friends I want to See Recipes I want to Try Activities I like / Bucket List

When I awoke in the middle of my emotional winter, forming these were a necessity. Sometimes (especially in depression), your windows of motivation are very small. You’re going through a hurricane of demoralization, when suddenly the clouds open up, and you have a brief moment of clarity. It’s the eye of the storm, so don’t waste it trying to figure out your options. Know your options ahead of time, and use all of your new-found energy to act!

Momentum = Change / Time

Over the years, I’ve gone through a lot of change. I ended a 6 year relationship, left that job I loved, and realized the mortality of my parents, ultimately losing my mother unexpectedly a few months ago.

One of the important things that helped me get moving in depression was to build momentum. With help, I identified the things I valued in my life (friends, creativity and exercise), and then I used this format to help achieve them:

“I should see friends at least 3 times a week.” “I need to run 4 times a week.” “I want to create or learn something at least twice this week.” “I want to try one new thing this week.”

These become the habits at the top of my list. I draw outlines of little boxes at the beginning of the week, and fill them in as I accomplish them.

This has helped me more than any other part of my planner, and pulled me out of multiple downward spirals in the past 15 years. Forget how I track it, but making these goals has helped me slowly build momentum with simple, measurable steps. Particularly “I should see friends 3 times a week.” I know what I have to do, I know how many I have left to do vs how much time I have left in the week. Often, I even try to get one out of the way early in the week, to take the pressure off. Suddenly, I have most of the week ahead of me, and I’m 33% there already!

“Show up, show up, show up, and after a while the muse shows up, too.” - Isabel Allende

I keep the goals achievable, even if I can do more. This was critical in the beginning, when I was so low on mental energy, and even still, on a rainy day. Make it as easy as possible to accomplish bite-sized things. Don’t be afraid to have a bad day, be afraid to skip a day. Doing any one repetition of a task poorly or slowly won’t spoil the goal, because the journey is not about a single step, but the culmination of steps. If you’ve never run a marathon, I can tell you, every step is not inspiring or pretty. But crossing the finish line (and giving yourself 45 minutes to regain consciousness) is.

So much of a goal is just showing up. So anything you can do to feel good just showing up is worth doing, including being ok setting the bar low. Remember, you can always do more than your goal. And, if you’re struggling with motivation, google “writing advice quotes from famous writers”. That crap applies to everything you do.

The Third Heat

Recently, a guest on The Brian Lehrer Show was discussing how to introduce kids to nature, and suggested we give them binoculars. “Tools,” she proclaimed, “make kids feel competent. When you hand them a tool, there’s an extra layer of excitement.” I have found this to be true, and have invested in a good notebook, and a fancy-ass pen.

While I advise you to keep the effort to a minimum, taking a little time to add flourish can keep you motivated to use your journal. For instance, adding little icons instead of words can declutter the page, and make recurring events easier to spot. This makes it easier to find things to brag about, which motivates me to keep going, even on the darker days.

Lastly, adding a weekly quote to my page was the best thing I ever did. It gives me a chance to look for something new or inspiring. It’s the Simpson’s Couch or The Special’s Board in Bob’s Burgers. It’s something fun to look out for, and it often has nothing to do with achieving your goals. The week Kobe died, I found one of his quotes. Other times I’d focus on my struggle-of-the-week. However, the first one I ever picked still gives me strength. It came from a message-of-the-day board in the London Underground:

“It’s OK if you fall down and lose your spark. Just make sure that when you get back up, you rise as the whole damn fire.”

About this Photo

Taken on May 5, 2020

ben helmer photography, journal, layout, planner

  • Canon EOS 5D Mark III
  • 1/125 sec
  • f/2.8
  • 50mm
  • ISO 640
Additional Details
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  • Not available for download.