Outgrowing What’s No Longer For You: 3 Steps for Brave Transitions in Relationships, Work, and Life
If you’re going through a transition right now—outgrowing a relationship, career, friend group, or way of life—and you’re experiencing a lot of self-doubt, self-criticism, or shame—
this article walks you through the 3 steps that have helped me make sense of, and proceed bravely through, some of the hardest transitions I’ve ever faced.
These 3 steps are based on the belief that we don't outgrow our old lives because we're “too picky,” “not trying hard enough,” “over-sensitive,” “ungrateful,” or any of the other self-critical messages our minds tell us.
We outgrow our old lives because our values have changed—and now, it's up to us to heed the call of our new values.
I'll kick things off with my story, and then offer the 3 steps you can use to embrace the transition you're facing with clarity, courage, and an inspiring vision of what's to come.
If what you read resonates with you, be sure to join me live on September 17 at my new hands-on workshop, Headed True North: Using Your Values As a Compass Through Transitions in Relationships, Work, and Life. (If you can’t attend live, the recording will be made available to everyone who purchases a ticket!)
My Story: Or, How I Realized I Didn’t Want the Life I’d Built
It was August 2023. I sat around a crowded restaurant table on the Seattle waterfront. It was the first time I’d seen my friend group in nearly two months, and despite the happy chatter all around me, I felt awkward and displaced. Socializing hadn’t been much of a priority recently, and honestly, I was afraid I’d forgotten how.
“Hailey, how are things going with the book?” a friend asked me.
The table quieted to listen. That spring, I’d gotten my book deal for STOP People Pleasing and Find Your Power. I shared with my friends that I’d just submitted the final round of major edits to my publisher.
One friend let out a whoop. Another wrapped her arm around my shoulders.
“Just look at you,” she said. “You’re living the dream right now!”
I laughed, accepted her compliment, and subtly steered the conversation in a different direction. My smile felt pasted-on.
If this is the dream, I asked myself, then why do I feel so hollow?
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Ever since I’d moved to Seattle six years prior, building a career in life coaching had been my priority. I’d started at zero, and now, my efforts were culminating in visible successes: a book deal. Press features. Financial security.
I entered the workforce at the pinnacle of Hustle Culture, which declared that happiness and fulfillment came from working your ass off and neglecting… well… pretty much everything else.
Hustle was the playbook I was handed for successful self-employment and, apparently, a happy life. I followed it unquestioningly. Saturday mornings found me with coffee in one hand and a dry erase marker in the other, doodling out workshop concepts on my whiteboard. In the evenings, I frequently cancelled plans in favor ticking Just One More Task off my infinite to-do list. When I was with friends, I was often distracted, replying to comments on the Instagram reel I’d uploaded earlier in the day.
My parents were proud.
My friends cheered me on.
My colleagues were encouraging.
For many years, I was content with this fast-paced, hustle-centric way of life. Sure, I saw my friends less than I used to, and sure, I hadn’t touched my guitar in months. But at the time, these sacrifices seemed small—if they registered with me at all—because I was helping people. I was making a difference.
Without me noticing, my identity was becoming overgrown with work like a brick wall becoming overgrown with ivy. Eventually, all you could see was the ivy.
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This is what our lives often look like before our values change: we’re happy, content, or at least reasonably satisfied. Even if we’re subtly dissatisfied, it doesn’t really register, because the rewards we’re receiving seem to outweigh the costs.
I might have carried on in this work-centric manner for many more years—but instead, something happened.
Within the same year I got my book deal, I underwent a slurry of paradigm-shifting events that challenged my notions of meaning, success, and happiness: that shifted my values.
(Now bear with me, because in just a moment, we’ll explore how Turning Points are playing a role in your story and transition, too.)
First, I supported my partner through a devastating health challenge that called all our plans for the future into question. The time with him that I’d always assumed was “guaranteed” suddenly seemed as fragile as a fraying thread.
Not long after, I lost a beloved family member to cancer. As the shockwaves of loss radiated through our extended family, I remembered our annual summer vacations, during many of which I’d been working and distracted.
They say when it rains, it pours—and as all of this unfolded, my little sister underwent a slew of unexpected medical emergencies—and I, myself, was swept under the tide of burnout.
