You’re smart. Experienced. Thoughtful. So why does your last career move feel… wrong?
I’ve spent two decades coaching senior professionals and C-suites across Asia, and if there’s one thing I’ve learned, it’s this: bad decisions don’t come from stupidity. They come from pressure, poor data, and rushed timelines.
So before you leap into a new role, pivot your career, or launch your side hustle full-time, here are five practical filters to run your decision through. They may just save you six months of misery and regret.
1. Making A Decision Under Pressure
When you’re told by your headhunter or friends “this is your only shot”, take a breath. Then walk away.
I once coached a senior executive who was aggressively courted by his headhunter for a “once-in-a-lifetime golden opportunity.”
The recruiter even visited his house to convince his spouse about how much more money he would be making. He accepted the offer after eight weeks of being pressured, but within three months he resigned. The role was completely misaligned with who he was.
Moral? Never make decisions under duress, especially not career-defining ones. Pressure warps perspective, and often leads to poor-fit choices.
2. Believing Everything You’re Told
It is the headhunter’s objective to get you to sign on the dotted line, because only then does he get paid. So he will whisper sweet nothings in your ear and flatter you to close you.
- “Our client loves you! You’re first on his list!”
- “The CEO said he’s planning to include you in his succession plan.”
Don’t get infatuated by the role or the team that’s courting you. Instead, ask the tough questions that no one dares to ask:
- What’s the churn rate on this team?
- Who’s succeeded in this role, and who’s failed?
- What’s the unspoken culture here?
Many career decisions are made on hearsay: “I heard it’s a great place.” But nothing beats first-hand data from insiders.
Speak to people in the company. Cross-check what other recruiters say. Treat this like due diligence for a million-dollar deal, because that’s what your career is worth.
3. Not Weighing The Pros And Cons
One of the simplest but most powerful tools I still use regularly to make important decisions? A weighted pros and cons list.
I map out each item, then rate each factor on importance. If you’re deciding on a job, you could consider:
- Work-life balance
- Learning curve
- Salary
- Career strategy alignment
This simple exercise helps you see clearly what’s often hidden under stress, ego, or emotion. Once you start weighing, the decision matrix becomes clearer. You’ll notice what matters, and what’s just noise.
4. Thinking Short-Term Instead Of Playing The Long Game
Career chess, not checkers.
Too many executives focus on this next job. But smart professionals ask: where will this take me next? Because that shiny title might box you into a role you’ll hate, or worse, one the market doesn’t value.
Is this role a springboard to bigger things… or are you being made to walk the plank?
Don’t just chase title or package. Look at trajectory. Does this align with your longer-term professional narrative?
I always ask clients: where will this put you in five years? Sometimes a ‘smaller’ role now unlocks far greater doors later.
Visualise your career three to five years down the road. Is this role a launchpad, or a dead end?
5. Getting Too Emotional
Start with heart, finish with head.
Yes, your gut matters. But gut alone can’t write your business case.
Some of us are heart-led. Others are head-first. The sweet spot? Use your heart to find what excites you, and your head to figure out how to make it sustainable.
Be honest with yourself: am I doing this because I’m passionate, or because I’m escaping something?
If you’re starting a business, start small. Validate your idea. Incubate it while employed. You can be bold without being blind.
Final Thought: Consult Your Future Self
Before any big decision, ask: will 60-year-old me thank me for this?
That question alone has stopped me from some costly mistakes, and encouraged bold decisions I’d otherwise have second-guessed.
If the answer is murky, don’t rush. Slow down. Gather intel. Check your blind spots. And if you need help, get it.
Your career is your most valuable asset. Treat it like one.
Need an objective perspective before your next move? Drop me a note.
