Stop Planning Your Career (Do This Instead)
Most career advice is backwards.
Everyone tells you to “plan your career” like it’s a neat 10-year roadmap.
That’s fantasy.
The world changes too fast. Companies fold. Industries vanish. New roles appear that didn’t exist five years ago.
Here’s what works.
Think Like an Investor, Not a Planner
Your career isn’t a ladder you climb. It’s a portfolio you build.
Every job has two sides:
Return: salary, skills, network, experience, location
Risk: layoffs, relocation, burnout, missed opportunities
Smart investors don’t put all their money in one stock. Smart professionals don’t bet everything on one path.
If you’ve been applying everywhere without a clear strategy, you’re stuck in the same trap I explained in The 10-Application Strategy That Works. Fewer, smarter bets always beat scattershot applications.
Your Risk Tolerance Changes
At 22: High risk, high reward makes sense. You can move cities, work 80-hour weeks, and join startups.
At 32 with kids: Stability matters more. You can’t uproot easily.
At 45 with savings: You can take risks again, but different ones, not climbing ladders, but creating value.
Most people make career choices like they’ll always be 25, or always 40.
They won’t.
Stop Judging Jobs in Isolation
Wrong question: “Is this job risky?”
Right question: “Does this risk fit my portfolio right now?”
If you’ve been playing it safe, the “risky” role might be exactly what balances your portfolio. If you’ve just taken two big bets, the stable corporate role might be the smart move.
This is the same mindset shift I talk about in Stop Networking. Start Building Career Capital Instead. Focus on building leverage, not just chasing “safe” moves.
The Real Risk Is Taking No Risk
Playing it safe feels comfortable. It’s also the biggest trap.
No risk means no breakthrough. You’ll have a fine career, but not a remarkable one.
The people who change industries, build companies, and become leaders? They all took calculated risks, while others stayed comfortable.
If you’re hesitating at the application stage, you may also be falling into the mistakes I broke down in Why Nobody Replies to Your Applications (Even If You’re Qualified).
Playing too safe gets you filtered out before you even have a chance.
Now you get the big idea. But here’s the problem:
Most people stop here. They nod along, think “that makes sense,” then keep making the same career choices they always have.
That’s why they stall out.
What’s the difference between people who build remarkable careers and those who drift?
→ They don’t rely on luck or gut feelings. They use systems.
Below, I’ll show you the exact framework I use with my coaching clients. The same tools that have helped over 100 professionals make career moves that doubled their salary, accelerated promotions, and opened doors they didn’t even know existed.
You’ll get:
The 15-minute portfolio audit that shows your hidden patterns
The decision matrix I use to kill doubt in under 10 minutes
A risk budget framework that tells you exactly when to take your next leap
Real examples from professionals who broke out of career ruts
This isn’t theory. It’s the step-by-step playbook you can use today.
🔐The 15-Minute Portfolio Audit:
(exclusive to my paid subscribers)