Career Advancement Strategy: Why Smart Executives Never Put All Their Leadership Eggs in One Basket

Personal GrowthLeadership LessonsCareer Transitions
Written By Lilah Jones

The painful rejection that taught me the most valuable lesson about professional growth and the career mistake 90% of high-performers make

"We're going to hire someone else."

Five words that knocked the wind out of me on a Friday afternoon I'll never forget.

I'd been working with this team for 2 years. Had glowing performance reviews. Support from skip-level leadership. The current role holder had mentored me for months. I knew every client by name.

I was a shoo-in for this executive promotion. Or so I thought.

The Career Advancement Trap Most Executives Fall Into

Here's what that rejection taught me about professional development: Never be the thirsty girl or guy at the bar.

In career terms, this means:

  • Pinning all your hopes on one leadership opportunity

  • Waiting for validation from a single decision-maker

  • Assuming your track record guarantees your next promotion

  • Putting your career trajectory in someone else's hands

Sound familiar? Most high-performers fall into this trap because they've been taught that excellence equals certainty. But in today's rapidly changing business environment, that assumption can be career suicide.

The Hidden Vulnerability of Being "The Obvious Choice"

When you only have one option, you're not negotiating—you're begging. You become vulnerable to:

  • Leadership politics (new bosses, budget cuts, strategic pivots)

  • Missed opportunities (while you wait, three better roles pass you by)

  • Weakened negotiating power (they control timeline, salary, terms)

  • Network stagnation (you stop building diverse professional relationships)

What Smart Executives Do Differently

The most successful leaders I coach approach their careers like investors approach portfolios—with strategic diversification:

✅ Multiple pipeline strategy (always nurturing 3-5 opportunities)
✅ Portfolio thinking (short-term wins + long-term relationships)
✅ Strategic networking (relationship-first, not transactional)
✅ Opportunity creation (don't wait to be chosen, create choices)

The Plot Twist That Changed Everything

That role I didn't get? The person they hired lasted six months.

By then, I'd already moved on to something 10x better. The rejection forced me to diversify my approach, which led to opportunities I never would have discovered if I'd gotten my "dream job."

Sometimes rejection is just protection you don't understand yet.

The Framework That Makes You Rejection-Proof

The most powerful position isn't getting the role you want—it's having three offers to choose from.

In Issue #13 of The Activated Leader newsletter, I share the complete story of this career rejection and break down the exact 4-stage framework I now use to help executives build "rejection-proof" career portfolios.

Read the full story and get the complete framework in Issue #13 →

Ready to Stop Putting All Your Career Eggs in One Basket?

If you're tired of waiting for someone else to recognize your potential, you're not alone.

Join 1000+ executives who get weekly strategies for creating career opportunities instead of waiting for them.

Because your worth isn't determined by who chooses you—it's determined by how many strategic choices you create for yourself.

Need help diversifying your leadership pipeline?

Lilah Jones https://lilahjones.com
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