Ten simple, hard, and potentially life-altering questions. Each one is a doorway. You only have to be willing to walk through.
Hello there, friend.
I want to ask you something today. Ten things, actually. And I want to ask them slowly — the way a good friend would — sitting with you in the space each question opens up, rather than rushing past your answer to get to the next one.
These are the kinds of questions that feel simple when you first read them. Then you stay with one a little longer than you planned, and something shifts. The usual answer falls away. And what remains is something truer.
That is what a great coaching question does. It holds open a space that ordinary conversation rushes past. It trusts you to carry the answer inside you already. It simply creates the conditions for that answer to surface.
So. Let’s begin.
What Does a Big Life Look Like for You?
This is the first question. And it is the one most of us have genuinely never answered with full honesty.
We have given versions of it. We have dressed it up in careful, reasonable language. We have qualified it with what seems realistic, what seems responsible, what our circumstances allow. We have answered the question we thought someone else was asking rather than the one that was actually asked.
So let me ask it plainly, with the qualifiers removed: what does a big life look like for you?
The answer lives beneath the socially acceptable version. It lives in the thing you daydream about at 6am before the rest of the world wakes up and tells you what the day is for. In the clarity that arrives after a long walk. In the rare hour when the noise goes still and you can hear yourself think.
Mary Oliver asked this same question in a different register: what will you do with your one wild and precious life? The big life is already inside you. The question is only whether you have been honest enough with yourself to describe it.
Sit with this one. Write your answer before you read the next question. Give it at least ten minutes of genuine attention. Let yourself want what you actually want.
What Has the Hardest Thing You Have Lived Through Given You?
I am asking this one gently, with full awareness that it lands differently for everyone who reads it.
Every one of us has something. The loss that arrived without warning. The door that closed when everything inside you was hoping it would stay open. The chapter that ended before you were ready.
The question I want to bring to that experience is a generous one: what has it given you that ease could never have developed? What exists in you now, because of what you went through, that would have had no room to grow in a life without it?
The capacity for deep presence. The ability to stay steady when others are panicking. The hard-won understanding of what actually matters. The specific intelligence that only comes from rebuilding something from the ground up.
Your difficulty has been doing that kind of work on you. The question is whether you have been receiving its gifts alongside the weight of it.
Name the hardest thing you have lived through. Then ask: what has it given me that I carry into the big life?
What Would You Do If You Knew You Could Handle It?
This one does something elegant. It removes fear from the equation by changing the assumption underneath it.
Most of us approach the things we most want with an unconscious assumption: that we might be destroyed by them. By the failure. By the exposure. By the cost of the attempt. And so we hold back. We prepare a little longer. We wait for a better moment.
This question replaces that assumption with a different one: you can handle it. You have handled hard things before. You will handle hard things again. Given that — given the full knowledge that you are the kind of person who finds a way through — what would you do?
The answer that arrives here is usually the real answer. The one that was there all along, waiting for the fear to step aside long enough for it to speak.
This connects to what we explored in the post on High Agency: the high-agency orientation begins with the belief that circumstances are an input to work with, rather than a verdict to accept. This question installs that belief deliberately — just long enough for the real answer to surface.
Complete this sentence in writing: “If I knew I could handle it, I would _______.” Write the first thing that arrives. Then write the thing beneath that.
What Are You Tolerating That Is Ready to Change?
Tolerating is a particular kind of activity. It is the low-grade hum of something that is off — something that takes a small but steady amount of your energy every single day because you have decided, consciously or otherwise, to live alongside it rather than through it.
It might be a conversation you have been postponing. A physical environment that drains rather than restores. A habit whose season has ended. A relationship running on old terms that have long since stopped serving either person. A professional situation that once made sense and now asks something of you that belongs elsewhere.
I bring some compassion to this question before you answer it. The things we tolerate are often things we are holding until the right moment of readiness arrives. There is wisdom in that. The question is a gentle invitation: is now that moment?
List three things you are currently tolerating. Beside each one, write one small action that would move you toward resolving it. Just one. Keep it achievable today.
What Would Your Future Self Thank You for Doing Today?
