How and Why I Track My Life

Unlike many people who I respect, I don’t believe in tracking for tracking’s sake. It’s not one of life’s intrinsic pleasures. Personally, I only have one reason to track: to increase the quality of my life. How? By identifying things that are either correlated or causally-related to increased quality of life and optimizing for those things. – Buster Benson

Because I anticipated that 2014 would be a year of intense learning for me, I kicked off the year by identifying Five Pillars for a Healthy and Happy 2014. These pillars would serve has my North Star and keep me pointed in the right direction.

I’m sure you have heard that you can’t improve what you don’t measure, so the remainder of this post highlights how and why I track my life. (Hint: to learn something new and valuable about myself.)

Weekly Goals

Every Sunday I prioritize 3 things that I want to accomplish during the week. Keep in mind that these are in addition to my day job responsibilities.

I put these goals on a shared document that my accountability partner and I use to keep each other on track. Below is an example of a two week span in May.

Like you, I have weeks that are busy and stressful at work and deplete my willpower for accomplishing additional tasks. Other times, I just need a quiet week to recharge. In other words, my weekly goals don’t always get accomplished, but doing something is better than watching hours and hours of mindless television.

The important part is ensuring that each of the things on this list align with my five pillars of happiness. Do achieving my weekly goals help me become happier, healthier, smarter, more spiritual, better at my job? More on how I evaluate that later in this post.

Excerpt from accountability document

About half way through the year, my accountability partner and I realized that our weekly goals were often too ambitious. We were hard on ourselves and beat ourselves up if we didn’t accomplish them all. Those pangs of guilt would sometimes get us down and carry over to the following week, adversely effecting momentum. How’s the saying go? You overestimate what you can accomplish in a day, but under estimate what you can do in an entire year. I think that’s true.

Anyway, as a result, we transformed our accountability document to look more like this:

Revised Accountability Document

This enabled us to do more of a week-at-a-glance analysis. By design, there’s less pressure to finish certain tasks because we share what we achieved after-the-fact. We also built in gratitude by acknowledging some of the good things that happened during the week while simultaneously analyzing what didn’t get done (and why) so that we can make adjustments accordingly.

Of note, when I mention the “10 action items” this was a (failed) experiment in which I was trying to shift from focusing on the outcomes of my three weekly goals to a systems-based model where I thought that I would inevitably achieve all my goals if I were able to complete each systems-based task.

The list of tasks included 10 things for each week (listed below), and like most of the things I set out to accomplish, it was a bit ambitious.

  1. One Yelp review
  2. 100 pages of a book
  3. 500 written words (preferably towards a blog post)
  4. Read ½ of a magazine
  5. Listen to and take notes on ½ of an RBT Interview
  6. One long run
  7. One shorter, speed work run
  8. One weight lifting session
  9. Add one person to Nat’l Networking doc who I can help professionally
  10. Add one person to Nat’l Networking doc who I can help personally

In Summary: I believe it’s important to push yourself to keep learning, growing and creating/sharing your art. This is how I hold myself accountable on a weekly basis, but can be a bit cumbersome. I’m exploring ways to streamline for 2015.

Your volume will depend on your life stage and your responsibilities (i.e. someone with a young family won’t have as much time to read and focus on personal development, but perhaps your goal would be to get home from work in time to eat dinner with your kids 3 times a week). The point is to push yourself to become a little better each day and to go beyond watching television for 3 hours every night before bed.


“Showing gratitude for the good things you have is the most powerful happiness boosting activity there is.” – Eric Barker

I’ve read and explored a lot of literature on happiness. The one thing, besides great relationships with family and friends, that always comes up? Gratitude.

Which is precisely why I keep a gratitude journal. Though I’m not as diligent about it as I probably should be, the mere act of starting a gratitude journal makes me more conscious of these thoughts in my day-to-day life. See someone getting rained on at the bus stop = thankful my vehicle gets me to and from where I need to go in a reliable way.

Here’s a small sample of a two week period in March. Notice the entries. In my experience a gratitude journal makes you more appreciative of the little things in life.

Gratitude is the key to happiness

“The more a person is inclined to gratitude, the less likely he or she is to be depressed, anxious, lonely, envious, or neurotic.” – Sonja Lyubomirsky

Here are a few additional resources for your reading pleasure:


So I’m setting and tracking targeted weekly goals and I’m honing my spirituality pillar by practicing gratitude, but how am I capturing and documenting all the information I’m consuming so that I can retain it and refer back to it for both personal and professional success?

