An Uncomfortable Self-Audit Blueprint
A comprehensive process for self-evaluation.
Prologue
How many times have you set a New Year’s Resolution? How many times have you tried to change a habit or create a new one? How many times have you found yourself failing to stick to a new routine or goal in February, only weeks after you set out to create a new you?
If this path sounds familiar, this post is for you.
If you want to skip ahead to the template, just scroll down to the header:
The Comprehensive Self-Audit.
If you want to understand the mechanics and evolution of how I got here, just keep reading from here.
An obligatory warning about Self-Audits:
We all want to improve ourselves, that’s normal. What’s unhealthy is expecting perfection. Perfectionism is the delusion that we should be whatever imagined ideal our brain envisions. This leads to inevitable self-loathing, guilt, shame, and a bunch of other fun emotions. If you’re not a brain scientist, let me explain why this is really bad.
We take in the world with our senses and then our brain tries to parse it. We feel and then we think. What we feel has a direct impact on what we think and how we see the world. How we see the world then continues to impact how we feel. The spiral continues.
All of this to say: this is not a path to perfection. This is a path to progress.
Before you dive into this template and start thinking about how to improve and be better, understand that your goal is not your goal. Your goal is a vector: magnitude and direction. That’s it. It’s not the outcome. The desire for perfection is just vanity, anyway.
The Evolution of the Audit
Year after year, I’ve checked in with myself in different ways.
I’ve asked myself many questions about my goals, my health, my mindset, my financial situation, and just about everything else. I’ve also used different tools to ask myself these questions so that I can stay consistent and accountable to my efforts.
I’ve changed my tactics incrementally and in spurts over the years, and I feel like I’ve learned a lot about myself but also about the process I put myself through.
Here are some of the iterations I’ve been through.
1st Iteration - The Personality Triangle
I think I can count my first effort at auditing myself when I was about 18 or 19 years old. I didn’t want to go to college, in fact I didn’t want to participate in life in nearly any way, so I was just working a retail job and reading a lot.
I started thinking about the characters I was reading in stories, but also about who I was. Engulfed in literature and philosophy, I saw pieces of myself everywhere. Classic. The strange thing was that I felt like I wasn’t completely whole or even solid. I felt like everyone around me was a monolith and I was an odd, inconsistent, fractured glue-job. I’m not saying this was all true, but it was how the world felt. I picked up my pen.
In order to call my thoughts into clarity, I drew out three characters who I felt represented different parts of me. They contradicted each other and were at odds with each others’ values. If I was one character in a moment, it was nearly impossible to also be the another character.
I developed them by giving them values, motivations, and even names. I tried, but I couldn’t find the notebook in which I first described them, but I still think about those three characters today and how much I’ve grown. Their definitions helped me choose, consciously, who I wanted to be.
My first self-audit had no spreadsheets, no pie charts, and definitely no input from others. It was purely introspective and I’ve kept it to myself for nearly my whole life.
It looked like this:
The Baron
The Baron was a wealthy philanthropist. He was generous, resourceful, creative, and someone who could appreciate quality. The Baron’s weaknesses were emotional dependency, ego, and confusing aggression with assertiveness.
The Wraith
The Wraith was the most prominent character for me at the time, and was also the most destructive. The Wraith was an eternal contrarian, infinitely self-critical, and unfortunately, highly addictive. Since The Wraith’s strengths were obscuring reality and convincing you that being yourself was scary and there was no realistic path forward. The obvious antidotes to this character were clarity of purpose, selflessness, and exercise. The only trouble was how hard it was to see clearly enough to know what to reach out and grab.
The Chief
The Chief was probably my favorite character. He seemed like the fully self-actualized version of my potential. Wise, calm, and fair, The Chief was my North Star. I wanted to be more like him than the others. The only downside to being The Chief full-time was that he could be quickly quieted by authoritarian rule, loud voices, and trusting others to do the right thing. The tragedy here is that I knew I couldn’t be The Chief full-time and also accomplish what I wanted because of his fatal weaknesses—which still upsets me.
I didn’t realize it at the time, but this introspection was the first real self-audit I ever performed. I don’t know that I’d recommend that you start in this way, but that’s for you to decide.
What was helpful about this first iteration was that it made me realize that I actually wanted to do something with my life. It made me realize that not seeking self-actualization was about the same as rolling over and dying—and that didn’t feel like the right thing to do. I still had a little gas in the tank.