Within the span of a year, life as I knew it—my safe, secure, privileged-as-hell life—no longer existed. I was confronted with a reality I’d always “known,” but hadn’t known: that nothing—not our health, our loved ones, or even our lives—was guaranteed.
Every day, I found a new gray hair in the mirror. Every time I went home to visit my parents in New Jersey, they looked older. The more I reckoned with these big, existential questions of love, loss, illness, death, and meaning, the less my perpetually-busy, hustle-driven striving made sense to me.
Frankly, it felt completely fucking absurd.
Beneath my feet, what I valued—what really mattered to me—had changed. I had undergone a Values Shift. And my heart was being softly called to slower, richer places.
After years of finding meaning in professional ascension, independence, and achievement, I ached to be present and connected with my family; I ached to be in deep community with my friends; I ached to be here, to be still, and to bear witness to the passing seasons.
But the timing of all this aching was, admittedly, not great. I was in the midst of the biggest professional milestone I’d ever reached: publishing a book. I had poured my heart and soul into writing that thing, and I was certain it would help people—but when friends and family offered congratulations and asked me about my work, I felt lost for words.
How could I tell them: “I’m afraid I’ve become somebody new, and the life I built for the old me feels wrong?”
How could I tell them: “In pursuit of happiness, I neglected the things that made me whole, and I don’t know how to find them again?”
How could I tell them: “I just realized I don’t want the life I’ve spent my life building?”
These are the shames, the doubts, and the worries we hold when we’re in the midst of a Values Shift. At first, we don’t know how to explain any of it to ourselves, much less to others. We feel broken, unreliable, ungrateful, “too picky.”
But we’re not. Something has changed inside of us—and we’re being invited to listen.
Step 1: Recognize That You’re Not Broken; You’re Undergoing a Values Shift
My story is mine, but it is not unique.
This is the story of a Values Shift: when the events of our lives prompt us to reprioritize what most matters to us—and we begin outgrowing old relationships, careers, communities, or lifestyles as a result.
It’s a story you’ve heard before:
After two years of therapy, a deferential wife realizes that the husband she married is a great fit—for the woman she was ten years ago. After suffering abuse in childhood, she had always valued harmony and security above all else—but as she’s healed, she’s begun to value authenticity and vitality more. As a result, she begins to feel like she’s outgrowing the marriage.
After forming friendships with folks outside of his religious community, a fundamentalist realizes that his religion has begun to feel more like a cage than a haven. He had always valued faith and obedience above all else—but as he’s gotten glimpses of the outside world, he’s begun to value freedom and self-expression more. As a result, he begins to feel like he’s outgrowing his faith.
After developing an interest in world news, a woman becomes disenchanted with her college friend group that only discusses superficial gossip. She had always valued fitting in and comfort, but as she’s become more aware of suffering unfolding around the world, she’s begun to value social change and integrity more. As a result, she begins to feel like she’s outgrowing the friend group.
Now, here’s the thing: If you were to ask the wife, the fundamentalist, and the friend what was happening (this sounds like the beginning of a bad joke, but I promise it’s not), they probably wouldn’t say, “I’m undergoing a values shift and my definition of what constitutes a meaningful life has changed! We’re all good!”
They would probably say something like: “Something feels off, and I don’t like it.”
Or: “I feel so ungrateful. This relationship/community/career/friend group has always been enough for me… How dare I suddenly want more?”
Or: “No, I don’t need to outgrow this relationship/job/community. I just need to work harder to make my internal dissatisfaction go away.”
Like plants sprawling out from tiny pots, Values Shifts almost always include a process of outgrowing. Our new insides are demanding new outsides to match—and restructuring our outsides isn’t always comfortable.
Sometimes, it means making major shifts, like leaving a career or relationship entirely; sometimes, it means making changes within the career or relationship (we’ll talk more about this soon).
Since making these changes would be uncomfortable, our first tendency is almost always to doubt ourselves: to see the transition not as a values-based evolution, but as evidence of personal deficits: too sensitive, ungrateful, selfish, broken, picky, etc.
The logic is: “Maybe I can just change my dissatisfaction so I don’t need to suffer the discomfort of changing my circumstances." This is especially true if we’re adopting new values that go against the grain of our families, our communities, or our culture’s definition of meaning, happiness, or success.
To counter this self-criticism, it’s crucial that we understand where our Values Shift is coming from: to identify the Turning Points in our story.
