10 Questions Every Man Must Ask Himself About His Life

There comes a time in a man’s life – usually at 1:30am on a Sunday night when he’s trying to sleep – when he starts to ask himself the deeper questions about life, such as:

These are big questions, and they can be nearly impossible to navigate on your own.

That’s why the men in The Great Man Within community have boiled down 10 of the most important questions that every man needs to ask about the quality of his life.

#1. Are you always busy…yet you feel like time is slipping through your fingers?

If the answer is yes, you’re not alone. 

In the spirit of “a problem well-stated is half solved,” let me introduce you to the two biggest culprits of why being chronically busy often feels like you’re letting time slip away:

  • “Drifting.” The state of being when your life is on autopilot and your unconscious habits, patterns, fears are running your life. This is opposed to you consciously and intentionally taking action in the most important areas of your life.   
  • “Lazy Busy.” Being in a perpetual state of busyness, wishing it were different, yet unwilling to take the actions necessary to and face the discomforts of creating change. 

#1 – Drifting is a term coined by Napoleon Hill in the #1 most important book of my life (of which I’ve read 200+) Outwitting the Devil.

Over a 20-year period, Napoleon Hill interviewed 25,000 people who at the end of their lives felt like they’d failed to live up to their potential. They’d left chips on the table. They’d allowed time (and subsequently, their lives) to slip through their fingers. 

How did this happen? Drift. 

Here are 5 signs you’re drifting in life:

  1. Your fears drive your behavior.
  2. You lack enthusiasm and initiative for anything you are not forced to undertake.
  3. You begin many things but finish very few.
  4. You publicly (or privately) criticize (or judge) others.
  5. You lack a major purpose in life. 


#2 – Lazy Busy is inspired by Tim Ferriss in the 4 Hour Workweek where he says (paraphrased): 

Being perpetually busy is the ultimate form of laziness. It’s merely indiscriminate action left unchecked over long periods of time.

Being busy can give you the illusion of being productive. For a time, at least. 

Until you wake up at the end of a year (or a decade) and ask yourself the question “where did the time go and what the hell did I do with it?”

Lazy Busy is a specific form of drift, typically arising from:

  • An inability to find peace in periods of stillness
  • A fear that if you’re not constantly in motion then something bad will happen






#2. Are stress and anxiety the primary fuel sources you rely on for motivation?

If I were your doctor about to give you your annual “motivation physical” (don’t worry, you can keep your pants on), I’d tell you stress and anxiety are the fast food fuel sources of motivation. 

Big Macs and Red Bulls are technically “fuel sources” too, but you wouldn’t want to make them your primary diet, would you? 

Use them sparingly. 

And yet, so many men have normalized chronic stress and anxiety in such a way they aren’t even conscious of it anymore. 

It’s like David Foster Wallace’s story of the fish:

“There are these two young fish swimming along and they happen to meet an older fish swimming the other way, who nods at them and says,

“Morning, boys. How’s the water?” 

And the two young fish swim on for a bit, and then eventually one of them looks over at the other and goes,

“What the hell is water?”

Why would anyone choose to live in a chronic state of low-to-high-grade anxiety? 

Because stress and anxiety have this nasty little habit of producing results.

It’s no secret that fear is a motivator, and when you’re motivated you can get a lot of things done.

But when you live 3, 4, 5, or more decades with fear as your primary fuel source, you may start to notice:

  • Wins don’t feel as exciting anymore
  • Losses feel increasingly worse
  • A numbness to any of life’s ups and downs 

This is no way to live a fulfilling life.

Therefore, the question is no longer simply “what do I want to achieve,” but rather “what do I want to feel on the road to those achievements?”






#3. Are you surrounded by men who call forth your best self…or men who make you feel comfortable?

There are 3 types of people in your life, and they relate to you in 1 of 3 ways:

1) Historical You: The people who see you as the man you were last year, 5 years ago, 20 years ago etc. They are stuck in the past. They want you stuck there with them because your growth is threatening to them. 

2) Here and Now You: The people who see the present-day version of you. They relate to your current capabilities, your current job, marital status, physical appearance etc. These people may support your growth and evolution as long as it’s incremental in nature. Changes that are too dramatic may also be threatening to them. They may call your big ideas weird or have a hard time relating to 

3) Highest You: This is the rare breed of man who sees you not for who you are today, but who you are your greatest potential. He’s the one who holds you to that highest of standards because anything less is unacceptable. He’s the one who knows when you’re trying to pass off a B- effort as an A, and he’ll call you on that bullshit. This is the man who is not always comfortable to be around. But he is the man who will always call you to live to your highest standard. 

