31: The Moment the Climb Slows Down
I remember the moment it hit me—I wasn’t climbing anymore. The momentum that had carried me through the early years of my career had slowed, and for the first time, I wasn’t sure what was next.
I wasn’t burnt out. But I wasn’t energized either. The rules had changed. The game had changed. And suddenly, I had to figure out how to play again.
At some point in our careers, we all encounter the long plateau—a moment where the rapid ascent of early achievements slows, and the path forward becomes less clear. The skills that once fueled our success—hustle, speed, execution—aren’t enough anymore. Promotions aren’t guaranteed. The rush of validation fades. And in that quiet, uncomfortable space, the real questions emerge:
Is this it? Do I still love what I do? Who am I beyond my job title?
No one tells you that success shifts. That at a certain point, your worth is no longer measured in promotions, but in how well you can redefine success for yourself.
The Shift: When Your Role Changes, But You Haven’t
I felt this shift in my career. But I also thought it in my role as a parent.
When my daughter was younger, she needed me for everything. And I loved that. But as she grew, she pulled away—not in a rebellious way, but in a natural, necessary way. Suddenly, I wasn’t solving every problem for her. I was just… there. A presence. A guide.
And it hit me: Who am I when she doesn’t need me like she once did?
The same thing happens in our careers. When the rush of external validation slows, the hands-on work shifts to leadership, and the promotions don’t define you anymore, you have to ask: Who am I beyond what I do?
The Side Hustle Is a Mindset, Not Just an Income Stream
A side hustle isn’t just about extra money—it’s about autonomy. It’s about experimenting with parts of yourself that don’t always get activated in your 9-to-5.
For mid-career professionals, satisfaction doesn’t come from climbing higher—it comes from expanding wider. It’s about stretching into new dimensions of yourself, staying relevant in a world that demands constant reinvention. A side hustle, passion project, or creative pursuit isn’t a distraction—it’s a strategy.
Think of it like parenting. When your child grows, you don’t disappear. You evolve. You find new ways to connect, new ways to be present. That’s precisely how you navigate the long plateau in your career. You don’t cling to an outdated definition of success. You expand the edges of who you are.
The Most Fulfilled People I Know Aren’t Just One Thing
Their job titles don’t just define the most engaged, resilient professionals I’ve met. They are:
Product leaders who are also artists
Strategists who are on an improv stage
Designers who teach and coach
Entrepreneurs who paint, code, or compose music
They’ve learned that their value isn’t tied to a single role or company but to the breadth of their skills, perspectives, and passions. They’ve embraced the idea that identity is fluid—you can simultaneously be more than one thing.
Similarly, the most fulfilled parents I know aren’t just caregivers. They’re mentors, friends, guides, and coaches—people who have found ways to grow alongside their children, rather than clinging to a past version of themselves or traditional expectations.
For Me, That Outlet is Art
While my professional work revolves around human-centered design, product strategy, and organizational leadership, my creative side finds expression in drawing and writing about art.
This isn’t just a hobby—it’s a vital part of who I am. It keeps me curious, sharp, and connected to a different side of myself. It reminds me that I’m not just a designer or a leader but a creator.
That multiplicity? That’s where true fulfillment lies.
How to Unbox Yourself: 5 Strategies for Expanding Your Identity
If you’re feeling stuck, if the path ahead feels murky, try this:
Map Your Identity Beyond Work: Who are you outside your job title? We often default to answering “What do you do?” with a singular label—Designer, Manager, Director, Engineer. But that’s not who you are. That’s just what you do for a paycheck. Take a step back and list every role you play in your life, beyond your work identity:
Are you a mentor? A teacher? A storyteller? A connector?
Do you create—whether it’s art, music, code, or experiences?
Are you a friend who gives advice, a parent who nurtures curiosity, a partner who brings stability, a sibling who encourages risk?
Do you thrive on organizing chaos, discovering new ideas, and challenging assumptions?
Now go deeper: What do these identities bring to your life?
What parts of yourself feel alive when you’re inhabiting these roles?
Where do you feel the most “yourself”—at work, home, creative space, or deep conversation?
If your work suddenly disappeared tomorrow, where would you still find meaning?
This isn’t just an exercise in self-awareness. It’s a way to permit yourself to be more than your title. The best careers—and the best lives—aren’t built on a singular track. They are layered, dynamic, and expansive.
