When Success Isn’t Enough Anymore

A few weeks ago, I was sitting in my apartment getting ready for a podcast interview. I had my matcha next to me, my prep notes open, and I was reading the title of the episode we were about to record: What Do You Really Want?

I smiled when I saw it because it’s such a simple question. 

And yet I know from experience it can be surprisingly difficult to answer in certain seasons of your life.

As we began recording, I found myself thinking about the version of me who had just moved to NYC after grad school, landed a job as a creative in advertising, with wide eyes and the sweet hope of living my dream life in the city of my dreams with the career of my dreams, WOW lucky me! 

Within a few years I was working on big brands, flying around the country for shoots, and climbing the ladder. From the outside it looked like I was hitting milestones with promotions, new projects, big opportunities…what I thought was my perfect recipe for success.

It certainly looked what I had always thought I wanted!

If you had asked me then what I wanted for my career, I would have answered with something along the lines of, “The next promotion with a shiny braggable title, bigger clients that people oooohed and ahhhhed at, working on cool projects and of course more money…always! 

I would have given the answer that looked like my next logical step up the ladder that looked impressive.

But there were many evenings when I would still be sitting at my desk long after everyone else had left, tearing up a bit, staring at my screen and feeling something I couldn’t quite name. It wasn’t that I hated my job or that I was ungrateful for the opportunities in front of me.

It was something much more subtle than that. Something that would surface as a light hum of sadness for the life I was building, before it quickly would get pushed aside, because, it didn't really make sense.

And in those moments, I’d catch myself asking, “Is this REALLY what I want?”

During the conversation on the podcast, we talked about why this question can feel so unsettling for high achievers, especially when things on the outside appear to be going SO well. We also explored a metaphor that has stayed with me for years about how easily we can keep moving forward without ever pausing to name where we actually want to go.

Here's what I have come to believe. It's natural to change.

The person who chose that career path many years ago is not the same person sitting here today. Your seasons shift. Your desires evolve. What once felt aligned may certainly not fit who you are anymore. 

And I don’t think that’s failure, I’d actually call it growth.

This is exactly what we explored in my recent conversation on the Find Your Dream Job podcast with Mac Prichard.

If you’d like to hear it, you can listen or watch the episode here:
What Do You Really Want?

You might be surprised what unfolds when you give yourself permission to truly ask yourself, what do you really want…now?

With ♡and gratitude,
Jennifer