Document Everything: The Secret to Measuring Progress

Do you ever feel totally lost? Do you ever feel unsure if you're making any progress? You're slogging along in your day job, or grinding away learning to code in the evenings, or putting in work on a side business, and you just have no idea if you're moving the needle towards any of your goals. This doesn't have to be work related, either. Maybe you're trying to lose weight or pay down debt and you never feel the end is in sight.

I've been in all of those situations and felt all of those things:

In my early-20s, I was scared I had made a huge mistake taking a straight commission insurance job during a recession and worried I wasn't going to pay my rent or keep the lights on.
In my mid-20s, I was frustrated working a lame day job with what felt like a useless liberal arts degree.
In my late-20s, I was worried I was going to immediately get fired from my first developer job after moving across the country to Portland .
At 31, I was worried my first video course would flop and the hundreds of hours I had put into it would be wasted and help no one.
At various times in my life, I've felt like I wasn't losing weight fast enough or that I'd never get out of debt.

Sometimes those fears materialized, sometimes they didn't (thankfully I didn't get fired from my first dev job). Either way, I got through them. Looking back over the long term, it's easy to see how those events shaped me and how I was making progress. My "useless liberal arts degree" taught me how to research and teach complex ideas. Commission sales made me more resilient and got me out of my shy, introverted shell. Spending hundreds of hours building a video course laid the foundation of my career in developer relations.

But in the day-to-day grind, it didn't feel like I was making progress. Objectively, I was making progress, but it wasn't happening as fast as I wanted or in the way I expected it to.

What if we could capture those feelings and be able to see our progress day by day? We would have objective proof we were making progress when we didn't feel it. It turns out we can do this and that it doesn't take nearly the amount of effort you might guess. In fact, it only takes a few minutes a day.

How to Track Progress by Documenting Everything

I recently stumbled onto a Google doc that reminded me of a habit I got into a few years ago that was a huge game-changer despite being so simple. For several months at a time, every day I would jot down whatever I was working on or thinking about. I call this documenting everything.

Documenting everything means writing down as often and consistently as possible:

Progress on projects
What you're thinking
What you're feeling
What you're worried about

You might be thinking, "You mean journaling? Great job bud, you've invented journaling. So glad I subscribed to your groundbreaking newsletter!" It's definitely a form of journaling (and I definitely didn't invent it), but for some reason for me journaling feels like this Big Process with lots of Rules. I'm talking about sketching notes and jotting down feelings with no other purpose or overarching plan. You might even consider it a "Daily Stand-Up" meeting with yourself. It's informal and just takes a few minutes a day, but it velds a huge amount of value.

Why document everything?

So why should you document everything? Here are a few of the benefits:

It helps us see progress. We're not good at judging our progress in the moment. We're too close to the action. When we document what we're working on, we can look back and see all of the little steps and daily habits that took us from point A to point B.
It keeps us honest about our progress. We have a tendency to think things were better or worse than they were in hindsight. I went through a huge period of personal transformation from 2013-2017. In 2017, I was really happy, feeling really fulfilled, and making a lot of progress. I started to romanticize the process and oversimplifying the advice I was giving to people (it was really obnoxious). Luckily I started reading back through my journals from that time period. The truth was that growth was painful! I frequently felt stuck, lost, angry, and frustrated. All of a sudden, in 2017, things clicked. It felt like waking up from a dream and I immediately forgot just how much work it took to get there. Reading my own writing and seeing just how much confusion and frustration I felt re-grounded me and caused me to take a more nuanced look at what actually helped me make progress (spoilers: it wasn't just believing in myself).
Self-awareness itself yields results. There have been many examples and studies that show that simply paying attention to a behavior tends to modify it. For example, a study at Oregon State University showed that just taking pictures of your food causes you to eat less. Paying with cash causes you to spend less money because the physical act of parting with your cash registers in your brain and causes you to pay closer attention. Writing down what you're working on and thinking about will start to subtly impact how you spend your time and what you think about simply by noticing.
It's good for performance reviews. You probably have some sort of annual review at your job. Usually this entails frantically trying to go back through your calendar, your code commits, and your sprint tracker to see what you've worked on. If you start documenting everything, you can do a quick scan over your notes and assemble a hit list of your biggest milestones with very little extra work.
It's good for gathering data and noticing trends. As you start to become mindful of what you're doing and thinking, you'll start to notice patterns. I tend to do my best creative work Tuesday through Thursday and my best admin, planning, and systems work on Mondays and Fridays. I tend to be more worried and restless when I don't have a clear project I'm working on.
It's good for creating content. There's no better way to source content than by using your own notes as a starting point, especially if you had to overcome some sort of pain or frustration in order to figure it out. Capture those thoughts and turn them into an article or a video. The gold mine here is in your language. When you're frustrated in the thick of debugging, you talk very differently than stoically and clinically prescribing a tutorial. Use that to your advantage and incorporate that authentic language into your content so people resonate with it. Well, maybe you don't want to incorporate all of the authentic language you use when debugging... 😬
It's good for building an archive. Over time, you can use your notes to build a library of your influences, thoughts, and feelings. There are countless ways to organize and use this data over time while also watching yourself grow as a person.

How do I start documenting everything?

If I've sold you on documenting everything, let me help you get started. Here's what you'll need to do:

Pick an app or format that you can stick with. When I first started, I used a running Google doc that I kept open in a tab all day. I eventually started creating a new document each month. Later on I moved to Markdown and an app called Drafts. Don't overthink this or over-research it, just pick something easy. Picking something and using it will help you figure out what you like or don't like.
You're going to create an entry for each day, so first write out the date.
For each entry, create two sections: what you're working on and what are you thinking or feeling (I always just called this "Notes.")
Keep this document open and, any time you have a minute or two, jot down notes in either section. In the first section, you might break it up by project or just jot down a few words of what progress you've made that day. In the second section, you might jot down reflections on previous days, what's working, what's not working, or what you're worried about. Think of this section as whatever is alive to you in that moment.
The next morning, copy and paste the previous day, update the date, and clear out the notes section to start over. You could also do this at the end of the day if it might be a helpful shutdown ritual.

That's it. Don't judge anything you write down. Don't think about someone else reading it. Write for no one else but you and be brutally honest with yourself. You can always edit it later if you decide to publish anything.

One other tip: don't say you're going to do this forever. You won't, at least not until you build the habit long enough to start seeing results. Pick a period of time and commit to it. It might be 4 days, a week, 30 days, or 90 Days. Start small and build the habit, then work your way up. I found 90 day stretches to be the most useful once I got into it. It might take you a month or so to start seeing the benefits, but once you do you'll start to get hooked. Another thing that helps with this is counting down instead of up. At the top of each entry, I would write "Day -90," then "Day -89," and so on. It helped me stick with it much more than slogging through Days 1 to 90 because I didn't want to break the streak.

How to Go Deeper

Once you've built the habit and are starting to notice patterns, you can go deeper. You can:

Optimize your notes for discoverability (processing or storing them)
Integrate your notes into content
Optimize your efficiency by automating your processes
Go down the rabbit hole of the Personal Knowledge Management system
Track your time

Don't worry about any of these things until you've got some experience under your belt. If you over-engineer too quickly, you'll burn out and stop doing it. Just build the habit and see where it takes you.

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