When the Career You Built No Longer Feels Like Yours
Updated: 16 hours ago
There is a kind of career problem that only shows up after things have worked. The title is good. The money is good. People respect what has been built. From the outside, leaving makes less sense than staying. And still, the work that used to create anticipation now creates dread.
Nothing has gone wrong. The person doing the work has become someone the old career was never designed to hold. That is harder than failure, because failure gives you permission and success does not.
In Episode 393, Laura Simms, Founder and CEO of Your Career Homecoming, talks about what she learned walking away from acting when acting was finally starting to work. She has guided high performers through career transitions since 2011. Her answer starts somewhere other than the job description. It starts with why you want to work at all.
Inspired by Paper Napkin Wisdom Episode 393 with Laura Simms.
Getting close enough to the dream to find out you don't want it
Laura's first career was acting. She earned an MFA, moved to Los Angeles, got an agent and a manager, and started doing the work. Her income came from acting. So did her community. She met her spouse through it.
None of that failed. That is the part worth sitting with. She was auditioning for the people who could make a full-time acting career happen, and getting good feedback. She could see the gap between where she was and where she wanted to be, and she could see a path across it.
Then a different question arrived. If she got to the fullest expression of this, would she even want it?
"And that answer changed," she told Govindh. "I didn't even want the thing I used to want. And I think part of it is because I got close enough to it to see what it was actually gonna be like."
Proximity did the work. The thing she wanted at twenty-two was not the life she wanted at thirty, and only getting near enough to see it clearly made that visible.
Asking the question felt like a betrayal of everything she had built. It sent her into what she describes as a spiral lasting a couple of years. The question wasn't just what am I going to do. It was who am I going to be. Because she had followed a passion once, she kept trying to find another passion to follow. Acting instruction. Web design. Nothing resolved it.
Then, in a small guest house in Los Angeles, one thought went across her mind the way a plane pulls a banner across the sky. What if it's less about what you do and more about why you do it?
The quadrant: looking underneath the activity
What Laura did with that thought is the practical part, and it is worth copying.
She took a blank sheet of paper and drew a giant plus sign. Four quadrants. She filled three of them with the things she had pursued that had genuinely been meaningful: acting, teaching acting, web design. Then she asked one question of each. What was it about this that made it meaningful?
The question was aimed underneath the activity, not at the activity itself.
What came up was connection, though she is careful with the word. More than connecting with people, she describes a real sense of communion, something closer to intimacy in doing a thing together. Making something from nothing. Service. Freedom and flexibility, which pointed her toward owning a business. Contribution she actually cared about.
Once those drivers were separated from the job titles that had been containing them, the list of possible next moves got much longer. Instead of how can I do acting, how can I teach acting, the question became what else rides on these same drivers.
Nothing happened immediately after she drew it. She says so. But the wheels turned differently from that point on.
Try the quadrant yourself
Three things you have done that mattered to you. One per quadrant. Then underneath each one, what was actually feeding you. Patterns show up on their own. You are not looking for a job title on that page.
The body knows before the mind will accept it
Govindh asked Laura how someone would know they are struggling with identity rather than circumstance. Are there signs?
"I think most of the time people will feel it in their body before they're ready to intellectually accept it," she said. The reason is that the alternative is threatening. It is the way people know you, how people depend on you, how you make your money, how you get introduced. It is what you tell the IRS you are.
Her own signal was a phone number. Early on in Los Angeles, a call from her agent or manager was electricity. She couldn't wait to hear what they had to say. Later, the same number on the same screen produced dread, because it probably meant an audition and she didn't want an audition.
The event never changed. Her response to it did.
So the things to notice are small and specific:
What has moved from anticipation to dread?
How does your body feel walking into that recurring Wednesday meeting?
How does Sunday evening feel? Laura is direct about this one. We joke culturally about the Sunday scaries, and they are not inevitable. "It's a version of work, but it doesn't have to be."
She is not telling anyone to quit. She is asking people to stop sweeping the signal under the rug and normalizing it as what work simply is.
Rough patch, or a cycle you've been in for years
Here's the thing about a rough patch. It's a reasonable explanation, and it works beautifully right up until you count how many you have had.
Laura describes the pattern. Things get rough, hard, all-consuming. Then a little breather arrives and you think, what was I so worried about, why was I so bent out of shape. Then the rough patch comes back. Rough patch, small reprieve, rough patch, small reprieve.
The small reprieve keeps you hooked for a long time, she says, because you keep thinking a longer one is coming. If the longer one never arrives, you are in a cycle.
One hard month is a hard month. Years of cycling is information.
Her own version wasn't that cycle. Acting has no predictable rhythm, no standing meetings to dread on a schedule. For her it was slower. She calls it a slow disintegration of something she used to be excited about, and the word that stayed with me is erosion. Erosion is close to invisible day to day. Come back a year later and the landscape has changed enormously.
