Welcome to The Quiet Rich, the weekly email to get “rich” in what matters most (like time, health, and a house full of love). Today I’m sharing the 7 rare questions that changed everything for me.👇
CONTEXT
A few years into my role at Google, I woke up wondering why—despite checking all the "success" boxes—something still felt... off. I had everything I’d been chasing, so what could possibly be missing?
The problem? We're so busy reacting to life that we never pause to examine it.
We don’t ask ourselves the tough but important questions that a coach might ask us. So we keep chasing goals that don't align with our values. And we maintain relationships that drain us. And we avoid taking a big leap on the thing that feels uncomfortable.
The most fulfilled people I’ve ever met aren't lucky. They just asked themselves the questions others avoid.
Here are 7 rare questions that led to my biggest breakthroughs:
THE QUESTIONS
1. What would 90-year-old you think of your life right now?
Are you living the adventure they dreamed about, or have you settled for less?
Your future self has the clarity that comes with perspective. They know which risks were worth taking and which "safe" choices led to regret. Every choice I make now is with 90-year-old Jade in mind—the person who will have to live the consequences.
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2. If you had 24 hours left on this planet, who would you call first?
For me, it’s my mom. Now ask yourself: When's the last time you saw them?
If it’s been a while, this question cuts through all the noise and reveals who truly matters to you. Yet we often take these people for granted, assuming we'll "always have time later." Life is too short to give these people your time leftovers.
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3. If you re-lived today's habits for the next 365 days, what would your life look like?
Would you be closer to or farther away from your goals?
We overestimate what we can do in a day and underestimate what we can do in a year. The person you’ll be in one year depends on the books you read, tiny habits you start, and conversations you have today.
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4. How many moments do you have left with your parents?
If you’re lucky enough to still have parents, do the math: Number of times you see them per year × their remaining years until age 80.
The number is probably smaller than you think. And suddenly, that weekly phone call feels less like an obligation and more like a gift.
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5. What are you avoiding that you know you need to do?
That tough conversation. That appointment. That decision. It's not going away.
The things we avoid don't disappear—they stack up. And the mental energy spent avoiding something is often greater than the energy required to face it.
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6. Imagine you walk into a room filled with everyone you've ever met. Who do you look for first?
This reveals your true north—the person whose opinion matters most, whose presence brings you peace, whose connection you crave above all others.
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7. If someone followed you around for a week, what would they say your priorities are?
Forget what you say matters to you. What does your calendar say matters to you?
You might think family is your priority, but if you're working 80-hour weeks and missing dinners, your actions might tell a different story.
CLOSING THOUGHTS
Self-awareness isn't a destination you arrive at once. It's a practice you return to again and again.
And you don’t need perfect answers to these questions. The goal is to be brave enough to ask them, and honest enough to sit with whatever comes up.
Once you can see the gap between who you are and who you have the potential to be, it’s so much easier to chart the path to get there.
Much love,
❤️ Jade
Send these questions to someone who will appreciate them.
And catch up on all The Quiet Rich newsletters here. I got the kindest notes about last week’s tips to be “rich” in work boundaries. Thank you to everyone who sent them.
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