When You Can’t "Be Sure", Be True

My sister and I are both going through it right now. Different stories, different circumstances, but similar emotional weight. The kind of weight that leaves you staring at the ceiling at 2am wondering how you got here and how you’re supposed to get out. We’ve been supporting each other through decisions that feel like no-win situations—ones where, no matter what you choose, something important gets lost.

As we talked last night, she mentioned she had written an email—the kind of email that feels like setting off an emotional smoke alarm. I asked the obvious question: “Did you send it?”

“No,” she said. “It’s just… burning a hole in my desktop. I want to make sure I’m doing the right thing.”

Make sure.

Those two words? Torture.

The Myth of Being “Sure”

Here’s what Oxford, Merriam-Webster, and Cambridge have to say about the word sure:

• “True beyond any doubt.”

• “Confident in what one thinks or knows; having no doubt.”

• “Having complete conviction about something; confident.”

Sounds nice, doesn’t it? So neat. So final. So… certain.

Let me be completely honest here: by these definitions, I am only sure of three things in my life. I am sure that I love my child with every fiber of my being. I am sure that I am not perfect, but I live in a way that I am proud for my child to see. And I am sure that those are the only things I am sure about.

Everything else? It’s on a spectrum of possibility. I wouldn’t bet my life on any of it.

So when someone says, “I just want to make sure I’m making the right decision,” I feel myself wince a little. Not because I don’t understand the desire—I deeply do. But because I also know how torturous that desire can be. My brain immediately chimes in: We can never be sure. Not in the way you think. Not in the way you want. Not in the way that makes it all feel clean and easy and settled.

Because that kind of certainty—the kind we crave when we’re scared or stuck or staring down a big life decision—it rarely exists.

And yet, we keep chasing it. We look for it in other people’s approval. We try to find it in spreadsheets or in pros-and-cons lists or in late-night internet rabbit holes. We wait for a sign. For validation. For permission. For clarity to come striding in through the front door, glowing and unmistakable.

But clarity doesn’t usually announce itself. And certainty? It almost never comes from outside.

The truth is, we could spend our whole lives waiting to feel sure—and miss the moments when we were actually being true.

True to ourselves.

True to what we value.

True to the voice inside us that doesn’t scream, but knows.

When You Stop Trusting Yourself

The most painful part of indecision isn’t the decision itself. It’s what happens inside when you stop trusting yourself.

It’s the silencing of your own voice. The way it starts as a whisper and eventually goes mute under the weight of everyone else’s opinions, judgments, expectations, and advice. You start outsourcing your authority—giving away the right to decide what’s best for you to anyone who sounds more confident, more experienced, or simply louder than your own instincts.

You begin second-guessing everything:

Your gut.

Your timing.

Your boundaries.

Your truth.

And the worst part? You start believing that they must know better. The people who don’t see your full life, who don’t carry your history, who don’t feel what you feel when your head hits the pillow at night—they start to sound more trustworthy than the quiet truth within you. So you defer. You comply. You wait for confirmation that may never come.

You hand them the pen to your story. And slowly, quietly, you begin disappearing from your own pages.

You shrink a little to keep the peace.

You nod when you really want to push back.

You stay when your soul is begging you to go.

You perform a version of yourself that’s more acceptable, less disruptive, easier to understand.

And maybe one day, you wake up and realize you don’t recognize your own reflection.

You’ve wandered so far from your own truth that you can’t tell which parts of you were real and which parts you edited to survive.

That moment? It’s gutting.

It’s disorienting.

It can break your heart.

But it can also become the beginning of something else—something sacred.

Because once you see the gap between who you are and who you’ve been re-written to be, you can begin the journey back. You can start asking the questions that bring you home to yourself.

The Only Way to Feel Sure

My candid opinion: there’s no such thing as being sure. But I think I can settle for a way to feel sure. And it comes from this: living in alignment with your values.

Not someone else’s values. Not your parents’ values. Not your workplace’s mission statement or your friend’s worldview or the “shoulds” that echo in your head. Your values. The ones that make your chest rise and your chin tilt upward when you speak them out loud. The ones that ground you when everything else feels shaky.

To take a little beat from Hamilton, when you know what you stand for—when you really take the time to define and own what matters most to you—you also start to realize what you won't fall for.

You know the line I'm talking about? That line hits. Because standing for something—really standing for something—means you stop letting people knock you over with their opinions, their projections, their discomfort with who you are. It means you’re no longer a blank slate for other people to write on. You’re not trying to bend or contort or prove. You’re rooted. And when you’re rooted, even in the face of uncertainty, you can feel a different kind of strength.

The strength of knowing what you will not tolerate. The strength of knowing what no longer fits. The strength of no longer abandoning yourself to keep the peace.

Living in alignment doesn’t guarantee a painless life. It doesn’t make hard decisions easy. But it makes them clearer. It allows you to make a choice and say, “This may be complicated. This may not be what everyone else would do. But this is what feels true to who I am.”

Because the goal isn’t perfection. The goal is integrity.

Here’s the real truth: the most important relationship you will ever have is the one you have with yourself. The most important person you need to trust is not someone else. Not your friend. Not your sister. Not your boss. Not your mentor. Not even your partner. It’s you.

