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On Planners and Habit Tracking

Four years ago, on one of those trips to Montreal, I was waiting for the girlfriend in a paper shop. Despite my lack of either need nor talent, I would walk out with yet another notebook. You see, I was in love with the allure of the written word, but I had nothing to write about. I even had a 70 Euro pen I had purchased in the Dreta de l'Eixample District of Barcelona, but what business did a computer programmer have with an analog medium?

This time, before I left that paper shop, I laid eyes on a beautiful Moleskin planner. It was full size, soft cover, like one of those teacher’s gradebooks. Nothing would make me more legit than carrying around the gradebook.

Recently, while listening to The Brian Lehr show discussing introducing kids to nature, an expert told us that we should give our kids a magnifying glass or binoculars. “Tools,” she proclaimed, “make kids feel competent. When you hand them a tool, there’s an extra layer of excitement.”

Armed with my Spanish Pen (it was German), and my French-Canadian Gradebook, I was ready to start a daily planner. Of course it was September, so as I waited for the year to begin, I also began a new job. My planning started from there. It looked very different then than now, but I think the tools really got me excited to dive in. They made me feel like an adult, and I carried them around the office, to meetings, even when there was no reason for me to use them. It just felt good.

For a long time, I simply tracked things like water and caffeine intake, my daily train delays, and appointments. I’d use the free page on the right for notes or to-do lists, but it would be two years before I would evolve that into what you see today.

The first evolution would come when I was going through a really dark time in my life, and knew I needed to get organized. In the span of a month, my 6 year relationship ended, my hero Anthony Bourdain died, and I would face mortality for the first time as my dad went into the hospital for what we thought might be the end.

Between working with a therapist, and my own ideas, I started writing down lists of friends to connect with, and activities I knew I enjoyed. The idea was that when the depression cleared, and I was motivated to contact someone, or do an activity, I didn't want to lose that energy trying to make a decision. If you have ever tried to watch a movie with dinner, only to watch your food grow cold while hunting for the right movie, you know what I'm talking about here.

Doing this meant I now had a weekly list of multiple categories to keep track of, and when you have many things, it's a good time to organize. I started taking that empty notes page, and with the help of Pinterest, got some ideas flowing to get a layout.

Over time, I switched to fountain pens (remember, children feel competent with fancy tools), and then multiple colors of ink. As I poured in more energy, the look improved, was more approachable, and my excitement to return to it began to swell. Over the years, I've had many dry spells, although since switching to this format, it's been easier to keep going.

On Setting Goals:

As for the habit tracking and goal setting, I've learned over the years to be conservative. Be honest with yourself. Sure, you might make it to the gym five times a week, but if you dream big too early, and fall short, you're more likely to throw in the towel and throw it away altogether.

When I first moved to NYC in 2011, I started a 365 Photo Project. Basically, the idea was to take at least one photo a day for a year, and post it. Early on, I realized just how exhausting this can be on the rainy days. I compromised with myself, and accepted that some days were gonna be harder than others. Every day wouldn't get a good result. How could it? Instead of beating myself up, I'd say "Just do the minimum." A buddy of mine allows himself 4 cheat days a month, for instance. For me, I always took a photo, but sometimes I'd keep an old shot in my back pocket for those rainy days.

Doing this photo project changed my life.

Within 3 months, I was published, and I would go on to do big things, from photographing one of my favourite actors, to working with several museums in NYC. It also led me to make connections that have introduced me to some movers and shakers of New York. As of this year, I've done some 100 gigs for just one of the organizations I met in my first 9 months of that project.

All of this is to say that missing a day or two of your weekly goals is nothing compared to where these habits can take you in the long run. Go easy on yourself. Building momentum with easy goals is more important for the long term than a few weeks of aggressive stats. And if you’re too proud to listen, I went on to complete 4 365 Photo Projects since 2011, and last year I trained for 5 marathons. I couldn’t have done any of that unless I was kind to myself, and I took it one day at a time.

My best advice on habits: Good quotes from famous writers. That crap applies to everything you do. Here are three relevant quotes from the first result in Google:




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 conservative, and being happy accomplishing tiny things over and over.

Looking Forward:

As I write this, I am just beginning the process of doing monthly summaries. “In these uncertain times,” living alone, I feel like I’m nowhere some days. Yet, as I began fact-gathering from April, I realized I had done a lot. I ran or biked almost 250 miles this month, despite being told 2 months ago that I will need back surgery. I cooked/baked a ton of things I’ve never dreamed of making before (Enchiladas Verda _and_ Chana Masala). I even attended several holidays, lectures and events (shoutout to The Moth!). I’m proud of all these things, but would have easily forgotten about them without a retro.

Summarizing things is not only a chance to check in on what you’ve done, but it gives you ammo to feel good about yourself. It’s OK to brag, especially to yourself. We all know life can be tricky. Especially now. But as Thoreau said, “Fools stand on their island of opportunities and look for another land. There is no other land; there is no other life but this.”

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
  • © All rights reserved
  • Not available for download.