The Career Question 90% of Leaders Never Ask Themselves


Hi Reader!

A few months back, I sat across from a talented CTO who looked exhausted.

For anyone around her, she had a stunning career — a senior leadership role, a great salary, and respect from her team. But when I asked what she wanted next, she went quiet.

"I don't know," she finally said. "A bigger role at a more established company? A risky startup? Maybe something completely different, like an NGO?"

She had options. That wasn't the problem.

The problem was that she didn't know which path actually fit who she was.

When Success Feels Like the Wrong Game

This happens more often than you'd think. Leaders build impressive careers, check all the boxes, then wake up one day realizing they're not sure what they're building toward anymore.

It's not about lacking ambition. It's about making decisions based on what is expected from you rather than what actually aligns with who you are.

That's when I introduced her to Ikigai—a simple Japanese framework that asks four questions:

  • What do you love?
  • What are you good at?
  • What does the world need?
  • What will the world pay for?

When those four things overlap, you've found your sweet spot. Not in a mystical way. In a practical, "I finally know what I'm doing and why" kind of way.

Two Very Different Outcomes

The CTO went through the framework. She realized her energy didn't come from climbing the corporate ladder or joining a mission-driven nonprofit. It came from building things from scratch, working with ambiguity, and helping other leaders navigate complexity.

Six months later, she launched her own consulting business. She always had it at the back of her mind, but never let herself take that leap until she realized it was the clearest match between who she was and what the world needed.

Another client—a department manager—had a completely different experience.

After mapping his Ikigai, he realized something surprising: he was already in the right place. His current role aligned almost perfectly with what energized him and where his strengths lived.

But he'd been so busy reacting to every request that he'd lost sight of what actually mattered.

He didn't need a new job. He needed to restructure how he spent his time within the job he already had. So he did. He declined projects that drained him, protected time for strategic work that only he could do, and took on an initiative that both benefited the company and played to his strengths.

Same role. Different experience. Completely different outcome.

Clarity Changes Everything

Both of these leaders were stuck—not because they lacked options, but because they lacked clarity.

Ikigai gave them a framework to cut through the noise and figure out what actually mattered.

If you're feeling that same misalignment—like you're succeeding at the wrong game—it might be time to pause and ask those four questions.

I wrote a full guide on how to use the Ikigai framework, complete with reflection questions and real examples from leaders who've worked through it.

And if you want support working through your own Ikigai, let's talk. Book a discovery call with me, and we'll figure out where your energy, strengths, and contribution actually align.

Because the truth is: you don't need more options.

You need clarity about which options are actually yours.

Talk soon,

Daria


P.S. The most common response I get after leaders work through their Ikigai? "I can't believe I didn't do this sooner." Don't wait until you're completely burned out to figure out what you're building toward.

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