Staying On Track

November 11, 2021

When you are working toward a sufficiently ambitious goal, it's easy to get distracted or discouraged along the way. By sufficiently ambitious, I mean something that requires sustained effort over a long period, like learning a new skill or a large project at work.

When you are working on something chunky like this, progress happens in small increments. You are just getting (at best) a tiny bit better every day, so it can sometimes feel like you aren't moving forward at all. In addition, many people have multiple ambitious goals in progress at any given time, which can make it more challenging to balance your time and energy effectively.

To combat this, you have to build a habit of reflection. Reflection gives you a chance to disconnect from the daily grind and celebrate the fact that you are actually moving toward your goal. It also helps you recognize areas that you can make adjustments to eliminate impediments or make your process more efficient.

I build reflection into my routine through journaling sessions, which I do on daily, weekly, and quarterly intervals. Here's how it works.

Daily Checkpoint

This is a quick session each morning that generally takes less than 10 minutes. The goal is to recognize and correct small things that might otherwise slip under the radar and get my head into a clear, focused state so that I take on the day as best I can.

Here are the questions I ask myself:

  1. What went well yesterday / what could have been better?
  2. What am I focusing on today?
  3. What am I grateful for?
  4. Is there anything causing me stress or anxiety?

The first two questions prompt me to think about what went well and what could be improved from yesterday and then set my intentions for the day. This includes any micro-corrections I want to make today. For example, one thing I've noticed is that if I spend the whole day reading and don't do any coding, I tend to feel worn out and less enthusiastic at the end of the day. To avoid this, I plan my day in a way that balances passive and active forms of learning.

The final two questions help me set the right tone for the day and build healthy mental habits. Research has shown that consciously expressing gratitude regularly for the good things in our life can lead to more positive moods and optimistic outlooks. I have found this to be true in my own experience. In a similar vein, consciously recognizing anything on my to-do list or in my life that is causing me anxiety tends to lessen the stress it causes. I think this allows my brain to recognize that no matter what the problem is, it's almost always solvable. Now I can start working out ways to approach it and get through the challenge instead of just ruminating about it aimlessly.

Weekly Checkpoint

This session takes about 30 minutes, and I typically do it on Sundays. The goal is to zoom out, recognize the progress made over the past seven days, and identify any macro-patterns that have started to develop. I ask myself the following questions:

  1. What went well yesterday / what could have been better?
  2. What progress did I make toward my long-term goals?
  3. Based on this, is there anything I am going to change this week?

It feels great to celebrate reaching milestones, and this helps keep intrinsic motivation levels high. You generally can also use this check-in to understand if you need to make any reallocations in how you are spending your time in relation to your longer-term goals. For example, earlier this year, I realized I wasn't making meaningful progress toward my goal of publishing more of my writing. I determined that this was because I was scheduling it for an hour at the end of the day, and it was often getting scheduled over when other projects ran long. I decided to adjust my schedule so that writing came first each morning. Now I'm writing and publishing more regularly.

Quarterly Checkpoint

The purpose of this session is to make long-term course corrections. The ultimate outcome is to set goals for yourself for the upcoming three months, but this can only happen productively if you feel good about the direction you are heading. Here are the broad questions I prompt myself with:

  1. What went well over the past 3 months / what could have been better?
  2. Am I happy with the person that I am and the path that I'm on?
  3. What do I want to continue doing/stop doing/add to my routine/accomplish over the next three months?

This session naturally takes more thought and consideration, so I generally return to it throughout the day or even over a few days. I recommend getting outside for a walk to get your reflective juices flowing beforehand. Give yourself time and space to slow down. Try and connect with who you are right now and how you've changed over the past three months. You might be surprised what you observe when you let the dust settle. From there, you can set new intentions for yourself for the upcoming quarter.


In this post, I presented a journaling system I use to keep myself on track. I think of this system as my personal operating system - it's a way to make sense of my life and create meaning for myself. This sounds fancy, but it isn't. It's just a bunch of questions in Google Docs that I ask myself on daily, weekly, and quarterly intervals. If you don't already have reflection built into your personal routine, I'd encourage you to try something like this out for yourself.

Finally, it's important to note that this system is really just a mash-up of many great tools and mental frameworks. If you are interested in learning more, I highly recommend the following resources: