You know how to make decisions. You’ve made hundreds of them for everyone else: for your family, your work, your household, the people who count on you. So why can’t you stop second-guessing yourself when the decision is your own?
→ Maybe you have weeks of vacation coming and no idea how you want to spend them.
→ Or you’ve set money aside for something you’d enjoy, and you still can’t choose.
→ Or someone asks you a simple question and you’ve said yes before you’ve even checked in with yourself…and later you regret it.
And when you finally do decide, your mind won’t let it go. You replay it, question it, picture everything that could go wrong.
Then you ask someone else what they think, and suddenly you’re right back where you started.
It’s exhausting.
And underneath the exhaustion, there’s usually something harder to admit…a voice that says:
I should be able to handle this. I’m someone who handles things. So why can’t I figure this out?
You’ve spent years being the one who sorts things out for everyone else. You might even be fabulous at helping other people make decisions.
So when you can’t make one for yourself, it’s easy to start wondering: What’s wrong with me? Why can’t I trust myself anymore?
Why it’s so hard to decide for yourself (when you’ve always decided for everyone else)
Nothing is wrong with you. There’s a reason this happens.
A lot of us grew up learning, in ways both obvious and subtle, that a good woman puts everyone else first. We check what they need. Consider how they’ll feel. Make sure everyone’s okay.
Do that for long enough and you get very good at checking in with everyone else…and very out of practice at checking in with yourself.
I learned this early. As the youngest of four, I was the family peacekeeper long before I had a word for it.
I read rooms. I smoothed things over. And when my parents fought, I’d sit at the kitchen table with my mom afterward and try to help her figure things out.
(I was about twelve years old, and that soooo wasn’t my job. But I didn’t understand it at the time.)
What I didn’t notice until much later was that somewhere along the way, I’d stopped checking in with myself. I was so practiced at tuning into everyone else that my own signals had gone completely quiet.
Now add a big change to the mix…
Divorce, an empty nest, retirement, a career shift, a loss, a move, a chapter you didn’t necessarily choose.
And suddenly the decisions are yours again. That can feel more disorienting than you expected.
From “I’m not good at decisions” to trusting yourself again
But you can learn to hear your own voice again. You can:
👉 Make a decision and leave it alone, without replaying it at 2 a.m.
👉 Quiet the arguing in your head.
👉 Get more comfortable with the possibility of getting something wrong.
I’ve watched this happen. When one client first came to me, she said “I’m not good at making decisions.”
She had an aging parent to care for and a big decision to make about the family home, and it all felt like “a tangled ball of yarn.”
Six sessions later, she told me she’d learned to trust her own instincts. The ones she’d always felt. The ones she’d been talking herself out of for years.
Here are three of the shifts that helped her get there, and that can help you stop second-guessing yourself too:
- Learn what your “yes” feels like
- Protect your first answer (before you ask anyone else)
- Make peace with the decision you keep replaying
1. Learn what your “yes” feels like
Most of us can recognize a no. Your stomach tightens, you feel heavy, and something in you says: I really don’t want to do this.
But what does your yes feel like? That can be much harder to name.
Because your yes tends to be quieter.
It might feel like a little more room in your chest, a lightness, ease, relief…a sense of this is right that doesn’t come with a long explanation.
And if you’ve spent years overriding yourself, you’ve probably learned to tune those signals out too.
Like one of my clients had, who put it perfectly: “I need to learn to listen to the positive side of my intuition, not just the warning signs.”
Why your yes is quieter than your no
Your intuition hasn’t gone anywhere. You’ve just gotten used to putting other things ahead of it.
Your brain is great at the practical stuff: money, logistics, other people’s needs. But once it gets stuck on the hamster wheel, more thinking doesn’t help. It just keeps you spinning.
Sometimes the only way out is to stop thinking so much, and start noticing.
In my coaching, I use what I call the Back to You Framework which has four phases: Reconnect, Clarify, Strengthen and Honour.
This strategy is at the heart of Reconnect: noticing the signals that have been there all along.
You don’t have to become someone different or learn some mysterious new skill. You’re remembering something you already knew how to do.
Try this: find your yes in your body
Think of a time something felt clearly right. It could be a decision, a place, a person, or something completely ordinary. Close your eyes and remember it.
What happens in your body? Do you feel lighter? More open? Calmer? More energized? There’s no right answer here. You’re learning your own language.