2nd Iteration - The Employee Review
By the time I’d passed through college and gotten my first “big boy job,” I was primarily interested in performance and management. After just a small taste of doing the work I wanted to do, becoming who I wanted to be, and getting some validation that I was valued on my team: I was hooked. I wanted to dial the knob all the way to 11. I made a Google Form with 2 questions on it. I then sent the form to people I’d worked with and to old friends who knew me well. I stressed to them that I’d made it anonymous because I didn’t want to make my own judgements about who saw what in me. I just wanted to look at the raw data as best I could. I repeated this, roughly annually, for several years.
The two questions I asked were:
What are my 3 biggest strengths?
What are my 3 biggest weaknesses?
What was helpful about this was that the patterns helped me validate my self-image and it gave me the opportunity to evaluate unexpected feedback. I was able to take these opinions and take them to people who knew me best and could help me interpret or dissect what might be useful.
Not only did the process show strengths and weaknesses that I could evaluate for myself, but it also required me to ask my community for help. This act was something I didn’t realize was important at the time, and showed to the people around me that I valued their perspective.
It also showed me that I cared about myself, which is a big deal when you’re a perfectionist.
3rd Iteration - Energy Audit
At some point, I started realizing how important my focus was on my career and life mission. I wanted to change education. I wanted to change kids’ lives. I wanted to make learning more fun. I wanted to make it possible for young brains to develop into amazing, productive, healthy, adult brains. I realized that the fire that burned inside me was a powerful tool that could help me put my ego aside and just focus on improving myself.
At the same time, I started thinking differently about productivity. After a conversation with a friend, it became clear that my productivity was less based on how I managed my time and more based on how I managed my energy throughout my day, week, and year. Working hard was working fine for me by itself, but I realized that I might be able to take some of the load off by balancing my work with things that gave me energy. I was less interested in managing my input and output, and I was more interested in creating a symbiosis.
Instead of asking about strengths and weaknesses, I asked myself questions like:
When do you feel the most alive?
When do you feel the most dead?
When you look back at your life, what are you afraid to regret most?
When you look back at your life, what memories will make you happiest?
(I stole these first two questions from a professor I had in high school: Mr. Ryan. It was one of the few things I took with me from my high school experience.)
Finally, in an especially hardcore and eccentric moment, I built what I called the “Death Bed Timer.” I made a rough estimate of how many days, weeks, months, and years I had left on the planet. And then I started counting down. And then I posted the timer on my website. And then I started logging my remaining number of weeks in my journal after each daily entry. I actually did this for a few years.
Here’s a screenshot of the timer from my website, back in August, 2018.
I didn’t realize it at the time, but this audit was less about the work itself and more about values. I was auditing how I spent my time, but only as it related to what I valued. This was a very, very formative iteration for me.
This was the foundation I would later use to create the work-life symbiosis I had been seeking.
4th Iteration - The Sustainable Balance
After the COVID pandemic began, I found myself in a low-stress, remote job, in a very comfortable home office. I was working with people I respected and loved, but something critical was missing. I was watching my work skills and experiences slide into a category I didn’t like: marketing. I was half-decent at it and most of the social impact companies I worked with genuinely needed help in this area—which was why I learned it—but I realized a few important things in my self-reflections:
It wasn’t a sustainable contribution for me.
It wasn’t my most uniquely valuable contribution.
Every day I kept going in this direction was making it harder to go in another direction.
This time, in my self-audit, I realized that I couldn’t just hold my foot down on the pedal and “red-line” my work engine anymore. It wasn’t healthy and I definitely couldn’t keep up the pace forever. I realized that I would regret how much of the rest of my life I’d miss, at the end, if I continued this way.
I needed to find a way to dovetail the intense purpose of my work with a sustainable effort, and also with enough fun to be able to look back and feel like I didn’t miss my own life.
So, I sat down, several times over the course of several days, and drew up some new guidance for myself. This time, I was thinking about how my work and personal life goals fit together. I think it was also probably the first time I let myself consider doing work that was easier for me, but still had high-value to others. For the first time, I wanted to carve out a life where the wind was at my back.
Here’s what I came up with:
I wrote a job description for an ideal job. I even allowed myself to have contradictory requirements in the description.
I wrote the “about us” page for a company I would be hypothetically obsessed with.
I reviewed my values. I wasn’t generating them for the first time, I was just looking over what I felt resonated with me in the past.
I chose “one big word” (A word that summarized my existence or purpose.)
I asked “Where are you holding yourself back?” (I stole this from a TEDx talk by Ashley Stahl)
I asked “When do you feel the most trapped?”
I asked “When do you feel the most freedom?