In my experience, 95% of the men in your life fall into the #2 category.

Hey, life is a lot more comfortable that way because they aren’t asking a whole lot from you. 

But if the old saying holds true “you are the average of the 5 people you spend your most time with,” then what implications does that hold for your ability to become your best self?






#4. How big is the gap between your “Public Self” and your “Secret Self?”

Not to impose an identity crisis upon you, but entertain for a moment that you might have three separate “selves”:

  1. Public Self: The persona you create to be accepted by work, family, friends, society etc
  2. Private Self: The parts of you that you’ve chosen to only allow certain people to see
  3. Secret Self: The parts of you that you hide for fear they won’t be accepted

There’s a critical difference between the Private Self and the Secret Self:

  • The Private Self is established by healthy boundaries and discernment.
  • The Secret Self is established by shame. 

The Secret Self holds your thoughts, feelings, behaviors, kinks, desires, stories from the past that, if exposed to others…you believe would lead to judgment, criticism, punishment, loss, make you unlovable etc. 

It can be exhausting to walk through life with a Secret Self.
It can be scary to always worry about that Secret Self being exposed. 

I speak from experience. 

I lived nearly two decades with sexually addictive behavior that was I terribly ashamed of. So I built a fortress around this part of me and spent a great deal of my life’s energy vigilantly defending it from being exposed.

In the process, I virtually guaranteed that no one would ever get to know the real me, and completely blocking my ability to experience intimacy that I deeply craved in my relationships. 

It was only when I dissolved the Secret Self was I able to stop hiding, liberate myself from shame and live authentically. 

I still keep certain things private. There will always be a place for a Private Self. Not everyone can or should have access to all parts of me. Not everyone has earned that right. 

What are the parts of you that you keep in the Secret Self?
What are the desires, thoughts, feelings, behaviors, stories you’re afraid of getting out?
What haven’t you allowed the closest people in your life to see?






#5. Despite all that you “should” be grateful for, do you still feel restless and unfulfilled?

Sure you have an enviable lifestyle, on paper.
You’ve got the income, the title, the material possessions and maybe even the family.

But something is off.

What once fired you up isn’t as interesting.
Your drive is diluted, and your mojo eludes you.
You can’t figure out why. 

All of this is happening at the same time as the responsibilities continue to mount and the chaos of your life accelerates.
You’re headed for a boring, predictable future of “more of the same” because:

You have not consciously designed your future*.
(I’m so passionate about this topic I even wrote a book about it: Design Your Future).  

You’re letting life happen to you.
That’s why it’s feeling predictable and uninspiring.
No wonder the restlessness, the boredom and feelings of being trapped.

But there is another way. 

Men who do “inner work” take command of their lives and create a future they can’t wait to live into by defining two critical things that shape their lives:

  1. The feelings you want to experience 
  2. The values that you want to live your life by

Most men have never defined with any level of precision what they actually want to feel in their inner worlds…nor have they consciously constructed a set of values that drives the most important actions they take in life. 






#6. Is how you’re spending your time aligned with the values you hold most important?

Do any of these sound familiar?

How you spend your time and the actions you take are far greater indicators of what you currently value than what you say you value.

As Richard Feynman said, 

“You must not fool yourself and you are the easiest person to fool.”

Once you wake up to that truth, you can take the power back: By creating values that you aspire to live into and organizing your time accordingly.

Of course, this is easier said than done when you have a lifetime of habits and inertia begging you to stay stuck in status quo. 

This is why charting a new course is rarely done without the support of a coach, mentor or community keeping you accountable along the way. 






#7. Is your inner critic preventing you from going after what you really want in life?

I’m not saying you’re crazy, but you’ve got a voice in your head telling you what to do. 


This voice is your “inner critic,” and he can be a nasty little tyrant, can’t he? 

Your inner critic is constantly looking for ways to protect your ego from criticism, failure and the infinite other forms of discomfort. 

This can feel like sabotage.

And when you take your marching orders from your inner critic, you are allowing the weakest part of you to run your life. 