Then try it with something small this week. Before you decide whether to accept an invitation, where to go for a walk, or what you’d like for dinner, pause for a moment and ask yourself:
What does my yes feel like?
Don’t worry about getting it “right.” You’re just practicing noticing.
Why I coach by phone
I coach by phone, and that’s intentional. Without a camera, there’s no one to perform for, so we can slow down and pay attention to what’s going on inside you.
I’ll often ask “How does that feel?” rather than “What do you think you should do?”
We slow down and notice what your body is telling you, not just what your thoughts keep circling back to.
One past client said coaching helped her pay attention to how something was making her feel:
“I’d often felt that, but before coaching I had a tendency to dismiss it.”
That noticing is where self-trust begins.
2. Protect your first answer (before you ask anyone else)
Have you ever known exactly what you wanted to do, right up until the moment someone else weighed in?
You think: Yes, I know what I want.
Then a friend asks “Are you sure?” or your sister thinks you should do something different, or your partner has another opinion…and suddenly you’re questioning everything.
That’s why I recommend protecting your first answer.
Before you ask anyone else what they think, get clear on what you think.
And it doesn’t need to be perfect.
It can be as simple as “I’m leaning towards…”
Or “My gut says no, but I’m not sure why yet.”
That’s enough.
Why other people’s opinions drown out your own
Often the problem isn’t that you can’t decide.
Your answer’s already there…but somewhere along the line, you’ve let someone else’s answer override it.
If you’ve spent years checking what everyone else needs before checking in with what you need, other people’s opinions can start to feel more trustworthy than your own.
Writing your answer down first gives your voice a head start. Then, if you want someone else’s perspective, you can listen to it without automatically handing over the decision.
Their opinion can be helpful, but you get to have the final say.
This is often where Strengthen, the third phase, begins.
You don’t have to confront anyone or announce a new boundary. You just get to know your own yes or no before you go looking for anyone else’s.
Try this: decide what you’d choose with no one to ask
The next time you notice yourself reaching for someone’s opinion, pause and ask yourself:
“If there was no one around to ask, what would I choose?”
Write down whatever comes up. It doesn’t have to make perfect sense. If you still want input after that, go ahead and ask, then check back in with yourself.
Did their opinion clarify something? Or did it drown out your own voice?
And when someone wants an answer before you’re ready, give yourself permission to pause: “Let me think about it and get back to you.”
You don’t have to say yes just because someone asked.
Hearing your own voice in our sessions
In our sessions together, you get a place to think out loud without anyone telling you what to do.
I’m not there to make your decisions for you.
I’ll reflect back what I’m hearing. And help you notice when the voice you’re describing sounds like your own.
Or when it might be someone else’s voice (like a parent, a friend, a partner, or an old “should”).
At the end of a session, you might choose one small area to practice before we talk again such as:
✅ Pausing before you say yes.
✅ Writing down your answer before you talk it over with a friend.
✅ Noticing what happens inside you when someone disagrees with you.
Small practices like these are how you start hearing yourself again in your everyday life.
That’s what happened for one client. She and her husband were trying to decide whether to sell the home they’d loved for more than 30 years, and once she checked in with herself, the answer was “not yet.” This time waiting wasn’t avoidance; it was a choice she felt at peace with.
3. Make peace with the decision you keep replaying
Now let’s talk about the decision you keep measuring yourself against. The one that “went wrong.”
Maybe you think: I should have known. I can’t believe I did that. The last time I trusted myself, I was wrong.
And now you’re afraid to trust yourself again.
But a decision that didn’t lead to the outcome you wanted isn’t necessarily a bad decision.
More often than not, it was a reasonable choice based on what you knew at the time.
So go back to that decision and get curious about it.
What did you know at the time?
What were you feeling?
What did you believe was important?
And was there a part of you that knew something wasn’t right, but you talked yourself out of it?
A bad outcome doesn’t mean a bad decision
When we look back at a painful outcome, it’s easy to treat it as proof that we can’t trust ourselves. But you know things now that you didn’t know then.
And sometimes the problem wasn’t that your judgment was bad. It’s that you overrode it.
That’s a very different problem, and a much more hopeful one. Because once you can notice when you’re overriding yourself, you can start making a different choice.
I know what it’s like to override yourself.
When I first discovered the training school to become a coach, I sat in their information session downtown and felt my whole body light up: this is it!
