The Career Strategy Most Leaders Don’t Have (2026 Edition)

Episode #382 The Career Strategy Most Leaders Don’t Have (2026 Edition)

If you aren’t actively driving your career right now, someone else is doing it for you.

And their plan for you has nothing to do with your long-term career success.

If you’ve been listening to this podcast for a while, you’ll know this is an episode we do every year.

The Crush Your Career Challenge has become a bit of a No Bullsh!t Leader ritual.

And there’s a reason for that.

Every year, the world shifts.

Every year, the mood, the environment, and the situation changes.

And every year, the leaders who manage to make progress are the ones who pay attention, and take deliberate action.

2025 has been a big year for that.

AI has moved from mildly “interesting”, to the unavoidably pressing.

Roles are changing faster than most organisations can keep up with.

Career paths are less linear, less predictable, and far less protected than they used to be.

In my father’s generation, after WWII, you could join a company and have a reasonable expectation of spending your whole career with the one firm.

My career, on the other hand, which started 40 years ago, spanned a dozen companies, beofre Em and I started to build this global business.

They say that the average teenager today is going to have 15-20 different jobs, with half a dozen distinct careers.  

And as for my granddaughter, Florence, who’s only 3? Who knows what she will face when she hits the workforce in 15 or 20 years’ time.

This makes it even more important to take control of your career. If you’re not actively driving your own career agenda right now, you’ll just end up bouncing from role to role, fulfilling someone else’s agenda.

Your current organisation has plans for you – or maybe they don’t.

Your boss has assumptions about you – maybe they’re right, maybe they’re wrong.

The system you’re operating in has a default path it will happily put you on.

None of those are inherently bad, but none of them are designed around your long-term interests.

Which is exactly why the Crush Your Career work matters more now than it ever has.

Before I go any further, I want to clarify something:

Last week, we ran our 2025 Review / 2026 Focus episode.

That was about reflection, learning, and closing out the year properly.

This is completely different.

The Crush Your Career Challenge isn’t a review. 

It’s about setting up a personal strategy for how you’re going to navigate the next phase of your career, in a world that is changing faster than most of us can keep up with.

Even if you’ve done this challenge before, it’s absolutely worth you doing it again.

Because your context has changed… as have the risks and opportunities that are on your path ahead..

For the last five years, we’ve run this challenge with thousands of ambitious leaders, and many of them have gone on to achieve some huge career outcomes.

Not because they “wanted it more”, but because they stopped being reactive, and started being deliberate about planning their careers..

And that’s what we’re doing again this year… except at a whole new level.

You’ll be joining close to 1,000 other No Bullsh!t Leaders inside our free No Bullsh!t Leadership Hub, all working through this together with me and Em.

That level of collective momentum and accountability changes everything.

It’s the day before Christmas, so we need to be realistic! 

You’re probably not going to sit down today and do a deep career strategy exercise… and that’s not the expectation!

But there is one thing I want you to do today.

I want you to go and register for the Crush Your Career Challenge at yourceomentor.com/cyc. 

That’s it. One action.

Because once you’ve registered you’ll get everything you need to access the challenge from this coming Friday.

And here’s why that matters.

Every year, there’s this strange little window between Boxing Day (which, for you non-Aussies, is 26th December) and New Year’s Day (which is 1st January).

Work doesn’t exist, the Christmas crazies are over, and you finally get a bit of mental space, while you’re still digesting your last slice of Christmas Pudding

That awkward in-between period is actually the perfect time to crack into this work with a clear head, away from the pressure of inboxes, meetings, and other people’s agendas. It’s a good excuse to sneak away from spending every moment with the in-laws too!

I had to move countries for that, but most of you won’t have to go to those lengths

Putting that aside, this only works if you put yourself in the right place.

If you don’t register now, life will roll on, January will hit, and this will quietly slide down the priority list.

So today, all I want you to do is register for the challenge – future you will be very glad you did.

Let me quickly walk you through how it works:

Once you register via the link in the show notes, you’ll get sent an email to access our free No Bullsh!t Leadership Hub on Skool – this is where we run the challenge.

Starting December 27th, you’ll be able to access the 5 day content series through a private podcast feed. Short. Sharp. Practical.

Designed to fit into your busy life.

Alongside each episode, you’ll get a worksheet that helps you apply the thinking immediately. No theory for its own sake.

Over the five days, I guide you through a very deliberate framework.

It’s part strategic thinking, part imagination, and part brutal honesty.

I’ve adapted the principles I used for years in corporate strategy, and distilled them for individual leaders navigating complex careers.

Here’s how the five days work.

Day 1 is about mapping your strengths.
Not just what you’re good at, but what actually gives you energy. Because long-term success comes when you can liberate your strengths by tapping into your capability and motivation.

Day 2 is about establishing your long-term vision.
This is where most leaders get uncomfortable, because it forces you to think beyond your current role, your current organisation, and the professional identity you may have built so far.

Day 3 is about building professional habits that stick.
Not hacks. Not motivation. Systems. Including a tool I’ve personally used every day for over 25 years.

Day 4 is about setting clear, high-value goals.
Not piling more busy work onto your plate. Not setting up vanity goals that feed your ego. Just the few outcomes that will actually move your career needle.

And Day 5 is about accountability and execution.
How to stay disciplined when things get messy, when motivation dips, and when competing priorities swamp you.

This methodology has been pressure-tested by thousands of leaders globally.

And in a world where AI is accelerating change, roles are being redefined, and it’s becoming even riskier to leave your career to chance, this work isn’t optional.

If you want to create a deliberate plan for where you’re heading.
If you want to stay relevant, valuable, and in control of your career trajectory.
This is the moment to do it.

Register for the free Crush Your Career Challenge, at yourceomentor.com/cyc and join us from 27th December!