The Philosophy That Changed My Life (How To Improve At Anything You Can Measure)

Tough reality: everyone has aspirations, but hardly anyone achieves them. Adopt the data-driven mentality that separates the top 1% from the rest.

I’ll tell you the kind of math I use every day, every hour of the day. If you don’t have this, you’re never going to be successful in business, politics or life.

— Michael Saylor

Everyone wants to lead a better life.

One full of health and well-being, financial stability, and meaningful relationships.

Yet the vast majority of people fail to live up to their aspirations.

The average person fails to solve their own problems, reliving them in perpetuity.

They fester in their discontent, neglecting the mental framework needed to break free.

Most people think of data and statistics as just a career path — not a way of thinking.

The data landscape is rife with educators focused solely on technical instruction and job interview advice.

They fail to communicate the value of a statistician’s frame of mind.

Data is a philosophy.

Data literacy provides a mental model applicable to EVERY facet of life.

I know from experience this is true.

I’ve always understood the usefulness of data from a high-level.

But it wasn’t until I studied the subject in graduate school that my worldview changed.

I realized the principles inside the textbooks could lead me to the life that I wanted.

I've since experienced a personal renaissance throughout my:

• Health and fitness

• Financial literacy & business acumen

• Personal relationships

• Mental health

• Societal views

I'm unrecognizable from my high school and college self.

But you don't need an advanced degree to yield these results.

The data-driven philosophy of Track > Synthesize > Iterate allows anyone to do the same.

Principle #1: Track

Data Modeling

Imagine if the map at your favorite amusement park lacked the “You Are Here” label.

Unless you're a seasoned pro, you’d have trouble figuring out your current location amongst the huge number of attractions.

You would have to collect data in the form of surrounding ride names, food stands, and gift shops to discern this.

Data is the way you model the world around you.

It is a vehicle for becoming objectively aware of your present state.

You want this model to reflect the indisputable realities of the world.

Once you have an unbiased view of where you stand, you can begin to set goals.

You can set a goal for any conceivable metric in your life.

Your intention is to create awareness of the gap between your present state and your goals — where are you now compared to where you want to be?

You want to leverage your data to diminish this gap over time.

But you need your data to be solid as bedrock.

Data is a double-edged sword.

While it can accurately model reality, it can also be responsible for its distortion.

Flaws can mislead you, resulting in wasted time, money, and effort.

Defective data is worse than none at all.

So how can you ensure the data you collect is fit for use?

Create a personal database.

A well-managed database emphasizes:

• Relevance - ensures data is relevant to your desired outcome

• Retention - solves recency & storage capacity constraints

• Organization - creates data integrity through structured & consistent storage practices

Here's an in-depth explanation of each of these standards and how you can align them with your own database usage:

1) Relevance

To garner insights from our data over time, the data you collect must be relevant.

Data is relevant when it has clear correlation to your desired outcome.

Tracking irrelevant data only serves to create clutter, wasting valuable time and storage space.

So how do you determine if the metrics you've collected are relevant to your desired outcome?

When you first start collecting data, the answer is simple.

You'll have to make an educated guess.

At the start, the amount of data you’ve collected (your sample size) will be small.

You won't be able to conclude which factors are significant to your success.

But as time passes, the size of your database will grow.

You'll be able to identify the building blocks of your success and discard the junk.

Statistics teaches us how to do this through empirical evidence.

You'll learn more in Principle #2: Synthesize.

2) Retention

Good things take time.

Often years.

You'll have to track your results throughout this entire duration.

This is impossible without a database.

A database can store context in perpetuity — to a degree that your brain can't.

Sole reliance on your brain to retain information is a losing strategy.

Your memory of events (your data) will decay over time.

Forgotten data is useless data.

Often times, a device or service will document data for you automatically:

• Fitness trackers

• Personal finance applications

• Smart appliances

But when you don't have these conveniences, data entry can be manual and impractical.

You'll have to devote time to inputting your memory of events into the database.

But sometimes life gets in the way — you might not be able to do data entry at the moment.

To avoid forgetting information, you'll need to develop systems for recording data promptly.

Assume you want to improve your social skills.

Nobody wants to be the person typing into a spreadsheet at a bar.

You'll detriment your goal by breaking up conversation instead of extending it.

Despite losing nuance, initially storing feedback as mental notes works best in social settings.

You can then convert your mental notes into data stored in your formal database when you return home that night.

As long as you have systems in place to ensure you record data in a timely manner, you'll be able to prevent loss of data quality.

3) Organization

As you collect data relevant to your goals, you must prioritize organization.

Failure to properly organize the data will hinder future analysis and make your life hell.

So how do you structure the data into schemas to ensure easy interaction later?

The format of your database will depend on the nature of the data you're tracking.

Most people already have experience with the top data models for personal improvement:

• Spreadsheet - tracking your daily macronutrient intake

• Document - daily journal entries

• Checklist - grocery store necessities

Luckily, these simplistic and sustainable models are often more than enough for personal data.

You don't need to be an expert at data modeling to build a quality database.

However, you will often use a data-driven approach to pursue many goals at the same time.

