Break Free From People-Pleasing in Business: How Assertiveness Drives Success
You say yes to every invitation and request, even though you’re already overwhelmed.
You agree with everyone, even those with conflicting opinions.
You have low self-esteem and need praise from others to feel good.
You really, really want to be liked, seen as the “best”, and accepted.
You’re a certified people-pleaser.
And you’re fucking sick of it…
This trait is hard to shake because it’s highly encouraged; after all, why would others tell you to stick up for yourself when you let them walk all over you?
But, as a seasoned mental health therapist and business coach in Portland, I’m here to tell you that your people-pleasing habit isn’t just annoying – it’s fucking toxic for your business and your mental health.
So buckle up, because we’re about to get real about people-pleasing in business, including why you’re doing this to yourself and how to cut it out before it’s too late!
Why Are You a People-Pleaser in Business?
Most of the time, people-pleasing in business is due to insecurity and a fear of rejection.
It stems from our deep-rooted need for acceptance and community.
We are wired to want and need others, so rejection threatens our sense of safety and belonging.
For entrepreneurs, this fear is SUPERCHARGED.
Not only does rejection mean a lack of community but also a potential loss of money.
Every “no” feels like you’re flushing cash down the toilet, and every boundary you set feels like you’re burning bridges.
It’s not just your social connections at risk; it’s your financial resources and stability, too. No wonder it’s easy to fall into the people-pleasing trap as a business owner, right?
But here’s the kicker – by trying to please everyone, you’re actually sabotaging your own success.
The Psychology of People-Pleasing in Business
Honestly, the root cause of people-pleasing behavior is usually childhood baggage. Maybe your parents had high expectations, or you were always the “good kid” who never caused problems. It could also stem from a demanding boss or relationship. At some point, maybe you learned to be the caretaker to manage your anxiety.
Whatever the reason, you’ve internalized the belief that your worth is tied to making others happy and comfortable – and you’ve learned to prioritize their desires over your own.
In daily life, people-pleasing can show up as:
Saying yes when you want to scream no
Apologizing for every little thing, even when it’s not your fault
Exhausting yourself to avoid conflict or confrontation
Putting everyone else’s needs before yours
… and that’s just a start!
What People-Pleasing in Entrepreneurship Looks Like
You might think that people-pleasing in business is helping you – I mean, who wouldn’t want to work with someone who bends over backward to accommodate every request?
But, I have been doing this for a long time… you trust me to be real with you, right?
Because, well, I can promise you that being a doormat is working against you!
Here are just a few ways your people-pleasing tendencies are shooting you in the foot:
You undercharge because you’re afraid to ask for what you’re worth
You take on/retain nightmare clients because you can’t say no
You overwork and burn yourself out trying to exceed expectations
You take on responsibility-heavy roles in your community hoping you will finally feel “reputable” enough
As a leader, you become a pushover.
Your clients and team walk all over you, and you resent them for it.
Your business growth is stagnant because you’re busy doing favors, putting out fires, and running around stressed instead of focusing on what actually moves the damn needle.
People-pleasing leads to incessant anxiety chatter in your brain, burnout that makes you want to quit your business, and self-esteem so low you need a shovel to find it.
See the problem here?
How to Break the People-Pleasing Cycle
The first step to stop people-pleasing in business is recognizing the behavior.
If you’re reading this and feeling called out, that’s good! That’s fucking progress!
So, take a deep breath because you can fix this!
I know, I know, you’re like “BUT HOW JENNIFER?!”
The next step is setting healthy boundaries.
You’ve got to decide what you will and won’t tolerate in your business and your life.
You must retrain your brain to value your time and energy as much as you value other people’s.
Developing this assertiveness takes practice, especially if it’s brand new to you, so start small with the tips below.
Strategies for Entrepreneurs
Now, let’s get into the nitty-gritty of overcoming people-pleasing in business.
