The Most Important Habit is Reflection

Not meditation. Not exercise. Not Reading. Reflecting.

Jacob Kerr
The Startup
Published in
10 min readJan 15, 2018


Over the holidays, I took some time to think back on 2017.

What were my successes this year?

What were my failures?

How should I adjust for 2018?

This piece is about all three, but my failures are the best place to start.

Failing at Habit-Building

Throughout 2017, I focused extensively on habit-building. I even posted pictures of my habit-tracking applications. Some weeks were better than others, but generally I focused on improving behavior change on a daily basis.

Daily tracking & metrics drove me crazy. (not actually my stats)

Unfortunately, the hyper-focus on tracking, data, and metrics alongside the habit-building was not healthy. I put too much pressure on myself to be perfect. My own emotional stress when I missed a habit outweighed whatever health benefits I received from my “well-balanced” lifestyle.

Burning out on a healthy habit isn’t healthy. After trying to build 5 new habits on top of a full-time job, a startup, and several tense personal relationships… I burned out. My habit-building deteriorated.

Besides my personal well-being to consider, I had to ask:

What good is habit building if it collapses under pressure?

Long-Term Change

I realized later that the best thing I did for myself in 2017 (and it’s not even close) was carve out time to reflect on a regular basis.

No doing. Just reflecting.

And since I’m super neurotic, I had to create some type of documented system to organize my reflection. Every Sunday, the only thing that’s hard-coded into my schedule is a Weekly Check-In:

I fill out this template every week, and it’s made me more consistent and generally happier as well.

The 1-page Google doc is a snapshot overview that basically answers, “How was last week and how does this week look?” It’s a nice blend of pragmatic and personal.

Blocking & Tackling

I start by focusing on monitoring my personal to-do’s and bills hitting me in the coming week — the URLs link to my Asana and Mint accounts. Every week, I look ahead to see what my to-do list looks like, and copy over some information to the weekly check-in. The process of moving over data is a good forcing mechanism for prioritization; I’m lazy, so I try to minimize the number of “priorities” in a given week. When I go to Mint, I make sure my transactions are being recorded and labeled correctly, and I check my budgets to ensure I haven’t been over-spending.

The personal reflection is where the magic happens.

Are you happy?

Most importantly, I start by asking myself… “Are you happy?” There’s no set criteria on how to answer this, it’s more about taking the temperature on life. When I answer “no” too many times in a row, then it’s time to make a change.

What’s the point in living life and building these great habits if I hate it?

Who are you thankful for? Who are you planning on re-connecting with?

Next, I prioritize relationships.

I’m terrible at staying connected with people. Truly abysmal.

When I get busy, involved, or stressed out, I go into a tunnel vision. Anyone in that tunnel with me gets attention, while anyone outside of the tunnel gets forgotten. It’s crappy to admit that, but that’s who I am. Recognizing this, I’ve made it a priority to reflect on “Who are you thankful for?” and “Who are you planning on re-connecting with?” The results have been staggering. I have been so much better about staying in touch with friends and family, and I regularly acknowledge the importance of others in my life.

This bullet alone ensured I maintained relationships that would have deteriorated otherwise.

What went well in the last week? What did not go well in the last week?

Again, two more broad questions to think back on the week.

One week, I wrote about running around Chicago. I hate running, and this is a major positive in my book (don’t judge!).

Some weeks, I wrote about arguing with others in unhealthy or unproductive ways. Other weeks, I wrote about watching too much Netflix.

The point is to call myself out for both positives and negatives. There are definitely some weeks I look back and realize…

Nope. Nothing positive or negative to write.

When that happens, I remind myself that every week had something in it that was a positive or negative. Every week has a lesson to learn. “Nothing” indicates I’m on cruise control and need to pick my head up out of the sand. Too many “Nope” weeks in a row means life is flying by and I’m not growing or I’m not paying attention.

What are you currently reading?

There are two bullets here…

Book, page:

Book, page:

The implied assumption is I’m always reading multiple books at a time. While not always true, it’s a good reminder to keep up reading. During my undergraduate years, it was easy to stop personal reading due to other commitments and reading for class. Now that I am done, I want to make sure it’s always a part of my life.

Have you been continuing and improving upon writing & personal brand pursuits?

This started out as just a question on “writing” but has since expanded to my own personal brand. In 2018, everyone has a personal brand, and I want to make sure I’m tending to mine semi-often. Brands are built over decades, so starting now — even small — will help in the long-run. The reminder to continue writing has ensured I post semi-frequently, even during periods of significant change.

How are the stress levels, sleep levels, meditation recently? (0–10) Why?

In this section, I give myself a quick score from 1–10, and then ask for a rationale.




This list keeps me honest and thoughtful about the pressure I put on myself and reminds me to be mindful. I’m going to be pretty stressed throughout life, so I better build in some mechanisms of handling it appropriately. Over the holidays, I added Sleep and Meditation to this section, because I found I did not prioritizing them enough during 2017.

How is the diet & exercise recently? (0–10) Why?

This tracking sheet auto-updates as I gain/lose weight over the time period.

