#TBCOverheard: He had 3 possible paths, 1 huge deadline, and 0 decisions made. Here's what changed in 2 sessions.

Blake came to me at the start of June with a problem most people would kill to have. Survived a round of layoffs at his corporate (Transport) job. Family business doing okay and waiting for him to join. Potential dream career in a different industry (Financial Services) he'd quietly kept watch over the years is hiring again.

And a wedding in the next calendar year. (I've become fond of weddings after deciding to have one of my own lol.)

Now Blake's sitting in front of me for the first of our 2 Next Big Move sessions. NBM is where you come as you are, just vomit all your thoughts, worries, and ideas about your future to me, and I'll help you arrange it into 3 possible paths. Then we discuss how to explore each possible path, and you walk out of it knowing exactly what your career's next big move is.


He framed it as a "too many options" problem. Which path should he pick? Everything's open and available right now so he's getting analysis paralysis. Which is why we're going to talk through his situation right now.

I got to work by asking him questions instead.

Had he actually talked to someone working at his dream career, not researched it, not thought about it late at night, but sat down with a real person and asked what the work is actually like? No.

Did he ever have a conversation with his family on expectations and timeline for him joining the family business? No. 

Had he done anything concrete, in the past 6 months, to move any of these paths forward? No.

And then he volunteered info that changed everything: he'd given himself a deadline years ago and missed it.

"1 more year here, then I'll start looking." That 1 more year had quietly repeated itself for several years running.

I’d heard enough and gave him my assessment:

Your problem isn’t that you have too many choices. It’s that you refuse to actively make one.
Not because you’re afraid of the outcome, you actually seem excited about all the changes and growth incoming, but because you don’t have the muscle for execution yet.

I likened it to this: if a friend introduced themselves as a filmmaker but had never filmed anything, you wouldn't believe them. Same logic applies to calling yourself someone who's "still exploring" while never testing a single path.

He left the call with a clearer mind and a ton of homework.


3 weeks later, and 2 hours before our call, Blake sent me 47 pages of notes and a lot of new confusion to untangle. Which is what happens when someone finally starts doing the work they'd been avoiding. So we untangled it. In 1 hour.

We found out that

  • the people he'd been talking to for insight were all peers, no seniors who actually knew what got someone promoted.

  • he'd been introducing himself as "the Transport guy" for years, but it was a label nobody but him had actually given him.

  • in the past 6 months, exactly 0 people had reached out to him about new roles even with all the layoffs and restructuring going on around him

Which led to my final summarization: that this wasn't bad luck. It was invisibility.

Then we mapped his skills and found what I call an upside-down T: 1 skill developed to expert level, everything else (like strategic thinking, people leadership, communication) sitting flat at the baseline. He'd sharpened the one thing his job rewarded and let everything else go untouched, waiting for someone else to hand him growth instead of building it himself.

Then we did the math that actually mattered.

What happens after the wedding? Kids, a house, tuition. Blake had a 5-year-max runway before real financial pressure hits. That meant he had a hard ceiling on how many job jumps he can make in that window without hurting his own trajectory. His current path wasn't going to get him there in time. And our 2 sessions showed him his reality.

By the end of the 2nd call, the fog was gone, curtain was lifted, he could actually see his situation for what it is. He didn't leave with more options. He left with 1 clear decision about his future and a hard deadline: he needed to leave his current job, start applying now, be settled somewhere new within 6 months so that he's regularized way before his wedding, instead of trying to negotiate for leave after.

That's the shift I want my students to make in every NBM session.

Not more clarity for clarity's sake. Clarity with a deadline attached. Because clarity without urgency is just a nicer way of stalling.

***

The Bumpy Career's Next Big Move is for the high achiever who isn't stuck because they’re option-less. They’ve usually got 2, 3, and sometimes, even 7 possible career paths. Yet every single one is still theoretical.

Meaning you're not short on potential moves. You're short on a decision. You've been "exploring" for long enough that it's started to look a lot like standing still.

That's where I come in.

We'll work together to turn your live options into one actual decision with a deadline attached. So you leave our sessions with a next move for the next instead of another year of "eventually."

If that sounds like where you are right now, you can book your own Next Big Move here and let's figure out what’s next for your career.