Step 2: Identify the Plot Twists in Your Story
Values shifts don’t happen out of the blue. Like I write in STOP People Pleasing and Find Your Power, our values tend to stay reasonably consistent over time.
However, our values often shift when we experience Turning Points: events that challenge our existing notions of ourselves, the world, or the meaning we make of life, such as:
Experiencing tragedy, losses, or grief
Confronting illness, disability, or aging
Having children or becoming grandparents/aunts/godparents
Experiencing radical shifts to your self-concept as the result of therapy, coaching, psychedelics, or other healing experiences
Being exposed to a radically different culture or lifestyle that challenges your existing values system
A few other cases we’ll explore at my workshop Headed True North: Using Your Values As a Compass Through Transitions in Relationships, Work, and Life on September 17
Understanding our Turning Points helps normalize and explain the evolution we’re undergoing. It replaces our self-bewilderment and self-criticism with self-compassion and understanding. Sometimes, it even helps us communicate the transitions we’re facing to ourselves and others in a way that makes sense.
My Turning Points were losing my family member, witnessing my partner’s and sister’s health emergencies, and burnout. These Turning Points shifted my values away from hustle, achievement, and independence and toward presence, community, and creativity.
In the chart below, you can see how the Wife, the Fundamentalist, and the Friend experienced something similar:
Identifying our own Turning Points helps us understand our transitions in an entirely new way. It’s not that we’re broken, lazy, weak, or ungrateful. It’s that our lives are perfectly assembled—around our old values.
When I assessed my lifestyle based on my old values of independence, achievement, and hustle, it looked exactly the way it should. But when I assessed my lifestyle based on my current values of presence, community, and creativity, it failed in almost every aspect.
Through this lens, my dissatisfaction with the state of things didn’t just make sense–it was unfolding exactly the way it was meant to. My dissatisfaction was trying to urge me toward a way of life that better reflected my values. And my guess is, yours is, too.
(Want support identifying your old values, your new values, and the Turning Points in-between? We’ll explore all of these questions in detail on 9/17 at my live workshop Headed True North: Using Your Values As a Compass Through Transitions in Relationships, Work, and Life. Can’t attend live? The recording will be made available to everyone who purchases a ticket!)
Step 3: Heed the Call of Your New Values with Vision
Once we accept that our new values are calling us in new directions, it takes courage to listen. Heeding the call of our values—in ways big or small—comes with both growing pains and great rewards.
The Deferential Wife, for example, might honor her values of Authenticity and Vitality by speaking up about her needs and desires in her marriage; taking a break from her husband’s passions to prioritize her own; or setting boundaries around the type of treatment she’ll no longer accept. If the relationship isn’t flexible enough to accommodate these values-aligned actions, she may decide to leave it altogether.
The Fundamentalist might honor his values of Freedom and Self-Expression by fostering a vibrant social life outside of the church; no longer abiding by edicts of the faith he finds overly restrictive; or creating his own rituals for introspection, service, and community. If the church doesn’t prove flexible enough to accommodate his values, he may decide to leave it altogether.
Personally, I decided to heed my values of presence, community, and creativity by dramatically repositioning the role work played in my life. When the time came, I knew I would have to divest time and energy from work so I could invest time and energy into avenues that embodied my new values (community, presence, and creativity)—and commit to working through the growing pains of doing so.
Yeah… That part, too! Values shifts almost always involve growing pains. They’re a normal and inevitable aspect of our inner evolution.
We might face pushback from the people affected by our new ways of living—like the husband with whom we’re setting boundaries, or the boss from whom we’re requesting time off—or pushback from our families, cultures, and communities if we’re pursuing a path that goes against the grain and contradicts the norm.
We might also face pushback from within in the form of identity crises: “Who am I without this person / career / community / lifestyle?” (For me, this growing pain was substantial as I released my old value of hustle. Embarrassingly, I cried when I got an A-minus on my report card in fifth grade. Like it or not, achievement had been baked into my sense of self-worth for decades.)
Growing pains are unavoidable—but they’re not the full story. In order to heed the call of our values, we can’t just focus on the things we’re leaving behind. We need a vision of where we’re heading that inspires us.
In the midst of my own identity crisis, I swapped the question “Who will I be without achievement and hustle?” (scary!) and asked myself, “Who might I become with community, creativity, and presence at my center? What could my life look like then?” (oh heck yeah!)
