Feeling Lost Career-Wise? A Case Study on What to Do

Figure out what to do when you're feeling lost in your career by extracting practical lessons from an example.


About once a month, I get an email from someone who is about to quit their job or is nearing retirement and feels lost about what to do next. Somehow, this leads them to stumble across my pretirement story, which compels them to contact me for help finding direction.

The most recent example came from someone we’ll call “Perdida.” After years of feeling like a hollow-living loser for trading her time for money and status in a career she hated, Perdida quit without a plan. Six months later, she feels lost and paralyzed.

Here’s her full story:

Perdida quit her career and is now lost and paralyzed

Perdida’s Story

I have hated every job I have ever had and thought that this meant that I was broken or defective. I know that I am more than my job title, conceptually, but I have defined myself by my title and paycheck for so long. I have hidden behind credentials. 

I have always felt like an imposter. Finance was the way that I could prove that I was smart. I worked in FP&A and built models but I think I was really bad at it. I feel like everyone could tell I had never been “formally trained.” I didn’t do investment banking so I was inferior and everyone knew it. 

I was always running. I’ve never taken a job that I was excited about, I was always taking a job to escape the role that I was currently in. In mid 2020, I decided moving from San Francisco to San Diego would fix things. I just needed a change in geography!  

After a year of working remotely and never stepping foot in my San Diego office, we realized that Zoom life was here to stay. We decided to put our stuff in storage and figure out where we wanted to live. We stayed in month-long Airbnb’s and traveled around for 18 months. 

I’ve always had this nagging voice telling me that my job was wrong and every once in a while, an overwhelming panic would wash over me “why was I wasting my life like this? Is this all there is?” I had decided that the paycheck was worth living as a Zoom zombie. Joining pointless calls, doing pointless tasks…It was so depressing. Is this why I worked so hard? So I could numb out and just get a paycheck while I slowly die?

Don’t get me wrong, the traveling was great but the trade off of my time wasn’t adding up anymore. The paycheck wasn’t worth it. I reached the point where the pain of staying in my current situation was greater than the fear of the unknown.  

So here I am now. I quit my job 6 months ago and I do not feel like I have figured anything out. We went to Europe for a month. We moved and settled into [some city]. I have started a podcast and write blog posts but my perfectionism is stopping me from sharing them publicly. 

It’s scary how easy it is not to work and for time to pass by. We are not stressed financially but I often feel completely lost and that I am being lazy and self indulgent. I am trying to not be overly critical of myself and think more expansively. I am devouring self-help books instead of moving into action. I love owning my time and energy but I feel paralyzed and don’t know what interests to focus on. 

I see a lot of similarities between Perdida’s story and others I’ve come across, including my own. So I think it helps to use her example as a case study for extracting some practical lessons that might help you or anyone stuck at a career turning point with no idea which way to go next.

Let’s break down Perdida’s:

Perdida's ego is shielding her princess snowflake of an identity.
Perdida’s over-protective ego and snowflake-princess identity.

Perdida’s Problem

So what’s Perdida’s problem?

To use a word I must have learned from Law & Order, Perdida’s email contains a preponderance of evidence hinting at it:

  • “I have defined myself by my title and paycheck.”
  • “I have hidden behind credentials.”
  • “I could prove that I was smart”
  • “I was inferior and everyone knew it”
  • “my perfectionism is stopping me”
  • “I am trying to not be overly critical of myself.”
  • “I am devouring self-help books instead of moving into action.”

The prime suspect for inflicting Perdida’s post-quitting paralysis?

Her over-protective ego.

Like a mother who coddles her child, Perdida’s ego has done everything it can to foster the development of a smart, esteemed, capable, and perfect sense of identity. This has had the negative knock-on effect of giving her identity low self-esteem and making it fragile, hyper-sensitive, and afraid to act.

No wonder Perdida doesn’t know what to do!

It’s not that she isn’t capable, it’s that she has little idea what she’s capable of. And that’s because she’s been too afraid to smash her inflated, precious, pristine identity piñata to see what’s inside.

On the bright side, Perdida:

  • Seems to be aware of her problems.
  • Shows a strong desire to make something happen.
  • Is comfortable enough financially to be able to work on it.

So let’s think about what she can do.

Perdida’s Challenge

Perdida’s challenge is to shove her ego aside and start whacking away at her coddled identity to see what she’s really got inside her.


Allow me to cherry-pick a couple of fruits of Twitter wisdom for suggestions:

Learn by doing.