I mapped these out across several blank, unlined pieces of printer paper. They are still sitting in a box in my office, 2 years later.
What was valuable about this was finally being able to see both my life and my work on the same page. For most of us, we spend most of our life at work. Auditing the integration seems pivotal, now.
5th Iteration - The Comprehensive Self-Audit
This last iteration was one of my most pivotal for me. It forced the merger of every part of me. It brought together my unreasonable aspirations, my personal baggage, my career achievements, my values, everything.
The only trouble was that it wasn’t super coherent or replicable. It was a series of drawings, questions, and journal entries. I still needed a way to repeat the virtuous cycle so I could track my progress.
Here are some of the new questions I integrated:
What are you proud of yourself for?
When are you disappointed in yourself?
Whose life do you wish you had? Talk to them and ask yourself if you still want that life. Are you willing to do what they did?
In what part of your life do you have the most control?
In what part of your life do you have the least control?
When are you too hard on yourself?
What motivates you?
One of the other main realizations I had during this process occurred while sitting on the toilet scrolling through Instagram. If you haven’t been on Instagram lately, let me tell you what it looks like. It looks like everyone is having the time of their lives on vacation while also in the world’s best relationship.
My realization was this:
Your life doesn’t look like others because you chose this path.
I chose social-impact work in the education sector over higher-paying sales jobs. I chose to risk my own, small, personal savings and start some entrepreneurial projects. I chose to stick to my low-paying career path while getting out of debt.
I chose this path. Of course it doesn’t look like everyone else’s.
What a productive trip to the bathroom this was.
The Comprehensive Self-Audit Template
Okay, finally. Story time is over. Here it is.
The Comprehensive Self-Audit Blue Print is just the latest iteration. It’s not perfect. In fact, I know that if it doesn’t change I’ve done something catastrophically wrong. What’s cool about it is that this is the best tool I’ve seen/developed that looks at us as whole people who are balancing life, work, aspirations, disappointments, emotional baggage, and everything else.
Keep in mind that it’s the iterative process that led us here, but it’s also how you’ll use the template.
How To Use The Template:
Use the resources to set values and rituals.
Move through the cycle to iterate.
Reiterate.
The Comprehensive Self-Audit Blue Print is broken up into a few categories:
Values
These are the guiding principles that help to realign and recalibrate our actions. They are principles, rules, or whatever other parameters we feel will help us remember who we are or where we’re going. These are the most important part of the entire process. Everything else is based on these, so it’s worth the extra time to evaluate and re-evaluate them as they inevitably change as you move through life.
The goal isn’t to belabor over your values and get them “right.” Just get close. As you continue audit yourself, these will feel more and more true.
Rituals
These are the habits and thought patterns that make up the practice. They are the metal that sharpens your values and show you the truth. What we know about the human experience of life is that we live from day to day. We chip away each day and it’s only when we look back at our life that we feel how fast the years have gone.
Days are slow. Years are fast. All we can do is operate within the realm of today, so that’s where we must focus our attention and action. By setting up systems of rituals today that consistently give us space to zoom out, we afford ourselves the convenience of focusing on the present and knowing our future is being planned for.
Resources
These are the tools, documents, and templates that get the job done. Unfortunately, this is where most people feel the secret lies because these are the easiest to focus on. They’re tangible. They may even require an account or a credit card, which makes us feel like we’re really investing in something that will help. Unfortunately, we are the operators of these vehicles—so try not to worry so much about having the right tools at first. The Values and Rituals are most important. The role and value of Resources will be revealed when you are deep in the process.
Start The Process
Set Your Values
Choose: 1 Big Word. 3 Values. 6 Areas of Focus. 11 Rules.
This is the format that worked for me. If you’re just starting this process for the first time, I’d say don’t worry about the 11 Rules. Focus on the high-level stuff and work your way down the list in each iteration.
I want to be really clear about something: these are the numbers that worked for me. You may find that you need a different number of rules—but you can’t have more than one big word and you can’t have more than 3 values. Those constraints are essential to this process.
1 Big Word
This is the highest-level focus that summarizes what your life is about. Don’t worry about picking the right word. Just get close. Iterate. Reiterate.
My big word right now is: Leadership
3 Values
It’s easy to write a long list of values. Instead of thinking of all the things you value, consider this approach: every value on your list must fight for it’s life to stay on the list.
My Values have stayed the same for the last few years. Here they are:
Simplicity
Authenticity
Fun
6 Areas of Focus
Sure, you can set goals based on your values, but I’ve found that it’s more helpful to be a bit more granular. In fact, it’s easy to think of work and life as the only things competing for our time and I wanted to make sure I was accounting for the things that I loved and that give me energy.
