Permission to disappoint: How and why to move beyond others' expectations
MONTHLY NEWSLETTER | August 2025
Three weeks ago, I wrote about liminal leadership—that disorienting space where the old maps no longer work and you're making it up as you go along. Here's what I've learned from the dozens of conversations that followed: You're not just navigating external change. You're navigating internal shifts as well. And that changes everything.
An executive who reached out after reading July's newsletter put it perfectly: "I'm starting to realize that the discomfort I'm feeling isn't just about uncertainty in my industry. It's about outgrowing who I've been professionally. But everyone expects me to keep being her—my team, my board, even my family. The thought of disappointing them feels terrifying."
If this resonates, what you're experiencing has a name in developmental psychology, the Self-Authoring Transition, and it's not a personal failing—it's a necessary passage that every authentic leader must navigate.
THE SOCIALIZED MIND’S BEAUTIFUL PRISON
Harvard psychologist Robert Kegan describes human development as progressing through distinct stages. Most of us spend our early careers mastering what he calls the Socialized Mind—learning to be successful by meeting others' expectations, following established rules, and gaining external validation. I call this living from the outside in.
To be clear, this stage serves us beautifully at first. We learn to read rooms, manage up, exceed expectations, and build careers by being who others need us to be. The feedback is often immediate and rewarding—promotions, recognition, inclusion in the inner circle.
But somewhere along the journey, often in midlife and when holding a senior leadership position, something shifts. The strategies that got us here start feeling constraining rather than liberating. The external validation that once energized us begins to feel hollow. We start sensing that we've become, as one client described it, "a professional people-pleaser with a corner office."
What's happening isn't a midlife crisis. It's a developmental transition. You're bumping up against the limitations of the Socialized Mind and being called toward what Kegan terms the Self-Authoring stage—the capacity to create your own internal compass rather than constantly seeking external direction. Far beyond a crisis, this is a mid-life awakening.
YOUR LOYAL SOLDIER’S FAITHFUL SERVICE
Franciscan mystic Richard Rohr offers another lens for understanding this transition through his concept of "discharging the loyal soldier." Your loyal soldier is the collection of adaptive strategies you developed early in life to ensure safety, belonging, and success. She has learned to read every room, anticipate every need, and manage every relationship to avoid conflict and secure approval.
For high-achieving women, this loyal soldier often becomes extraordinarily sophisticated. She masters the art of being indispensable, of exceeding expectations, of making everyone comfortable. She builds an impressive career by being exactly who each situation requires her to be.
This loyal soldier isn't the enemy—she's been protecting you. She has kept you safe in family systems where approval was conditional and helped you navigate organizational cultures where fitting in was essential for advancement. She has enabled you to succeed in a professional world that often rewards women for being accommodating rather than authentic.
Unfortunately, the strategies that protected and propelled you in your 20s and 30s can become a prison in your 40s and 50s. The loyal soldier who once served your growth now constrains it. The very adaptability that made you successful prevents you from accessing your authentic power.
The cost of her continued service shows up everywhere: in the exhaustion of constantly managing others' emotions, in the resentment that builds when you consistently prioritize others' needs over your own, and in the growing disconnection from your own desires and values.
Most importantly, it shows up in your leadership. When you're constantly reading the room instead of leading it, when you're managing up more than empowering down, when you're avoiding difficult conversations to maintain harmony—you're leading from the loyal soldier's playbook, not from your authentic authority.
It’s time to transition into living from the inside out!
THE DEVELOPMENTAL INVITATION
This feeling of constraint isn't pathology—it's possibility. The discomfort of realizing you've been living someone else's version of success is actually your psyche's way of inviting you into the next stage of development.
The Self-Authoring stage doesn't mean becoming selfish or disregarding others' needs. It allows you to develop the capacity to make conscious choices about which expectations to meet and which to thoughtfully decline. It means creating your own internal scorecard rather than being driven by external metrics. It calls on you to learn to disappoint others because staying true to them would require betraying yourself.
This transition requires what Rohr calls a "discharge ceremony" for your loyal soldier, a conscious process of thanking her for her faithful service while recognizing her time of service is ending. Don't reject her entirely; retire her from active duty and give her an advisory role.
This process isn't about becoming ruthless or uncaring. It's about developing what authentic leadership actually requires: the capacity to hold your own center while remaining genuinely connected to others. It's about learning to lead from internal authority rather than external approval.
THE LEADERSHIP IMPACT: FROM REACTIVE TO CREATIVE
The Leadership Circle Profile, one of the most comprehensive leadership assessments available, maps exactly how this developmental transition shows up in leadership effectiveness. Leaders operating from the Socialized Mind tend to score high in what the model calls "Reactive Tendencies," organized in 3 broad categories: complying with others’ expectations, shielding our true self, and controlling our output and environment.
While these tendencies can help you climb the corporate ladder, they ultimately limit leadership impact. When you're constantly reading and managing others' reactions, you can't access the creative competencies that drive breakthrough results: visionary leadership, authentic self-expression, and the courage to make difficult decisions that serve the larger purpose even when they disappoint individual stakeholders.
