AI-Proof Your Career? Think Again.

Everywhere you turn these days, there’s another headline about Change.
More specifically: change brought by AI.

And one question seems to be coming up repeatedly: How do I pivot my career, to AI-proof my job?

Some are responding by signing up for every AI course they can squeeze into their calendars.

Learning, upgrading, collecting certifications; yet somehow feeling more overwhelmed.

Which course is actually right for me? How much do I need to learn?

Others are “switching back to the Trade life” as a Director I was speaking to recently described it.

Analogue skills like carpentry, plumbing, repair work — that feel perhaps, reassuringly human.

And yet, somewhere in the back of their minds wondering: Am I missing out?

Some are altogether choosing to ignore AI.
It feels too complex, and they don’t even know where to start.

Life already has so much going on, so perhaps it’s easier to simply carry on doing what I’m doing.

Less overwhelming in the short term, but is this a realistic approach in the long term?

> Read more: The Two Shifts That Make Busy Feel Different


Before you jump into the career pivot…

When we think about career transitions, we often jump straight to: What should I do next?

But there’s a stage that comes before that.
You first need to make sense of where you are, and the direction you want.

It’s the part where you start peeling the onion. Exploring and discovering, rather than simply reacting to what the latest headline is telling you that you should want.

This part doesn’t happen by chance.
It requires intentional work and effort, and is often overlooked because it doesn’t ‘look visible’.

And when the change is as fast-moving as AI, this stage can feel particularly difficult.

> Read more: The Hardest Part of Change Isn't the Change. It's the Waiting.

“What happens next?”

In meeting change, our brain is constantly trying to predict what happens next.
That’s useful, when the world is relatively predictable.

But with AI?
The ground keeps shifting, everything’s being built as we go along. Just when you think you’ve got one part figured out, another evolves. A role that looked secure may be changing, new capabilities expectations emerge.

And you might begin to wonder:
Where is this all going? Am I wasting my efforts, should I just give up?

So when you’re thinking about ‘pivoting my career to AI’, the question behind that really is:
‘what does this mean for my future?’

And underneath that, the real question you’re weighing: ‘is a career switch worth it?’
Is it worth the rebuilding, the learning, the uncertainty, can I afford my time and effort, will it yield the results?

When your brain can’t find a convincing answer, it can become very good at keeping you in place.
You might have:

  • a list of career paths you’ve researched — still sitting on your desk three months later.

  • taken five AI courses in six months, yet still feeling you’re ‘not ready’ to decide.

  • decided what to do, but are somehow not taking the first step.

  • told yourself that next month (the ‘perfect month’) is the right time to start planning.

  • hidden behind “I’m too busy to think about this right now.”

And suddenly, ten months have passed.
You’re back in almost exactly the same place you were when you started thinking about the change.

You’re stuck.

You’ve spent the last ten months responding to what feels most urgent or threatening, rather than creating the space to work through the decision itself.


So, what can be more helpful?

Instead of playing the busy game (more courses, more research, more tabs open), help your brain gather the information it actually needs.

The question you were asking:
How do I pivot my career to AI?

> now becomes:
Is a career switch actually worth it for me?

> and then:
What would my career look like if it aligned more closely with the life I want?


> Read more: Why Capable People Still Get Stuck in the Same Cycles

Here’s how you can start:

1. Make it less costly

Big career decisions can feel paralysing because the perceived cost of getting them wrong is high.

So don't start with the big decision. Begin with small experiments.
Try out experiences that give you new insights about what energises you, and what you really don't want.

Keep these micro-experiments low-cost and reversible.
For instance:

  • Try a small AI-related project on your own, perhaps building an AI assistant for your year-end travels.

  • Volunteer for a small AI initiative at work, rather than deciding you need to become an AI expert.

  • Spend a few hours actually doing the work, rather than only reading about it.

The point isn't to immediately decide, but to lower the stakes so you can gather new data.
And that information helps your brain update its predictions about ‘what happens next?’ so you don’t stay stuck.

You don't have to jump off the deep end.
Chunk it down, so you can move forward.

2. Some Friction is good

“Friction forces us to engage, to pay attention, to confront the messiness of the world.”
‍ ‍- Brad Stulberg, author

And perhaps this is something we could use more of when thinking about career change.

When we move outside what is familiar, we experience Friction.
A certain prickliness, a sense discomfort. Sometimes even the feeling of ‘this isn’t me, I don’t like this’.

But that discomfort isn't necessarily a sign that you've made the wrong choice.
Often times, friction is information.

It can show you where your comfort zone lies, and where you need to pay attention to, as you make your decisions.

Maybe you've been following a certain career path because you've always done things that way.
Maybe something new feels too risky.
Maybe you're more capable of handling the unknown than you thought.
Or perhaps the friction is telling you: Actually, this isn't for me. That's useful too.

Your micro-experiments let you encounter small, manageable amounts of friction — to observe what happens.

  • How much uncertainty can you sit with?

  • What kind of work makes you lean in?

  • How do you feel, working on the micro-experiments?

  • What happens if you don’t make a switch?

Those answers are more useful than asking: What is the hottest (AI) career to move into right now?

Asking the questions that matter

This isn't just about AI. AI merely makes the challenge more visible.
The same questions apply whenever you're standing at a career crossroads.

Instead of needing more information, you might need better information about yourself.
And that comes from creating the space to think, experiment, notice and reflect

Give these a try.
Build in a bit of friction, get a little uncomfortable and put yourself in situations to run micro-experiments.

I experimented in a similar way, exploring my own career pivot. It was a significant jump going from corporate life, to running my own coaching practice.

Some questions I wrestled with:

  • Can I actually do this?

  • How difficult will the switch be?

  • Will I regret it?

  • Is this pivot (new industry) for me?

  • Will I enjoy it?

I couldn’t answer all of those questions from my desk. So I built in some friction, explored and gathered data.

The process was eye-opening—even after spending a good 2 decades in large companies. Some things that I learnt about myself made me go ‘you’ve gotta be kidding me ...’.

I leaned on my own coaches to help me make sense of what I was discovering, and eventually made the switch that worked for me.

Thinking about a career pivot?

That’s the kind of transition work I love doing with clients.

If you're somewhere between ‘I know I need to change’ and ‘I have no idea what that change should look like’, let's work this through.

Reach out for a complimentary discovery call.
Let’s explore what this next evolution of you might look like.


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A new title on the door doesn’t make you  Automatically ready