A few weeks ago I was sitting at my regular cafe drinking my regular coffee when I got swept up in the conversation at the table next to me. A bunch of work friends were thick with worry because word on the street was that their workplace – a tech company – was about to do a round of redundancies. Thanks to my boots on the ground journalism (read: eavesdropping) I deduced that:

• Whispers of layoffs had been doing the rounds in their office and on Slack

• The reason for said layoffs was that “AI is taking over the world” (their words, not mine)

• Claude can now do parts of their job infinitely better than they can and they’re stressed about their once-lucrative skills becoming redundant

• Gary from Finance has a thing for Linda in Sales

The conversation was a touch dramatic (especially when discussing Gary’s unrequited office romance) but their feelings aren’t far from some of the recent chats I’ve had with mentoring clients on Zoom and my friends over drinks at the pub. There seems to be one question on everyone’s lips:

“How do we future-proof our careers when we don’t know what the future will look like?”

I, for one, am thinking about this question approximately 76.6% of my waking hours. I’m wondering which parts of my generalist skillset have longevity and whether the things I’m paid for today (advising startups, educating people around portfolio careers, talking about the future of work, writing) will still be worth paying for in 5 years. At this point it’s anyone’s guess, but I’m keeping my nose to the ground to try and understand how the value of certain skills is trending:

• The value of some skills is shrinking. It’s now faster and cheaper for Claude to spin up a first draft of a brief, strategy doc or an email than it is to engage a real life human. It’s more effective for AI to synthesise huge amounts of information than it is for any of us to trawl through it for days. Routine knowledge work seems to be trending downwards

• Some pundits speculate that the value of some skills is expanding. Stakeholder management, leadership, persuasion, community building and certain elements of sales fall into this bucket. Anything centred around human connection and communication seems relatively protected (at least for now). AI simply could never!

• Then there are emerging skills whose value is not yet quantified, but appear to be trending upwards. Vibe-coding, building swarms of AI agents, pretty much anything AI-adjacent lives here

Figuring out how skills will be valued in 5-10 years is tricky. Even AI can’t predict how AI will play out (I asked Claude and she said “honest answer: nobody knows”). Despite this vast uncertainty, I’ve made some tiny decisions about where to focus my energy from here on out:

• I’m diversifying, baby. I’ve said it before and I’ll say it a million times over: income and option diversification is the only sane way forward. With eggs in many baskets, you’ll always have something to eat.

• I’ve become obsessed with craft. Specifically the craft of writing. It’s tempting to use AI to write my Substack (because convenience!) but more often than not it makes me sound like everyone else. Instead, I’m studying great writers, reading fiction and comedy, spending hours walking around the park to come up with a zingy metaphor, noting down interesting sentence constructions, tinkering, finessing and agonising over each word. It’s not the most efficient process but that’s ok. I’m optimising for humanness, not speed.

• I’m bringing the personal back into personal brand. Related to the above. I’m differentiating myself by telling more personal stories and being more transparent about how I’m building my business in real time. AI can’t replicate real world experience so I’m putting more of that onto the page.

• I’m developing my soft skills. The ones made of flesh and bone. Specifically facilitation, community building and public speaking.

• I’m trying harder to fail. This is specifically about doing the most to improve my judgement by experimenting in a way that AI can’t. Being in the arena, doing and reflecting, shipping and iterating, taking action and figuring it out. The more reps I do, the better my judgement gets

This is where my brain’s currently at and you might be hovering around a similar set of assumptions. You might be looking around, looking forward and looking inward to figure out what’s next. You might be starting to diversify your income (smart), build your personal brand (smarter) and invest in skills that are moving up and to the right (smartest).

If that sounds like you, I’ve created a free 14 day email series that walks you through how to future-proof your career. You’ll learn how to diversify your income and risk, and build a portfolio of skills, opportunities and income streams so that no matter what happens, you have options. Sign up for free here.

I’ve been thinking a lot about the work friends I overheard at my favourite cafe. I don’t know what became of them, or whether Gary finally approached Linda and asked her out on a date. I hope they kept their jobs. I hope they are alright. I hope they know they have options. I hope they’re thick with determination to move through whatever comes their way.

A few additional thoughts on the importance of craft, how I’m bringing the personal back into personal brand and why I’m investing in my soft skills:

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