When the Path We Imagine Isn’t Theirs: Rethinking How We Define Career Success
This week, I had what I used to call, as a five-year-old, a “first time in my life” experience.
Apparently, I said that every time something new happened to me. My dad loved the phrase so much that he continued reminding me of it long after I was grown.
This week brought another one.
My daughter was performing in Vancouver, British Columbia—close enough for my husband and me to drive up and see her.
She and a friend have a musical band, and Vancouver was one of the stops on their tour. Later this month, they’ll be performing in several cities in Europe.
Sounds like a pretty big deal.
The irony is that, until recently, I didn’t fully understand how big a deal it was.
A friend’s college-age kid told me that she had been bragging to friends that she had known my daughter since childhood because they follow the band.
That got my attention.
I started looking more closely at what my daughter had built.
And I realized that while I knew she had been performing, traveling, and earning money from music, part of me still assumed she was doing it before moving on to a more conventional career.
That realization was uncomfortable.
The career I had imagined for her
I come from a family that deeply valued education and intellectual achievement.
Education opened doors. A good degree led to a good professional career. Success followed a path we understood.
Without consciously deciding to, I had carried some of those expectations into my own parenting.
My daughter studied journalism and political science at a prestigious university. People around us naturally imagined what might come next—a recognizable organization, a journalism career, perhaps a conventional professional path.
Music was not the future I had pictured.
And she knew that.
For a while, she didn’t tell us how seriously she was pursuing it because she expected us to discourage her.
That realization hurts.
It is difficult enough to choose a path that is different from what society expects.
It may be even harder when you know the people who love you most imagined something different for you.
Then I realized something else.
As I watched her perform, I began seeing the situation through a different lens.
She had not rejected the values I had tried to teach her.
She was living them.
I wanted her to become independent.
She has.
I wanted her to pursue excellence.
She does.
I wanted her to work hard at things that matter to her.
She works extraordinarily hard.
I wanted her to become resilient and resourceful.
I’ve watched her stay steady through canceled flights, complicated travel, unexpected problems, and the countless logistical challenges that come with building something yourself. She doesn’t wait for someone else to solve them. She figures out the next step and keeps moving.
The form is different from what I imagined.
The values are not.
That distinction has mattered to me.
How do we define career success?
People who care about us often develop pictures of what success should look like.
Usually, those expectations come from love.
A particular profession feels secure.
A prestigious employer seems promising.
A certain title signals accomplishment.
A predictable path feels safer than an uncertain one.
I understand that perspective because part of me still carries it.
But defining career success only by the path we recognize can make it difficult to see other forms of achievement clearly.
Sometimes success looks like climbing.
Sometimes it looks like changing direction.
Sometimes it looks like building something no one around you fully understands yet.
And sometimes it means disappointing people who care about you.
I have been on the other side of this
There is another reason I can relate to both sides.
Seventeen years ago, I made a career choice that disappointed some of my own well-wishers.
I had a solid career in technology and leadership. Leaving that path to become a coach did not make sense to everyone around me.
From their perspective, I was stepping away from something established and respectable toward something uncertain.
At the time, I had to learn to trust a path that other people could not yet see.
Looking back now, that experience helps me understand my daughter differently.
I know what it feels like when people who love you have a picture of success that no longer matches the life you feel called to build.
And now I also understand the other side more deeply—the instinct to want security for someone you love, and the challenge of making room for a path you would not have chosen yourself.
Perhaps that is why this experience feels so full-circle.
Seventeen years ago, I had to give myself permission to define career success differently.
Now I am learning to extend that same permission to my daughter.
Two generations, two different creative paths
There was another moment during the evening that stayed with me.
After the show, I watched my daughter signing merchandise for people who had come to hear her music.
Only a month ago, I sat at a table signing copies of my own book, Mid-Career Momentum.
The images made me smile.
Two generations.
Two very different creative paths.
Both of us putting something we created into the world.
My path probably looked much more familiar to me than hers did.
But perhaps that is part of the lesson.
Our children are not here to reproduce our choices.
And neither are we required to reproduce the choices that were imagined for us.
The expectations we inherit
This is not only a parenting story.
Many of us reach points in our careers when the life we have built no longer completely matches the life we want next.
And yet changing direction can be remarkably difficult.
We carry expectations from our families.
From our cultures.
From our education.
From colleagues.
From the organizations where we built our reputations.
And sometimes from an earlier version of ourselves.
We may have spent years becoming successful according to one definition—and then discover that the definition no longer fits.
That does not necessarily mean abandoning everything we have built.
But it may mean becoming curious about something deeper:
Whose definition of career success am I following now?
And:
What might I choose if I permitted myself to define the next chapter differently?
Those questions sit at the heart of much of what I explore in Mid-Career Momentum: Design Your Next Phase with Purpose and Joy.
Perhaps this is part of parenting, too.
I used to think one of my responsibilities as a parent was helping my daughter find a good path.
I’m beginning to think the responsibility is slightly different.
It is helping her develop the values, judgment, resilience, and confidence to find her own path.
And then comes the harder part:
Trusting her when that path looks different from the one I imagined.
That doesn’t mean I will never worry. I am still her mother.
It doesn’t mean I will understand every decision.
It means remembering what my role ultimately is.
Not to create a replica of myself.
Not to prescribe the life that makes the most sense to me.
But to help another human being discover her own core—and build a life around it with courage, zest, and diligence.
This week, I got the added bonus of some pretty wonderful VIP treatment at her show.
But what I came home with was something much more valuable.
Another “first time in my life” experience.
A chance to see my daughter more fully for who she is becoming—not who I once imagined she would become.
And perhaps that is something we owe not only our children, but ourselves:
The freedom to define success for ourselves.
Mid-Career Momentum: Design Your Next Phase with Purpose and Joy is for professionals who have achieved much and still feel another chapter is waiting—one with greater fulfillment, purpose, and joy.
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