Question Everything: How to Reexamine what You’re Doing

As a society, we’re asking questions. In fact, we’re questioning everything.

We’re questioning why and where we work the ways we do? Why are we educating our kids the way we are? Why do we police our communities the way we do? There’s no topic or area of life that’s off limits.

What about you? What about your life?

I’m fond of saying there’s only 50 Saturdays a year. While I understand there are more than that, the idea is to maximize every single one of them. To spend our favorite day of the week doing our favorite things, with our favorite people.

Take that one step further, I think life’s too short to do anything other than that. To be ruthless with how and with whom you spend your time. Don’t agree with me? Look up the top regrets of people who are on their deathbeds (Here’s a post on it).

As Jack Kornfield famously said, “The trouble is, you think you have time.” Here’s my take on that, “You and I have time to do whatever we want, but not enough time to waste.”

There’s a cost of waiting. The longer you wait to pursue financial priorities, the harder they are to reach. As we get older, our physical and mental capacity can be reduced, and it can become harder to make meaningful change. Bottom line- we’ve got to get started living the lives we truly want to live.

The best time to plant a tree was 30 years ago. The next best time is today. Looking at this correctly means viewing it as an opportunity to break free of the expectations of others and of society, and to begin living on your terms.

While I don’t think I’ve got everything (or anything) all the way figured out, I’m trying. And it’s that intention and pursuit which is the starting point for living the way you want. It’s my desire to help you on your path.

Here’s what we’ll cover:

First principles

Challenge the assumptions you’re living under

Rebuild the life you want

Handling resistance

The way forward

Let’s get started.

First principles

While I’m fond of questioning things, I don’t believe the truth is up for debate. First principles thinking seeks to get down to fundamental truths.

Wikipedia defines it as a basic proposition or assumption that cannot be deduced from any other proposition or assumption. Again, it’s what is true.

When Elon Musk decides he wants to create a new industry, or disrupt an existing one, he uses first principles thinking. Instead of taking cues from existing car companies or rocket manufacturers, he looked at the problem in a new way. This helped him avoid getting caught up in existing assumptions and limiting systems. Whatever you think of Mr. Musk, he certainly gets things done.

What assumptions and systems are you subject to?

Challenge the assumptions you’re living under

Do this, don’t do that. You can’t, you shouldn’t. Think this way, don’t think that way. Whose life are you living? On whose terms are you living them?

Hopefully, you don’t feel like your entire life is like this, but I’ve met plenty of people who do. What’s happening in your life that you don’t like? That you’re sick of? Are you spending your most important resources, your time, attention and money, on things you don’t want to be? On things you don’t like?

The systems you’re living in and the assumptions that you may be living under, are unique to you. That being said, we all feel pressure in these six key areas of life:

Family
Community
Money and career
Personal development
Wellbeing
Peace of mind

In each of these areas, I want to talk about applicable first principles and common assumptions. Once we’ve done that, we’ll talk about breaking free of them and building the life you truly want.

Family first principles

Love unconditionally
Show up for one another
Provide safety and security
Respect one another’s autonomy
Always have their backs
Listen to one another
Respect thoughts and feelings

Family assumptions

You need to get married
You don’t get divorced
You need to start a family
You need to live here
You need to spend time with X
You need to be straight
We vote this way
You need to vacation here
We have family dinner on Sundays

Community first principles

Be a good neighbor
Clean up your own yard
Do unto others as you’d have done unto you
Be kind
Respect others
Be an active member
Be supportive

Community assumptions

Keep up with the Jones’
Live in this neighborhood
Have this kind of house
Belong to this club
Drive this car
Go to these places
Dress a certain way
Do this, don’t do that

Money and career first principles

Spend less than you make
Don’t run out of money
Maximize your income
Pay yourself first
Play for emergencies/stay insured
Build your credit
Save for retirement
Risks requires a reward
Money has time value
Market prices are generally right
Don’t borrow what you can’t repay

Money and career assumptions

This is what we spend money on, this is what we don’t
This is the career we have
This is how we invest
We take risk, we don’t
We don’t change jobs
We start our own businesses

Personal development first principles

Be a lifelong learner
Become an expert
A curious mind is a healthy mind
Make up your own mind

Personal development assumptions

Don’t waste your time on X
Courses are a waste of money
You only need to know one language
You’re fine the way you are

Wellbeing first principles

Eat healthy food
Exercise consistently
Be mindful of your mental state
Be intentional

Wellbeing assumptions

Be vegan/vegetarian/carnivore
Drink/don’t drink
Drugs/don’t do drugs
Run marathons/do yoga
Meditation is woo woo

Peace of mind first principles

We’re all unified by our impulse to find happiness
Know yourself
Consider what makes a happy life
Do the things that bring you peace
Pursue contentment

Peace of mind assumptions

You’re a Catholic/Muslim/Etc
We go to church every sunday
We pray before meals

Now, it’s time to think about how you’d like each of those six areas to look. Specifically, I’d like you to focus on how you’ll spend your three most valuable resources: time, attention and money.

Rebuild the life you want

The only way to live how you want, is to know how you want to live. With that in mind, it’s imperative you get crystal clear on what you want. In service of doing that, please access our Goals course, it’s free.

For each of the six areas, spend time thinking and writing about how an ideal life will look.

Family