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Question Everything: How to Reexamine what You’re Doing

George Grombacher June 23, 2022

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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.




How will you spend your time, attention and money?




How will you spend your time, attention and money?


Money and career


How will you spend your time, attention and money?


Personal development


How will you spend your time, attention and money?




How will you spend your time, attention and money?


Peace of mind


How will you spend your time, attention and money?


Focusing on how you allocate those three resources will help you to get a better sense of what’s most important to you, and what you can live without. 


Inevitably, when making big changes, we’re going to encounter resistance. This resistance will come from inside ourselves, as well as external sources. 


Handling resistance


Knowing it’s coming will help us successfully navigate it. 


Internally, you’ll be fearful of some of the changes you want to make. This is our body’s normal response, because our brains want to keep us safe. When we depart from our regular and predictable patterns, we’ll feel pulled back to the way things were. 


You may also require new learning in order to implement the changes you’re looking for. If you’re trying to lose weight, you may need to learn about nutrition and fitness. In each area that requires new learning, where will you find it? What resources are available to you, and when will you get them?


And then there’s the external resistance. Family, friends and people in your community will notice your changing. Some will be supportive, and others will not be. For the most part, people want you to be happy and to succeed, so they’re probably just looking out for you.


Take their resistance with a grain of salt. 

You’ve questioned everything. You’ve made the decision to make substantive changes and to pursue the life you want. Shut out the chatter, move through the resistance, and get to work. 


The way forward


It’s one step at a time. Like all things worthwhile, it will be difficult to make this happen. But it’s worth it. 


Also, don’t throw the baby out with the bathwater. I’m confident there are many aspects of your life which are wonderful, and you should leave those as they are. 


For those areas you’re going to change, give yourself patience and grace to pursue them. You’ll slip up, back slide, and make mistakes. Get some sleep, wake up early and try again tomorrow. 


If you’d like to kickstart your transformation, I welcome you to enroll in our Strive Online Bootcamp. It’s a two-week program to detox your mind, body and money. It could be just what you’re looking for. 


You’re someone who can have the life they want, let’s go!


We’ve got three free courses as well: Our Goals Course, Values Course, and our Get Out of Debt course. 


Connect with one of our Certified Partners to get any question answered. 


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