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Breaking Free from People-Pleasing: A Guide for High-Achieving Women

April 10, 20255 min read

Have you ever found yourself saying "yes" when you desperately wanted to say "no"? Or perhaps you've taken on extra work despite being overwhelmed, just to avoid disappointing someone else? If this sounds familiar, you might be caught in the cycle of people-pleasing that so many high-achieving women experience.


What Is People-Pleasing, Really?

People-pleasing is when you prioritize another person's perceived comfort over your own needs. I emphasize "perceived" because what's happening is usually a projection of what we ourselves are uncomfortable with.

For example, if I am uncomfortable with rejection, I automatically assume and project that others feel the same way. This leads me to do everything in my power to make sure that you do not feel rejected—even if, for you, it doesn't really bother you that much.

This pattern creates a lose-lose situation: you sacrifice your wellbeing while addressing a discomfort the other person may not even have, ultimately hindering the discovery of the best solution.


Why High-Achievers Struggle More

There's a reason why high-achieving women struggle so much with people-pleasing. At a young age, many of us were taught that our feelings don't matter. We learned that to gain acceptance or approval, we must perform or achieve. Our ability to suppress our own feelings in the name of achievement is at the core of what made us "great."

And it did make us great!

…At least according to external metrics. We excelled in school, advanced in our careers, and checked all the boxes society deemed important. But at what cost?

The same skill that propelled us forward also made us miserable. We became disconnected from our authentic desires, exhausted from constantly performing, and trapped in a cycle of external validation seeking.

overwhelmed woman at work

The Counterintuitive Path to Freedom

I know this is going to sound really counterproductive because you've probably been suppressing your own emotions for so long, but the key to overcoming people-pleasing is actually to start tuning in to your own feelings and to honor them.

Yes, you read that correctly.

After years of pushing your feelings aside, the solution is to bring them front and center.

This means:

  1. Acknowledging when something doesn't feel right

  2. Giving yourself permission to have boundaries

  3. Recognizing that your needs and wants are valid

  4. Understanding that honoring your feelings isn't selfish—it's necessary and benefits everyone in the long run

Start doing more of the things that you enjoy, that make you feel good, and less of the things that don't. This practice builds your "authentic feeling" muscle, a gut you can trust, that has likely atrophied after years of neglect.


The Connection Between People-Pleasing and Burnout

People-pleasing doesn't exist in isolation—it directly contributes to burnout. Think of burnout as trying to sprint a marathon on empty. When we keep pushing, driven by our fear of not being good enough, suppressing our negative emotions, or relying purely on willpower, we inevitably crash.

But the surprising truth is that you can stay driven without sacrificing your health and happiness. This comes from:

  • Knowing authentically what you want (hard to do when people-pleasing)

  • Acting consistent with your intrinsic motivations

  • Owning and working from your strengths and superpowers

These elements, paired with understanding that rest is actually a vital part of performance, create sustainable energy that allows you to finish your marathon and pursue many more down the road.


The Higher Cost of People-Pleasing

Beyond the personal toll, people-pleasing impacts your effectiveness in all areas of life. When you're constantly accommodating others at your own expense, you:

  • Make decisions based on others' expectations rather than sound judgment

  • Fail to establish necessary boundaries in professional relationships

  • Diminish your authentic voice and unique contributions

  • Exhaust your energy on low-priority tasks that don't align with your values

Ultimately, this isn't just about feeling better (though that's super important too). It's about being more effective, making better decisions, and creating a sustainable approach to success.


Practical Steps to Break the Cycle

Breaking free from people-pleasing doesn't happen overnight, but these steps can start you on the path:

  1. Practice the pause. When asked to do something, say "Let me think about that and get back to you" instead of automatically saying yes.

  2. Start small. Choose low-risk situations to practice honoring your needs and setting boundaries.

  3. Get curious about your discomfort. When you feel the urge to people-please, ask yourself: "What am I afraid will happen if I don't accommodate this person?"

  4. Reframe "selfish." Recognize that taking care of yourself isn't selfish—it's necessary for sustainable success and actually being able to help others effectively.

  5. Create a "feelings inventory." Take time each day to check in with yourself about how you truly feel, not how you think you should feel, and process those feelings without judgement.

  6. Celebrate boundaries. When you successfully honor your needs, acknowledge it as an achievement rather than something to feel guilty about.

businesswoman presenting to team


The Counterintuitive Result

Here's what might surprise you: When you start honoring your own needs and setting healthy boundaries, your professional life often improves rather than suffers. You'll have:

  • More energy for meaningful work

  • Clearer focus on what truly matters

  • More authentic relationships

  • Greater creativity and problem-solving ability

  • Sustainable long-term success

This approach leads to way more sustainable success in the long run because you're no longer draining your resources by constantly accommodating others at your own expense.


The Journey Forward

Breaking free from people-pleasing isn't a destination but a journey. There will be setbacks and moments when you slip back into old patterns. You are becoming a new you that you’ve never been fore, and it’s a normal part of the transition process.

What matters is the overall direction. Each time you honor your feelings, set a boundary, or make a decision based on your authentic needs, you're strengthening a new pattern that will serve both you and others better in the long run.

Remember that the world needs your authentic self, not just your accommodating self. Your unique perspective, energy, and contributions matter—and they can only fully emerge when you stop prioritizing others' comfort over your own authenticity.

In the end, overcoming people-pleasing will not only help you feel much better; it’s about showing up as your whole, authentic self so you can make your greatest contribution to the world!

Drawing from my own experience and background as a performance and life coach, I created The DREAM Method to teach high-achieving women how to tap in to their inherent inner confidence and wisdom for sustainable, aligned success. Learn more at www.dream-method.com.

Personal Development Coach for Busy Women Entrepreneurs
Founder of The DREAM Method

Jen Katsev is a Silicon Valley recovered people pleasing overachiever, serial entrepreneur of 7 businesses, #1 bestselling author, former real estate syndicator and founder of BACOMM Investment Club. Despite her outward success, she felt trapped by the reputation she had built. Seeking change, she moved to Bulgaria to start a honey company, sparking an unexpected five-year journey of self-discovery and transformation. Now happily married and loving her life, Jen combines her journey and 7 years of life coaching experience to help others find authentic fulfillment and work-life alignment through her innovative DREAM Method.

Jen Katsev

Personal Development Coach for Busy Women Entrepreneurs Founder of The DREAM Method Jen Katsev is a Silicon Valley recovered people pleasing overachiever, serial entrepreneur of 7 businesses, #1 bestselling author, former real estate syndicator and founder of BACOMM Investment Club. Despite her outward success, she felt trapped by the reputation she had built. Seeking change, she moved to Bulgaria to start a honey company, sparking an unexpected five-year journey of self-discovery and transformation. Now happily married and loving her life, Jen combines her journey and 7 years of life coaching experience to help others find authentic fulfillment and work-life alignment through her innovative DREAM Method.

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