Oh hi there, I'm Vivianne Castillo ✌🏾
You know that feeling when the job looks good on paper and still costs you something you can't name? I know it too.
So I built HmntyCntrd, an award-winning consultancy, into a 7-figure business and then walked away from UX to build Choose Courage Inc., where I help creatives and aspiring corporate escape artists break free from systems that were never built for them and build businesses that pay well, feel good, and protect their peace.
Everything I share here comes from that work, not from theory.
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This post pulls from a conversation with Lauren Celenza, a UX researcher, writer, and founder of moonpaws, about why so many of us stay in careers that have stopped fitting us, and what it actually takes to leave. We get into trauma bonding at work, the difference between discipline and hustle, and the sunrise-sunset way Lauren thinks about career transitions. Note: this post may have affiliate links and we donate 100% of those funds to non-profits and a children's group home🫶🏾
Feeling stuck in a career rarely shows up as a single bad day. It shows up as a slow accumulation: the Sunday dread, the meeting you sit through without hearing a word of it, the calendar that somehow fills every week with the same three problems dressed differently. Most people who feel this way assume the fix is motivation. A new planner, an earlier alarm, a pep talk from a podcast. What Lauren Celenza and I got into is a harder and more useful idea: staying stuck usually isn't a discipline gap. It's an attachment, and most of us have never been taught to name it, let alone leave it.
The Attachment Nobody Names
Lauren has spent years thinking about work as a relationship rather than a place you go for eight hours a day, and that shift changes what "stuck" actually means. A job or an industry can trauma bond you the same way an unhealthy relationship does. It's an intense, unhealthy attachment to the thing that's hurting you, and it forms because the people closest to the pain end up closest to each other. You bond over the shared boss, the shared frustration, the shared sense that none of this is quite right. Lauren has watched it happen inside UX design, an industry that markets itself as human-centered while running on the same extraction as everywhere else. I've watched people leave a company and grieve, not the job, but the people they thought they were close to, only to realize what actually held the group together was the shared pain and nothing underneath it. Take the pain away and there isn't much left. That's a hard thing to sit with, and it's also the reason so many people stay long past the point where staying makes sense: the bond feels like belonging, even when the thing you're bonded to is what's hurting you.
Lauren's own path into this question started early. Her father worked fourteen and sixteen-hour shifts at a warehouse; her mother ran a donation call center from home, one of the first work-from-home jobs of the 1990s. Watching that as a kid gave Lauren a set of questions that didn't resolve, they just changed shape as she grew up and eventually entered UX herself, doing work she'd been told was creative that mostly felt like staring at the same Figma file on repeat. The questions she asked as a child (why is Dad always gone, why does work make the adults around me so tired) became a different question as an adult: who gets to shape our relationship to work, and what is it costing us to let them.
Why "Stuck" Rarely Means What You Think It Means
If you search around for feeling stuck in career advice, most of it treats stuckness as a mindset problem to be solved with a worksheet. Lauren's framework treats it as a tension between two real, legitimate pulls: staying safe in the familiar, which usually pays the bills, and yearning for something more, which usually doesn't, at least not yet. Spend too long in the safe zone without tending the yearning and resentment builds. Spend too long chasing the yearning without any practical scaffolding and you lose the stability you need to actually get somewhere. Neither side is the villain. The trouble starts when people attach shame to whichever side they're currently standing in, telling themselves the safe choice is boring or the risky choice is reckless, when really it's just where they are in a transition that has its own timeline.
Lauren compares it to a sunrise. The sun doesn't jump from night to day in a single second; it moves through a slow gradient most of us don't consciously watch but trust completely. A career shift works the same way. You can be doing the thing that pays the bills while deliberately, weekly, carving out time for the thing you're not ready to leap into yet. That's not indecision. That's the transition working the way transitions actually work.
"I don't think UX was ever really human-centered." — Lauren
Where I Had to Do My Own Work
I came into UX from a background in counseling and human services, and from day one I understood human-centered design differently than most of the industry did. What I didn't expect was how long it would take me to notice that the work was starting to feel like a cage instead of an expression of anything. I've always poured myself fully into what I build, whether that's a company or a community, and for a long time I read that intensity as commitment. It took me longer than I'd like to admit to see that the relentless push to prove myself, to keep growing, to keep matching external expectations, was draining me in a way that had nothing to do with how much I was accomplishing. I looked successful from the outside. I did not feel like I was thriving on the inside, and those two things being able to coexist for years is exactly the problem.
The belief I had to unlearn sits underneath most of this: that my worth is tied to my output, that I have to keep proving my value by doing, achieving, producing more. Some of that is upbringing. Some of it is the plain fact of being a Black woman who has had managers tell me, in so many words, that I was already operating at the director level while they withheld the promotion to match. Creativity and courage don't grow under that kind of pressure to perform. They need room to be messy, to fail without the failure becoming a referendum on your worth. Rest, in particular, is not a reward you earn by working hard enough first. It's a requirement, and treating it as optional is how people end up holding onto jobs, relationships, and identities that were never built to hold them in the first place.
Discipline Is Not the Enemy Here
People conflate discipline with hustle constantly, and it's worth separating the two before you try to plan any kind of exit. Hustle culture treats constant motion as proof of worth. Discipline is what actually protects the thing you're trying to build, including your rest. Lauren color-codes her calendar every week specifically so the yearning-for-more space doesn't quietly get crowded out by whatever's loudest and most urgent. James Clear's observation that we don't rise to the level of our goals, we fall to the level of our systems, is doing real work here: the goal to leave a stuck career means very little without a weekly structure that actually protects the hours you'd need to build toward something else.
None of this requires an overnight overhaul. Diversifying income, even in small ways, does more to loosen a stuck feeling than any single bold leap, because it removes the trap of needing one revenue source, one employer, or one industry's approval to survive. And it's worth naming plainly who you tell about a transition while it's still forming. Not everyone in your life is equipped to be a good steward of a dream that isn't fully built yet, and the wrong audience at the wrong moment will talk you out of something you were right to want.
Where to Start
If you recognize yourself in any of this, the honest starting point isn't a five-year plan. It's an audit of what's actually keeping you attached to your current situation and whether that attachment is pain or genuine alignment. That's the exact work our free Life Audit walks you through, and it's built for exactly this stage: sensing that something's off before you've decided what to do about it.
Lauren and I didn't get to close the loop on what happens once you've named the stuckness and started moving toward something else, which is really its own conversation about what you're moving toward. That one's coming.
If feeling stuck in your career is something you're sitting with this season, The Life Audit is the place to start untangling what's actually yours to keep and what you've been carrying out of habit.
Originally aired as Episode 7 on the Choose Courage Inc. podcast.