5 Questions I Ask Myself When Everything Looks Right But Feels Wrong
When the strategy is solid but your gut says “no,” it’s time to pause and dig deeper.
It usually sneaks up when I least expect it. Everything looks fine on paper—the plan is mapped, the systems are humming, the work is moving forward. But inside? I feel off.
That tension used to keep me stuck. I’d push harder, double down on effort, or throw more tools at the problem. But none of it fixed the core issue: I wasn’t clear on why I was doing what I was doing. It wasn’t that I needed another answer. I needed to ask a better question.
I still remember one afternoon clearly. I was scheduling a website launch and a big product reveal that had been put off more than once. I wasn't feeling the excitement. Finally, I stopped, took a breath, and asked myself, "Why am I forcing this into my schedule?"
That moment changed everything—not because it gave me the strength to schedule it, but because it clarified that forcing the schedule wasn’t the solution; recognizing my actual needs was.
We think we need to do more to fix our problems.
More strategies, more tools, more hacks. But often, it’s not a lack of action—it’s a lack of clarity.
This mindset sticks because the culture around us celebrates hustle, overcomplication, and constant busyness. It tells us that slowing down to reflect is lazy or inefficient. But skipping the self-questioning phase leads to burnout and work that we resent.
I’ve learned that I build things I don’t want without good questions. And then I have to undo them.
The Moment of Truth
My shift happened gradually. I started noticing that whenever I paused to ask myself a few key questions, I moved forward faster, not slower. This wasn't an attempt to stop forward motion; it was about finding the right route.
A coach once told me, “Your best comes when you trust yourself enough to ask the hard questions.” That hit. I realized I needed to design a set of anchor questions—not as a checklist, but as a compass.
The New Mindset: Core Principles and Go-To Questions
Here are the questions that anchor me:
1. Does this fit the way I want to live and work?
It’s probably not a good fit if something disrupts my lifestyle.
2. Am I doing this to prove something or because it’s aligned?
This checks if I’m chasing external validation or making choices that genuinely serve me.
3. What would this look like if it felt easier?
Ease isn’t laziness. It's embracing ease instead of struggle.
4. What’s the actual goal here?
Not the feel-good or ego-driven goal—the real, practical milestones that move me forward.
5. What am I afraid will happen if I do it differently?
This uncovers where fear—not strategy—is guiding decisions.
6. Who am I trying to be with this choice—and do I even like that version of me?
Sometimes, the person I’m trying to be isn’t someone I respect or want to become.
7. What would I do if no one else were watching?
This strips away the need to impress others and focuses on what truly resonates with me.
Living This Mindset: Real-World Impact
Business Decisions: I regularly use these questions before adding new tasks or tools, helping me avoid busywork.
Client Relationships: I bring these questions into consulting to help clients reconnect with their true motivations.
Personal Wellbeing: These questions keep me aligned and focused and lower my stress.
Long-term Vision: They help ensure I’m designing a business I want to live inside, not just one that looks good on the outside.
Overcoming Resistance to Change
Common resistance sounds like:
“I don’t have time to stop and reflect.” → Reframe: What’s the cost of not stopping?
“I should already know the answers.” → Reflection: What if the power is in admitting you don’t?
“Slowing down will make me fall behind.” → Reminder: Clarity accelerates the right progress.
Invitation to Reflect
Which of these questions resonates most with you right now?
Where are you making decisions on autopilot?
What might open up if you asked one of these questions today?
How could you build a habit of pausing for reflection in your own process?
The Bigger Journey
For me, questions aren’t just tools—they’re lifelines. They pull me back to myself when I drift. They remind me that success isn’t about keeping up but staying aligned.
Wherever you are, remember: the right question can open a door you didn’t even know was there.
I’d love to hear—what’s your go-to question when things feel off?