How I moved from second-guessing myself to trusting my yeses and nos.

For years, I thought keeping the peace meant putting myself last. I’d say yes when I wanted to say no, soften my words so no one felt uncomfortable, and carry guilt anytime I tried to prioritize my own needs. Sound familiar?

That’s the cycle of people-pleasing — and it quietly chips away at your confidence. A few years ago, I started writing about becoming more assertive without feeling guilty. Back then, I had some helpful scripts and ideas, but not a lot of real-life practice.

Now, after walking through motherhood, marriage, career shifts, and countless everyday moments, assertiveness feels different. It’s less about theory and more about tools I’ve tested in the messy middle of life. These seven lessons are the ones I keep coming back to — and I just had to share them with you.

8 Assertive Lessons to Go From People-Pleasing to More Confident

1. Pause, Then Answer Clearly

This one is non-negotiable. Sometimes it looks like a few quiet seconds before I respond. Other times, it looks like me signing up for a restorative yoga class because the request feels so heavy, I need to regulate my nervous system before I can answer.

Almost every time, we already know the truth. We just need our bodies to catch up to what our brains have decided.

The pause is powerful, but it only works if it’s followed by clarity.

In the past, I softened my “no” or left doors cracked open, thinking it was kinder. What I really did was create false hope. Now I know clarity, even when it stings, is a lot more compassionate than indecision.

Maybe you’ve done this too — saying “Let me see if I can make that work” or “I’ll try to be there” when you already knew the answer was no. Those words might feel polite in the moment, but all they really do is delay the truth.

My scripts now sound like: “What is the best thing for me/my family at the moment? Does this help or take away from that?” Another one I use often: “If I actually wanted to do this, it wouldn’t feel like a negotiation. Yeses are clear and LOUD. Anything else is a no.”

What about you? What would it look like to pause long enough for your body and brain to line up — and then give one clear answer instead of softening the truth?

2. Stop the Habit of Overriding Yourself

For years, I thought being “flexible” was a strength…I’m sure you’ve been there before.

I’d bend, rearrange, and say yes when every part of me wanted to say no. That constant override of my own needs looked like:

Saying yes to late-night calls even when I was exhausted.
Agreeing to plans that clashed with my family’s rhythm.
Putting off rest or movement because someone else “needed me more”.

At first, it might not seem like a big deal. But every time we override ourselves, we chip away at trust with the one person who needs us most: ourselves.

Here’s what I’ve learned: Someone is always going to be disappointed. It doesn’t always have to be you.

These days, I check in with myself before I automatically agree to anything. If I notice that saying yes means betraying my own needs — whether that’s sleep, peace, or family time — I choose me. Because the truth is, no one wins when I’m resentful, depleted, or silently wishing I’d said no.

What about you? Can you think of a time you said yes when you meant no? How did it feel in your body afterwards? What would it look like to stop overriding yourself, even once this week?

3. Listen to Your Body’s Response

My body almost always tells me before my words do.

Headaches, raised shoulders, eye-rolling, audible sighs—this is no territory. On the flip side, if I catch myself outfit-planning, scrolling menus, or feeling giddy? That’s a yes.

These cues guide even small choices, like whether to make lunch plans or invite someone over to our home. It’s become one of the most reliable tools I have and the sooner we tune in to what our bodies are saying, we’ll be that much closer to honoring what they’re asking for and deserve.

What does your body do when something is a “no” for you? Do your shoulders rise, your jaw clench, your stomach twist? Paying attention to those cues might give you the answer faster than your words can.

4. Protecting Your Tone (and Your Ground)

Tone carries weight. If I know mine will come out shaky, I don’t force the conversation yet. I wait until I’m steady. We’re too grown to be arguing with other adults about what works best for us.

But here’s the tricky part: what if the person pushing against your boundary has some kind of power over you, even if perceived? That’s when tone matters even more, because the conversation isn’t just about what you say, but how you say it.

Here are some things you might find useful:

Prepare your words in advance. Even if it’s just a sentence or two, decide what you’ll say and practice it out loud. That way, you’re less likely to soften your stance under pressure.
Stay neutral but firm. Instead of raising your voice or over-explaining, keep it steady: “I understand you’d prefer I do X, but this is what works for me right now.” Calm doesn’t mean passive — it communicates clarity.
Don’t match their energy. If they get louder, guilt-trip, or push harder, resist the urge to escalate. Matching their tone pulls you into an argument. Holding your calm creates contrast — and clarity.
Name the boundary once, then hold it. Repeating yourself in circles only wears you down. State your boundary clearly, then let the silence do some of the work.

