Aging Gracefully in a Tech-Driven World

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I know what you’re thinking, “What the hell does this kid know about getting old?”

Alright, hear ye hear ye.

First of all, I don’t get along with anyone my age. A significant majority of my friends are twice my age. I’ve always worked primarily with executives in their late forties to early sixties. Toss a few golden agers in there too. Working with people at least 10x smarter than me has been intentional.

I’ve always found immense value in listening and learning from those with significant life experiences. I’m one of those whipper-snappers that respects my elders. Go figure.

Disclaimer aside – let’s get to it.

The Digital Age Hates The Aged.

If working in the tech industry for 15 years has taught me anything it’s that these damn kids have ruined everything. (I wonder if that’s what our parents thought, too).

Technology and information is outpacing anything that we’ve ever experienced in human history. Humanity is currently doubling its data consumption every 18 months. And maybe this is a stretch, but if you’re not learning at a similar pace, that means you’re getting left behind in this new hell that we made for ourselves.

It’s not your fault.

You’re not necessarily lazy, yet we’re all learning how to evolve in a world of increasing digital noise, media fear, data points, and goldfish attention spans.

Our expectation of immediacy, frictionless customer experiences (on a phone, watch, or even by voice), and the fear of missing out on the cutting-edge has most definitely ruined society.

If I’m being truly candid, this game sorta sucks. I’m ready to flip the table, send the Monopoly board flying, and further estrange everyone with my grumpy demeanor.

If you’re feeling that frustration, you may also be letting the age game ruin your career, too.

Don’t Play Kids’ Games.

Some games are specifically designed for ages 2-12. Adults aren’t the target.

For example, Candyland is absurd. They had to rig a game with so much luck that a 3 year old could actually feel like they had a shot at beating a mentally superior adult. And they do! (I’m not bitter, my nephew is just lucky, okay.)

Most self-respecting adults know what they get into when sitting down to play a game of Candyland with a child. If they were concentrating on (metaphorically) smashing faces and bringing tears to children’s eyes, they’d suggest a game of Chess—or another strategically or logically superior game.

Your career is no different.

Often, I’ll be working with a dominant executive. I’m talking about a stout resume with 20-25+ years of career ass-kicking. Leading teams of 80-120, 9 figure P&Ls, and a tenure of standout companies. Match that with a great degree—bachelor’s, master’s, Ivy League, the whole type-A try-hard track record of trouncing the competition.

Then I hear, “Jacob, I can’t compete with kids these days. I’m not up to snuff with what’s needed to be competitive with these new frameworks, trends, growth trajectories, yada yada…”

Excuse me?

If you aren’t up to snuff—the rest of society must be a hopeless mess.

What I’ve observed is that we (as a society and as business leaders) tend to look toward the hottest trends and innovations with rose colored glasses. And then compare ourselves to them recklessly.

  • Crypto and Web3 is the hotness. That is a sexy place to be.
  • It’s all about big data and natural language processing. That’s the future, baby!
  • Forget enterprise sales—the now now is Product Led Growth. We all need to do it yesterday or we’ll die on the vine!
  • (Insert something about building an engaged community for your never-been-heard-of product here)

Look, there is always going to be something new. There is always going to be someone younger than you doing something new, better. Maybe it’s Candyland luck, or maybe they created a new game and designed the rules in their favor. Then they make sure to beat the drum over and over until you are forced to drink the Kool-Aid too.

Sounds familiar? It’s the game plan for most Silicon Valley PR.

Sell The Rules Of Your Own Game.

I’d like to re-establish that to this point, I’ve sufficiently proven that taking a game of Candyland seriously is a fool’s errand.

But if everyone at the family table wants to concentrate on Candyland, how do you suggest playing something more sophisticated? Something more in your favor, perhaps?

It’s time to lean into your executive presence and unique expertise.

For example, let’s say that you’re a seasoned executive entering a discussion about just how much you know about the latest trends and tactics.

If you’re being honest with yourself, you aren’t really the right person to ask about the specifics, but you’re expected to know the right answers regardless. Feelings of imposter syndrome may begin to creep.

You know that you shouldn’t be deceitful—and with a track record like yours, you sure as hell don’t need to fake or over-exaggerate your skills.

So, what do you do?

It’s time to own the conversation and steer the discussion into an area that highlights your strengths (and eases the internal tension with the voice in your head).

Here’s the game plan for discussing the new trends with teams, fellow execs, or through an interview process.

  1. Acknowledge the topic with confidence. You have nothing to hide.
    “It’s an exciting time to be thinking about (trend) and how it will improve how we do business moving forward. It’s certainly been a big reason for the success of (company), (company), and (company).”
  2. Inquire about why the topic is relevant to the business now, collect more information to better inform your answers, and showcase how you (as the badass executive you are) can turn a trendy idea into action.
    “How specifically are you thinking about how this (trend) will make an impact with your organization? Are you considering a similar approach to how (company) executed the (trend)? I’d love more context about your thought process here.
  3. Strategize about the actions that should be taken, insert relevant previous experience if applicable, and turn the corner to concentrate on your expertise and comfort zone.
    “Thank you for sharing more detail about how you’re thinking about (trend) within the company. It sounds like there may be an opportunity to invest effort here—and it could mean significant financial growth. Have you considered communicating this approach like this (past experience)? Or perhaps we could consider an approach like (company/past experience) did to find success with? I’ve experienced some of the pros and cons of each… Look out for… This was surprisingly effective… etc.

The play here is no nonsense. You’re not pretending that you know each detail about a new game. Or that you’re an expert.

Rather, you’re being authentic and sharing how you work through a trendy idea in a challenging and thought-provoking manner—using your unique experience as a foundation.

You’re leading with soft skills that you’ve sharpened over decades of being in the trenches.

You’re showcasing your executive presence, expertise, and leading confidence to steer the conversation in a direction that more junior professionals cannot compete with.

You’ve succinctly said, “I’m not interested in talking about a high-level overview of Candyland. I’d like to discuss how our knight is going to take our competition by surprise and steal their queen. These are the moves we make to maximize this trend.”

If you’re truly an executive, you need to prove it. And stop complaining about kids that are trying to get you to play a kids game.

Show them why you’re the executive and win a game of chess.

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