Stuck on a Career Decision? Start With Why and Stop Asking How

When senior leaders get stuck on a big decision, whether it's a move to a new sector, a step up to the C-suite or going independent, it's rarely because they lack options. It's usually because they've started in the wrong place.

They start with how.

The trap of asking how first

How would I make the move? How would it work financially? How would I compete with people who already have the experience? How would I explain it to my current employer?

These questions feel responsible. They're the questions a sensible, experienced person should ask. But asked first, they bury you in detail before you've decided whether the thing is worth doing at all. The result is overthinking, hesitation and months of going round in circles.

Simon Sinek made "Start With Why" famous. The less discussed half of the idea is just as important: escape the how until you've earned it.

A better sequence

Work through three stages, in this order.

1. Why

• Why does this matter to you?
• Why must you do it, rather than simply would like to?
• Why now, and not in two years?

A strong why gives you energy and clarity. A weak one is useful information too: it might tell you this isn't the move after all.

2. What

• What are the possibilities, including ones you've dismissed too quickly?
• What resources do you already have: experience, network, reputation, savings?
• What are your priorities and non-negotiables?
• What's the best next step you could take this week?

This is where momentum builds. Options appear that weren't visible when you were stuck on the mechanics, and confidence starts to grow.

3. How

Only now do the strategies and tactics come in, and by this point they tend to reveal themselves. Once you know why you're moving and what you're aiming for, the how is mostly a matter of execution, which is something senior leaders are already very good at.

An example

Picture a finance director who has spent a year "thinking about" a portfolio career of non-executive roles. Every conversation starts with how: how to get the first board seat, how to replace the salary, how to explain it.

Go back to why, and it might turn out the real driver is broader strategic influence and more control over her time. That changes the what: perhaps one non-executive role alongside a part-time interim CFO assignment, rather than a leap straight into a full portfolio. With that settled, the how tends to follow quickly.

The short version

Start with why. Clarify what. Let the how emerge. Reverse the order and you'll keep postponing the decision you already know you need to make.

If you're weighing up your next move, book a free 20-minute clarity call. No pitch, just a clearer view of where you are and what to do next.