Then I walked out, thought about how much it would cost, and promptly talked myself out of it.
“I can’t afford it. It’s not the right time. You need to be more responsible, Kerry.”
I went home that weekend and fell into a mini depression. So I drove to the ocean, sat on the beach with my journal, and just started writing. Within an hour I’d written my way back to what I already knew: I was going to enrol in the coaching program.
Because the knowing was never the problem. I just needed to stop arguing with it.
This is Honour, the fourth phase of my framework…holding self-trust and self-compassion together. Because you can’t rebuild trust with yourself while you’re still beating yourself up for the past.
Try this: look back with kindness
Think of one decision you keep replaying, and write down:
- What did I know at the time?
- What was I feeling?
- What did I want?
- What was I afraid of?
- Did I notice any signs that something wasn’t right?
- Did I dismiss or override any of them?
Then ask yourself:
“What would I say to a friend who made this decision with the exact same information?”
You’d probably be much kinder to her. You might even remind her she was doing the best she could with what she knew.
You deserve that same kindness.
If you’d like more support with this, my free guide, How to Stop Second-Guessing Yourself, walks you through the Try It On Method, a simple way to test a decision before you commit and tell the noise in your head apart from what you actually know.
Looking at old decisions together, without blame
This is where it helps to have someone alongside you. It’s hard to see your own story clearly when you’ve been in the middle of it for years.
In our sessions, we’ll look at those old decisions together, gently and without blame, until they stop being used as evidence against you.
Instead of “How could I have been so stupid?” we’ll ask:
“What was I noticing? What did I need? What did I override? What do I want to remember next time?”
Before we hang up, you decide what you want to take with you: one or two small things to try, at a pace that feels right to you.
One past client said I gave her “the tools I needed to solve my problems/concerns in my own way” and helped her realize she “already possessed a lot of these skills.”
That’s the goal. For you to trust yourself more, not to need me forever.
But what if my gut is wrong?
You might be thinking: “What if my gut is wrong? The last time I trusted myself, it didn’t work out.”
Ok that’s fair. And it’s often what makes it so hard to stop second-guessing yourself.
But what if the lesson from that experience isn’t “I can’t trust myself”?
What if instead it’s “I need to get better at listening to myself, and at noticing when I ignore what I already know”?
Self-trust doesn’t mean you’ll always make the perfect choice.
Or know exactly what will happen. Or never change your mind.
It means you can make a choice with the information you have, keep listening to yourself along the way, and trust that you’ll handle whatever comes next.
That’s a confidence you can actually build. And it takes a lot of the pressure off.
You don’t need every detail settled before you move forward. You don’t need all your ducks in a row, or a guarantee that nothing will go wrong.
As one client put it:
“I feel lighter. There’s no more ‘or else.’ I’m slowly learning there won’t be consequences.”
Three small shifts to stop second-guessing yourself
If you’re in the middle of a big change, it makes sense that decisions feel harder than they used to.
But you haven’t lost your ability to make good decisions. You’re just learning how to make them for yourself again.
✨ Start by noticing what your yes feels like.
✨ Protect your first answer before other people’s opinions get involved.
✨ Separate the decisions you’ve made from the outcomes that followed, so you stop using your past against you.
These are small shifts, but small shifts add up. They’re how you stop second-guessing yourself and start trusting what you already know.
Over time, you can say yes when you mean yes, and no when you mean no. You can make a choice without needing to know exactly how it’ll all turn out.
And you can feel at peace with yourself again.
Ready to hear your own voice again?
If any of this landed for you, I’d love to talk.
Next Step Back to You is my six-session coaching package, one-on-one and by phone.
It’s where we work through all four phases of the Back to You framework together, so you can hear your own voice again and trust what it’s telling you.
Together, we’ll practice noticing your yes, protecting your answer from everyone else’s opinions, and making peace with the decisions that have been weighing on you.
At the end of each session, you choose your own next small step, so you leave knowing what you want to try, in a way that works for you. I trust you to take it from there, and if something comes up between sessions, you can always email me.
The first step is a free, no-pressure 20-minute conversation. We’ll talk about what’s going on for you and whether Next Step feels like the right fit.
You don’t need to have it all figured out. You just need to be curious.
Kerry xo
P.S. Not ready for a call yet? Start with my free guide: How to Stop Second-Guessing Yourself. It’s a gentle place to begin practicing this on your own.
