I was stuck in the same patterns for years until I started asking myself these 7 brutal questions

For almost two decades in finance, I lived my life on autopilot.

Wake up at 5:30. Commute. Analyze spreadsheets. Attend meetings. Pretend everything was fine. Rinse and repeat.

I was earning six figures, had the respect of my colleagues, and by every external measure, I'd "made it." But here's the honest truth: I was miserable.

At 36, burnout forced me into therapy, and my therapist asked me something that stopped me cold: "When was the last time you made a decision based on what you wanted, not what you thought you should do?"

I couldn't answer. And that inability to answer revealed something terrifying. I'd spent years building a life that looked successful from the outside but felt empty on the inside. My achievement addiction, born from being labeled "gifted" as a kid, had me chasing external validation like it was oxygen.

The path out of those patterns wasn't comfortable. After leaving finance at 37 to become a writer, I discovered that transformation required asking myself questions I'd been avoiding for years. Questions that made me squirm. Questions that challenged every belief I held about success, worth, and identity.

Now, every morning after my trail run and meditation practice, I sit with my journal and work through these seven questions. They're not gentle. They're not meant to make you feel good. But they will shake you awake if you let them.

1) What am I pretending not to know?

This question cuts through denial faster than anything else I've encountered.

When I first asked it, the answers came flooding in. I was pretending not to know that my 70-hour work weeks were destroying my health. I was pretending not to know that money wasn't making me happy. I was pretending not to know that I'd chosen my career to please my achievement-oriented parents, not myself.

We're brilliant at selective blindness, aren't we? Your body sends signals. Your relationships show cracks. Your Sunday night dread speaks volumes. But it's easier to pretend these signs don't exist than to face what acknowledging them would mean.

Think about it. What uncomfortable truth are you dancing around right now? Maybe it's that your relationship isn't working. Maybe it's that your drinking has become a problem. Maybe it's that you hate your job but feel trapped by golden handcuffs.

The thing about pretending not to know is that it requires enormous energy. It's exhausting to maintain illusions. When I finally admitted what I'd been avoiding, the relief was immediate, even though the path forward wasn't clear yet.

Try this: Write down the first three things that come to mind when you ask yourself this question. Don't edit. Don't judge. Just let them surface. The clarity might be uncomfortable, but it's the first step toward actual change.

2) If I lost everything tomorrow, who would I become?

When the 2008 financial crisis hit, I watched colleagues who'd built their entire identities around their net worth completely crumble. One day they were masters of the universe, the next they were lost souls who didn't know who they were without their titles and bonuses.

This question forces you to examine how much of your identity is tied to external things. For years, I was "the financial analyst." Strip that away, and who was I? The answer was terrifying: I didn't know.

During my transition from finance to writing, I had to rebuild my sense of self from scratch. Without my six-figure salary, without my corporate title, without the validation of being the "smart one" who made it in a tough industry, I had to find out who I actually was underneath all those labels.

Ask yourself: If you lost your job, your savings, your home, your relationship status, what would remain? What parts of you exist independent of circumstances? This isn't about catastrophizing. It's about finding your bedrock, the parts of you that can't be taken away.

What I discovered was that my curiosity, my desire to understand human behavior, my love of early morning runs, my commitment to growth, these things were mine regardless of my bank balance or business card. They became the foundation I rebuilt on.

3) What story am I telling myself that keeps me stuck?

We're all walking around with narratives we've never questioned.

Mine was: "I have to be perfect to be worthy of love." This story, planted in elementary school when I was labeled "gifted," shaped decades of my life.

It drove me to work those 70-hour weeks. It made me stay in relationships where I couldn't be vulnerable. It kept me in a career that was slowly killing my spirit.

During my first marathon training at 42, I had hours of running to think about the stories I'd accepted as truth. "Rest is lazy." "Asking for help is weakness." "Success means constant achievement." Each one was a bar in the cage I'd built around myself.

Your story might be different. Maybe it's "I'm not the kind of person who..." or "People like me don't..." or "I've always been..." These narratives feel like facts, but they're just stories. And stories can be rewritten.

I learned this the hard way when I met my partner Marcus at a trail running event. My story said successful women intimidate men, that I'd have to choose between love and ambition. But he showed me that was just one possibility, not an inevitable truth.

What narrative are you carrying that isn't serving you anymore? What story would you tell if you could choose any story at all?