Knowledge Capture

To capture knowledge, I employ Ryan Holiday’s notecard system for organizing and remembering key insights and takeaways from all the books, magazines and blog posts I read. This is how I capture (mostly) single thoughts and nuggets of information.

On the left-hand side of the card, I indicate where I found the quote/passage and who to attribute it to. In the top right hand corner of the card I put the theme or category the card belongs to. I flip back through these cards often for inspiration. Because I keep them sorted by my themes, I’m able to grab a handful from a certain theme and thumb through them whenever I need to engage that topic.

Here are a couple of examples:

Matt Goldenberg on Mindset

Ramit Sethi on Criticism

To convolute the system a bit I *also* keep a commonplace book. I reserve the commonplace book for long(er)-form notes.

“A commonplace book is a central resource or depository for ideas, quotes, anecdotes, observations and information you come across during your life and didactic pursuits. The purpose of the book is to record and organize these gems for later use in your life, in your business, in your writing, speaking or whatever it is that you do.” – Ryan Holiday

The pages in my commonplace book typically consist of three things:

  • A handful of takeaways from an interview of someone I respect and want to learn from
  • A compilation of quotes or ideas that all fit together under one category/theme
  • Notes from a book that I want to keep together in one place


Here two examples:

The first is some of my favorite quotes (mostly from books) about long distance running:

Quotes About Running

And this one is from Simon Sinek’s Ted Talk on “How Great Leaders Inspire Action“:

Notes from Simon Sinek's Ted Talk

The knowledge I capture on these note cards and in my commonplace book have immediate practical application, both in my personal and professional life.

I cannot tell you how many times someone has asked me about something and I was able to cite scientific research from an article I’d captured, quote an expert on a relevant topic, or even deep dive a methodology, help solve a problem, and/or come up with the perfect solution by referring to notes in my commonplace book — typically  from an expert who’s way more knowledgeable than myself on said topic.

Beyond that, it’s just a great source of inspiration for offering advice and for writing this blog.

Sleep and Exercise

These are my two main priorities of my physical health pillar. The scientific benefits of these two are undisputed.

To track my sleep, I use the Sleep Cycle Alarm Clock, which tracks what time I go to bed, average time in bed by day of the week, sleep quality, and things I’ve indicated might have an effect on my sleep.

Some of these include:

  • Had 3+ drinks (slight negative effect)
  • Afternoon coffee (surprisingly, I sleep a little better)
  • Worked out (no effect)
  • Stressful day (slight negative effect)
  • Napped (no effect)
  • Ate late (biggest negative effect – mostly because it usually means I was out late and went to bed late)

Sleep Quality

Each month, I aim for at least 80% sleep quality. I’ve learned that 80% (or better) ensures that I’m well rested, alert and productive at the office.

Interestingly enough, my worse night of sleep is Fridays. This is because I tend to go out to dinner with friends, have a few drinks, stay up and watch a movie, etc. and yet I still get up at the same time (or earlier) than I do for work to ensure I get my long run in before it gets too hot. (I still love you Texas!)

In a perfect world, I’d get 3-4 runs and 2 lifts in each week, but given how much I worked this past year, it simply wasn’t feasible. I try to practice self compassion and tell myself that everything beyond 2 runs and 1 workout a week is a bonus.

I rarely track my lifts because mass, strength, etc. are not part of my current goals. Setting a PR in the half marathon in January is one of my goals. As a result, I keep a close eye on all my runs in Garmin Connect.

October Mileage


Weekly (personal) goals, gratitude, knowledge capture, sleep and exercise are all things that are ultimately critical for my career success; however, virtually all of the action-items and tracking for those things occur outside of the office. The exception being a quick note of gratitude or a note card on something I’m reading that has direct applicability to a current project.

This category is something I do not track outside of work, but find it important to track while I’m at the office.

The danger for high-achieving people is that they’ll unconsciously allocate their resources to activities that yield the most immediate, tangible accomplishments. This is often in their careers, as this domain of their life provides the most concrete evidence they’re moving forward. — Clayton Christensen

It probably took me longer than most people, but I now realize that as important as my career is to me, it’s also *very important* that I have time to spend with friends and family, exercise, get adequate sleep and pursue my passion projects (including sharing with the readers of this blog). While my career might provide more immediate returns, I cannot unwittingly neglect my relationships with my family, friends, health, etc.

In order to ensure I have time for all of those things, I have to be uber productive at work so that, unless we’re on deadline for a high priority project, I can leave the office on time.