Leaders who have developed beyond the Socialized Mind show up differently. They can have difficult conversations because they're not dependent on universal approval. They can make unpopular decisions because their sense of worth isn't tied to others' ease or comfort. They can disappoint people strategically because they understand that trying to please everyone ultimately serves no one.
This isn't about becoming uncaring, it's about caring more skillfully and purposefully. When you're anchored in your own values and vision, you can actually serve others more effectively because you're not constantly managing your own need for validation.
Consider the difference between these two leadership approaches:
The Socialized Leader spends a significant portion of her energy reading the room, managing up, and ensuring everyone is comfortable with decisions before moving forward. She avoids difficult conversations until they become crises. She says yes to requests that drain her energy because saying no feels selfish.
The Self-Authoring Leader seeks input and considers others' perspectives, then makes decisions based on her assessment of what best serves the larger purpose. She has difficult conversations early, before emotions run high, because it’s more efficient and creates space for creative solutions and she’s willing to embrace the temporary discomfort to serve a larger purpose. She says no to good opportunities that don't align with her vision, freeing up energy for extraordinary ones.
Both leaders care deeply about people. But only one has the developmental capacity to lead authentically in complex, ambiguous situations.
THE PRACTICAL PATH FORWARD
So how does a leader make this transition? How do you discharge your loyal soldier and develop authentic authority?
Start with recognition, not rejection. Your loyal soldier developed sophisticated strategies that served you well. People-pleasing, conflict avoidance, and hypervigilance about others' comfort—these aren’t character flaws. They are intelligent adaptations to the environments you had to navigate. Thank her for keeping you safe and helping you succeed.
Practice strategic disappointment. Start small. Decline a meeting that doesn't serve your priorities. Share an opinion that might be unpopular. Set a boundary that others might not like. Notice that the world doesn't end when people are temporarily disappointed in you.
Develop your internal compass. Get clear on your values, not just your goals. What matters to you independent of what others think? What kind of leader do you want to be when no one is watching? What legacy do you want to create through your work?
Reframe disappointment as development. When you disappoint others by staying true to yourself, you're not being selfish—you're modeling what it looks like to live authentically. You're giving others permission to develop beyond the need for universal approval.
Get support for the transition. This developmental passage is challenging because everything in you has been wired to seek external validation. Working with a coach, therapist, or trusted advisor who understands this transition can provide the external support you need while you develop internal authority.
THE GIFT TO OTHERS
Here's what I've witnessed again and again: When leaders develop the courage to disappoint others in service of their authentic truth, something remarkable happens. The people around them—their teams, their families, their peers—suddenly have permission to be more authentic too.
Your willingness to stop performing to maintain perfect harmony gives others permission to bring their real thoughts to meetings. Your willingness to set boundaries models healthy self-care for your team. Your willingness to make decisions based on vision rather than popularity creates space for others to access their own creativity and courage.
The ripple effect is profound. Organizations led by self-authoring leaders consistently show higher levels of innovation, engagement, and resilience because people feel safe to bring their whole selves, including often-silenced concerns and their bold ideas, to their work.
It’s pure magic.
YOU CANNOT SERVE FROM AN EMPTY WELL
The permission to disappoint isn't about becoming callous or self-centered. It's about recognizing that you cannot serve others authentically if you are betraying yourself. You cannot lead with genuine authority while constantly seeking permission. You cannot create the conditions for others to thrive while you're depleting yourself to manage their ease and comfort.
The loyal soldier who protected you for decades deserves recognition and immense gratitude. And she deserves to be relieved of duty so you can step into the authentic authority you've been developing all along.
The discomfort you're feeling isn't a problem to solve—it's a threshold to cross. On the other side waits not merely personal liberation, but professional effectiveness you've never accessed before. The kind of leadership that changes not just results, but cultures. The kind of influence that comes not from managing others' reactions, but from the magnetic pull of someone who has learned to live from the inside out.
You are not selfish for wanting to be authentic. You are not difficult for having boundaries. You are not failing for questioning the expectations that once defined you.
You are developing. And that is exactly what the world needs from you right now.
Kindly,
THIS MONTH'S REFLECTION QUESTIONS
Recognizing Your Loyal Soldier
What specific behaviors or strategies did you develop early in your career to ensure approval and success? How are these same strategies now limiting your authentic expression as a leader?
Exploring the Cost of External Validation
When was the last time you made a decision based purely on what you thought was right, rather than what you believed others expected? What did that feel like?
Identifying Your Internal Compass
If you could lead without worrying about anyone's approval for one month, what would you do differently? What conversations would you have? What decisions would you make?
Strategic Disappointment Practice
What is one small way you could practice strategic disappointment this week? What boundary could you set or expectation could you not meet in service of your authentic leadership?
COMING NEXT MONTH
Next month, we'll explore The Courage to Redesign
You've started questioning the expectations that once defined your success, but you haven't yet built new structures to support your emerging authentic authority. This is exactly where you're supposed to be. September offers the perfect moment to move from recognition to redesign. Because authentic authority isn't just about changing how you think—it requires consciously architecting how you operate. It's time to redesign your leadership from the ground up.
"The cave you fear to enter holds the treasure you seek."
—Joseph Campbell