Get inspiration and motivation by doing.

What kinds of actions?

Let’s rattle off some quick ideas:

  • Publish her precious podcasts and blogs to expose them to the harsh feedback of reality (or crickets).
  • Take classes in something she sucks at to rediscover the pleasures of incompetence.
  • Join a peer group that pressures her in a positive way to push herself.
  • Sign up for Toastmasters.
  • Do some David Goggins-esque physical challenge to start building mental callouses.

She could even have fun with it by setting a 30-day challenge of taking a different daily action that ignores her ego and toughens up her identity.

Perdida’s ego’s going to rebel against these actions. Her identity will cower and cry about it too. But if she keeps at it, she’ll toughen up her self-identity and get an idea of what she’s made of.

This leads us to our next question: How can Perdida find the motivation?

Thought experiment of doing anything to rescue your husband
These aliens really want to see Perdida’s content.

A Thought Experiment

To get an idea of how Perdida might find the motivation to do things that harden her identity, consider this thought experiment:

Imagine aliens abduct Perdida’s husband. They tell her they’ll only give him back is if she manages to get ten thousand people to read her blog posts or listen to her podcasts.

What do you think Perdida would do?

Would she keep perfecting the posts and episodes she already has? Would she read dozens more self-help books in search of the perfect strategy?

Of course not! She’d publish the stuff she’s been sitting on, promote the crap out of it, incorporate whatever feedback she gets to improve her work and publish more, better stuff. And she’ll keep going until she gets her husband back.

Perdida would probably get her husband back before she even starts to miss him!

Am I trying to say that Perdida should get her butt in gear to pursue a career in blogging and podcasting?

Probably not. My point is bigger than that.

Find a purpose to overcome your ego, toughen your identity, and fuel your motivation.
Find a problem that fires you up and pushes ego to the background.

Trump Your Ego

The best way I can think to explain the alien thought experiment is with a quote I found in legendary psychiatrist Viktor Frankl‘s “sledgehammer” of a book, Man’s Search for Meaning:

“He who has a Why to live for can bear almost any How.”

Friedrich Nietzche

And let me to layer on another quote from another classic book, The 7 Habits of Highly Successful People:

“The successful person has the habit of doing the things failures don’t like to do. They don’t like doing them either necessarily. But their disliking is subordinated to the strength of their purpose.”

Stephen Covey

So if Perdida wants to beam her ego into outer space instead of her husband, she has got to stop picking at her belly button and take charge to hone in on a purpose, a Why, a problem, she’s willing to sacrifice her identity to pursue.

Then she’s got to take swings at it in whatever ways she can. Reality will whack her back even harder and knock her down. But if she cares enough, she’ll get back up again, adjust her strategy, and keep at it. This will make her tougher and stronger.

Eventually, Perdida will find a way to make an impact.

Then she’ll have fought her way into a new career because all work is about solving problems. And if something’s a problem for you, it’s a problem for many others. Once you get good enough at taking it on, people will pay you to help them with theirs.

Update: Follow Perdida’s Journey!

Perdida’s real name is Kendall.

She has decided to do away with anonymity to start publicly promoting her thoughts, challenges, and progress in her “Still Small” newsletter and podcast.

Check out Kendall’s content and subscribe to motivate her and get motivation from her!

Go Find a Problem to Pick On

Perdida’s problem doesn’t have to be as intergalactically dramatic as alien kidnapping. It can be something as humble as what my wife Kim’s working toward with her blog, Feed My Friends: people’s inability to host fun, low-fuss, but meaningful gatherings. Or the problem I’m taking on here with The Zag: the conundrum of figuring out what to do next to make life more fulfilling.

There’s no shortage of problems in the world. And there are infinite ways to take on each of them. So Perdida, like you, me, and everyone else, can find a way to contribute if she keeps swinging. It all starts with keeping an eye out for things you have a problem with, then using that as motivation to shove aside your ego’s protective instincts to take it on and see what you’re really made of.

If your problem is finding a problem, you might want to choose to check out these posts:

About the author

👋 I'm Chris. Everything you read on TheZag.com is my fault. This site is like a gym for your comfort zone, full of challenges to make your status quo sexier. Join my 'Consider This' newsletter for a fun new challenge every 10 days. Try it!

Leave a Comment

Latest Articles


The Zag shares my adventures off of the boring beaten paths of life and ideas for finding your own unfollowable path.