It was this question that sparked a cascade of inspiration and gave me the courage—and a step-by-step guide—for how to move forward.
The process of building this vision and distilling it into action steps is too broad for this article, but we’ll go over it in detail on September 17 at Headed True North: Using Your Values As a Compass Through Transitions in Relationships, Work, and Life. Here’s a glimpse into what mine looked like:
💭 When I envisioned my life with presence at its center, I imagined myself with a quieter mind, fully engaged with the people, places, and things in my environment. I imagined myself spending ample time in nature; attentive, focused time with my loved ones; and long stretches of time away from my phone and computer.
A few ways I’ve heeded the call so far: Once my book was published, I took a full month off of work to rest, travel, visit family, and be completely offline. I no longer work on evenings or weekends, and I’ve committed to a regular meditation practice. I’ve also dramatically changed how I use social media: no daily posts, no responding to comments, no DMs, and I delete those suckers off my phone the moment I post my content. I feel like I have my mind back.
Growing pains I’ve faced along the way include: Working less and being “less online” comes at a financial cost. Part of heeding the call of my values has been interrogating the cost I’m willing to pay for my presence. Turns out, it’s pretty high.
💭 When I envisioned my life with community at its center, I imagined myself embedded in thick webs of connection with various friend groups; being a good neighbor and making a contribution in my town; staying connected to my family members near and far; and hosting regular gatherings for friends old and new.
A few ways I’ve heeded the call so far: Instead of letting texts from friends or family go unanswered for weeks, I carve out 30 minutes every night to respond to everything. I’ve updated my budget to include a “visiting friends and family” fund, which I’m using, and at my suggestion, my closest girlfriends have started a weekly Monday dinner tradition. I’ve started also actively seeking more opportunities to collaborate with organizations/individuals in my capacity as a coach for more community at work.
Growing pains I faced along the way: Community takes time to build, and after years of over-working, mine is smaller than I’d like. Sometimes, I feel lonely, like I’m starting from square one. Instead of being paralyzed by shame over this, I do my best to put myself out there and build from the ground up, even when it’s hard.
💭 When I envisioned my life with creativity at its center, I imagined myself making music, short films, games, and other projects with creative collaborators—with no intention of monetizing them or turning them into “work.” I imagined myself setting aside regular time to connect with myself through art and becoming a member of creative communities in my town.
How I’ve heeded the call so far: I’ve made a commitment to attend artistic events—improv classes, music open mics, and more—a couple of times a week. Every day, I spend an hour writing music and playing my guitar, even when I’m not particularly in the mood. My friends and I pick one another’s brains about art, and I intentionally expose myself to new ideas (books, podcasts, articles) that spark my curiosity.
Growing pains I’ve faced along the way: My creative life was barren after years of neglect, so I’ve had to work through some perfectionism, self-doubt, and insecurity as I began prioritizing music, performance, and art again.
Your New Values Deserve Your Commitment
Trust me: I know that transitioning into your new values isn’t always easy. But on the other side, you no longer have to grapple with the dissonance of living a life that doesn’t align with you.
You get to experience the freedom and integrity of an outer life that matches your inner values—and as far as I’m concerned, this is the only definition of achievement that really matters.
Once you experience a Values Shift, there’s no unknowing: there’s no going back to the way things were before. You are being called to evolve, grow, and honor what matters most to you in life. Now, your only task is to listen.
If this article resonates with you, join me on September 17 at my live workshop, Headed True North: Using Your Values As a Compass Through Transitions in Relationships, Work, and Life. If you can’t attend live, a ticket gets you access to the event recording 48 hours afterwards. In this interactive, hands-on workshop, I’ll guide you through the process of:
Getting clarity on where your transition is coming from—including defining your old values, your new values, and the Turning Points in your story
Building a inspiring, values-based vision of what it would look like to heed the call of your new values
Determining a step-by-step process for getting there—one that you can start today
Building courage to stay the course, even when you get pushback from within or from your family, workplace, community, or culture.
👉 Learn more about the event and get your tickets here.
(Did you know that members of The Self-Advocacy School attend all of my events and workshops for free? For less than the cost of a workshop ticket, you can learn more and enroll here.)
(PS: If you’re seeking one-on-one support navigating your transition, consider working with me in private coaching You can learn more and apply here.)