This section is pretty self-explanatory: I give myself another score on my eating habits and my exercise routine. If I have 4 “average” workouts in a week, I might give myself a 7. If one of those workouts is awesome, I bump it up to an 8.

The diet links to a tracking sheet (left) I use to monitor my diet. The tracking sheet auto-updates the “Target Weight-loss per week” according to my current weight and goals. Over time, I am going to build this section out to assess the quality of my diet —i.e. Am I taking in enough fruits, vegetables, and nutrients on a consistent basis?

Anything else important to note (major events, thoughts, etc.?)

This section is as open and broad as it can be. If something major happened that is important to record, this is where I do it. Writing it down is cathartic and can help me process when shit-hits-the-fan, or something great happens and I want to remember it for later.

As an aside — I predict there will be some interesting nuggets to explore when I eventually dig through these files later on and can spot trends.

What’s this? Every time there was a major life event, Jake ate worse, exercised less, but slept more? Hmm…

Why is this the most important habit?

This is the first year I have really stayed consistent with healthy habits. In years past, I would start a new habit (e.g. a New Years Resolution to exercise more consistently), and drop off in just a few weeks.

When I started doing this weekly reflection, my consistency picked up dramatically. I wasn’t perfect, but I was trending in the right direction. This template is quick, easy, and comprehensive. When juggling tons of little balls in the air, it’s nice to step back and breathe for a second. The time and overhead was relatively minimal, so there’s rarely an excuse for missing a quick Weekly Check-In.

Downstream Habits

Keep in mind, the whole thing described above is a 20-minute Google doc. It’s generally the first thing I do on Sunday mornings or the last thing I do on Sunday evenings, but it doesn’t actually get anything done; it’s just reflecting.

From this 20-minute process, however, flows all the other things in life I want to cultivate for the next 30+ years. I’ve been asking a lot of people, especially adults, “What do you wish you had known when you were 22? What’s something you wish you started doing earlier? What can I start today that 55-year old Jake will appreciate?”

The answers usually fell into a few categories:

  • Prioritize relationships
  • Save your money.
  • Take care of your health.
  • Live in the moment.
  • Don’t worry so much.

There are plenty of other answers, but I found that my Weekly Check-In template hit them all. By consistently asking myself the above questions, I would be tending to all of those suggestions along the way. The low-stress, low-overhead template helped me get back into the gym, read more, and stay connected with friends on a consistent basis. All these other habits were tied to one larger habit of reflecting.


There were many, many weeks where I dropped the ball on individual habits. Some weeks, my answer to a prompt was “Absolutely not. I’m drowning and can’t make time for going to the gym/writing/reading.” And that’s ok. I always got back on, eventually.

I got back on eventually because I only missed my weekly check-in 9 times over the year. That’s 43/52 weeks! In the aggregate, I became more consistent than I ever have in the past.

When starting this, my goal was to find a balance between consistent, rigorous, and flexible. There are some weeks when I didn’t hit everything. Actually, I would say I RARELY hit everything on my list. However, filling out this template was the right balance for me and it’s made a world of difference.

That little red light in the back of your head

Over the holidays, I realized much of the anxiety I experience on a day-to-day basis comes from the feeling of “I’m not doing what I should be doing.” Part of this feeling arises because I don’t even know what I “should” be doing. For me, this creates “that little red light in the back of your head.” When I took a break for the holidays, I realized many of the things I “should be doing” are artificially created — by me. They’re not “do or die” they are “do or get annoyed at yourself.”

Many of the things I “should be doing” — like health, relationships, etc. — are already captured in my Weekly Check-In. Basically, if I keep up the bullet points on my template, almost everything else takes care of itself.

Looking Forward: Optimization & Iteration

My Weekly Check-In was also a forcing mechanism for optimizing routines which are better automated & verified than done manually. For example, when I started doing this last January, I paid bills manually. By creating a weekly check that forced me to assess this manually, it encouraged me to set up auto-pay. Now I verify bills were paid on time and look ahead to see the bills that have payments pending. Seems obvious, right? It is obvious, but the weekly annoyance pushed me to find better ways to automate parts of my life.

By creating this template, I also created a framework for future iteration. By the end of 2017, I added sleep, meditation, and personal brand building to the template. If I want to prioritize other aspects of my life — perhaps my children in the future, or painting, or travel — I can add those to my template.

Final Thoughts

The reminder at the top of my template was helpful. I frequently hear people look back at hard times in life and reflect on it: “I wouldn’t change a thing. It made me who I am, despite the negatives.” Why not appreciate that wisdom in the current moment? Why is this a learned lesson twenty years later? The reminder helped me keep life in perspective, especially when I felt overwhelmed.

You are on a path of constant challenge and growth to becoming the person you want to be.

Sometimes it’s going to suck. Sometimes it’s going to be great. It’s all part of the process.

Keep growing. Keep helping others. Don’t forget to take a moment to look around and enjoy life.

What do you think about my habit of weekly reflection? Do you have something similar? What did I miss? What did you add to your weekly reflection? I’m always looking to learn and share with others, so please reach out!

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Jacob Kerr
The Startup

Helping orgs find their Hamilton or Daenerys by day… Building @AlumniVentures by night. Every strategy, change, mission starts with people! @NorthwesternU '17