This requires you to manage multiple data models simultaneously, adding complexity.

To solve this, you can store your data models within a all-in-one environment.

Some of the most popular solutions include:

• Notion

• Evernote

• Google Workspace (Docs, Sheets, Keep)

• Microsoft Office (Word, Excel, OneNote)

• Apple iWork (Page, Numbers, Reminders)

Regardless of your platform choice, storing the various schemas you create under a single umbrella will streamline your database management system.

Over time, utilizing your database to document your life will become second-nature.

Through a conscious routine of continuous observation, you'll accumulate relevant data that represents your present state.

However, merely possessing data does not translate to an understanding of it.

Without proper interpretation, the data you've worked hard to ensure the quality of is rendered useless.

So how can you interpret the data that you've collected?

Further, where do you go from that interpretation?

How do you know what the first step toward your ideal life should be?

You'll learn these frameworks in the next section: Synthesize.

Principle #2: Synthesize

Regression

The second stage of creating value from data involves the combination of analysis & strategy.

As you create your game plan, you'll want to conduct your analysis and strategic planning in a specific order.

Your analysis should be performed first, while your strategy should be based off your findings.

The awareness you'll gain from analysis empowers you to form your strategy around the most influential factors.

You'll be able to fixate on the details in your life that empirically drive the results you want.

Regression teaches you the correct mental framework for analysis.

You must question your most deeply rooted assumptions and view your data objectively.

The quality of your analysis is only as good as your ability to properly interpret the data.

When building your database, you created standards to ensure the underlying data was solid.

Now you'll need to ensure that your interpretation of the data is sound.

It ain’t what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so. — Mark Twain

Data can only maintain its objectivity if you don't introduce preconceived notions and biases.

As you analyze the data, you need to separate personal beliefs from empirical evidence.

Consider an overweight person tracking data related to their weight loss journey.

Their goal is to lose 20 pounds within three months.

They diligently track their daily exercise routine, calorie intake, and weight fluctuations.

But as the weeks progress, this person isn't losing any weight.

Despite "following" their exercise plan and calorie-restricted diet, there's been no progress.

In this scenario, the average person will become biased towards the data they've tracked.

They won't accept that they've remained stagnant despite the effort they've put in.

They'll gravitate toward the days where they perfectly followed their diet and exercise regimen.

Yet ignore their overeating and the workouts they skipped.

They'll try to explain away their lack of progress through water retention, muscle gain, or fluctuations in metabolism.

Most people will tell themselves anything to blunt the truth — most people aren't successful.

Failing to be objective about your present state doesn't do you any good.

Remove the excuses, cop-outs, and biases.

It's only then you unlock the benefits that proper analysis provides:

• Relevance - validation of whether the data you're collecting is relevant to your desired outcome

• Granularity - determine the relative importance of each behavior to your desired outcome

• Trajectory - quantify your improvement and see if you're moving in the right direction

Important:

If you haven't yet taken any action toward your goals, you'll only receive two of these insights.

You'll be able to better understand the relevance/granularity of your behaviors.

But there is no improvement without action — thus no ability to determine your trajectory.

You're now aware of your present state.

But where do you go from there?

How do you actually decide what actions to take toward your goals?

Bayesian Priors

Take a second mental visit to your favorite amusement park.

The map at the kiosk is now too faded to read.

It's impossible to discern the shortest path to your destination.

There are seemingly infinite roads to take — many of which may lead you even further away.

So what should you consider before choosing one?

Start with prior knowledge.

Prior knowledge comes from two data sources:

• The experience of others

• Your own experience

But you shouldn't treat these two data sources with equal weighting.

Step-by-step advice from the experience of others is often appealing.

In the absence of clear direction, people crave the clarity that guidance offers them.

But this luster only exists on the surface.

There is no guarantee this advice will work for you.

The variation in how success is achieved negates the ability to prescribe a cookie-cutter approach.

• Two people eating the same foods may illicit radically different responses.

• Two people seeking the same financial standing may require contradictory wealth management strategies.

• Two people seeking to build a stronger relationship may be advised to spend either more or less time with each other.

This means some advice may be broadly applicable to you, but some may not be.

So how do you avoid being lost in a sea of clashing advice?

How do you separate signal from the noise?

There is only one true way of knowing what actions precede your success — you must experience success and evaluate what got you there.

Personal experiences are inherently applicable and tailored to your unique situation.

This is why adhering to what has worked in the past produces the highest success rate.

You already know it works for YOU.

Nonetheless, you'll often find yourself without prior knowledge.

In life, you'll inevitably develop interest in new pursuits — ones where you are devoid of any prior knowledge at all:

• Learning a new skill

• Traveling outside of your home country

• Your first love

What should you do when you have no prior knowledge to build off of?

Seek it out.

The internet is a vast repository of data available for anyone to leverage.

You can build your knowledge from the ground up using the information that lives there:

• Articles

• Podcasts

• Videos

• eBooks

• Databases

But these are ALL external sources.

As we know, they aren't directly relevant to your own life circumstances.

We need a system to assess the relative validity of their claims.

What is the likelihood what they say will work for me?