And when life hands you one of those impossible decisions—where every road feels uncertain, every option comes with risk—your values become the flashlight in the dark. They’re the way you start to feel your way forward, even if you’re still scared.

So where do you start?

You ask questions that don’t necessarily have immediate answers. But they open a door. They invite you back into conversation with yourself:

1. What feels most important to me in this situation—and why?

   When you zoom in on what’s stirring you up—whether it’s anger, sadness, or confusion—you’re likely bumping up against something deeply meaningful. That’s a sign. Pay attention to what you’re trying to protect or preserve. That’s where your values live.

2. What do I need in order to feel like I can look myself in the mirror?

   This is about self-respect. When all is said and done, will you be proud of how you showed up? Did you advocate for yourself? Did you stay quiet to keep the peace, or did you protect your peace by speaking up?

3. What am I afraid will happen if I choose this option?

   Naming fear is powerful. Are you afraid of being judged? Of losing something or someone? Of looking selfish? Get curious about the fear—not to shame it, but to understand it. Fear often points to where we’ve been conditioned to abandon ourselves.

4. Who or what am I trying to protect?

   This one stings. Sometimes we make decisions to protect others from discomfort. Sometimes we’re trying to protect a version of ourselves that no longer fits. Sometimes we protect systems, relationships, or roles that don’t protect us in return. That’s worth noticing.

5. If I could change one thing about this situation, what would it be?

   This helps you uncover what you long for. Maybe it’s transparency. Maybe it’s fairness. Maybe it’s freedom. Our wishes and frustrations tend to reveal the environments where we feel most (or least) ourselves.

6. When have I felt proud of how I handled something—and what was I honoring in myself?

   Think back to a time when you made a decision that felt right in your bones, even if it wasn’t easy. What were you standing up for? What were you unwilling to sacrifice? That can offer clarity on what guides you when you’re at your strongest.

   
   

These aren’t easy questions. They’re not checklist questions. They’re the kind that simmer. The kind you might need to ask in a journal, in a therapy session, or on a long walk by yourself. But they’re the kind that bring you home.

They bring you back to your core—not the version of you that’s been watered down or molded to fit someone else’s comfort, but the version that’s always been there. The one that knows who you are, what you care about, and what you’re no longer willing to tolerate.

And here’s the thing: when you make a choice from that place—even if it’s scary, even if it comes with loss—what you gain is trust. Trust in yourself. Trust that you can handle hard things. Trust that you’re building a life that aligns with who you are, not who you’ve been told to be.

That kind of trust? That’s what makes you feel sure.

Even when nothing is certain.

“Let Them”—And Let Yourself

There’s this concept I love from Mel Robbins. It’s simple, and also wildly freeing. It’s called: “Let Them.”

When people mistreat you?

Let them.

When people make assumptions about you, twist your words, or project their own insecurities onto your story?

Let them.

When people decide who you are—without actually knowing you, without asking, without listening?

Let them.

At first, this might sound passive. Like you’re just letting people walk all over you. But that’s not what this is about at all.

Let them doesn’t mean you accept the behavior. It doesn’t mean you roll over, stay quiet, or deny your hurt. It means you recognize something critical: it’s not yours to fix.

It is not your job to carry the emotional immaturity of someone who refuses to take accountability.

You are not obligated to convince anyone of your worth.

It is not your responsibility to rewrite their assumptions or clean up their messy projections.

Because let’s be honest—when someone is committed to misunderstanding you, there is probably no way to explain yourself that will suddenly make them see you clearly. And every ounce of energy you pour into trying to prove yourself to them is energy you’re taking away from your own healing, your own clarity, your own self.

So instead of spiraling in defense mode or begging to be seen, choose something far more powerful:

You let them reveal themselves.

You let them continue to be who they are.

You let them show you, over time, whether they are someone who deserves proximity to your life.

And while they do that?

You let yourself walk away from conversations that aren’t respectful.

You let yourself leave environments that demand you shrink or stay silent.

You let yourself honor your truth—even when it’s messy, even when it’s misunderstood.

You let yourself hold your own hand and say, “I’m still with you. I believe you. I trust you.”

Because here’s the thing: they don’t get to decide who you are. You do.

And in a world where people are constantly trying to define, label, judge, or narrate you—standing firm in your own self-definition is a radical act.

Let them spin their stories. Let them whisper, assume, dismiss, and distort.

Because the more they do, the clearer you get on what you will and won’t allow. The more they show you who they are, the more free you become to protect who you are. Not by fighting them—but by refusing to give them the power to shape your identity.

You don’t need to argue.

You don’t need to defend.

You don’t need to convince.

You just need to choose yourself, over and over again.

Let them. And then, let yourself be better.

Final Thoughts

We think the goal is to be sure. But really, the goal is to be true.

True to your voice.

True to your values.

True to your boundaries.

True to the person you are and the person you’re becoming.

So if you’re standing at a crossroads, stuck between two impossible options, don’t wait until you’re “sure.” Wait until you feel honest. Wait until you feel aligned. Wait until you feel you in the choice.

And when you do?

Hit send.

"The Let Them Theory" by Mel Robbins