The Worst Question People Pleasers Ask Themselves & What To Ask Instead
Blog post by Heidi Gustafson
Mindset & Transformation Coach
Mastering Midlife with Heidi is dedicated to helping middle-aged women live their lives with confidence and joy, instead of merely surviving.
As we go about our day, our internal monologue is filled with questions — whether we are aware of them or not.
We’re constantly filtering through information, making decisions, and selecting what we’re going to pay attention to. From figuring out what to make for breakfast to paying attention to other drivers on the freeway, everyone is buzzing with questions.
Tony Robbins said the quality of your life is determined by the quality of the questions you ask. But typically the questions we ask ourselves start with ‘why’ and stem from frustration or disappointment.
"Why do I always procrastinate?"
"Why can’t I get control of my money?"
"Why am I so messy?"
"Why did I eat all that crap last night?"
“Why am I always late?”
Asking ourselves “why” doesn’t usually get us anywhere because …
1 — It puts people on the defense
Whether you’re asking yourself or another person, why questions put people on the defensive automatically because “why” carries a certain amount of judgment. Think about it. If you ask your friend or kid or partner, “Why did you do that?”, you’ll probably notice them coming up with reasons and excuses. If you ask yourself the same question, your subconscious is going to give you a justification. You’re going to hear yourself rationalizing why you did it. In both cases, nothing has changed for the better.
2 — We go into justification mode
In an attempt to answer why, we end up making up reasons for our actions, which doesn’t promote genuine self-reflection. This cycle reinforces negative patterns without addressing the root issues.
3 — It causes you to relive the past
When we go to the past, we relive those experiences, right?... whether a little or a lot, and our subconscious mind doesn’t know time. It doesn’t know the past from the future. It only sees the present moment. So it thinks what you’re dwelling on is happening right now and that it’s real.
Your subconscious ALSO can’t distinguish between what’s real and what’s imagined. It thinks whatever you’re thinking or worrying about is happening right now and in the present moment… that it really IS happening.
Because the subconscious mind’s job is to keep us safe, dwelling on the past to figure out “why” most likely puts us into fight or flight mode… a stressed state.
Think about it: How often do we ask “why” about something that doesn’t stress us out? You’re not saying, “Why do I feel so amazing today?” “Why did I nail that presentation?” “Why did I have so much fun playing with my grandkids?”
4 — It keeps us stuck in fear, not possibility
Since our “why” questions are driven by fear, there is no logical answer … yet we keep pursuing it as if there is. This keeps us on a one-track path — a path that’s heading to the past — instead of allowing us to tap into our creativity and intuition.
It’s time to stop regurgitating and start allowing ourselves to do what we were all divinely given and born to do… to create.
If you stay on the “why” path long enough, your brain will start to make up stories to answer your question. Then that lie, created out of fear, becomes a part of you.
How are “why” questions even worse for people pleasers?
1. It can intensify negative self talk, leading someone who people pleases to blame themselves excessively for actions or situations.
2. “Why” questions can lead to Overthinking and Overanalyzing. People pleasers in particular tend to overthink their actions and decisions and asking "why" can trigger this overanalysis, making situations appear more complex than they are. “Why” can get us into analysis paralysis.
3. The uncertainty associated with “why” questions can raise anxiety for people pleasers. They already fear judgment and disapproval from others, and deeply scrutinize their own actions. When they ask themselves “why” they did something or made a certain decision, this is often stemming from a concern about how others perceive their actions. They fear not meeting others’ expectations and the “why” questions amplify that fear.
4. People pleasers often carry a burden of guilt. Asking "why" can make the guilt worse by focusing on feeling like you've let others down.
5. People pleasers also might pose "why" questions as a way of seeking external validation. This means they ask "why" to understand how their actions align with others' expectations, hoping for approval or acknowledgment.
The bottom line is: it doesn’t matter WHY we or anyone else does something.
Knowing why doesn’t bring change. Instead, it reinforces negative aspects of ourselves. It doesn’t matter “why” you are who you are.
A better question is: who do you want to become? What kind of transformation do you want?
Phrasing questions and asking “what” or “how” instead of “why” encourages us to look at things more constructively and with possibility. This helps shift to solutions and empowerment — taking us away from judgment to curiosity.
When you get curious about what’s happening, that leads to creativity, which leads to change.
If you're feeling stuck, it's time to start asking yourself "how could this be different?”
Reframing "why" questions into more constructive "what" or "how" questions gives a more solution-oriented perspective.
These new questions help move away from overthinking about why we do things and instead get us to focus on the practical steps we can take to actually bring resolution to the situation.
Having a positive, problem-solving mindset also creates more self awareness and self acceptance because it helps us realize we DO have a choice and the power to make things different.
💡 Also… remember that using what or how instead of ‘why’ when interacting with OTHERS will lead to more open conversations because the other person doesn’t feel the need to defend themselves.
I have a list of almost 100 questions I use with my clients to help them get unstuck.
Almost everyone is striving for growth in various aspects of life—whether it's in their spirituality, more success in their job, more financial stability, deeper relationships, more self awareness and acceptance, or experiencing more joy and fun. The list goes on for what most of us want MORE of in our life. However, we often find ourselves stuck in challenges when seeking that increase we desire.…. and asking ‘why’ NEVER helps us to get unstuck.
I’ll close with this quote by Jim Rohn. He said, “Your life does not get better by chance. It gets better by change.”
Until next time, embrace change, ask empowering questions, and keep mastering your midlife journey.
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