Why You Keep Second-Guessing Yourself (and How to Stop).
- Jennifer Bonilla
- Aug 23
- 5 min read
Updated: Sep 7
You finally make a decision, maybe about dinner, texting someone back, or saying yes to that project at work. For a moment, you feel relief... but then, almost instantly, the spiral begins.
“Was that the right choice? What if I regret this? Did I overreact? Should I have said yes instead of no? What are they thinking about me now?”
Suddenly, a simple choice spirals into a marathon of overthinking. Instead of moving forward, you end up doubting yourself, replaying conversations, and scanning for reassurance.
Sound familiar? Trust me, you’re not alone! Many women I work with in therapy describe this constant self-questioning as a near-daily occurrence. It’s draining, it eats away at your confidence, and it leaves you feeling disconnected from your own voice.
Here’s the important part: second-guessing yourself doesn’t mean you’re broken. It usually means you’ve been carrying self-doubt for a long time, shaped by experiences that made it harder to trust yourself.
Let’s take a closer look at why this is happening and how things can begin to shift.
Where Second-Guessing Comes From
Self-doubt rarely comes out of nowhere. It’s often learned, woven into family roles, cultural expectations, and the way you were treated growing up.
When Childhood Pressure to Achieve Leads to Self-Doubt
Maybe your childhood was filled with pressure to achieve. Good grades, awards, or recognition mattered more than how you felt. Mistakes weren’t safe; they led to criticism, disappointment, or silence.
Over time, you learned: “I have to get it right, I have to be the best.”
Now, even small choices feel risky. You replay them endlessly, trying to avoid the discomfort of failure or judgment.
How Family and Cultural Expectations Shape Self-Trust
In many immigrant and culturally rich families, there are unspoken rules: Don’t make us look bad. Put family first. Be strong. Don’t be selfish.
These messages can create a sense of closeness and resilience, but they can also start to blur the line between what you need and what others expect. If you’ve always been in the role of caretaker or peacekeeper, it makes sense that your own voice feels unsafe now.
When Your Feelings Were Dismissed
If you were told things like:
“Stop being so sensitive.”
“You’re overreacting.”
“Don’t be dramatic.”
…it’s no surprise that you came to doubt your feelings. When emotions weren’t taken seriously, you learned to minimize them or look to others for approval. The persistent self-doubt you’re experiencing is often a reflection of that invalidation.
What all of this has in common is survival. Self-doubt became your way of staying safe in environments where independence, mistakes, or vulnerability weren’t always welcomed.
How Second-Guessing Shows Up in Daily Life
The impact of just “being indecisive.” It shows up in deeper, more frustrating ways:
Emotional Overwhelm: Feeling everything all at once, then shutting down or numbing out to cope.
Anxiety in Relationships: Overanalyzing texts, re-reading conversations, or worrying about rejection. Dating can feel like a rollercoaster filled with uncertainties and “what-ifs.”
Family Guilt: Setting boundaries can feel overwhelming. If a parent gives you the silent treatment or reacts defensively, it often leaves you feeling resentful and guilty.
Decision Fatigue: Even simple choices (dinner, weekend plans, taking a break) can feel daunting. You run through every scenario until you’re paralyzed.
Instead of living from your authentic self, it can feel like you’re stuck on the sidelines, always wondering if you’re doing it “right.”
What You’re Really Longing For
Beneath all the doubt is something deeply human: the desire to feel safe, connected, and free.
You want to:
Feel your emotions without shame or fear of being “too much.”
Be valued in relationships (romantic, family, friendships) for who you are, not just what you give.
Set boundaries without guilt, say no without panic, and make choices that align with your needs.
In other words, you want to trust yourself. To move through life without that constant background noise of doubt.
What Can Help You Stop Second-Guessing Yourself
The good news? You can learn to overcome self-doubt. Therapy is one space where this transformation happens. Together, we can work on:
Emotional Awareness and Regulation
When you’re stuck in uncertainty, emotions can feel too big or too scary. Therapy helps you:
Name your feelings without judgment.
Practice grounding techniques so emotions don’t spiral out of control.
Build self-compassion so you can meet feelings with curiosity instead of criticism.
Mindfulness plays a crucial role here. It’s about slowing down, noticing what’s present, and remembering that emotions aren’t enemies; they’re signals worth listening to.
Boundaries and Family Dynamics
Boundaries can be one of the most challenging areas, especially when cultural expectations and guilt come into play. Therapy helps you:
Reframe boundaries as an act of care, not rejection.
Navigate guilt and emotional pushback with compassion for yourself and your family.
Redefine your role so you’re no longer stuck as the fixer, pleaser, or emotional caretaker.
This isn’t about cutting people off; it’s about creating some breathing room so you can show up without losing yourself.
Rebuilding Self-Trust
Ultimately, second-guessing is about a lack of self-trust. In therapy, you practice:
Listening to your instincts.
Making decisions without the endless reassurance.
Affirming your feelings are valid, even when others disagree.
Learning that mistakes aren’t failures, they’re part of being human.
Eventually, you stop depending on others for your decisions and start listening inward again.
A Kinder Way to Change
Here’s something I want you to remember: doubting yourself has served a purpose. It was your way of staying safe, of protecting yourself from rejection, criticism, or conflict.
You don’t need to shame yourself into changing. You don’t need to force yourself into being “confident.”
What you need is a gentler shift, one that moves you out of survival mode and into a space that feels freer, calmer, and more connected.
Small Steps to Stop Second-Guessing Yourself
While therapy gives you the deeper support, here are some everyday practices to begin breaking the cycle:
The One-Question Reset: Ask yourself, “If no one else had an opinion, what would I choose?”
Name the feeling before the doubt: Instead of replaying decisions, pause and say: “I feel anxious” or “I feel pressured.” Naming reduces intensity.
The small wins journal: Each day, write one decision you made without spiralling. Even tiny ones count (yes, your coffee order makes the list). These reminders help retrain your brain to trust yourself.
Spot the “shoulds”: When you catch yourself thinking, “I should…” pause. Ask: “Is this my value, or someone else’s expectation?”
Final Thoughts
Self-doubt is not a sign of weakness; it reflects how you learned to navigate environments that didn’t always welcome independence or emotions.
But survival isn’t the whole story. With the right support, you can learn to trust yourself again. To feel safe in your emotions, secure in your relationships, and free to live in alignment with your own needs.
Therapy isn’t about fixing you. It’s about helping you come home to yourself with clarity, compassion, and confidence.
Want Support Moving Forward?
Curious to keep exploring? Subscribe to Dear Overthinker, my monthly newsletter with gentle support and practical tools to help you feel more, fear less, and trust yourself again.
Ready for the next step? I offer virtual psychotherapy for adults across Ontario. If this resonates, I’d love to connect. Click here to book a consultation.
You don’t need to suppress your doubt; you just need the right support to regain your self-confidence.
✨Thank you for being here! For every version of you, across every season of life.
Kindly,
