Ever notice how the word question begins with quest? When you think about it, every great question really does send us on a quest of some kind. Sometimes, a great question leads to something positive and profound, like a fresh, new perspective on life. Other times it leads to something more tangible, like profit.
But this assumes we’re asking ourselves and others well-worded questions in the first place—something most people have never even thought about. Many of us fail to realize the powerful role questions play in our daily lives…
If that’s you, you’re about to learn how to change that.
Most of the questions we ask in life are the questions we ask ourselves.
Most the questions we ask in life are the questions we ask ourselves.
Think about it: Aren’t you asking and answering questions pretty much all day long?
Do I like my job?
When is this due?
Who should I vote for?
Should I ask for a raise?
What should I do today?
Does this make me look fat?
What should I have for lunch today?
Should I start my presentation this way, or that way?
We’re teeing up questions and answers in our brains all day long—it’s how we think.
I hate to say it, but most folks aren’t asking themselves the types of questions that are conducive to the life they want to lead.
Most people ask poor questions, which leads to poor results…
For example:
- You don’t feel motivated, so you ask, “Why can’t I ever get motivated?“
- You have difficulty comprehending some of the lingo your co-workers were using at a recent meeting, so you ask, “How come I’m so stupid?“
- Your last business idea was a failure, so you ask, “Why can’t I ever get my ideas to succeed?”
☝️ None of these questions are helpful.
In fact, they’re downright harmful…
Bad questions lead to bad answers.
When we ask bad questions, our brain gives us bad answers.
For instance, when you say, “Why can’t I ever get motivated?“, your brain literally looks for answers to this question and spits out something like: “Well, I can’t get motivated because I’m a loser.”
And that’s not the answer you’re looking for, is it?
It sounds more like a statement that reinforces a poorly worded question.
Here’s how you might transform that question into something that helps you rather than hurts you:
- 🛑 Stop asking: “Why can’t I ever get motivated?”
- 👍 Start asking: “What actions/habits will help me generate motivation consistently?”
The quality of your life is proportionate to the quality of your questions.
I believe that the quality of our lives is in direct proportion to the quality of the questions we ask ourselves.
Sometimes, our questions lead to something negative, like a dysfunctional belief system that keeps us from being our best.
But as I mentioned at the outset of this article: When you drop the last three letters of the word question, you’re left with the word, quest.
That’s the part I like to focus on when I ask questions of myself…
Because every question we ask gives us an opportunity to embark upon a quest—a new path or direction in life.
This path can be positive, negative, or transformative… It all depends on your questions.
The power of a question.
One of the most powerful questions I’ve ever asked myself is this:
What does success mean to you?
To me, success is being able to do what I want, when I want, and with whomever I want. Success is freedom.
If I had never paused to actually think about that question—to ponder upon what “success” means to me—I’d likely still be stuck in a career I hated because it fit everyone else’s definition of success.
I’m grateful I took my time all those years ago to think about and answer that question. Because it sent me on a quest that eventually led to building a life and career that aligns with my personal definition of success.
In some ways, we each embark on a quest of our own each day of our lives… The sum total of which results in one long quest—from the day we’re born to the day we die.
So, here’s my question to you:
How’s your quest coming along so far?
If it doesn’t look like you want it to, maybe it’s got something to do with the questions you’re asking.
Better questions lead to better answers.
Sometimes, a single, powerful question can change the trajectory of your entire life.
Ask the right question, and it can send you on a quest that reveals your life’s purpose.
Ask the right question, and it can lead to an answer that takes your business to the next level.
Ask the right question, and it can cause you to quit a job you hate so you can embrace a job you love.
Ask the right question, and it can spark a deep and meaningful conversation with your next best friend.
10 empowering questions to ask yourself and others.
By now, you might be wondering what kinds of questions you can ask to begin your own “quest.” Lucky for you, I’ve gotcha covered…
Below, I’m going to share 10 empowering questions with you. You can ask + answer them yourself, journal about them, or use them as conversation starters to get to know other people on a deeper level.
Let’s dig in.
- What’s one piece of advice you’d give to your younger self?
- What are three things you love about yourself?
- Describe a time when you had to forgive someone. What was the outcome?
- What haven’t you accomplished yet that you want to?
- What has failure taught you?
- When was the last time you cried?
- What story are you telling yourself, about yourself?
- How do you live out your purpose each day?
- What’s the craziest thing you’ve ever done, and would you do it again?
- If you could thank one person who isn’t alive anymore, who would it be and what would you say?
☝️ These are the types of questions that unlock true meaning in life.
Think about them.
Journal about them.
Or use them as conversation starters to get to know other people on a deeper level.
They might just send you on a powerful quest of your own.
And if you think these questions are as powerful as I do, I invite you to check out my latest project…
The Journey Deck.
Back in 2020, in the heat of the pandemic, four friends and I started a weekly men’s group as a way to bond, motivate each other, and have meaningful conversations.
It didn’t take long for us to realize we’d started something special.
So, we began recording our sessions and documenting the most inspiring nuggets we got out of each meetup. At the time, we had no clue what we would do with all that footage. But we knew something good would come of it.
A few years later, we stumbled on an idea:
What if we sifted through ALL of our meetings to find our most thought-provoking questions + conversations, then compiled them into a product that could help other men?
And that, my friend, is how The Journey Deck was born…
The Journey Deck contains 52 conversation cards with 52 essential questions to inspire men of all ages to become the best version of themselves through meaningful (but manly) conversations.
These cards contain the same inspiring questions that helped my friends and me improve our own lives.
Our mission is to help men unlock the same magic we did—without having to go through the pain of figuring out which questions to ask.
You can use these cards as a way to get to know yourself on a deeper level OR you can use them as a fun way to bond with your buddies, bros, coworkers, acquaintances, and anyone you’d like to have a meaningful conversation with.
A quick side note for the ladies: Although we don’t have a Journey Deck for women yet, I’m confident you’ll still benefit from getting The Journey Deck for all the men in your life. Here’s why: Men are FIVE times lonelier today than they were in 1990.
There are a ton of factors that have contributed to this sense of loneliness in men. I believe one of them is this: Many of us are involved in superficial friendships—and we don’t even realize it.
The Journey Deck changes that by helping men go beyond surface-level chit-chat, with fun and powerful questions that spark deep and meaningful conversations. Whether you get one for your spouse or partner, boss or coworker, brother or father, or all of them at once—every man in your life can benefit from The Journey Deck… So hook him up with a gift he’ll forever be grateful for.
Here’s how to get The Journey Deck.
Preorders are officially open as of TODAY and our first batch of Journey Decks ship out to customers on December 1st.
If you want to ensure you receive yours in time for the holidays, be sure to stock up now to be included in our first batch of shipments. 👇
The Journey Deck
$34.99 • The Journey Deck contains 52 conversation cards with 52 essential questions to inspire men of all ages to become the best version of themselves through meaningful (but manly) conversations.
With love,
—Dean.
