8-ish Questions That Make Me Pause

The instinct is to look for answers, but the truth is that questions that teach us most. It can also be that the rhetorical questions—the ones that don’t even seem to have answers—that push and push the hardest. Who do you think you are? What does all this mean? Why? Why? Why?

The right question at the right time can change the course of a life, can still a turbulent mind, or heal an angry heart. While every situation can generate its own, there are twelve questions, I think, that deserve to be asked not just once but many times over the course of a lifetime, some even many times over the course of the day. I have gathered them from some of the wisest and most incisive thinkers, greatest leaders and most awesome badasses that ever lived.  I question whether I really know the answer to any of them, but I can say there is value in letting them challenge you. If you let them. If you let them do their work on you—and let them change you.  It has for me.

Start now by asking:

Who Do You Spend Time With? 

Philosophers would say “Tell me who you spend time with and I will tell you who you are.” Who we know and what we do that influences more than any other factor, who we will become. Because what you do puts you around people, and the people you’re around affects what you do.

Think about your friends and colleagues: do they inspire you, validate you, create unnecessary stress or drag you down? We seem to understand that a young kid who spends time with kids who don’t want to go anywhere in life, probably isn’t going to go anywhere in life.

What we understand less is that an adult who spends time with other adults who tolerate crappy jobs, or unhappy/unhealthy lifestyles is going to find themselves making similar choices.  Or those with who you are always having to validate and reaffirm, versus share in the confidence that the relationship doesn’t change just because something changes. 

Same goes for what you read, what you watch, what you think about. Your life comes to resemble its environment – it is the proximity effect.  So choose your surroundings wisely.

Is This In My Control? 

Stoic philosophers would say that the chief task of the person is to make the distinction between what is in their control and what is not—what is up to us and what is not up to us?

We waste incredible amounts of time on the latter and leave so many opportunities on the table by mislabeling the former. Our actions, our thoughts, our feelings, these are up to us.  Other people, the weather, external events, these are not.  But here’s where it comes full circle: our responses to other people, the weather, external events are in our control. 

Making this distinction will make you happier, make you stronger and make you more successful if only because it concentrates your resources in the places where they matter.

What Does Your Ideal Day Look Like? 

If you don’t know what your ideal day looks like, how are you ever going to make decisions or plans for ensuring that you actually get to experience them on a regular basis? It’s important to take an inventory of the most enjoyable and satisfying days of your life. What did you do? Why did you like them?

Now be sure that your job, personal life, even the place you’ve chosen to live takes you towards these, not away from them. More importantly, ensure that your habits are ingrained in you such that they are the building blocks for your day.  Without positive habits (even recognizing the bad ones), there is little direction towards what you are looking to achieve.

What Am I Missing By Choosing To Worry or Be Afraid? 

When you worry, ask yourself, ‘What am I choosing to not see right now?’  What important things are you missing because you chose worry over introspection, alertness or wisdom?”

Another way of putting it: Does getting upset provide you with more options? Obstacles in life make us emotional, but the only way we’ll survive or overcome them is by keeping those distracting emotions in check—if we can keep steady no matter what happens, no matter how much external events may fluctuate.

It is hard to live with the absence of irrational or extreme emotions.  I find myself battling this too often.  But I try to reflect when indulging in those emotions and get back to reminding myself of the cost they incur:  That I’m missing something by being nervous, scared, or anxious. That I’m taking your eye off the ball to do it. Can I afford that? Probably not.  Can you?

What Is The Most Important Thing? 

If you don’t know what the most important thing is to you, how do you know if you’re putting it first?

How do you know if you’re taking the right steps to get it? Maybe the most important thing to you is family (this is it for me, but it has not always been that way).  Awesome, so that’s your priority.

What it means is that not only do you have to start measuring yourself by family-related metrics, but you must stop comparing yourself to people with different priorities. Maybe money is the most important thing to you. That’s perfectly fine. Know that and own it.  You must know and own whatever it is. Only then can you understand what matters and what doesn’t.

Only then can you say no - can you opt out of stupid things that don’t matter, or exist? Only then is it easy to ignore “successful” people because most of the time they aren’t - at least relative to you, and often even to themselves.

Only then you can develop the quiet confidence that stoics called “euthymia“- the belief that you’re on the right path and not led astray by the many tracks which cross yours of people who are hopelessly lost.”

Does This Actually Matter? 

The reason that wise people never let the very real fact of their mortality slip too far from their mind (memento mori – look it up) is because it helps them ask this question: Given the shortness of life, does this thing I’m thinking about, worrying about, fighting about, throwing myself into even fucking matter?

Sadly, the answer is usually no. We want to ask ourselves this question before we throw good time after bad, before we waste more life than we must. “You could leave life right now, let that determine what you do and say and think.” Considering that, does this thing you’re so worked up about actually matter?

Will This Be Alive Time or Dead Time? 

Early on in my career I had a pivotal conversation with a business mentor who the world lost earlier this year – I miss him greatly. 

At the time, I was working long hours and sacrificing much of my life towards building my career (at the time, family was not the highest priority).  I remember telling him about all the great things I was going to achieve, all the money I was to make and the “richness” I would showcase to others.  Ridiculous now thinking about it. 

He said, Jayme, there are two types of time: Dead time - where we are just waiting and Alive time - where we are learning and active and leveraging. And then he left it there with me to decide which I would choose. Alive time or Dead Time? 

So let that question catch you the next time you find yourself sitting on your hands or goofing off as you wait. Let it jolt you back into line. 

Pick up a book, listen to a podcast, grab coffee with a friend who has something to teach you, and get back to work. Resist the temptation to get distracted with silly politics or wanderlust.

Make the most of every moment as you prepare for the next move or the next event. If you want to be productive, be fully alive.

Am I Being Who I Want Me To Be? 

Our mind has the cunning ability to make the distinction between what we do and who we are. The problem is that this is complete nonsense.

You can’t be a good person if your actions are consistently bad. You can’t be a hardworking person if you take every shortcut you can. It doesn’t matter that you say you love someone, it only matters if you show that you love them.

I read somewhere, “In your twenties you’re in the process of becoming who you are, so you might as well not be an asshole.” This is true for life itself.

You are what you do - so ask yourself whenever you’re doing something: Is this reflective of the person I want to be? That I see myself to be? How we do anything is how we do everything. It is who we are.

So ask this question about every action, thought and word. Because it adds up in a way that no amount of self-image or belief ever will.

**

Last question. Sort of.

What is the meaning of life??

Who the hell knows and I’m not smart enough to think in these dimensions; however, I think life is demanding that we answer the question with the actions and decisions we make. That we create meaning in our choices and our beliefs. I think we create it in doing our best to challenge ourselves with the questions above:

What am I here for?

Who do I spend my time with?

Who do I want to be – am I being that?

What’s up to me – can I control it?

What does a good day look like?

Some are simpler than others, sure, but the answers rarely are—and the act of asking is the most important thing.