The Questions That Changed Everything
Hey there beautiful soul,
I’m writing this from my kitchen table at 6 AM, coffee still brewing, because I can’t shake something that happened this week.
My buddy called me Tuesday night, completely spiraling. “I feel like I’m sleepwalking through my life,” she said. “I’m 32, decent job, nice apartment, but I wake up every morning feeling… empty.”
Sound familiar?
Here’s what I told her (and what I wish someone had told me when I was burning through my twenties on autopilot):
The life you want exists. But it won’t build itself.
The Brutal Truth About “Finding Yourself”
We’ve been sold this lie that our purpose will just appear one day like some cosmic Amazon delivery. That we’ll wake up and suddenly know exactly what we want to do with our lives.
Not really.
Your dream life isn’t hiding under a rock waiting to be discovered. It’s designed. Built.
Crafted through intentional choices, uncomfortable questions, and the courage to act on what you find.
My friend’s problem wasn’t that she didn’t know what she wanted. Deep down, she knew. The problem was she’d never asked herself the right questions.
The Questions That Actually Matter
Most people read lists like that and do absolutely nothing with them.
So here are the 5 questions that will actually change your life if you have the guts to answer them honestly:
1. “If I could wave a magic wand and have my life exactly as I want it in 3 years, what would that look like?”
Not “what job would I have” or “how much money would I make.” What would your days look like?
How would you feel when you wake up? What would you be excited about?
My friend’s answer: “I’d wake up excited about my work. I’d be helping people solve real problems, not just pushing papers. I’d have time for my art again. I’d live somewhere with natural light and plants everywhere.”
2. “What am I pretending not to know?”
This one hits different. We all have that voice in our head telling us what we need to do, but we ignore it because it’s inconvenient or scary.
My friend’s answer: “That I hate my corporate job and I’m good at graphic design. That I’ve been making excuses for three years about why I can’t freelance.”
3. “What would I do if I trusted myself completely?”
Most of us don’t trust our own judgment. We’ve been conditioned to seek external validation for everything. But you know yourself better than any career counselor, life coach, or well-meaning friend.
My friend’s answer: “I’d start taking freelance clients on weekends. I’d save up a 6-month emergency fund and then quit my job to go full-time.”
4. “What’s the cost of not changing?”
This is where it gets real. We focus so much on the risk of change that we ignore the guaranteed cost of staying the same.
My friend’s answer: “I’ll be exactly where I am now in 5 years, except more bitter and with more regrets.”
5. “What’s the smallest step I can take today?”
Big dreams without small actions are just fantasies. What’s the most ridiculously small thing you can do right now?
My Friend’s answer: “I can update my portfolio website tonight.”
What Happened Next
Here’s the thing about asking yourself real questions: you can’t un-know the answers.
My friend updated her portfolio that night. By Friday, she had her first freelance client (a friend of a friend who needed a logo).
By the end of the month, she had three more clients and a plan to go full-time within 6 months.
Did she have moments of doubt? Absolutely.
Did she want to quit when her first client was difficult? Of course. But once you see what’s possible, it’s hard to go back to sleepwalking.
The Design Process
Building a life by design isn’t about having all the answers upfront. It’s about:
1. Getting brutally honest about where you are
Most people lie to themselves about their current situation. They say they’re “fine” when they’re actually dying inside. You can’t navigate to where you want to go if you won’t admit where you are.
2. Getting specific about where you want to be
“I want to be happy” isn’t a destination. “I want to wake up excited about my work, have $10K in savings, and spend my evenings painting” is a destination.
3. Closing the gap with small, consistent actions
The gap between where you are and where you want to be is filled with daily choices. Sarah didn’t quit her job on day one. She built a bridge first.
4. Course-correcting when you get new information
Your plan will change. That’s not failure—that’s intelligence. Sarah’s original plan was to save for 6 months. She ended up having enough client work to quit in 4 months. Adapt.
Accountability
Here’s what nobody tells you about changing your life: motivation is garbage. It comes and goes like the weather.
What works is systems and accountability.
My friend and I text each other every Sunday with our wins and our commitments for the week.
Not because we’re accountability buddies (though we are), but because naming your intentions to another human being makes them real.
This week’s challenge: Find one person who will check in with you about your progress.
Not someone who will judge you or give you advice (unless you ask), just someone who will witness your commitment.
The Stories We Tell Ourselves
“I’m too old to start over.”
“I don’t have enough money to take risks.”
“What if I fail?”
“What if I succeed and it’s not what I expected?”
Every single one of these is a story. And stories can be rewritten.
The most expensive thing you’ll ever buy is a limiting belief. My friend’s story was “I’m not creative enough to make money from design.” The cost of that story was three years of her life.
What story is costing you yours?
No Regrets
I had a chat Amy a 75-year-old woman who always pass by where I do my pull ups last week. She told me something that’s been stuck in my head:
“The things I regret most aren’t the things I tried and failed at. They’re the things I never tried at all.”
You know what you need to do. The question isn’t whether you’re ready (you’re not—nobody ever is). The question is whether you’re willing.
Your Turn
Before you close this email and go back to scrolling, do this:
1. Pick one of those 5 questions above
2. Set a timer for 10 minutes
3. Write your honest answer
4. Text that answer to someone you trust
5. Take the smallest possible action today
That’s it. Don’t overthink it. Don’t wait for Monday. Don’t wait for the perfect moment.
Your future self is counting on the decision you make right now.
What I’m Up To
Reading: “The Courage to Be Disliked” (again—some books deserve multiple reads)
Experimenting: blogging everything I cook daily, with short form video and all that. I’m on a good roll, things are starting to be like part of breathing.
Check out hundreds of delish dishes here 👈
And here 🌱👇👇👇👇👇
I learned that much resistance is of the mind and can be let go. Just stay committed to the action and watch results blossom.
Track your inputs. Increase and double down on actions that yield results. Purify and clarify this each day. Like sharpening a knife. You get sharper and sharper as time goes by.
Thinking about: How many people are living lives that look good on paper but feel empty inside, and what it would take for them to change
One More Thing
If this resonated with you, forward it to someone who needs to read it. Don’t wait—do it now.
And if someone forwarded this to you, subscribe here to get these doses of real talk every week.
Until next Sunday,
- Paolo
P.S. my friend launched her design studio last month. She’s booked solid through May and finally sleeping through the night. The only thing she regrets is not starting sooner.
The Sunday Reset is written by someone who believes your life should be intentional, not accidental.
If you’re tired of living on autopilot, you’re in the right place.
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Those questions are great Paolo. It’s the ones we don’t want to answer because the answers make us realise we need to start taking action right now where we are. Otherwise we continue to accept that we’re not doing anything to change our situation and the regret of not trying eats you up.
Cool that you were able to help your friend, and your dishes look delicious!
👏👏👏🙏🙏🙏