The Power of Questions

When it comes to getting the life, career, and financial independence you desire, one of the most effective tools you have at your disposal is understanding and internalizing what I call the power of questions.  Combined with a checklist, asking the right questions can help you evaluate where you are, introspectively examine your own heart so you can better understand where you would like to go, and gain some degree of objectivity in evaluating your progress on that journey, making course corrections as necessary.

I touched on this back in 2019 on my 37th birthday when I shared three questions that I have used for a long time to guide my plans and behaviors. If someone young wanted to emulate my success, there are few more important articles on this blog. Another post in this same school of thought, and almost as important, is The Power of Intention from 2017 in which I gave actual examples of questions I use when crafting my own plans and strategies, both business and personal. If you haven’t read either, I recommend starting there before proceeding.

The “Designing Your Life” Questions

The first, and most important, question you should ask yourself when you are thinking about the bigger picture of your life is, “What do I want?”.

This question is important because it serves to clarify your desires and acts as a defense against the sad fate of a majority of people in this world who go through life, carried from birth to the grave on waves of inertia, never truly choosing their destiny.  In many cases, they reject, through inaction, passivity, or negligence, the opportunity to grow into, and become, their best, whole, most authentic selves.  Sometimes, this rejection is the by-product of ignorance; of never truly understanding there are alternatives and different ways of living due to a lack of exposure.  In other cases, this rejection is the by-product of fear, peer pressure (social proof), or incentives; sacrificing the chance to live in true happiness and harmony for the cheapness of the mediocre but familiar and comfortable. Society has insidious ways of forcing compliance.

The best way to figure out what you want is to sit silently, with no distractions, and run through two checklists, envisioning your ideal life.  At this stage, you should not be concerned with trade-off decisions – e.g., your current situation, income, time limits … none of that should matter.  You’re trying to get a picture to develop of what you want, not what you think you can have.

The List of Positive Questions (Checklist A)

• What does my best life look like?
• How do I spend my time?
• With whom do I spend it?
• How do I generate an income?
• What level of income do I generate?
• What does my ideal family situation look like?
  • Am I married?  If so, to what kind of person?  Man or woman?  My age?  Personality?  What is the relationship dynamic?
  • Do we have kids?  If so, how many?
• What skill sets am I developing or improving?
• What task, project, goal, circumstance, or situation am I working on improving and/or achieving?
  • What am I hoping to accomplish through this effort?
• What are the aesthetics of my personal and professional life?
  • What is my style (clothing, automobile, shoes, haircut, etc.)?
  • What does my home look like?
  • What does my work environment look like?

The List of Negative Questions (Checklist B)

• How do I refuse to spend my time?
• With whom do I refuse to spend it?
• What types of ways to generate an income would cause me unhappiness or dissatisfaction?
• What type of family situation would cause me deep unhappiness or provide no utility?
  • Am I married?  If so, to what kind of person?  Man or woman?  My age?  Personality?  What is the relationship dynamic?
  • Do we have kids?  If so, how many?
• What skill sets am I developing or improving?
• What task, project, goal, circumstance, or situation am I working on improving and/or achieving?
  • What am I hoping to accomplish through this effort?  (In other words, referencing a post linked in the introduction, what is the intention?)
• What are the aesthetics of my personal and professional life?
  • What do I not want my style to be (clothing, automobile, shoes, haircut, etc.)?
  • What sort of home do I not desire?
  • What kind of work environment do I want to avoid?

As the image develops, it is also important to ask yourself a question we’ve discussed many times over the years: “Is this something I actually want, or is this something I think I should want because that is what has been modeled for me by my parents, friends, co-workers, society, institutions, etc.?”  If you’re not careful, it can be easy to fill in predetermined scripts that you picked up in the past.  If you don’t know an answer, be honest with yourself and say, “I’m not sure, yet.”  This is a process, like perfecting and reducing a sauce when cooking.  It doesn’t happen instantaneously.  It requires attention, care, and refinement.

The “What Could Go Wrong” Questions

After gaining clarity on the first group, the next category of questions I like to answer and revisit from time to time include those designed to identify things that, to the extent you can control them in an uncertain world, might lead to higher probabilities of catastrophe or wipe-out risk. Those wipe-out risks can involve finances, reputation, relationships, injury, or death.

