EP 393 - Laura Simms on Career Change After Success: When Your Old Identity Still Works but No Longer Fits | Paper Napkin Wisdom

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There is a particularly difficult kind of career problem that tends to arrive after things have worked.

The title is good. The money may be good. Other people respect what has been built. From the outside, leaving makes less sense than staying.

And yet something has changed.

The work that once created anticipation now creates dread. The promotion that should feel like progress feels more like another lock clicking shut. Nothing has necessarily gone wrong. The person doing the work has simply become someone the old career was never designed to hold.

That is a much harder problem than failure.

In Episode 393 of Paper Napkin Wisdom, Govindh Jayaraman sits down with Laura Simms, Founder and CEO of Your Career Homecoming, to explore career change after success, professional identity, and the quiet signals that tell high performers they may have outgrown a career that still appears to be working. Laura has guided high performers through career transitions since 2011, after first living through the problem herself. (Your Career Homecoming)

When the Dream You Chased Is No Longer the Dream You Want

Laura's first career was acting.

She earned an MFA, moved to Los Angeles, found representation and began getting work. Acting provided her income, her community and even introduced her to the person she would marry. This was not a dream that had failed. She had gotten close enough to the life she had wanted to see that there was a real path forward.

Then she began asking a far more unsettling question.

If she actually got everything she was pursuing, would she still want it?

Her answer had changed.

That created a crisis that was larger than choosing another profession. If acting was no longer what Laura did, she had to confront who Laura was without it.

For proven entrepreneurs and experienced leaders, that distinction matters. A role can become so intertwined with identity that questioning the role feels like questioning everything that came before it. The business can still make money. The skills can still work. The reputation can still open doors.

The mask still works. It just may not be your face anymore.

Laura spent years trying to find another passion to replace acting. Acting instruction. Web design. Other possibilities. Nothing resolved the question.

Then, sitting in a small guest house in Los Angeles, one thought appeared with unusual clarity:

“What if it’s less about WHAT you do and more about WHY you do it?”

That question became the foundation of Laura Simms' career change philosophy. Instead of searching for another activity she could become passionate about, she started examining what had made her most meaningful experiences meaningful in the first place.

She drew a large plus sign on a piece of paper. In separate quadrants she wrote about acting, teaching acting and web design. Then she looked beneath each activity.

What was actually feeding her?

She found connection that went deeper than ordinary interaction. She loved making something from nothing. She wanted service, freedom and meaningful contribution.

Once Laura separated those drivers from the job titles that had previously contained them, her options became much larger.

1. Career Change After Success Starts With Separating Identity From Role

Experienced people rarely leave only a job. They may be loosening an identity that has been reinforced for decades.

Laura described the crossover after acting when she would still tell some people she was an actor while beginning to tell others she was a coach. That overlap gave her enough distance from the old identity to experiment with the new one without pretending the previous chapter had never mattered.

For an entrepreneur, the equivalent question may be uncomfortable: If the company no longer required the version of you who built it, who would you become next?

2. Your Body May Recognize Career Misalignment Before Your Mind Accepts It

Laura remembers the early days when a call from her agent or manager created electricity. Later, seeing the same number appear on her phone produced dread because it probably meant another audition.

The external event had not changed. Her response to it had.

She suggests paying attention to those signals. What has moved from anticipation to dread? How does Sunday evening feel? How does the body respond before a recurring meeting?

One difficult month may be a rough patch. Years of cycling between strain and brief relief may be telling a different story.

A Promotion Is Not Progress If It Takes You Further Toward a Life You Don't Want

Some of Laura's clients arrive after receiving raises or promotions.

They should be celebrating. Instead, they leave the room and cry.

“The golden handcuffs just got tighter,” Laura told Govindh.

For high performers, advancement can hide career misalignment because the external scorecard keeps improving. More compensation, authority or recognition cannot answer a more fundamental question: Do I actually want the life this success is creating?

4. Meaningful Career Change Is Hundreds of Micro Decisions

One of the most useful distinctions Laura makes is that changing careers is rarely one enormous decision made on one dramatic day.

It is hundreds of smaller decisions, made in the right sequence.

That matters because experienced leaders can put enormous pressure on themselves to discover the complete answer before taking the first step. Laura's own experience was far more iterative. She worked with people. She noticed which problems held her attention. She began writing an ebook for career-transition clients and discovered she had far more original thinking there than she expected.

The work taught her what the work wanted to become.

5. Leaders Should Ask What Growth Means Before Offering Advancement

Laura's message also carries a warning for entrepreneurs leading teams.

Managers frequently assume that the next title, larger responsibility or promotion is something a high performer will naturally want. Govindh recalled promoting a team member who became miserable and asked for her previous role back two weeks later.

Laura advocates beginning much earlier with conversation. What does fulfillment inside the organization mean to this person? What do they want more of? What kind of development matters to them?

The strongest career development plan may not resemble the ladder the leader had already drawn.

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?