While everyone else is making resolutions they'll abandon by February, these nine gut-punch questions will strip away the comfortable lies you tell yourself and reveal truths you've spent years avoiding—because deep down, you already know the answers.
New Year's Eve used to terrify me.
Not because of the parties or the pressure to have plans, but because of the quiet moment that came after midnight. When the champagne bubbles settled and everyone went home, I'd be left alone with the one person I couldn't escape: myself.
At 38, after burning out so spectacularly that I couldn't get out of bed for three days, I finally understood why. I'd been avoiding the hard questions for years, building a life that looked perfect from the outside while feeling empty on the inside.
That breakdown became my breakthrough. And now, every January 1st, I sit down with my journal (I've filled 47 notebooks since I started) and ask myself the uncomfortable questions most of us spend our whole lives avoiding.
These aren't your typical "What are your goals?" questions. These are the ones that make you squirm, that force you to look at the parts of yourself you'd rather keep hidden.
Ready to get uncomfortable? Let's dive in.
1. If I stripped away my job title, salary, and achievements, who would I be?
This question nearly broke me when I first asked it.
After leaving my six-figure financial analyst position at 37, I realized I had no idea who I was without that corporate identity. For years, I'd introduced myself as "a financial analyst at..." as if that job title was my entire personality.
When you peel away all the external markers of success, what's left? Are you kind? Curious? Creative? Or do you discover, like I did, that you've been so busy achieving that you forgot to actually become someone?
Most people avoid this question because the answer reveals how much of their identity is borrowed from external sources. But until you know who you are at your core, you'll keep chasing achievements hoping they'll finally make you feel like enough.
2. What am I pretending not to know?
You know that relationship that drains you? That job that makes Sunday nights feel like a death sentence? That habit you swear isn't a problem?
Yeah, you know.
We're masters at selective blindness. We tell ourselves stories to avoid making hard decisions. "Maybe things will get better." "It's not that bad." "I can handle it."
I pretended not to know I was heading for burnout for two years. Every morning, my body screamed at me to stop, but I kept pushing. I pretended the anxiety attacks were just stress. I pretended the insomnia was temporary.
What truth are you avoiding because acknowledging it would mean you'd have to change?
3. If I had one year left to live, would I spend it the way I'm planning to spend this year?
Before you roll your eyes at another "live like you're dying" cliché, hear me out.
This isn't about quitting your job to travel the world. It's about examining whether your daily choices align with what actually matters to you.
Would you spend 60 hours a week in an office trying to impress people you don't even like? Would you keep postponing that conversation with your parent? Would you keep saying "next year" to the things that light you up?
When I asked myself this during therapy at 36, I realized I was living for a future that never came. Always sacrificing today for a tomorrow that would supposedly be better. But tomorrow kept looking exactly like today, just with more exhaustion.
4. What would I do if I knew nobody would judge me?
The fear of judgment is a silent killer of authenticity.
How many dreams have you buried because someone might think they're silly? How many times have you stayed quiet when you wanted to speak up? How many pieces of yourself have you hidden to fit in?
I spent years hiding my desire to write because "serious professionals" didn't leave finance to become writers. What would people think? What would former colleagues say?
Turns out, most people are too busy worrying about their own lives to care about your choices as much as you think they do. And the ones who do judge? They're usually jealous of your courage to do what they can't.
5. Am I addicted to being busy because stillness forces me to feel?
This one stings, doesn't it?
Look at your calendar. Is every minute accounted for? Do you feel anxious when you have free time? Do you immediately reach for your phone when there's a quiet moment?
Busyness is the most socially acceptable addiction. People praise you for it. "You're so productive!" "I don't know how you do it all!"
But constant motion is often just sophisticated avoidance. When I finally slowed down during my burnout recovery, years of unfelt feelings crashed over me. Grief I'd never processed. Anger I'd swallowed. Dreams I'd abandoned.
What are you running from that stillness would force you to face?
6. Do I love myself, or do I love the idea of who I could become?
We live in a world obsessed with transformation. New year, new you. Before and after photos. Success stories.
But what if you never lost the weight? Never got the promotion? Never found the relationship?
Would you still think you were worthy of love and respect?
For years, I lived in the future tense. I'll be happy when I make more money. I'll feel successful when I reach this milestone. I'll finally relax when I achieve that goal.
My achievement addiction meant I could never enjoy where I was because I was always focused on where I needed to be. External validation was never enough because there was always another level to reach.
Can you love who you are today, flaws and all, without conditions?
7. What story about my life am I accepting that isn't actually true?
"I'm not creative."
"I'm bad with money."
"I'm too old to change careers."
"I need to work this hard to be valuable."
These aren't facts. They're stories. And stories can be rewritten.
I believed for 37 years that leaving a stable career meant failure. That story wasn't mine; it was inherited from well-meaning people who valued security above fulfillment. When I finally questioned it, I realized security without purpose is just a comfortable prison.
What limiting belief are you treating as truth?
8. If my life is a message, what am I actually saying?
Not what you post on social media or say at dinner parties. What does the way you actually live communicate?
Do your actions say that work is more important than relationships? That other people's needs matter more than yours? That money equals worth?
When I looked at my life before burnout, the message was clear: "I will sacrifice everything, including my health and happiness, to prove I'm successful."
That wasn't the legacy I wanted.
Look at how you spend your time, energy, and attention. What message are you actually sending?
9. What do I need to forgive myself for?
This might be the hardest question of all.
We carry so much shame about our perceived failures, mistakes, and shortcomings. We replay our worst moments on loop, punishing ourselves over and over for being human.
I needed to forgive myself for ignoring my intuition for years. For choosing achievement over authenticity. For waiting until I collapsed to make changes I knew I needed to make.
Forgiveness isn't about excusing what happened. It's about releasing the weight so you can move forward.
Final thoughts
These questions aren't meant to be answered once and forgotten. They're meant to be revisited, wrestled with, and explored over time.
Some answers might surprise you. Others might confirm what you've suspected all along. All of them will probably make you uncomfortable.
Good. Discomfort is where growth happens.
This January 1st, while everyone else is making resolutions they'll abandon by February, dare to ask yourself the questions that actually matter. The ones that cut through the noise and force you to confront who you really are and what you really want.
The honest answers might be uncomfortable, but living a life that isn't truly yours? That's unbearable.
