Flamingo Fix 017: When Boundaries Feel Mean: Why Good Leaders Struggle to Enforce Great Systems
Successful, intelligent business owners and leaders undermine their own systems and boundaries when standing on those systems feel selfish, mean, unsafe or domineering.
You might have client onboarding mapped out beautifully… but still bypass it when you're afraid of seeming “too rigid.” You might be clear and confident with your team on Monday… but spend Wednesday tiptoeing around giving real feedback. You might enforce your scope boundaries with one client at 2 p.m., only to completely abandon them by 3 for fear of rejection from an old client.
This isn’t a failure of strategy. It isn’t you being “too nice”. This is your nervous system doing what it was trained to do: survive.
You only shift out of survival mode when you journey through the four stages of people-pleasing recovery. These stages affect how you sell, serve, and lead during different business scenarios.
You stick to your systems easily when you acknowledge your current stage and implement mechanisms that strengthen your ability to handle those scenarios.
Let’s look at each one.
Stage One: Pre-recovery
In this stage, you are focused on keeping others happy. You are concerned about fairness for others at the expense of yourself. Perhaps you don’t see this pattern as a problem - or you have, but you’re not doing anything about it.
You are what I call the “Them-Focused” Flamingo. You’re still building your business around exceptions. Still responding to every client text. Still working evenings and weekends even though you have “office hours” written down somewhere.
Your business feels chaotic because it is. But the chaos isn’t random. It’s just a mirror of your unhealed habits.
At this stage, structure is just an ideal – a theoretical concept. Even if you got it, your SOPs and boundaries won’t hold. They’re not bad, but they aren’t rooted in your identity.
Stage Two: Identity Recovery
This is your turning point. It is the stage where you begin to see you. You realize you’ve been building success around sacrifice.
You start noticing how often you’ve accepted less than what you’re worth. Maybe you even admit (like I did) that you’re tired of looking successful but feeling resentful, used, or stuck.
So, you get curious about healing, about who you were created to be, and maybe about God.
That curiosity always creates a shift into another dominant identity state. You shift from focusing on “fairness for others” to either “fairness for yourself” or “fairness for yourself and others” or “fairness that honors God, you and others”. I talk more about the “Me-focused”, “Us-focused” or “God & Us-focused” identity states here.
It is at this stage that many business owners and leaders create business systems and structures to match their dominant identity state. But there is a high risk of bypassing those systems if they never address stage three: emotional recovery.
Stage Three: Emotional Recovery
You will struggle with any business system and structure you implement if there is an emotional gap between:
Your chosen identity state and who you are.
E.g. if you build “me-focused” systems but you have a heart for people. Stepping on others to please yourself feels mean.
Who you are becoming and how you still respond.
E.g. if you build “Us-focused” but you’re still emotionally “Them-focused”, your new actions will feel unsafe, so you second-guess, procrastinate, lizard-brain to what feels emotionally safe, etc. This gap shows up in business as:
Sales: You set prices that reflect the value of your services, but you still dread tough pricing convos. You create a great client screening process but feel like a bad person for not helping so you accept a bad-fit client.
Client Fulfillment: You feel triggered when clients push back… or even question a deliverable. You have the policy to stop work if clients don’t pay but you fear hurting the relationship, so you continue working despite nonpayment.
Team Leadership: You’re inconsistent: clear one day, overexplaining the next. You delegate today and then step in and take over tomorrow because it's a high-value client.
These gaps cause your recovering nervous system to revolt and scream at every business situation that feels emotionally unsafe or unfair. You’re not failing, you’re feeling. Your emotions are demanding alignment with your identity.
It’s an opportunity to finally notice and address the emotional mask you wore to stay liked, needed, and safe. Typically, this is when you start the deeper healing work: you go to therapy, get emotional fitness tools, and reflect deeply.
Similarly, you need your business systems and structure to feel safe as you stretch emotionally into your accepted identity. You need to feel confident that you are being fair to yourself and your prospects, clients and team – that your actions and processes are designed to set them and you up for success. That’s how you prevent your sense of safety and fairness from fighting against the business systems you create. If you do anything less, you will struggle with control, perfectionism, and overthinking. You’ll people please every time a situation occurs that makes you feel unsafe.
This is actually where we let business founders and leaders hire us 1:1. Because they are committed to doing the personal emotional work, we can trust them to implement any structure we design together instead of it living on paper. Our work focuses on designing fair and safe sales, fulfillment and team leadership systems that give leaders the confidence they are being fair to themselves and their team, prospects and clients. It positions them for stage four, a space where they can lead with confidence and grow profitably without burning out or self-sacrificing.
Stage Four: Releasing Control and Leading With Confidence
This is active recovery. This is when who you are and how you operate in business integrates. You’re not ‘performing’ confidence anymore. You’re living it.
You start showing up fully in your emotions, your voice, and your decisions. You feel at ease.
And more importantly… you no longer need to control everything to feel safe.
In business, that looks like:
Delegating without obsessing
Letting clients manage their own emotions and adhere to your processes
Trusting your systems to hold
Allowing team mistakes without spiraling
You’re not fighting your business anymore. It does not mean things are perfect. And even if situations come up where standing on your planned policy feels selfish, mean, unsafe or domineering, you recognize that your feelings are not always valid. You remember that what your new processes are designed to “honor you and your people” or “honor God, you and your people”.
So, you adjust faster and regulate yourself even if you need a little help. That’s why our 1:1 work is not just about developing those structures. We also mentor our clients as they 1) build consistent habits to adhere to their new business structures and 2) fix blindspots so they don’t lizard-brain themselves into old patterns when pressure hits.
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You’re not a bad leader who needs to work harder to stick within your systems. You can lead without feeling guilty when you hold a boundary or stick to your systems. You can lead in a way that allows you to thrive as your clients, prospects, and team members thrive. Your leadership can honor you, your clients, your prospects and your team (and God).
It’s what happens when you stop choosing between doormat and tyrant and start leading from a healed identity (click here if you need support from a personal perspective). It’s what happens when you have systems and structures that reflect your healed leadership and feel safe and fair to you and your people. Take the first step toward business freedom that feels good and does good. Book your curiosity call now.
💡 Need a Fix?
Here are other ways we can help.
OPTION 1: Join CEO Like A CEO - our high-touch mentorship for growing CEOs and leaders. Step out of the weeds, scale smarter and lead stronger with structure, strategy, and sanity backed by human-centered business optimization tactics and data-driven decision-making.
OPTION 2: Ever felt frustrated because you are healing and recovering, only to realize that you have screwed up really badly once again? Ever wished someone would hug you, let you know that you’re normal, and to provide you with practical advice and know-how to navigate your journey? That’s what The Pink Flamingo Way's resources, books and the Pink Flamingo Club are about. Head on over to get support along your personal people-pleasing recovery.
OPTION 3: Invite us to speak or do a business workshop/training. Drop us an email.
OPTION 4: Grab the "How to Train Your Clients" Workshop. Just $99 to learn how to set rock-solid boundaries (and get clients to actually respect them).
OPTION 5: Subscribe to Flamingo Fix. Weekly, no-BS strategies to scale smart, enforce boundaries, and build a business that actually feels good to run and grow. As a bonus, the first issue shares our proven client onboarding process, complete with the tools to create a red-carpet onboarding experience that wow your clients without utter chaos or losing your sanity.