This is essentially working the problem backwards. For example, if one of your goals is to build an extreme multi-generational fortune that sets your family up for the next 50 to 100 years, time is one of the most powerful ingredients in the compounding calculation. Therefore, simply living as long as you can to protect the money is key. (Consider arguably the most famous investing duo of all time: If Warren Buffett or Charlie Munger had died at, say, 50 or 60 years old, besides their friends, family, and colleagues, they would predominately be remembered by financial geeks. Most of the money they amassed in their lifetime happened in those later decades; their late 70s, 80s, and 90s.) To figure out how to live a long time, first identify the things that might make you fail at that goal:

• Being chronically under-slept leading to more rapid aging and mental decline over time.
• Being morbidly obese.
• Living a sedentary lifestyle.
• Heavily smoking tobacco, drinking alcohol, or using drugs. This can include even drugs that are otherwise not as harmful at first glance. For example, it is one thing for a 70+ year old woman to take THC. It is insane for any biological male (XY karyotype) under the age of 25 to do so because there is a non-zero chance the exposure sets off a series of changes that trigger schizophrenia which otherwise might never have been activated. In other cases, for those who likely would have developed it, anyway, certain varieties can accelerate the onset of symptoms by three years. This is especially true if there is any family history of psychiatric conditions or disorders.
• Frequently finding yourself in the social vicinity of violent people or those engaged in criminal activity.
• Flying or being a passenger in single-engine planes.
• Skydiving.
• Cave diving.
• BASE jumping.
• Backcountry skiing.
• Riding a motorcycle at high speeds, especially without a helmet.

You get the idea. It should go without saying that you might not succeed at all of these all of the time. The point is to use them as a north star to guide your way. Also, if your passion is skydiving, it is what it is. Life is meant to be enjoyed. The point: You have to accept that there is a significant potential trade-off and arrange your affairs accordingly. Identify the risks and exclude those that are not offering you commensurate benefit or pleasure as they fall into the category of “non-compensated risks” that I tell you to avoid at all costs if possible.

Another example of applying the “What Could Go Wrong?” questions involves starting a business. One of the best ways to succeed is to identify all the common ways businesses in your industry fail, then work to not do those things. For a lot of companies, failure comes from not building a sales organization that is supported and drives the growth pipeline. For most, it is basic execution. If you start a hamburger chain, you can’t be serving cold french fries. If you provide a plumbing service, you can’t show up two hours late to every appointment. (Absolutely, you can flip this around, too, and identify the things successful businesses do. That seems to be the approach many folks take and every bit helps. In my case, I’ve found that if the business model is right, success takes care of itself. It’s the pitfalls and disasters against which you need to mitigate.)

The “What Are My Implicit Assumptions?” Question

One of the most important questions I run in nearly every process I undertake is, “What are my implicit assumptions?”. I take time to explicitly identify them; to state the things that I am taking for granted so I can acknowledge where a blind spot might be. Interest rates. Inflation. Tax rates. Picture your life in fifteen years. Do the math: Who is likely to not still be alive? Things won’t look like they do now. Think about the processes running below the surface. So many things go unspoken and exert staggering pull on the direction of our lives when they may or may not be true. Force them into the light and decide how much weight to give them. Life can be remarkably ordinary, but sometimes it gets very strange, very quickly.

I Cannot Emphasize Enough How This Framework Is Foundational to Everything I Do

All day, every day, I essentially read, synthesize information, and ask questions. Questions let me test the boundaries of my thinking. They let me assess probabilities. It would be impossible to estimate how many times a year I think or say, “What if … [insert test condition here]?”. I sometimes think of questions like a chisel on marble. Each bit, you chip away to reveal the answer. You go at it from different angles. A form emerges, not quite in focus at first but becoming a bit clearer.

Wake up every day and ask yourself, “What are the two or three things I’d like to accomplish before the sun sets?”. Take out a pen and paper and ask yourself, “What things in my life are causing me the most stress, anxiety, or apprehension?”. Identify them. Then follow up, “What is the worst that happens if each manifests?” and “How can I eliminate or, at least, mitigate the blast damage radius if that worst comes to pass?”. Over and over just attack it. Questions are the key. “Why?”, “Why not?”, “Why not me?”.