Probability & Significance

Almost nothing in life is a guarantee.

There is always a risk things don't play out in your favor.

A probabilistic mindset can help you minimize that risk.

There is a reason intelligent gamblers choose blackjack over slot machines.

They can weigh potential outcomes and their likelihoods to take intelligent action.

A probabilistic mindset allows you to perform scenario analysis when making decisions in life:

• What are the odds a certain event happens?

• What is the outcome if the event happens? What if it doesn't?

• How can I best position myself to succeed across all possible outcomes?

Chances are (no pun intended) you're already using probabilistic reasoning without realizing it:

• What are the odds of rain tonight? Should I wear my coat out later?

• Is it likely there is traffic at this hour? Should take a different route?

Implementing a conscious pattern of probabilistic thinking as you pursue your aspirations is a catalyst for better decision-making on the topics that matter to you.

The concept of significance should be equally connected to your decision-making process.

For billionaire Michael Saylor, the real-world benefit of statistics can be boiled down to the capability of “understanding how significant the thing someone is telling you is.”

In statistics, the significance level is a probability threshold — anything below it is rejected.

You can apply this concept to your online search for knowledge on where to start your journey.

How confident are you that the ideas you're sifting through are beneficial to you?

By creating standards for the advice you encounter, you create your own idea filtration system.

Here are the benchmarks that have helped me separate the highest quality ideas from the rest:

• Consensus - high success rate by others, testimonials & research supports validity of advice

• Personal Context & Intuition - advice aligns with personal situation, resonates with you

• Logical Reasoning - the advice makes logical sense to you

It is important to note that these guidelines aren't mutually exclusive.

You don't have to check every box before being allowed to implement advice into your life.

For example, if an argument makes logical sense to you but isn't the consensus view, this doesn't mean you should discard it.

In fact, much of the advice that will lead you to success is NOT part of the consensus view.

Instead, take note of the advice in your database and mull over how it fits into your action plan.

Over time, you'll build up a vast repository of potentially actionable advice.

Alongside analysis of your present state, your repository will form the basis of your strategy.

Principle #3: Iterate

A second Mark Twain quote:

Continuous improvement is better than delayed perfection.

Machine Learning

Up to this point, you've completed the following steps:

• Collected & analyzed your data, giving you an objective view of your present state

• Utilized your knowledge to help you plan the strategic first step toward your goals

You've constructed the best blueprint to achieve your aspirations you know how to create.

Now execute on your plan of action.

Put the behaviors you believe will benefit you into practice.

Continue to track your performance over the following days, weeks, months, and years.

Once your sample size is large enough, there's only one thing left to do.

Iterate.

Evaluate your new present state.

Analyze whether your new behaviors have improved your outcome.

Conduct research to inform your decision-making.

Synthesize your analysis and research to upgrade your strategy.

Implement your findings into your daily life.

Repeat.

Repetition is key — taking a single step in the right direction isn't enough.

It's virtually guaranteed you won't have the optimal model from the get go.

Usually, you'll be laughably far off.

It doesn't matter.

Failure is an essential part of actualizing your aspirations — it's counterintuitive, but it's true.

You'll often implement advice that doesn't benefit you and even slows you down.

Yet, your failures will also reveal insights that will 10x your rate of progress.

You have to risk taking a step backward to take two steps forward.

Create a feedback mechanism fueled by your failures.

The lessons you learn will enhance your knowledge base, and allow you to update your beliefs in light of new empirical evidence.

You can focus on course correction from there.

Once you’ve taken your first step toward your goals, you immediately gain personal experience (the most powerful prior) you can use to iterate further:

• Are the metrics you're tracking able to reliably predict your desired outcome?

  • No? Research which metrics would be more lucrative to track.

• Are you channeling the majority of your energy into the aspects that truly drive results?

  • No? Work on distributing more of your time and effort toward those areas.

• Is your current strategy yielding positive results?

  • No? Ensure your sample size is large enough, reevaluate your interpretation of the data, devote more energy to your research, and determine if you need to pivot toward a new strategy.

Even if the answer to the above questions is yes, you shouldn't stop there.

Finding success on your first try is possible, but isn't likely the highest form you'll experience.

Ask yourself:

• How can I systematize the actions that have led to me to my initial success?

• How can I remove the challenges or obstacles I encountered along the way?

• How can I allocate my resources (time, energy, finances) more efficiently across all my aspirations?

No man ever steps in the same river twice, for it's not the same river and he's not the same man. — Heraclitus

Much like a river, the entropy of life ensures the landscape you pursue your goals in will change over time.

These changes are largely out of your control.

Economic downturns, technological advancements, and other black swan events all contribute to the dynamic nature of your environment.

They produce new challenges, opportunities, and uncertainties you must address as you pursue your ideal life.

But the evolution of a person is different.

You can control the degree to which you grow.

You can will your aspirations into fruition by adapting your strategies to the changing context.

Or you can stay stagnant, passively hoping your ideal life will materialize.

At the end of your lifetime you'll remain the same person, except for one realization:

Standing still gets you nowhere.

Until next time.

— Landon