Here are the 6 Areas of Focus that I’m using to set goals.
Career
Creativity
Relationship
Finance
Fitness
Environment
11 Rules
These are the rules I set out for myself many years ago. They’ve changed only slightly. I have these sitting on my wall in my office to remind me of the person I need to be when I make decisions.
I wrote a complete blog post detailing these already, so I won’t dive into explaining how I came up with each one. If you choose to read that old blog post, be aware that I wrote it in my old style of “rah-rah-motivation-guy” writing. You’ve been warned.
Set Your Rituals
Consider A Daily Launch Sequence Or Reflection
By starting each day the same way, we condition our brains and bodies to be ready for what we throw at it. I wrote an in-depth blog post about this years ago, which gets the point across but the routine has evolved.
Since this blog post isn’t about productivity or habits, I won’t dive into that—this ritual is designed to help you collect data about yourself. Consider it a log of whether or not you’re making space in your day for the essential.
For me, my Daily Launch Sequence is about checking off the essentials before getting lost in the day. It’s about making sure I take care of my brain and body first, so I can be set up for success.
Also, this isn’t prescriptive. You choose a “wind down” sequence instead, or in addition to something like this. This is just a framework with a bunch of ideas. This is one that’s worked for me. That’s all.
Warning: Don’t make Rituals a huge string of activities. One or two habits are plenty.
Review How You’re Allocating Your Time
I only recommend this for beginners who are just starting their journey. If you feel like you could be more clear on your values or you want to calibrate your integrity (how well your actions line up to your values), consider logging your time.
I used to do this for years and I still do it in my work—just not as much in my personal life anymore. Any timer will work. I like Toggl.
You may not need to be super strict about logging your time in an app, in fact, the more I audit myself, the more easily I’m able to realize that I’m spending more time than I want to on things that don’t matter or that aren’t serving me.
You know yourself best. You may just need to set a reminder to look back at your calendar each week or maybe you just need to set a recurring smartphone reminder that asks you how you spent your time that day. Reflection and introspection is the secret here, not meticulously tracking every minute of every day—that’s not sustainable. See the next section about using different types of reminders.
Warning: Don’t track everything. Just track high-level categories. If you can’t get to the end of your day and roughly assign what time was spent doing what activity, then you’re getting too specific.
Set Some Reminders And Micro-Checkins
There are two main types of reminders I would consider here.
Timed Reminders, which you can set up through your phone or calendar system, and Visual Reminders, which can be physically placed in your environment to keep something top of mind—like a post-it note, or the poster of the 11 Rules I mentioned above.
The only flaw with this method is that if you set up too many reminders, the system becomes overwhelming, perfectionism will start to get louder, and then you’ll start to ignore reminders and the system will break. I can’t express how important it is to start off small, here.
I promise, if you’re sitting there thinking “there’s just no way this could possibly be enough,” then you’re doing it right.
Pro-tip: Try sticking with 3-5 time reminders and 1-3 visual reminders like wall art or post-it notes. More than that will make your visual field cluttered and surely lead to burnout.
Pro-tip 2: Your calendar is not your to-do list. Don’t try to “check” things off. The purpose is to remind you to create a task to do something or it’s to remind you to think about something. Don’t ask too much of reminders.
A good example of using reminders would be as a “micro-check-in” with yourself.
This is just a quick, simple pulse check and they can easily take the form of smart phone reminders.
I currently have a reminder set on my phone that asks me, every 3 months “How are you progressing on your fitness goals? Do you need to change anything about your approach?”
This doesn’t mean I need to stop what I’m doing and re-evaluate everything. It’s just a helpful nudge that will inform my deeper reflections. The Purpose of the Micro Check-in is not to solve anything, it’s just to take your temperature.
Gift Yourself Private Space For Deep Retrospectives
These are quarterly and annual check-ins that give you the time to look at what’s working and where you have opportunities to improve your system. This is a chance for you to review your values, goals, and progress to see if you need to change your strategy or put more gas on the fire.
No value, ritual, or focus area is off-limits for assassination. Everything in your audit must fight for it’s life to stay on your list of to-dos. If it’s not serving you, stop doing it. You can always add it back later on if you discover that there was something useful about it after all. Your goal in these retrospectives is to reduce friction and audit the things that give you energy and require energy from you.
I have found that quarterly check-ins are super helpful, but only if I can contain them to 90 minutes or less.