Of all ten questions, this one most consistently surprises people with what it reveals.
The answer is almost always something small. A conversation begun. A habit initiated. A page written. A phone call made. A boundary spoken with love.
Your future self rarely thanks your present self for grand gestures. They thank you for the quiet, consistent, unglamorous acts of building. For the morning you chose to begin even when the conditions were imperfect. For the day you kept your word to yourself when keeping it was inconvenient.
“The small daily choices are the architecture of the big life. They compound in silence, and then one day you look up and something extraordinary has been built.”
We explored this same question in the Book of Life practice: the annual question of what Future You would thank Present You for doing. This brings it into the daily register. Just today. Just this morning. Just this hour.
Answer this question before you do anything else. Write it down. Let the answer govern the next three hours.
What Energizes You So Completely That Time Disappears?
This question is a compass. A body-level compass that bypasses the thinking mind and goes straight to the signal that actually matters.
You know the experience it is pointing at. The complete absorption in something that is calibrated perfectly to where you are right now — demanding enough to require your full attention, alive enough that the demand feels exciting rather than exhausting. Time stops being a dimension you are aware of. The self-consciousness that monitors and judges and worries goes quiet. What remains is the pure experience of doing the thing.
Most people can name two or three activities that reliably take them there. The question I am asking is: how much of your life is organized around those things? And if the answer is very little, the more important question follows: what would it take to change that ratio?
The big life expands the proportion of your days lived inside that state. It is built around the things that call forth the best of you without requiring you to manufacture the energy to show up for them. The energy is already there. The question is whether the structure of your life is allowing it to flow.
Name the three activities where time most consistently disappears for you. Then look at next week. Where do they appear? Add one.
What Story About Yourself Are You Ready to Set Down?
Every person carries a personal mythology. A collection of stories about who they are, what they are capable of, what happens to people like them, and what the world is likely to offer them.
Most of these stories were written in childhood, in adolescence, in the first significant failures and first significant rejections. They were written at a time when you had very limited information and very limited perspective. And yet you carry them forward as if they were facts. As if the story of who you were at seventeen — or twenty-three, or thirty-one, in the worst moment of that year, with the least resources available to you — is an accurate and permanent description of who you are now.
I want to ask you: which story is ready to be set down?
The one that says you are someone who gives up under pressure. The one that says the big things happen for other people. The one that says you missed your window. The one that says you are too much, or too little, or somehow the wrong shape for the life you want.
The releasing of a story is one of the most powerful acts available to you. It requires looking at the story clearly, acknowledging where it came from, feeling genuine compassion for the version of yourself who needed it — and then setting it down. The story served its purpose. It kept you safe at the time it was written. It belongs to a chapter that is complete.
This connects to what we explored in the wisdom of Neville Goddard and Florence Scovel Shinn: the inner life is always writing the outer life. When the story changes, the conditions built on top of it begin to change with it.
Write the most limiting story you carry about yourself in one sentence. Then write the truer, kinder, more generous version. Keep the second sentence somewhere you see it each morning.
Who Do You Want in Your Corner for the Next Chapter?
This question is about intentional community. About the radical act of choosing, with full awareness, who gets to be in close proximity to the life you are building.
The people around you are shaping the way you see what is possible. They are either expanding your sense of what you are capable of, or quietly confirming a smaller version. This is true whether or not either of you is aware of it. Proximity is influence, and influence compounds.
The observation that you are the average of the five people you spend the most time with has become almost a cliché through repetition. It remains entirely true. So the real question is: are those five people pointing in the direction you want to go? And if the answer is only partially, what would it take to bring the right people closer?
This connects to what we explored in the post on Shaan Puri’s zero to million framework: the loser’s edge includes the willingness to reach toward people who are already living in the territory you are moving toward. One genuine connection with someone further down the road can accelerate a decade of solitary effort.
Name three people who represent the next version of you. Consider one concrete way to bring yourself into closer contact with each of them this week.
What Would You Attempt If the Outcome Were Guaranteed?
This question removes fear of the outcome. And in doing so, it asks you to name the desire itself — stripped of its protective uncertainty.