She uses another word for what it does to people. Self-erosion. Shrinking. Clients tell her they feel like a shell of themselves. They are not dating, not traveling, not making anything. They are surviving.
And she is honest about the limits of the fix. Getting into the right job, on its own, does not necessarily change a life. You can carry the misery straight into a brand new one.
What she has noticed is something else. When people live in congruence with who they are and what they care about, and spend their time in a way that feels worth it, something comes back. It isn't that people don't want to work. They want the work to feel worth the hours they are putting in, and to be a contribution they actually care about.
Why advancement can feel like the trap closing
There is a story people tell about career change, and it is a story about underperformers. You weren't a star. You weren't advancing. Of course you should move.
Laura's clients break that story. They are high performers at the top of their game.
Some of them come to her right after a win. They got the raise, or the promotion, accepted it, walked out of the room and broke down in tears. "No," she said, describing the thought, "the golden handcuffs just got tighter."
"It doesn't feel like advancement when you're advancing towards something that you don't want. It feels like you're pulled deeper into the trap."
For an established owner, that is the dangerous part. The external scorecard keeps improving. Compensation, authority, recognition, the respect of people whose opinion you value. None of it answers the question underneath, which is whether you actually want the life this success is building.
The other thing to put down here: changing careers is not one enormous decision made on one dramatic day. Laura calls it hundreds of micro decisions made in the proper sequence. A transition, not an abrupt stop and start. That matters for proven leaders, who tend to demand the complete answer before they will take a first step.
And while it is happening, feelings are an unreliable instrument. Sometimes the process feels great. Sometimes it feels awful, because people are challenging beliefs they were raised on and what their parents modeled, and wrestling with identity, meaning, service, legacy and money all at once. Laura works with clients on the strategic hallmarks that say the work is on track, since the feelings indicator can't be trusted on its own.
Her own path proves it. She started broad, more watered down than she would advise anyone to be. She worked with two buckets of people: business owners needing marketing help, and people in career transition. She decided to niche into the business clients and wrote an ebook for the career people so they would at least have a resource. Writing it, she found she had far more original thinking there than she expected. She let the business clients go.
"Engage with the thing so the thing can teach you what it wants to be."
Ask before you promote: what to do this week
This lands on leaders too, and it lands hard.
Govindh told Laura about promoting a team member who was miserable in the new role and asked for her old job back two weeks later. They gave it back. She had been miserable for the whole two weeks.
It is easy to assume someone will be happy about the next advancement you have to bestow. Laura's alternative is a more collaborative, slightly awkward conversation, started earlier than the opening exists.
Her questions, close to how she put them:
What about this would interest you?
What does fulfillment or success in this organization look like for you?
What's working well?
What do you think you're missing and could use more of?
Open-ended first. Roles and titles after. Come in with the question instead of the assumption.
She is also clear that this is complex, and that it isn't a wish list. You may be looking at several people with competing wants, plus what the organization itself needs. Nobody is handing a leader a list for Santa Claus and expecting every item delivered. It is collaboration toward a place where people feel valued, can grow, and have the circumstances that make the work feel worth it.
It is hard. It is harder when you skip it. Get the next rung wrong and you hurt the person, you hurt the company, and most often you lose both.
Three things to do this week
Draw the plus sign. Three things you have done that mattered. Underneath each one, what was actually feeding you. Look for the drivers, not the roles.
Track one signal for seven days. Pick the recurring meeting, the Sunday evening, the name on the incoming call. Notice where anticipation has become dread, and write down what you notice rather than explaining it away.
Ask one person on your team the growth question before there is a vacancy. What does success here look like for you, what's working, what are you missing. Then stop talking and let the answer surprise you.
And for yourself, if the company no longer needed the person who built it, who would you become next? That question is worth more this week than any answer about what to do.
The Napkin Moment
Laura Simms actually wrote the central insight of this conversation on her napkin:
“It’s less about WHAT you do and more about WHY you do it.”
There is enormous permission in that sentence.
The career, company, role or identity that carried someone through one successful chapter does not have to remain the container for everything they value. Purpose can survive a change in form. Skills can travel. Nothing meaningful about the previous chapter has to be discarded simply because the next one requires a different expression.
Laura eventually called her work Your Career Homecoming because she noticed something surprising. The greatest change was not simply that clients discovered different work. People seemed to come back to life. They dated again. They returned to creative pursuits. They travelled. Their energy returned.
The destination was never merely another job.
For the entrepreneur who has spent 10, 15 or 25 years becoming extraordinarily good at one version of themselves, Laura Simms' career change story raises a harder possibility:
Maybe nothing is wrong with what you built. Maybe you are simply no longer the person it was originally built around.
What might become possible if the next chapter did not begin with What should I do? but with Why do I want to do any of it?
Related Insights
If the identity that built your business has stopped fitting the person running it, that is depth work, and it goes faster with peers who will ask you the harder question. Build the Field
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