Rescue Time is a great way to measure your productivity
Photo Credit: Naveen Dittakavi

To keep track of my productivity at the office, I often employee the pomodoro technique (3 uninterrupted sessions in one day is amazing, FYI) and use RescueTime to spot inefficiencies in my day so that I can maximize the use of my time. I have not upgraded to the premium version so I don’t track offline time like meetings, but it still gives me a good sense of how I spend my time each day.

I also leverage customized categories to define what constitutes my most productive time. For example working on a strategy document or deck is considered “very productive” time, while e-mail is considered productive time (and that’s giving it the benefit of the doubt). Getting distracted by a trending topic on Facebook would be considered “very distracting time” and should be reserved for at home, after dinner.

At the conclusion of a successful pomodoro session, I might read a pertinent article, stretch, do push-ups or check in on colleagues. Sometimes, if I’m really in a state of flow I’ll opt to skip the break and keep hammering away.

If you’ve made it this far, you have a really good idea of all the things I track in my life and why I think it’s important to keep up with each one, but how does it all come together in a useful way?

Monthly Reviews

This is how I perform my monthly reviews:

  1. At the end of each month I collate all of my weekly goals together in chronological order.
  2. If applicable, or the week was especially noteworthy, I’ll add a bit of commentary that I can go back and reflect on.
  3. I identify the following:
    • The biggest win of the month
    • Things I skipped (and why)
    • The “not so good stuff” (i.e. causes of stress, anger, insecurity)
    • What I learned (i.e. any big takeaways that were unsuspected and/or applicable moving forward)
  4. I list out 3-5 bullets for each pillar of my five pillars for a healthy and happy 2014. (Below are examples for each).
    • Personal Relationships: “Even if I sometimes want to stick my routines, I rarely regret spontaneous meet-ups with friends.”
    • Physical Health: “Only 2 runs over 5 miles this month; definitely reflected in total mileage (48 miles), which is just a little over half of last month’s 82 miles. Our week long vacation contributed a bit to less mileage.”
    • Mental & Emotional Wellness: “Asking for and receiving a quieter work space has helped me realize that it is worth asking if something will make me more happy, motivated, better at my job, etc.”
    • Spirituality: “One area of spirituality where I really need to improve is to forgiving myself when I don’t meet all the expectations and to-do’s I assign myself every week.”
    • Career: Talking about Kickstarter – “I was working crazy, unsustainable hours. A “sprint” like this is necessary from time to time in your career and can pay dividends, but I do think there would be diminishing returns *very* quickly after 4-6 weeks.”
  5. I look at all the weekly goals holistically, review the commentary, review the big wins/lessons learned, review how well the weekly goals aligned with my five pillars and write a 2-3 sentence executive summary so that I can always come back to these monthly reviews and have actionable takeaways and understand the month’s impact on the things that matter in my life.

These are quite a bit more personal/introspective so I don’t share them with anyone except my wife. If you’re *really* interested in seeing the format so that you can create something similar, let me know and I’ll try to revise one to share.


In addition to the “main” things I track, I also keep up with the best/most interesting things I read each month. Here are my 11 favorite reads from October. It’s often quite telling which articles/blog posts are resonating with respect to my current situation and/or station in life; as well as, situations I’m navigating both personally and professionally.

In addition to the best things I read online, I also captured highlights from informational interviews and some of the best things I read offline (see: books). In an effort to give back to my community, I try to publish comprehensive notes and takeaways when I have the time and think you all will find them valuable.

Here are a few of my favorites:


I track where I’m at (or rather where I’ve been) with Swarm. Though, for how much longer, I don’t know as the data is no longer compelling since the decoupling with Foursquare.

When I remember, I track what beers I drink with Untappd. It’s a good way to remind myself of beers I don’t have very often and whether or not I liked them. It’s also useful for recommendations. If you’re curious, here a few of my favorites.

I tried Reporter app for a couple of weeks after reading “How I Track My Life” by Buster Benson, but felt it was too labor intensive and didn’t like pulling out my phone when I was around people.

The key is not to track just for the hell of it, but because it adds value to your life, hence the likelihood that I continue to use Swarm isn’t very high (unless I can get summarized check-in data to get an over-arching look at the types of places I go most often, outside of the obvious: work and my apartment.

In Conclusion

It’s not perfect (not even close), but I get an immense amount of value from tracking these things in my life.