It also helps not to need someone’s approval or financial support. Boundaries are much easier to hold when your life stands independent of their opinion. But if you’re not fully there yet, tone becomes your ally — it communicates both self-respect and steadiness, even when the situation feels unbalanced.

5. Be Loyal to Your Principles, Not People

Trent Shelton said this on the Mel Robbins podcast (43:10) recently: “I’m loyal to my principles, not loyal to people.” That landed hard with me.

Blind loyalty to people can push you to compromise the very principles you’ve already decided matter most. It’s up to you to define those principles — they become your GPS, your roadmap to the life you actually want.

An example of this for me is peace. Peace has to lead in every area of my life—environmentally, internally, relationally, and through the actions I take. That means some things, even if they’re “good,” become automatic no’s. As much as I love Christmas, for example, staying in a big cabin with 20 people during the holidays screams chaos to me. Chop. Same goes for spending time with someone where I constantly feel emotionally drained afterwards. Chop.

With this core principle in mind, asserting myself in a confident manner becomes easier because my decision is no longer about the other person—it centers on whether something violates the principle itself. That shift makes the decision clearer, faster, and less guilty.

But let me be clear — this is hard. Old habits of loyalty will tug at you, and it’s easy to slip back into reminiscing about “what was” or feeling guilty for choosing differently. That’s why this practice has to be exercised like a muscle. The more often you use it, the stronger and more natural it becomes.

Remembering your principles can be easier than building a case for every single decision. If something contradicts mine, I simply say: “That doesn’t work for me or my family right now.” Done.

What principles matter most to you — peace, money, stability, honesty? If you had to write down two or three guiding ones today, what would they be?

6. Be Okay With the Outcome

For confidence to be assertive, you have to be okay with the outcome.

That starts with clarity — knowing what you want, where it aligns with the priorities you’ve made for yourself, and trusting that if all else fails, you’ll still keep the thing you value most.

Maybe that’s peace. Maybe it’s your freedom. Maybe it’s money not spent. Sometimes it could also mean missing out on certain things and that’s okay.

For example:

Family gatherings: Especially for new families trying to create their own traditions in the middle of legacy ones. Saying no to an invite may sting in the moment, but it protects the bigger “yes” you’re building for your own household.
Different core values: When your priorities don’t match those of your family or current friend group, clarity helps you avoid getting swept back into old dynamics.
Relationships: When you set a boundary or express what you need, you’re giving people the opportunity to show up. If they don’t, your job isn’t to obsess over why. Your job is to make sure the path to that boundary stays clear — so your need can still be met, even if it’s by someone new.
Money: Let’s say you decline an expensive trip with friends because it doesn’t align with your financial priorities. They may not get it — but your job isn’t to justify. It’s to stay rooted in your boundary, knowing that the peace of financial freedom is worth more than explaining yourself over and over.

Don’t get me wrong, some of this can feel really difficult in practice because it can mean saying no to the people and things you love. This does not change how much you love them, though.

But, when you can accept the outcome — whether it’s someone’s disappointment, silence, or even a relationship changing — you stand on steadier ground. Assertiveness isn’t about winning the other person over; it’s about staying loyal to what you’ve already chosen matters most.

7. Dropping the Guilt Around “Good Things”

TBH, the guilt isn’t entirely gone for me—it’s just quieter. What used to last days now lingers for a few hours, at most.

I used to feel guilty for choices that brought me joy. An expensive yoga membership, a weekend retreat, moving across the country, even buying something small that made my home feel cozier. If a friend did those things, I’d cheer them on without hesitation. But when it was me? Suddenly, the inner critic showed up with a list of reasons why I didn’t “deserve” it or happiness.

That double standard was exhausting. So now, I practice being my own friend. If I’d celebrate someone else for saying yes to joy, peace, or growth, I celebrate myself too.

This shift has helped me push back against conditional self-worth — the idea that I can only deserve good things once I’ve hustled hard enough, sacrificed enough, or earned enough.

The truth? We deserve joy because we’re human. And the more we practice choosing it without guilt, the stronger our confidence becomes.

Where do you notice guilt creeping in around “good things”? What’s one area this week where you can practice celebrating yourself the same way you’d celebrate a friend?

Closing Reflection

Years later, assertiveness feels less like a skill I’m learning and more like a compass I live by. It’s not about being louder or harder. It’s about protecting my peace, honoring my principles, and giving answers that match the life I want to build.

If you’re still in the messy middle of this, here’s your reminder: your body knows the truth, your principles can keep you steady, and your yeses should be loud. As you reflect, I’d love for you to jot down one principle you want to live by this week. What would shift if you stayed loyal to that above everything else?

With Love,
Ambyr

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7 Assertive Lessons to Go From People-Pleasing to More Confident