Stop Checking If Your Boss Is Happy: How to Break the Approval-Seeking Cycle

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Derrick sits at his desk, staring at the email he sent three hours ago. His boss hasn't responded yet. He rereads it for the fourth time, wondering if his tone was too direct, if he should have added more context, if the subject line was clear enough.

He checks Slack. His boss is online, green dot glowing. So they're definitely seeing messages...

Derrick types a follow-up, deletes it, types it again. Finally hits send: "Just wanted to make sure you got my earlier email about the client presentation. Let me know if you need any clarification!"

Sound familiar?

If you've ever found yourself refreshing your inbox, overanalyzing response times, or second-guessing every interaction with your leader, you're not alone. And you're not being "thorough" or "proactive" — you're caught in one of the most exhausting cycles in modern work: constantly checking to see if your boss is happy with you.

Let's call it what it is: approval seeking and the need for validation.

The Hidden Reason You Seek Approval from Authority Figures

That urge to constantly check — Am I doing this right? Are they happy with me? — it's a strategy your brain picked up somewhere along the way. A way to stay safe. Stay liked. Stay employed. You rely on other people's responses — their tone, mood, facial expressions, how quickly they reply — to gauge how well you're doing.

But when you're always looking to someone else to prove you're okay, you're building your self-worth on something you can't control. Sure, getting that "looks good" reply feels like relief in the moment. You exhale. Okay. I'm safe. But that feeling doesn't last. Because the next project comes. Your boss doesn't respond as quickly. They have a bad day. They change their tone.

If your success depends on someone else being in a good mood, available, and communicative at all times... you're never going to feel secure.

Psychologically, it's tied to "external referencing," where you're trained to look outside yourself to figure out what's "right."

• Maybe you worked for a boss who was never satisfied.
• Maybe you grew up where praise was rare and success meant keeping the peace.
• Or maybe you've been in high-pressure roles so long that your brain automatically scans for threats, approval, or rejection.

This skill probably helped you rise in your career. You're attentive. Thoughtful. Adaptable. But like most strengths, if left unchecked, it becomes a weakness. What starts as smart managing up turns into mental gymnastics.

• Holding back in meetings until you've gauged their reaction.
• Changing your tone mid-sentence because you saw their expression shift.
• Staying online an extra 30 minutes to wait for a reply.

It's subtle. Automatic. It seems harmless — even responsible. But this is one of the most exhausting ways you give away your power at work. You start outsourcing your sense of success to someone else's mood, tone, or response time. Pretty soon, your time, energy, and focus are tied up in trying to read between the lines instead of doing your actual job.

How to Let Go of an Excess Need for Validation at Work

The solution is shifting from external referencing — where your confidence depends on how other people react — to internal referencing — where you know how to ground yourself, even when the room is quiet, the email is ambiguous, or the feedback isn't glowing.

This doesn't mean ignoring everyone else and charging ahead with blind confidence. It's about balance. Listening to your own voice alongside others, not only after you've gotten a green light.

1. Do a gut check

Before you hit send on that "just confirming" email, pause. Ask yourself: Do I already know the answer? Am I reaching out for clarity...or comfort? Creating that pattern interrupt helps you slow down long enough to distinguish what's really driving the behavior instead of just going on autopilot.

2. Name your perspective before inviting others in

If you tend to hold back and let others speak first, it's easy to fall into the habit of deferring. You wait to see what your boss or teammates say, and then adjust your opinion to match.

Instead, get in the habit of going first. You can say:

• "Here's what I'm thinking right now — let me know if I'm on the right track"
• "I'll share where my head is at and then I'd love to get your thoughts"
• "This is how I'm leaning, but I'm open to feedback"

Others will be more likely to treat you as someone worth listening to. Not because you have all the answers, but because you're bringing something original to the table.

3. Let discomfort be a data point (not a danger signal)

The next time you feel that familiar wave of unease — the urge to explain yourself again, to soften your opinion, to double-check one more time — pause. Not everything that feels uncomfortable is a sign that something's wrong.

Sometimes, it's just your nervous system doing what it's been trained to do: scan for threats, avoid rejection, stay safe. But discomfort is just a sensation. Let it be there. Don't try to push it away or immediately soothe it by over-explaining or checking in. Instead, imagine it like a wave cresting. If you let it rise and fall without reacting, it usually passes faster than you think.

4. Don't treat someone's silence as a judgment

Silence is neutral, even if your brain doesn't think so yet. A delayed response can feel like a sign you messed up. You reread the email you sent. You start filling in the blanks: Maybe they didn't like it. Maybe I came across too strong.

But most of the time, silence means nothing more than what it is. People are busy. Emails get buried. A short Slack reply doesn't mean your idea was bad — it might mean your boss is juggling three priorities or reading from their phone.

5. Be your own debrief

Before you start hunting for feedback or validation from someone else, stop and run your own assessment first. After you finish a presentation, submit a report, or complete any significant task, take two minutes to ask yourself:

• Did I communicate what mattered most?
• Did I show up in a way I feel good about?
• What worked well? What would I do differently next time?

When you evaluate yourself first, you're building a strong internal reference point — something solid to come back to. You become a filter, not a sponge. A filter takes in what's valuable and lets the rest pass through. When you have a strong internal perspective, you're not rejecting feedback — you're able to process it.

FREE TRAINING: 5 Steps to Speak Like a Senior Leader

In this value-packed session, you'll discover:

✓ Exactly what's going wrong if you aren't commanding credibility and respect – even if you're doing the work of someone two levels up

✓ What it REALLY means when you're told "you need executive presence" (hint: it has nothing to do with being louder or wearing nicer clothes)

✓ Small tweaks you can make TODAY to articulate yourself with such polish and precision, your boss's boss says, "We need you looped in earlier"

✓ My 5-step system that gets our clients at top Fortune 500 companies tapped for 6-figure promotions (without annoying buzzwords or 10 hours of prep)

This isn't about changing who you are or becoming someone you're not. It's about making sure your expertise finally translates into the influence, recognition, and compensation you deserve.

The training is completely free, and yes, replays will be available – but only if you register.

>> Save your spot for July 16th at 3pm ET

See you there,

Melody

P.S. At the end of the training, I'll also be publicly opening enrollment for my new program Speak Like a Senior Leader™. But even if you're not interested in that, this free session will give you immediately actionable strategies you can use ASAP.