Asking Better Questions To Live A Happier, Healthier Life

The self-improvement industry is built upon rules to live by.

Do this…don’t do that…gets old quick.

I’ve always bristled at rules…unless of course I’ve made them up myself.

There’s an insane number of rules written in thousands of self-improvement books sitting on thousands of shelves that go unheeded. Some are good, some are not, but in most cases we don’t pay attention because we generally don’t like being told what to do…even when it’s good for us.

If you have children, you’ve definitely seen this in action. You can tell your son or daughter to do or not do something a thousand times. Then one day they discover the key to solving their problem is precisely through following your instructions…but that’s not how they see it.

They had to discover it for themselves and maybe you’ll get a token of gratitude when they drunkenly toast you for all your “help and support” at their wedding that you paid for. Insolent little shits!

We’re no different. As a physician, a consultant, a CEO, and a coach I’ve been in the business of giving people advice for over 20 years, and I’ll let you in on a little secret.

Advice, even good advice, is rarely followed.

Again, most people just don’t like being told what to do and much less what to think…at least not consciously.

This is where having an arsenal of good questions can be a game changer.

Whether you’re trying to improve your own life, that of your coworkers, or that of your family, one good question can accomplish more than a 2-hour powerpoint presentation about how they’re doing it wrong.

I’ve heard it said many times from thinkers I respect like Derek Sivers, Tim Ferriss, Naval Ravikant, Seth Godin and others that the key to finding good solutions to our problems is through asking better questions.

I believe the reason for this is that questions are interactive where rules are often unilateral and by their nature demand strict adherence to justify their existence.

A rule can even take on a life of its own. You've seen it. Workplaces, political systems, local governments, homeowners associations, and even our own brains have rules that exist simply to perpetuate their own existence.

Think on that for a moment...

Rules are exclusive and static while questions are interactive and dynamic.

Life is complex and constantly changing, so the systems we use to make sense of and navigate life should be also adaptive and dynamic.

Realistically we can’t live without rules. In fact, our brain is making them unconsciously all the time, but we can improve the rule making process and build better, more adaptive rules.

One way to do this is through intentionally constructing and asking ourselves better questions.

Where a static rule usually gives us a specific course of action toward one outcome, a good question gives us the vantage to see a problem through multiple angles. We can then apply our best effort along the most viable course toward the most favorable outcome.

Here are few examples of a some of my favorite questions

1. What am I not seeing or unwilling to see about this situation?

We are hobbled by our own historical, intellectual and emotional biases. The person who’s capable of getting a foothold over their own biases is one step closer to developing the superpower of clear insight.

We suffer from our biases for two reasons:

First, we’re often unaware of them and keep stubbing our toe on the same stupid brick over and over because it’s just outside our visual or perceptual fields.

Second, we’re unwilling to take the time to simply crouch down and move the thing out of our way.

Asking ourselves what we’re not seeing, or even better, unwilling to see about a certain situation, is powerful. It makes us slow down, expand the scope of our vision, and gives us the ability to take some action toward a different path.

It’s one thing to illuminate something we were unconscious of. It’s another thing entirely to be unwilling to see it, and to then intentionally bring it into the light for examination. This takes courage in addition to a masochistic type of curiosity…but it is very effective!

I believe essential questions like this are the seeds for authentic self-actualization. They can help us turn off the autopilot that’s flying us down the same unfulfilling and unproductive flight paths.

2. Am I more focused on the process or the accomplishment right now?

We’ve all heard it before…be present…the power of now…etc. Repeating to myself “be here now” is rarely helpful, especially when I really need to focus on the task at hand.

I’ve noticed that when I look back at something I’ve done and I’m not completely happy with the quality of the outcome, I was usually rushing toward the end goal.

My dad’s voice in my head telling me “if you’re going to do something, then do it right the first time” still gives me an itchy middle finger.

But, when I notice I’m rushing through something or having problems keeping focused or motivated, I’ll simply ask myself “am I more focused on the process or the accomplishment right now?”

If I’m struggling to complete a task or am unhappy with the result, I’m usually focused on just getting the thing done rather than actually doing it.

Take writing for example.

There are times I love to write and times I simply loathe it. The main difference between the times when writing puts me in a state of flow and times when I’d rather be organizing my sock drawer is how invested I am in the process.

When I take each idea as something to spend time with, and the process of writing as a way to help me think more clearly about that idea, I deeply enjoy it.

When I give myself an arbitrary deadline or a goal like “write 2000 words per day,” I’d rather dig holes in the frozen ground in my backyard; at least then I’d be getting some exercise.

For me, sitting in one place and writing can be an onerous chore or it can be the very thing that unlocks my creativity and helps me sharpen my thinking process. It all depends on my approach.

When I sit down to write, I remind myself to give each thought its due and to revise one sentence or paragraph as many times as necessary until it fully clicks.

Then I move from one "click" to the next, and before I know it, I’ve completed the project and feel a sense of fulfillment with how I’ve spent my time.

The feedback I get from my readers is also reflected in whether or not I was invested in the process or simply trying to put something out there.

Another question I use to connect me to the process is simply asking “what’s happening right now?” I use that as a trigger to recalibrate my efforts toward a process-based focus instead of an outcomes-based focus. Simply asking "what's happening?" takes me off autopilot so I can have more agency and choice with where I put my attention and effort.

Becoming A Question Alchemist By Stacking Questions

I use the questions above almost every day, especially when I’m tackling hard problems. I also use them when I'm midway through a long and challenging project and want to prevent attentional attrition.

To really maximize the effectiveness of this process you can stack multiple questions together which can provide even better breadth and depth of insight.

For example, once I’ve finished a process-oriented writing period, I usually take a short break before I return to re-read and revise it. As I go through the document, I’m looking to see that each idea makes sense, is clearly written, grammatically correct, and flows within the context of the piece.

Once I’ve made all the obvious changes and if the piece still doesn’t completely click, I’ll take another short break and then ask myself…”ok what am I not seeing or willing to see here?”

Then I reread the piece, looking for the unknown factors that keep the document as a whole from feeling right.

I imagine this is what professional painters and musicians do. They sit with their art, attentive and curious, tinkering here and there until it all comes together.

Aside from my writing, I try to do this for all the other areas of my life that really matter.

The result has been that when I’m truly attentive to my life, it feels so much more open and full of possibilities.

It’s like walking into a dusty old log cabin in the springtime; throwing open all the doors and windows, and inviting the light and fresh air to breathe new life into the room.

Good questions can do this.

They can push you off the treadmill you’ve been stuck on and reinvigorate your career, your relationships, your art, and your life in general. One good question can change your life.

As a “rule,” if it’s worth doing, it’s worth asking the right questions.

What are your good questions?