Your Career Is Trying to Tell You Something
You know the one thing I absolutely hate? Not being able to sleep at night, replaying every decision you made that day. Especially when you mess up at work - like the major PowerPoint snafu in the board meeting or the report you wrecked that your co-worker won’t stop reminding you about.
What’s worse is when you start spiraling, thinking about every mistake you’ve made in your career - or at least all the major ones. You find yourself conducting an impromptu 2 am resume review, reflecting on all of your shortcomings and wondering where you went wrong in your decision-making. Did it start with the first promotion you took solely for the money? You knew you’d hate the trajectory it’d put you on, but man, that paycheck was amazing. Or was it the new startup you joined because it was going to be the next FAANG? Or maybe it was that one role where you stayed two years too long and sabotaged everything.
If you’re thinking, “Oh, this is definitely me,” you’re not alone. Most people either beat themselves up for the choices that didn’t work out, or they simply swallow their pride and tell themselves it will all make sense eventually.
But what if none of those experiences were mistakes at all? What if they all served as important data for strategic decision-making for the future?
Let me show you why you might be looking at this all wrong…
What We Get Wrong About Career Decisions
Remember the term “career ladder"?
Of course you do, you’ve heard the term since the early days of high school (and maybe even middle school). Whether it was your parents or your guidance school counselor from back in the day, you were encouraged - no - expected to follow it.
The concept of a job or career ladder (in case you need a refresher)refers to the mechanism through which workers ascend to better employment opportunities over time. Job ladder theory states that individuals start their careers at lower-paying and potentially less-desirable jobs but gradually "climb the ladder" as they gain experience, skills and qualifications.
Most professionals treat their career exactly like this - a linear path where every decision either moves you forward or sets you back. Skipped over for a promotion 3 years in a row? Automatic career failure. Making more money at the Fortune 100 company you landed a job at? You’re on the path to automatic success.
By that logic, anything that didn't work out was a wrong turn. But that’s not how it works, especially at the mid-career level.
Psychologist Donald Super spent decades studying how people actually develop their careers and his research makes one thing clear: career decisions aren't single moments of clarity. They're the cumulative result of everything you've experienced, learned, and discovered about yourself along the way.
Experiences both good and bad, mind you.
That VP who spent three years in a role she hated learned something irreplaceable about what she values. The Director who turned down a promotion and still wonders if he made the right call learned something critical about what success actually means to him.
Every single one of those moments generated information. The problem didn’t lie in the decisions itself, it's that nobody taught us how to use what they revealed.
Your Career Has Been Asking You Questions All Along
When you go to a job interview, you’re asked a series of questions ranging from behavioral to performance based. Whether you like them or not, recruiters need to ask these questions to gauge your level of "fitness." But what if you took time to internally interview yourself about your current job to see if it’s the right fit for where you are now? Every job, role, boss, and project you’ve had has been secretly interviewing you, asking versions of
the same questions for you to answer and track:
What kind of environment brings out my best?
Where do I feel confident and capable, versus where I am just performing?
What did I keep doing even when nobody asked me to?
Whether you know it or not, you've been answering these questions throughout your entire career: how you felt on Sunday nights, in the projects you stayed late for without being asked, in the meetings that made you want to disappear, in the moments you felt most alive professionally.
There is hidden value in all of this data. It’s just a matter of perspective.
So, What Is Your Career Telling You?
In the words of psychiatrist Mena Mirhom, “Climbing the career ladder can sometimes be a journey of self-discovery.”
And reflection should also be included in that journey.
It requires you to sit down and look at everything in a very different light.
But as a mid-career professional, can you wade through the emotions, actions, and decisions of your career portfolio to uncover the hidden gems to lead you into your next move? That’s the million-dollar question, because the data is there. Whether you're ready to read it and do something about it, is another.