The point of this post isn’t so that you will duplicate my (time intensive) system, but that you’ll slow down and think: “How do I spend my time? What do I want to get out of life? Am I proactively working towards my big goals as a result of systems I create, habits I form and smaller goals I tackle each week?”

If you’re not thinking about these things, I encourage you to. And I highly recommend that you also track some of the most important metrics — at least at first. You might be surprised the effect it has on your life.

Not only have I learned a ton about myself (what makes me happy, healthy, productive), but also how the things I track impact where I ultimately want to go and what I want to accomplish in this life.

I’ll use the remainder of 2014 to determine the best way to streamline my weekly goals and monthly reviews in 2015, which will ultimately mean less time tracking and more time reading, writing, thinking and sharing.

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  • Carolynn

    I recently had a talk with a mentor of mine — a very successful businessman who came to America with a few bucks in his pocket and an offer to sleep on a stranger’s couch. He’s since become a millionaire many times over, married the woman of his dreams, and dedicated his life to making the world a better place. Oh, and he gets to play often with his grandchildren.

    By anyone’s measure, my mentor is a rich man.

    Anyway, he invited me to do something with him, and I said I’d find the time between everything else I was doing.

    “My dear,” he said gently, “the moments between all the stuff you do is LIFE. You’re missing it.”

    That made me stop dead in my tracks. I realized my calendar had become my master instead of the other way around.

    To be very honest with you, I care less about systems now that I did 6 months ago. Systems are great, they help with growth, but ultimately they’re tools. I worry less about productivity nowadays and more about being present.

    The #1 tool I use to track my “richness” now is asking myself every day, “How am I feeling right now?”

    Sometimes I have to ask myself several times a day.

    If I’m feeling excited about what I’m doing, or another happy feeling, I keep doing it.

    If I feel drained, or angry, or sad, that’s a red flag. Sometimes it’s subtle, like a slight feeling of agitation and I don’t know where it’s coming from. Then I have to dig until I uncover what’s going on.

    Once I have a good bead on where I’m at emotionally, mentally, spiritually and physically at any one time, I redirect as needed.

    Sometimes that means using Google Drive or my calendar or another system I have, but they’re really secondary to this constant check ins with myself. In focusing so much on the apps, I’d become too mental and had begun to forget myself.

    The interesting this is I’ve noticed when I’m very present, the productivity comes naturally anyway.


    Ryan Stephens Reply:

    First and foremost, thank you for taking the time to share the advice of your mentor and your own experience tracking your “richness.”

    I think you’re right. The first couple of monthly reviews I did, I thought it was an invaluable tool; however, as summer rolled around the monthly reviews began to feel a bit like a chore.

    A theme that started to surface was that if I was spending more time tracking than I was doing the things I track, then the entire process had become too cumbersome. (This is *mostly* true of the monthly reviews and *NOT* many of the other things (sleep, my runs, etc.) that I track easily and efficiently).

    The monthly reviews started out as a very worthwhile exercise because they made me infinitely more mindful of how I was spending my time. Now that I have a good inclination, I plan to streamline for more real-time feedback (i.e. “How am I feeling right now?) and a much less laborious way of periodically checking in to ensure that I’m on the right path.


  • “I tried Reporter app for a couple of weeks after reading “How I Track My Life” by Buster Benson, but felt it was too labor intensive and didn’t like pulling out my phone when I was around people.”

    Yes. To the end part especially! I don’t like so many tracking (and other) apps because I consciously do NOT like being on my phone when I’m around others. But once you open it “to check one thing” the rabbithole is RIGHT THERE! :


    Ryan Stephens Reply:

    So great to hear from you, Elisa!

    As result of all the tracking I did in 2014, one of the big things I’ll be focusing on in 2015 is creating more than consuming (as efficiently as possible) to ensure ample time to slow down and savor life by spending more time with friends and family having great conversation, listening to awesome music and partaking in some delicious libations.

    In other news, we *must* catch up soon. You’re live on the news and launching news businesses and I want to hear all about it.


    Elisa Doucette Reply:

    Creating is a big one for me in 2015 as well. I keep going back and forth between Creation and Completion; have lots of creative project ideas, but never bring them to completion. Plus, living the past 3 years in a very disjointed, thrown together on the road style, I look forward to having a bit more planning and stability in the next 12 months. 🙂

    We will definitely have to catch up! Been a crazy week, the result of a good six months of work and planning (well, the press stuff was the fluke of a well-written article that somehow gained a ton of unexpected attention and traffic!)


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