As a therapist in Portland, I’ve found a few exercises that actually work — not the fluffy stuff you’ll find in self-help books:
The “No — Period” Challenge: The next time someone asks for something unreasonable or that overextends your schedule, just simply say, “That doesn’t work for me.” No explanation or alternative offers are needed. And guess what? The world won’t stop turning, even though you said No PERIOD.
The “Hell No” Challenge: For one week, just say “no” to every non-essential request. Every. Single. One. You’ll probably feel like an asshole, but trust me, you’re not. You’re just finally setting boundaries and putting yourself first. Buffer: if it helps you with this experiment, let a close friend, partner, or loved one know you are trying this new thing out. Not everyone will be “in the know”, but at least it’ll make it easier knowing the safe people in your life can cheer you on (and not be miffed with your abrupt pivot).
The Cost-Per-Minute Calculator: Next time a client or someone else in your field asks you for a “quick favor,” calculate how much money you’re losing per minute. Then ask yourself if you’d pay that amount to make them happy. Spoiler alert: you wouldn’t.
The Ghosting Experiment: Pick one low-stakes, annoying request and just... don’t respond. The world won’t end, I promise. You might even find it liberating.
The “What Would They Do?” Game: Think of the most successful, no-nonsense person you know. When faced with a people-pleasing dilemma, ask yourself what they would do. Then do that.
The Discomfort Diary: For a week, jot down every time you feel the people-pleasing urge. At the end, tally up how much time and energy you wasted on other people’s priorities. BONUS: Also take note of your somatic experience each time the people-pleasing nag comes up. Bringing awareness to the physical sensations you notice in your body will help you manage them differently.
The “Fuck It” Fund: Set aside a small portion of your income as your “Fuck It” fund. Use it to cover potential losses when you need to walk away from toxic clients or situations. Just having this in place will make you feel more confident in business dealings, so it’s easier to say no when people want to waste your time.
The People-Pleasing Purge: List all your current commitments (business-related or otherwise). Ruthlessly cut anything that doesn’t directly contribute to your goals or well-being. It’s not personal, it’s business – and it’s completely fucking okay.
Building Authentic Relationships
Here’s the paradox…
When you stop being a people-pleaser, you actually start building better, stronger relationships.
Why?
Because they’re based on authenticity, not obligation. You genuinely enjoy and value the people you stay connected to, and vice versa.
In your personal life, this means having fewer but deeper friendships.
In business, it means attracting ideal clients who respect your boundaries and appreciate your work.
It means clear expectations and mutual respect with those you interact with.
Sounds pretty damn great, right?
The Power of Authenticity in Business
Let’s talk about why this matters beyond just making your life less miserable:
Genuine Brand: When you aren’t being everything to everyone, your brand becomes clearer and more attractive to potential clients. Which brings me to…
Ideal Clients: The right clients appreciate your honesty and directness. And the ones who don’t were never going to be a good fit anyway.
Sustainable Business: When you model healthy boundaries, your business becomes capable of caring for you and your life becomes more fulfilling.
Remember, breaking the habit of people-pleasing in business isn’t just about setting boundaries with clients. It’s about being kinder to yourself. It’s about building a sustainable, profitable business that doesn't slowly kill you. It’s about becoming the kind of leader who inspires respect, not resentment.
People-pleasing is a habit, and like any habit, it can be broken. It takes work, courage, and a willingness to be uncomfortable. But the payoff – a thriving business, better relationships, and a hell of a lot more self-respect – is definitely worth every awkward moment.
And hey, if you’re struggling to make these changes on your own, there’s absolutely no shame in seeking help. Sometimes you need an expert to call you on your bullshit and (gently but firmly) push you to make real changes.
As a therapist and business coach in Portland and beyond (I do remote sessions for coaching), I’ve helped countless entrepreneurs navigate this exact process.
Remember, you are here because you are ready to stop being a doormat and start being a Bad Bitch in Business!
I know it’s not easy, and you’ll probably feel like a jerk at first, but I promise you, your future self – and your business – will absolutely fucking thank you.
So, what are you waiting for?
Your recovering people-pleaser journey starts now. Go forth and disappoint some people – I dare you!