Welcome to Reframed, where high-achieving professionals come to rethink their careers. Because doing things the “right” way only works if it’s actually right for you.
I'm Ashley Rudolph—a former tech executive turned coach for leaders and next-gen execs in the creative, tech, and lifestyle industries.
For the next few months, I’m experimenting with a more condensed essay format. It’s summer and I want the option to keep it light. Enjoy!
If you would’ve asked me five years ago whether I wanted to launch a podcast, I probably would’ve laughed. Not because I didn’t love them…I did. Serial unlocked something in me back in 2014. I had just landed my first role in tech and was adjusting to a new pace, a new culture, a new version of myself.
I remember texting my friend
about podcasts, trying to convince her to listen so I’d have someone to unpack them with. Ten years later, we launched a podcast together. The Impactful Conversations Effect is our outlet for unpacking the conversations behind entrepreneurs, executives, and creatives’ career moves.This week on the podcast, we’re talking to Rachel Kourakos. She started her career in investment banking, then decided it was time for change. Before pivoting, her sister encouraged her to try a simple exercise: describe her resume without using any finance jargon.
That one exercise gave her the clarity she needed to reframe her banking experience; Rachel realized she was great at things like project management, cross-functional leadership, and problem-solving at scale. That clarity helped her land her dream job at Google. You’ll have to wait to hear the full story and what came next in tomorrow’s episode :) We get into how disorienting it is to outgrow the version of success you built your entire career on.
Am I the only one who’s noticed more existential questioning lately? Not just in my clients, but culturally. There’s a shift happening. A desire for authenticity and more in person connection, a rejection of the illusion of perfection we see online. I see it on Substack, we’re seeking out real perspectives written by real people. Books are “back” (as odd as it feels to write that statement) and people are craving self-expression instead of “quiet luxury”.
And of course this theme is showing up at work too.
As I was writing this post, I stumbled upon a clip of Denzel Washington. He was breaking down the “Learn, Earn, Return” career phases, a concept coined by Bert W. M. Twaalfhoven years ago (read about it here).
It made me think about seeing Othello back in April. That entire performance felt like the Return phase. His presence. His generosity and the space he made for others on stage. There was an intention behind his acting; like he knew exactly what he wanted to leave behind.
Since there were no phones allowed, I have no photographic evidence - sorry! But I did walk away with inspiration for today’s post.
We’re exploring the Learn, Earn, and Return career phases and the existential questions that often come with each one.
THE 3 CAREER PHASES
Learn: The Early Career or Post-Pivot Phase
Learn is the phase where you're mostly saying yes — to growth, opportunity, and things you're not sure you even want yet. It’s about stretching and developing expertise. As you’re learning, you might feel:
Restless but unclear about what’s next
Anxious about “getting it right”
Torn between proving yourself and questioning your path altogether
Disillusioned with “hustle culture” but unsure what the alternative is
This is when we see things like job hopping and professionals deciding to pursue advanced degrees (MBAs, MPP, MFA, M.Ed, etc).
In my Learn phase, I wondered if I’d already made the wrong career choice and was too far in to back out. That’s why Rachel’s story sticks with me. Her sister’s exercise of describing her resume without using any finance jargon, gave her the clarity she needed to reframe what she already knew how to do and pivot out of investment banking and into tech. If you’re in the Learn phase, try this:
Describe your strengths without using your current job title
Track what excites you (and what drains you)
Treat your restlessness like a data point, not a problem
Earn: The Mid-Career Professional Phase
In Earn, you’ve found your lane and now you want to be seen for your expertise and your impact. It’s no longer about trying to prove you can do the job. One of the biggest questions for people in the Earn phase is understandably: Do they value my contributions?
You might feel:
Overextended and under-recognized
Stuck in “high performance, low visibility” cycles
Confused why impact isn’t translating into influence
Unsure whether to keep climbing, chasing perfection, or pausing and reassessing
Earn is where most people enter into management, increase their scope of responsibilities, or take ownership of more complex problems.
My toughest career moments in the Earn phase came down to feeling a major compensation / perceived value misalignment.
Value is a funny thing. We’re told not to tie our worth to it (and you shouldn’t!). But when you’re investing a lot — time, creativity, leadership, late nights, emotional labor — of course it hurts when the return doesn’t match the output.
This is where many of my clients start seeking leverage, not just skill-building, but support: better managers, more aligned sponsors, work that feels reciprocal. If that’s you, I recommend my Career Influence Quiz, not because it has all the answers, but because it helps you name the kind of shift you might need next: visibility, negotiation, sponsorship, or even a new chapter altogether.
Return: Those in Senior Leadership
This phase is about reconnecting to your purpose. At this point, senior executives have built a track record. Led teams through chaos and calm. Hit milestones most people dream of. But after a long, successful run or a major milestone like an exit — something shifts.
The pursuit of “more” stops feeling gratifying. I hear this often from execs I coach: “I’m great at what I do. I just don’t want to keep doing it like this.”
Sometimes it’s a signal that they’re ready to lead differently. Other times, it’s the first nudge toward legacy work: mentoring, writing, joining boards, or shaping culture instead of just running business operations.
Not everyone walks away. But many people redefine what success looks like. And when that happens, they need the space to pursue it.
MISTY COPELAND’S RETURN PHASE
I loved listening to Misty Copeland’s interview on The Daily this weekend. She talked about stepping away from ballet after nearly two decades at ABT, saying:
“I feel like I’ve done everything I can do as a dancer…I’m not striving to reach other people’s standards anymore.”
She’s choosing alignment and what she’s leaving behind — the cultural shift, an audience newly engaged with the ballet, the dancers who saw themselves in her — is just as meaningful as her years of performing on stage.
CLOSING THOUGHTS: THE WRAP UP
So Where Are You?
Learn? Earn? Return?
For you, maybe the real shift isn’t a big ‘aha’ moment. Maybe it’s admitting to yourself that you’re ready for something new and letting that be enough, for now.
And honestly, I don’t think it matters whether or not you’re in the Learn phase, try describing what you do sans jargon this week and see how it feels. It’s summer time, you’ll be socializing — be the person who makes people lean in when the topic of work comes up 😉
Good luck. See you next week!
Ashley
PS, I heard you - after my post: A Tale of Two Performance Reviews, a few of you asked for a follow-up on how to talk about your accomplishments — in meetings, in emails, in ways that feel human and strategic (read: not cringey). I’ll work on a piece that dives into just that.
Thanks
and , for the recommendation!WORK WITH ME
If you’re feeling stuck in the Learn, Earn, or Return phase, it’s time to pivot.
In my 1:1 coaching, we focus on uncovering what you want to do next.
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Yet another great reframe and excited for the upcoming post Ashley - thank you!
"There’s a shift happening. A desire for authenticity and more in person connection, a rejection of the illusion of perfection we see online." i'm seeing this shift in both personal and professional realms! i'm excited to try the challenge of describing my work without jargon — thanks for sharing!