No matter what you end up accomplishing in your life, if you don’t take reclaim the throne and put the inner critic back in the court where he belongs, you will never feel fully liberated or empowered to go after the life you want most. 

I can’t tell you how many men have dreams, desires and talents that could fuel a lifetime of adventures…
…that instead stay shackled on the sidelines by the tyranny of the inner critic.

Ask yourself: 

How many dreams do I have…that simply remain dreams?
How many desires do I have…that I never fully pursue?
What have I wanted to create…that I’ve been too afraid to bring into this world and share?

What if, instead of giving credence to your inner critic, you built the muscle of listening to your “inner genius” instead? 

The part of you that’s creative, bold, powerful?

Making that switch isn’t easy – your inner critic is loud and you’re used to listening to it. That’s why doing inner work with a coach, mentor and supportive community of other men matters. 






#8. Do you have untapped potential…but don’t know how to get at it (or even know where to begin)?

A constipation of potential.
Is there any worse feeling? 

It’s an awful experience to know you’re under-clubbing this game of life. 

To see your gifts on the sidelines.
To never truly put yourself to the test.
To never know what you’re capable of. 

Why does this happen? It comes back to our old nemesis: Drift.

Remember, drift is rooted in fear. When you’re not tapping your potential it’s because there is some underlying fear – or likely, many fears – paralyzing you. Keeping you stuck. 

Most men will try to un-stuck themselves on their own.  

We call this approach “lone wolfing.” 

Sometimes, it works. Most times, you end up stabbing around in the dark and wasting precious time. 

Most men will only find their true potential when they belong to a group of men who are also actively striving to find their greatest potential. 

Why do you think Navy SEALS and elite athletes can do the seemingly impossible?
They’re surrounded by others who are striving for excellence…every moment of every single day.

The question becomes: 

Are you surrounded by men who are actively seeking their greatest potential?
Or are you an army of one?






#9. Are you “Lone Wolfing” your life?

The Lone Wolf is the man who:

  • Is self-reliant and takes extreme pride in his independence
  • Navigates his biggest challenges on his own
  • Shares very little of his inner emotional world with others
  • Is surrounded by people yet feels alone because he’s never truly allowed others in
  • Feels he loses “man points” for asking for or receiving help

Lone wolves don’t trust groups of other men.

  • They’ve been burned by groups of men in the past.
  • They haven’t found a place where they feel they belong. 
  • They often trust women with their emotions, but not men.
  • They believe a group threatens their freedom and independence. 

In our society the Lone Wolf is heralded.
He is praised for his independence and rugged individualism.
But the fact of the matter is, Lone Wolves starve.

Wolves are a pack animal, as are you.

Which begs the question:

Do you have men who you trust implicitly for questions about life, career, relationships and the most vulnerable dealings (hardships, secrets and fears) of your inner world?

Thoreau’s “quiet desperation” ceases to exist when you find your band of brothers – your community of men – who call forth your best self and who you can reveal all parts of your inner world without judgment or criticism. 

As we like to say in The Great Man Mastermind: “Personal development on your own is slow, shallow and incomplete.”

Here are 5 signs you’re Lone Wolfing:

  1. You believe your problems aren’t important (so you share them with no one)
  2. You feel no one really knows you (because you hide big parts of yourself)
  3. What you project externally doesn’t sync up with what you feel internally
  4. No one’s there to celebrate your wins…or support your struggles
  5. You play the small games but stay on the sidelines for the big ones. 






#10. Are you living in such a way that, at the end of your life, you can say you lived your purpose and left a legacy you’d be proud of?

It’s been said that men have two lives:

  1. The life you currently live
  2. The unlived life within you

That unlived life within you is what we call The Great Man Within you.

The Great Man Within is who you are when:

  • You relentlessly pursue your greatest Potential
  • You live in alignment with your Purpose
  • You walk with men who call forth your Highest Self

Too many men will settle for a life of comfort, safety and predictability…therefore never stepping into their Great Man…and instead careening towards that Definition of Hell.







BONUS #11. Where Do I Go from Here? 

Hungry for more? Here are your 3 options:

  1. Stay tuned for the next article in this series: 10 Payoffs from Pursuing Your Best Self
  2. Subscribe to The Great Man Within Podcast: “New Listeners Start Here Playlist” on Spotify
  3. Learn more about our communities of men – The Great Man Masterminds – in pursuit of their best selves.