“All progress starts with telling the truth.” (D. Sullivan)
I keep coming back to this quote. Because in my work coaching cybersecurity professionals, I’ve noticed something.
The question that tends to paralyse people the most isn’t “Am I ready?”
It’s this one: “What do I actually want?”
And it’s terrifying. Not because the answer doesn’t exist, but because, deep down, most people already know it. And knowing it means having to do something about it.
Why We Avoid the Question
We’re very good, in cybersecurity, at optimising. At planning. At mapping a route from A to B.
We’re less practiced at stopping to ask whether B is actually where we want to go.
It’s easier to keep moving. To aim for the next certification, the next promotion, the next logical step on the ladder… without ever pausing to check whether the ladder is leaning against the right wall. (Thanks, Stephen Covey.)
And it makes sense. The industry moves fast. There’s always something urgent. The work is absorbing and meaningful. Why stop and question something that seems to be going well?
Because going well and going in the right direction are not the same thing.
The Questions Worth Sitting With
When I invite clients to slow down and get honest with themselves about what they want, these are the kinds of questions that tend to surface:
What is it that I keep putting off thinking about?
What would I choose if the title and the salary didn’t matter?
Am I moving towards something — or just away from discomfort?
Is this really what I want, or what I thought I wanted five years ago?
What would I do differently if I already believed I was ready?
These are not comfortable questions. I get that.
But what I’ve observed, again and again, is that when clients finally start telling me the truth and as their coach, I’m essentially a mirror, so they’re really telling it to themselves that’s where things start to shift.
A weight lifts. Clarity arrives. And from clarity, we can actually move.
The Difference Between Optimising and Choosing
There’s a version of a cybersecurity career that looks impressive from the outside: growing responsibility, strong technical reputation, clear progression; and feels slightly hollow on the inside.
Not because anything has gone wrong. But because somewhere along the way, the career became something that happened to you rather than something you were consciously choosing.
This isn’t unusual. It’s actually very common among high performers.
The drive that got you here (the curiosity, the work ethic, the ability to absorb and execute) can also mean you respond so well to external demands that you never fully stop to ask what you are demanding of yourself.
What kind of work energises you versus drains you?
What does leadership mean to you — and do you actually want it?
Is the goal more seniority, or more impact? Are those the same thing for you?
What does a career you’re proud of look like in ten years?
These are not questions to answer quickly. They’re questions to sit with, honestly, over time and ideally with someone who will hold the space and hold you accountable to the truth.
A Note on Truth-Telling
One thing I’ve learned: truths are best declared in simple language.
No skirting around. No euphemisms. No longwinded explanations that soften the thing you’re actually trying to say.
“I’m bored.”
“I want to leave.”
“I don’t actually want the CISO role — I want to go independent.”
“I’ve outgrown this company.”
Simple. Direct. And often accompanied by a mix of relief and mild terror. 😊
That’s how you know you’ve hit something real.
What Happens When You Get Clear
Here’s what I’ve seen happen when cybersecurity professionals allow themselves to answer the question honestly:
They stop wasting energy. When you know what you want, you also know what isn’t it and you can stop pursuing it, waiting for it, or pretending it matters to you.
They make better decisions. Clarity about values and direction makes every subsequent decision easier. The job offer, the stretch assignment, the conference to attend — all of it becomes easier to filter.
They show up differently. There’s a kind of quiet confidence that comes from people who know what they’re doing and why. It’s not loud. But it’s unmistakable.
So — What Do You Actually Want?
If you feel like you’re moving in circles, or simply moving fast without a clear sense of where you’re headed, it might be time to ask yourself that scarier question.
Not “Am I ready?” but “What do I actually want?”
And if you’d like some support finding an honest answer to it, I’d love to talk.
Book a free 30-minute consultation at cristinamagro.com and let’s find out together.