Are You Holding Yourself Back?

As an assistant you like to know that you are tracking with your executive and that your priorities and objectives are aligned with theirs. You like to see things from their perspective so you can anticipate what they’ll need next and provide it before they even ask.

But…. what happens when you begin to care a little too much what your executive thinks of you? You begin to get worried because it’s been a long time since you’ve received a “thank you”, or any sort of recognition. You begin to question yourself, and the relationship you have with your exec. Why can’t they just say, “thank you”? 

You, my friend, have crossed over into people pleasing territory.

On the surface, people pleasing seems harmless. You’re just trying to do everything perfectly and make sure other people are happy with your work….right?

Unfortunately, under the surface, people pleasing is extremely detrimental. At its root, it’s essentially tying your identity and self-worth to another person. 

Instead of standing in your self-sufficiency, and knowing that you produce good work, you look to your executive to tell you that you’re good enough. 

When you don’t get the recognition you feel you deserve you desperately try and control what they think of you by making them happy. Again, you don’t get the level of recognition you deserve, and the cycle repeats.

Eventually, this leads to extreme frustration and resentment, and fails to serve anyone.

How do you let go of people pleasing and embrace the kick-ass assistant you know you are? 

Here are a few tips:

1. Know the difference between inserting yourself into other people's shoes vs. their brain. Looking at things from your exec’s perspective is very different from trying to control what they think about you.
2. Decide that you, and your contribution, are enough. It really is a decision.
3. Realize that it’s not your job to make everyone, even your executive, happy all of the time. (No, really! It’s not.) In the same way your happiness is yours to own, their happiness is their to own. Allowing others to experience the bad along with the good allows for them to get to experience the fullness of the human experience.

Here’s the irony… We people please to make everyone else around us happy thinking this will bring us happiness, but it seldom does! Most of the time it only leads to bitterness, entitlement, and frustration.

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Annie Croner is the founder and CEO of Whole Assistant, an online platform & community, formed to provide a positive place where assistants can go to transform their lives and level up their careers. Annie has made it her focus to help assistants achieve their goals and manage everything on their plates, while finding freedom from overwhelm and burnout. Over her 20+ years as an assistant, Annie has worked for boutique companies across multiple industries including accounting, marketing, nonprofit, and private wealth management. Working in a variety of settings has led to a diverse understanding of the assistant role and the many challenges that often come with it. Annie lives in Denver, Colorado where she enjoys green smoothies, her family, and an occasional evening of Latin dancing.

To learn more about Annie, please visit her website: WholeAssistant.com or connect with her on LinkedIn.

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Frequently Asked Questions

How can you tell when people pleasing is hurting your performance?

A common warning sign is when your confidence depends on constant external validation. You may overextend, second-guess good decisions, and feel increasingly resentful even while delivering strong work.

What is the difference between being supportive and being a people pleaser?

Being supportive means aligning to business priorities and helping your executive succeed. People pleasing crosses the line when your decisions are driven by fear of disapproval rather than clear goals and professional judgment.

What is one practical step you can take today to break the cycle?

Start by naming one boundary you will protect this week, then hold it consistently. Small, repeatable boundaries rebuild self-trust faster than occasional big resets.

Why does this pattern lead to burnout so quickly?

Because you are carrying emotional labor on top of operational workload. Over time, trying to manage everyone’s perception of you creates stress that no productivity system can offset.

How do you stay high-performing without tying your worth to praise?

Measure yourself by outcomes, reliability, and values-based execution. Recognition is still welcome, but your baseline confidence comes from the quality and consistency of your work.