Because one of the ways we manage the pain of wanting something we are afraid to pursue is by keeping our desire vague. By holding it at arm’s length. By never quite naming it, so that if it does arrive, we can tell ourselves we were always moving in that direction, and if it does stay away, we can tell ourselves we were never fully committed anyway.
This question requires you to name it. Clearly. With the outcome guaranteed. What would you attempt?
The book you would write. The business you would build. The conversation you would begin. The place you would go. The person you would become. The thing you have been circling for years without quite committing to land on it.
That is the thing. That is what this question is asking you to see clearly and hold without flinching.
And here is the follow-through the question deserves: the outcome being guaranteed is the condition for seeing the desire clearly. The attempt itself is the point. The attempt is where the big life gets built. The outcome, guaranteed or otherwise, is what arrives afterward.
Write the thing you would attempt if the outcome were guaranteed. Then ask: what is the smallest version of that attempt you could begin today?
What Does Living Well Actually Mean to You?
The final question. The widest one. And in some ways, the most personal of all ten.
Living well is different for everyone. For some it is presence — the felt sense of being fully alive in each ordinary moment. For some it is contribution — the knowledge that the work you did here mattered to someone, to something beyond yourself. For some it is freedom — the ability to move through the world on your own terms, shaped by your own values rather than borrowed ones. For some it is depth — the experience of being known, fully, by people who choose to stay.
“The well-lived life belongs to the person willing to ask the honest questions and stay long enough to hear the honest answers.”
This question asks you to define it for yourself. With full specificity. With the courage to want what you actually want rather than what seems like a reasonable answer.
And then it asks the harder question underneath it: are you building those conditions now? In today’s choices? In this week’s priorities? In the shape of the year you are currently living?
Because the well-lived life is built daily, from the inside out. It is made of moments, choices, and the slow accumulation of decisions made in alignment with what you believe actually matters. It is available to you in this decade, in this year, in this morning, in this very hour — regardless of what has come before or what the circumstances are currently asking of you.
Write your definition of living well. Make it specific to you. Then ask: am I building that today?
All Ten, Together
Here they are, gathered in one place. Read them slowly. Let each one land before you move to the next.
- What does a big life look like for you?
- What has the hardest thing you have lived through given you?
- What would you do if you knew you could handle it?
- What are you tolerating that is ready to change?
- What would your future self thank you for doing today?
- What energizes you so completely that time disappears?
- What story about yourself are you ready to set down?
- Who do you want in your corner for the next chapter?
- What would you attempt if the outcome were guaranteed?
- What does living well actually mean to you?
You can find Vickie M Lanthier’s original free resource, including her own version of these questions, at vickiemlanthier.com/resources.
The questions are available to you right now. This morning. In the quiet before the day claims you.
Pick one. Stay with it. Write what arrives honestly.
Start today. Start early. Start with the question that already has your name on it.
With love,
Paolo
Try This Today
- The one question. Choose the single question from the ten that landed most powerfully. Set a timer for fifteen minutes and write freely in response. Let the first answer come, then push past it to the answer underneath.
- The story release. Write the most limiting story you carry about yourself in one sentence. Then write the truer, more generous version. Keep the second sentence somewhere visible each morning.
- The future self letter. Write a single paragraph from the perspective of your future self, three years from now, thanking your present self for something specific you are choosing to begin today.
- The flow audit. List the three activities where time disappears for you. Look at next week’s calendar and add one of them intentionally.
- The attempt. Name the thing you would attempt if the outcome were guaranteed. Then name the smallest possible version of that attempt. Do that smallest version before the week ends.
Keep Going
- You Are the Author of What Comes Next: Three Frameworks for Becoming Who You Already Know You Can Be
- How High Agency by Caelin Kompass Teaches You to Bend Reality to Your Will
- Your Inner Life Is Writing Your Outer Life
- The Book of Life: Mark Pincus’s Most Powerful Idea for Becoming the Author of Your Own Story
- The Framework That Takes You From Zero to Your First Million: Six Ideas From Shaan Puri
- How The Almanack of Naval Ravikant Teaches You to Build Wealth and Find Happiness