What Happens When You Did Everything Right… And The Future Changes Everything?

I was speaking at a private corporate event last week and during the Q&A session a senior executive pointed out to me that they had done “almost” everything right during the last digital transformation (Web… social… mobile…)… but they are currently in a place where they feel like they could “lose” because of AI.

…Ouch…

It wasn’t just the executive’s perspective on their company/industry… it was about them as an individual and professional. That’s a particular (and frustrating) kind of work anxiety when you believe you’ve done everything right… and still feel like you might “lose.” In fairness, I’m hearing this a lot (and, it’s from very senior, experienced and smart folks). They went to school… got the degree… built the career… developed expertise… learned how their industry works… became valuable… took risks along the way… made decisions based on their assumptions about the future. And they did this with a social contract that was something like this: invest in yourself today and those skills will become more valuable tomorrow.

What do you think… is that agreement broken or is it absurd to believe that it ever existed?

I’ve been thinking about this even more since my conversation with Fredric Marshall on this week’s episode of Thinking With Mitch Joel. Fred is an entrepreneur, investor and author of Thrive – The Antidote To Future Shock. This surfaced when Fred made the observation that people can have agency (the word everyone hears when it comes to being valuable in this AI age)… and still not feel like they have any. We talk about artificial intelligence as though the primary challenge is technological adaptation. Learn the tools… develop new skills… become AI fluent… tinker and experiment… stay curious… and *poof* you are re-skilled. I tell audiences many of these things. But imagine hearing that advice when you’ve already spent twenty years becoming great at something that AI can suddenly do in seconds… or you’re already using it and realizing how many things you can now get done without calling on others from your team.

“Adapt” probably lands differently.

Fred and I talked about younger people being terrified of never even getting onto the bottom rung of the corporate ladder… not even getting a shot… and struggling to plan because they simply don’t know how to get started. There’s a strange symmetry here. Senior people are wondering whether the expertise they spent decades building will retain its value… while younger people are wondering whether they’ll even get the opportunity to build that expertise in the first place. How do you invest in a future when you’re no longer sure which investments will matter?

That question goes well beyond AI.

For most of modern working life, we’ve encouraged people to build expertise. Become exceptional at something. Accumulate experience. Create economic value around capabilities that are difficult for other people to replicate. That was the deal. Now we’re introducing technologies whose entire economic promise is based, in part, on making difficult capabilities easier to access. That doesn’t make expertise worthless… but it does make the future harder to price. And I wonder if leadership is underestimating the psychological impact of this uncertainty? It’s easy to tell people that every technological revolution creates new opportunities. Historically, that’s true. It’s much harder to tell someone what opportunity they should prepare for right now. Fred and I are both optimistic about where AI ultimately takes us while still being realistic that the benefits will not be evenly distributed.

Agency requires more than having choices… it requires some belief that your choices can influence what happens next.

Maybe that’s what feels “off” right now. In my travels, people aren’t necessarily afraid of change. Many have spent their entire careers changing. They’ve learned new technologies… survived economic cycles… switched companies… reinvented themselves. Maybe the map itself suddenly feels unreliable. And it’s hard to exercise agency when you’re no longer sure that the map and the territory have anything to do with one another. Telling people to embrace change is easy when you’re not acknowledging what they believe they might lose. People did what we told them to do. Now the future is knocking and telling them to do something different. The leadership challenge isn’t convincing people to change again…

It’s giving them a reason to believe that investing in their future will still be worth it.

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