Design ‘Micro-Experiments’: Most people think reinvention requires a drastic change—a new career, a significant pivot, an all-in leap. But growth often happens in small, deliberate experiments.
A micro-experiment is a low-risk way to explore an interest or expand your skill set without upending your life.
Ask yourself:
What’s one thing you’ve always been curious about but never pursued?
What’s a creative outlet you abandoned years ago that you could revisit?
What slight shift in your daily routine could reintroduce play and exploration into your life?
Try this:
If you used to write but stopped, set a timer for 15 minutes and free-write once a week.
If you love photography, challenge yourself to take one meaningful photo daily.
If you’ve always wanted to teach, offer to mentor a junior colleague or give a guest lecture.
If you’re fascinated by a new industry, create curiosity conversations with people working in that space.
It’s not about turning every passion into a side hustle or adding more pressure to perform—it’s about reconnecting with the parts of yourself that get buried under daily responsibilities.
I started sketching again. No agenda, no expectation of mastery. Just time for me to listen to an audiobook, unwind from work, and put pen to paper. Sometimes this turns to 2 hours. Someday, I have 15 minutes. I’ve done this for a year, and I can tell you something has changed. Drawing—not for work or a project, but just for me—reminded me of a part of myself that had been dormant for years. That’s the power of a micro-experiment. It reignites something that’s already inside you.
Audit Your Success Metrics: What would make you feel accomplished if your job title disappeared tomorrow? Many of us have spent years chasing external validation—titles, promotions, performance reviews, public recognition. But at some point, those markers stop being reliable indicators of fulfillment.
Try this exercise:
Look back at your past five years. What were the moments that felt deeply satisfying? Were they tied to external rewards, or something more personal?
Now, project forward five years. If you could design a career (and life) that felt meaningful, what would be at the center of it?
If success weren’t measured in promotions or money, how would you measure it instead?
I realized that profound impact, creative autonomy, and mentorship mattered more than chasing the following job title. Once I reframed success on my terms, I started making career decisions differently—not based on what looked good on paper, but on what aligned with who I was becoming.
Cultivate a ‘What’s Next?’ Mindset: Careers evolve. So should you. The most resilient people I know don’t have the perfect 10-year plan. They’re the ones who stay curious about what else they could be.
Instead of feeling stuck, start asking yourself:
What am I drawn to right now?
What skills do I keep wanting to build, even when I don’t have to?
What parts of my work energize me, and which ones drain me?
What would it be if I could spend the next five years mastering one thing?
The most exciting careers aren’t linear—they’re adaptive. Staying relevant isn’t about rigidly sticking to one path; it’s about learning to pivot, explore, and embrace reinvention.
For some, this means deepening expertise in their current industry. For others, it means stepping sideways into new opportunities. For many, it means expanding into areas that don’t fit neatly into a job description—teaching, writing, advising, or creating. The best question you can ask yourself isn’t What’s my five-year plan? But what’s my next experiment?
Reframe Growth: Most of us have been conditioned to think of career growth in vertical terms—promotion, title changes, moving up the ladder. But growth isn’t just about going higher—it’s also about going deeper and broader.
Ask yourself:
Instead of chasing upward mobility, how can I focus on depth and mastery?
Instead of looking for a title change, how can I expand my influence and impact?
Instead of feeling like I must “start over” to make a change, how can I layer new dimensions onto what I already know?
Some of the most interesting careers are built at the intersections of skills, industries, and perspectives. The most dynamic people aren’t just specialists or generalists—they’re hybrids.
For example:
A designer who understands business strategy becomes a design leader.
A marketer who leans into behavioral psychology creates deeper customer engagement.
A writer who experiments with visual storytelling develops a whole new communication medium.
The question isn’t just What’s next? But what else could I be?
The Power of Multiplicity
In a world that constantly asks, “What do you do?” the most compelling answer might be: “Many things.”
Embracing multiple identities isn’t about being scattered—it’s about deepening your sense of self and expanding your capacity for growth. It’s about recognizing that you’re not just one thing, and that’s your superpower.
So as you navigate mid-career (and beyond), ask yourself:
What else could I be?
What other parts of myself am I ready to explore?
Because the truth is, you’re not just a professional, a parent, or a partner. You’re a mosaic of identities—each adding depth, color, and meaning to your life.
And that’s where true fulfillment lies.