The real magic comes when you do annual audits that look across all of your logs, notes, calendars, and focus areas. If you don’t have a space at home that is guaranteed to be free of interruptions, I suggest you invest in yourself and gift yourself your own personal retreat. Get an AirBnB cabin in the woods. Go drive to a lake and sit in the sun. Being “off-site” can sometimes be an important, refreshing factor that can put your brain in a new mindset.
Resources
The Essential Tools
Here are some tools I’ve used to help me throughout the self-audit process:
All of these things exist in my personal VAULT of resources. This is just a public Google Drive folder that I’ve been adding to for the last 15 or so years. It’s totally public and totally free, so take whatever you want from it. I made it for you.
A Physical Journal
I use this exact journal. I like these because they’re small and simple. I date each one and file it away in a box when it’s full. I have years of journals for reference at my fingertips. If you wanna be all smart and put these in a digital format, that’s cool—just do yourself a favor and don’t underestimate the value of writing by hand.
You can type faster than you can write. Writing things by hand allows your mind to think more slowly. You can choose the right words more easily and you can be free of digital distractions that interrupt your flow.
I strongly suggest doing this the old fashioned way—but do what works for you.
Final Thoughts
Set targets as aspirations, not goals.
You’ve heard the platitude “we overestimate what we can do in a year and we underestimate what we can do in 10 years,” but it’s true. We have wild ideas about what we could do or be, but we don’t know the path to making it reality. For me, the times that I’ve had success in achieving a dream have been when I follow my current curiosity.
The only path that’s been fruitful for me has been to focus on what’s right in front of me and then pause to take frequent and momentary breaks to pick my head up and see if I’m digging in the right direction—hence this audit blueprint. Sometimes there’s no way to know where curiosity, interest, or motivation will lead, so I think my new perspective is to just be present for the ride.
I didn’t come up with this idea. I heard it from someone on the internet and I can’t find the original source. I’ll post a link to it as soon as I remember where it came from.
In times of great stress, you can’t expect this system to work the same way.
Several years ago, I broke up with a romantic partner, quit my job, and moved into a new place all in the same month. I found that journaling every single day was insanely useful. I made it part of my launch sequence, which was effective because it allowed me to process the thoughts and feelings I was waking up with and put them away so I could focus on my work. This was really, really hard—but I would have been a complete mess without this outlet.
Just because something is working really well right now doesn’t mean it will continue to work when life throws something at you. I don’t journal the same way anymore because my needs have changed. This process is really just a simple, continuous evaluation of “is this working for you right now?” If not, it’s time to adapt.
Days are long, years are fast.
We live in the present, but all of our memories are in the past. This makes it easy to do what’s pleasurable right now and regret all the ways we didn’t spend our time more wisely. It means that we are flying around the sun, orbiting at a wild speed, but have no sense of pace.
These rituals and check-ins are designed to help us calibrate and see if we’re doing the things we said we would without going too far down a path we don’t like.
Kintsugi
Literally “golden joinery,” the Japanese word “Kintsugi” encourages us to embrace imperfection. When we drop a plate and it breaks, we glue the pieces back together with gold filament instead of throwing it away—making the object unique and shaped by it’s experiences.
A few years ago, one of my mentors said something very important to me that I still refer to when I feel beat up or when I feel like I can’t keep going.
I’ll close with his immutable words:
“I had an old favorite t-shirt back in the days when my wife and I were full-time rock climbers.
Years of living full-time in the elements, carrying heavy packs up approaches, stuffing hands into cracks, and never quite having enough money for great food or shelter made a gradual but fairly dramatic change to our physical appearance. We became stronger in many ways that were essential, despite the fact that there were some inevitable injuries, deformities, and damage.
In the end, we were obviously much better off than when we started. We had adapted to the struggle, and it was precisely those adaptations that allowed us to perform well at our craft.
In small writing, the t-shirt simply said:
Shaped by the pursuit.
It’s a quality that I still notice about the form of people or tools or objects that have been subject to a lot. It often brings a beauty and a purpose to what otherwise might have been considered merely ‘wear and tear.’“
-sw
Have fun. Don’t pull your hair out.
As you develop your own self-audit blueprint, remember to seek progress, not perfection.
This is your life.
Invest in the things that serve you. Audit your time but give yourself permission to be imperfect. Keep your focus but remember that energy comes in waves.
If it feels good, you’re doing it right. Obsess over what gives you energy. Watch yourself become shaped by the pursuit.
Wow. "Shaped by the pursuit." This!