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Thinking Of Mailing It In Because You Fear AI? Keep Dancing

Daily Legal Briefing by Daily Legal Briefing
September 29, 2026
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Thinking Of Mailing It In Because You Fear AI? Keep Dancing
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I attended the 8am Kaleidoscope conference this past week. And like most legal tech conferences, much of the talk was about AI. AI and lawyers. AI and law firms. AI and your future.

But perhaps recognizing there is only so much AI we humans can absorb before it leaks out our ears, the 8am folks gave us a free night to frolic on our own. My little frolic was to go see Carlos Santana in concert at the House of Blues. I’ve always been a fan of Santana, but frankly I didn’t know what to expect. I’ve seen too many music acts who were at the top of the charts back in the day return to concert tours years later and mail it in. After all, Santana is pushing 80, so he could be forgiven for coasting a bit after a long career.

Well, Carlos don’t coast. And he sure as hell doesn’t mail it in. He gave an almost two-hour show. No breaks. And those famous guitar riffs that he’s known for? He himself played them all. No reliance on some guitarist back in the shadows who played the solos while the headline performer stood in the spotlight clumsily and pitifully trying to act like he was playing. 

One thing’s for sure. By the time the show ended, the whole place was dancing.

There’s a Connection to Legal Here Somewhere?

So, I know what you’re wondering. Great, Embry went to Vegas, saw one of his childhood idols, and now we’re getting a concert review. (BTW, I’m not as old as Santana.) What does Carlos Santana have to do with AI and legal technology? More than you might think.

The well-known podcaster and lawyer, Ruby Powers, graciously asked Carolyn Elefant and me to be on her Power Up Your Practice podcast that was recorded at the conference. During our discussion, Elefant, a practicing lawyer who also advises law firms about technology among other things, said she is seeing more and more older lawyers throwing up their hands when AI comes up. They’re saying, “I’ll just retire.” Go out to pasture or the golf course. As in “That’ll show ‘em.” As though ChatGPT is sitting around thinking: Dear God. Bill retired. I really screwed that up.

Then there is the other group. You know the ones. They aren’t retiring. (Unless retiring in place counts.) They’re simply pretending none of this AI stuff is happening. They stubbornly keep trying to practice exactly as they always have.

I talked to Elefant after the podcast, and she told me she is seeing the retirement option mainly from lawyers around 60 and older. They are fearful of AI and the changes it may bring. For some of them, Elefant says it’s just too much. Sort of the straw that is breaking the camel’s back. And from what I see, it’s not helped by all the pundits harping on how AI is going to change everything and the perception that older lawyers just can’t keep up.

But retiring, mailing it in because you’re frightened of learning something new. Come on.

Yes, It’s Human Nature

I do get it, sort of. I even felt some of this myself at Kaleidoscope. I sat through some sessions at the conference where a presenter talked about AI and what they were doing with it. What they outlined was over my head and probably a lot of others in the audience. It was tempting to say, “I don’t get it. I don’t understand what they’re talking about. So, I’m just not going to listen.” But that’s a cop out as well. And just because someone can’t explain in ways I can understand doesn’t mean there isn’t something there I might need to know.

But there’s a big difference between thinking occasionally “I’m too old and tired for this shit,” and then actually deciding I’m too old and tired.

I Don’t Like Your Attitude

It’s a piss-poor attitude, frankly. You spend years mastering your craft. Years cultivating your clients. Decades protecting them. And now, when you have something that really challenges you again, a challenge the likes of which you may not have seen in a long time, you just throw up your hands and quit?

Or maybe worse, you mail it in, determined to keep working while ignoring AI. That’s insanity, not to mention a malpractice bomb set to explode.

But I’m Entitled

But after all, you deserve it, you say. Elefant says many, in fact, do have a sense of entitlement that contributes to their desire to leave. Maybe so. But do your clients deserve it? Do the younger lawyers in your firm who need your help and guidance now more than ever deserve it? Do your partners deserve it? What about the profession that gave you a pretty damn good living for all those years?

Think back to your first trial. Do you remember how stressed you were? How the challenges of it seemed insurmountable? I’m sure the thought crossed your mind then to just give up. I know it did mine. But we didn’t, did we? We didn’t walk away right before the opening statement. We didn’t say, “Your Honor, this is all a little overwhelming. I’ve decided to retire.”

Nor did we mail it in. And when the next trial came along, it wasn’t quite so terrifying. Nor was the next one, and the one after that. We survived. We persevered.

Your Firm and Your Future

Elefant brought up another good point: the “I’m just hanging it up” approach deprives your firm and colleagues of any kind of succession plan. A plan the implementation of which, she says, could ironically be made much easier by engaging with AI. Succession planning is often put off because frankly it’s hard to figure out how to get at and transfer all the knowledge and experience of the departing lawyer. But Elefant is right. Using AI and automation to do that can make the process a whole lot easier.

Retire to What?

Think of this. Yes, there are lots of reasons to retire. Lifestyle. Family. Sitting on a beach drinking something with an umbrella sticking out of it. Like me, the desire to pursue another career. But chickening out? Do you seriously think you will be happy when you quit out of fear? That’s not a plan. 

And this: approaching so-called retirement ought to be like approaching your next career. Ask yourself the question: I am leaving my current career to do what? Good lawyers who practiced for 35 years fighting fires day in and day out aren’t going to be to happy sitting around watching TV all day.

Fear is a lousy career counselor.

It’s Just One More Challenge 

AI and technology are just another challenge we as a profession must step up to. It’s a challenge that threatens to upend what we do and how we do it. So, the profession needs you, your experience, and your steady hands. It’s a challenge we can’t walk away from.

We All Have Doubts — Even Carlos

Maybe you’re a bit long in the tooth. But that doesn’t mean you shouldn’t give back in some way to clients, younger lawyers, partners, and to the profession for what it’s given you. Sure, you have doubts whether you can sufficiently master AI to be relevant and credible. I wonder that about myself.

Then I think of Carlos Santana. He may have sat down for much of the show and played some of those glorious riffs from a chair. And God knows he probably didn’t need to be giving two-hour flawless concerts. But I like to think he did it for his fans. For his band. For himself. 

When he decided to do this tour, I’m sure the thought occurred to him: Can I still do this? Can I still perform at a high level? Can I still be relevant and credible? Can I still make the audience dance to Smooth? To Oye Como Va?

Wednesday night in Las Vegas, I got my answer. It’s hell yes. So, if you’re thinking about mailing it in because of AI, or because you’re too old, sit down if you need to. But keep playing. And keep dancing.


Stephen Embry is a lawyer, speaker, blogger, and writer. He publishes TechLaw Crossroads, a blog devoted to the examination of the tension between technology, the law, and the practice of law.



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