4) What would I do if I knew I couldn't fail?

This question seems cliché until you really sit with it.

When I asked myself this at 36, the answer was clear: I'd write. I'd spend my mornings running trails and my days exploring psychological insights. I'd build a life around understanding and sharing what makes us human.

But here's what stopped me: the fear of giving up financial security. The fear of being seen as someone who "threw away" her potential. The fear of my parents' disappointment. The fear of starting over in my late thirties.

Fear of failure keeps us in situations that are slowly failing us anyway. Staying in finance was its own kind of failure, just a socially acceptable one. I was failing at being authentic. Failing at honoring my values. Failing at living a life that felt meaningful to me.

When I finally took the leap, I struggled financially for two years. I lived off savings. I faced judgment from former colleagues. My mother still introduces me as her daughter who "used to work in finance." But I also discovered that understanding human behavior was infinitely more fulfilling than understanding market trends.

The question isn't really about eliminating failure. It's about recognizing that not trying is its own form of failure, just one that feels safer.

5) What am I tolerating that I don't have to?

Here's what nobody tells you: most of what we tolerate is optional. Yes, life includes inevitable suffering, but so much of our daily discomfort comes from situations we could change if we were willing to be uncomfortable for a short time to create long-term relief.

When I started saying no to things I'd been tolerating, people were shocked. No to networking events that drained me. No to maintaining friendships that were actually just professional obligations. No to the voice in my head that said rest was laziness.

The pushback was real. But here's what I learned: people's resistance to your boundaries says everything about them and nothing about the validity of your needs.

What are you putting up with that drains your energy? What have you accepted as "just the way things are" that could actually be different?

Start small. Pick one thing you're tolerating and change it this week.

6) Who am I becoming if nothing changes?

Picture yourself in five years if you change nothing. Same routine. Same patterns. Same compromises. Who is that person? Are they who you want to be?

When I did this exercise during my burnout, I saw a bitter woman in her forties, successful on paper but dead inside. She had money but no meaning. Achievements but no authenticity. She was my nightmare future, and she was exactly where I was headed.

This isn't about dramatic life overhauls. Small patterns compound over time. The daily choice to prioritize work over relationships. The habit of numbing discomfort instead of addressing its cause. The tendency to say yes when you mean no.

When I started my gratitude journal, I was skeptical. How could writing three things I was grateful for change anything? But it shifted my attention. Trail runs became meditation. Cooking vegan meals became creative expression. Small changes in daily patterns led to fundamental shifts in who I was becoming.

Look at your current trajectory honestly. If your daily choices continue unchanged, where will they lead? Is that destination one you're choosing, or one you're sliding toward by default?

7) What would the person I want to be do right now?

This is the question that turns insight into action. It's one thing to know you're stuck in patterns. It's another to break them. This question becomes your compass for decisions both big and small.

When I was debating leaving finance, I asked: What would the authentic, creative, fulfilled version of me do? She'd take the risk. When I was learning to set boundaries with my parents, I asked: What would the person with healthy relationships do? She'd have the difficult conversation.

This question bypasses the endless analysis that keeps us stuck. Instead of "What should I do?" or "What's the right choice?" it connects you to your future self, the one who's already made the changes you're contemplating.

I use this question daily. When I want to skip my morning run: What would the person I want to be do? When I'm tempted to say yes to please someone: What would the person I want to be do? When I'm avoiding a difficult truth: What would the person I want to be do?

The answer isn't always what I want to hear, but it's always what I need to know.

Final thoughts

These questions aren't magic. They won't transform your life overnight. What they will do is start disrupting the automatic patterns that keep you stuck. They'll make you uncomfortable. They'll challenge beliefs you've never questioned. They'll reveal gaps between who you are and who you want to be.

That discomfort? That's not a bug, it's a feature. Comfort is what kept me in a career that was killing my soul for almost two decades. Discomfort is what led me to a life where I wake up actually wanting to face the day.

Every morning, after my trail run, I sit with these questions. Some days the answers come easily. Other days they reveal work I still need to do. But they keep me honest. They keep me growing. They keep me from sliding back into unconscious patterns.

You don't have to ask all seven at once. Start with one. The one that makes you most uncomfortable is probably the one you need most. Write your answers. Don't just think them, write them. There's something about putting words on paper that makes truth harder to avoid.