Keeping up when everything is getting faster

How to grow and advance against a backdrop of constant change

Last year, when I published my book Say Good Morning, Like a Humana career guide for young professionals—I included a chapter titled "Map out a plan, but shift course often."

The basic premise of the chapter is that we need to have a North Star in our careers—a sense of direction—but we also need to be humble enough to realize that many factors are going to change along the way, necessitating frequent course shifts.

The funny thing is that just a few weeks before finalizing the manuscript, I re-read the chapter, which at the time was called "Map out your 20-year plan" and realized that what I was saying wasn't actually true. I was basically advising young people to very specifically imagine where they wanted to be in 20 years and then to trace the steps backward to get there.

The problem, I realized, was that the career paths of almost everyone I knew looked quite different than that in reality, including my own.

So just a few weeks before finalizing the book, I scrapped the chapter and rewrote it—with the emphasis much more on 'shifting course often.'

The question this left me with was: Why? Or more specifically, why do so many people's careers appear to develop randomly rather than follow orderly, logical steps?

Hindsight is 20/20

What I have since come to appreciate is that careers really only make sense in the rear-view mirror—when we look back.

Perhaps no one expressed this better than Steve Jobs when he said:

“You can't connect the dots when you're moving forward. You only can when you're looking backwards.”

In other words, our careers—and our lives—are murky, disordered messes when we're in the middle of them, but when we look back, every move looks logical, linear, and even considered.

Of course, in reality, they weren’t that at all. All of those moves were accompanied by uncertainty, fear, and a thousand other emotions.

But even if our career-path reality fails to match the theory, it doesn’t mean that we shouldn't have a plan.

Rather, it means that we need to take Mike Tyson's advice to heart when he famously said:

"Everyone's got a plan until they get punched in the mouth."

Life has a way of punching us in the mouth—figuratively (I hope), if not literally.

Our best-laid plans inevitably get thrown off course. And it's not just because of bad things that happen or challenges that emerge.

The reality is that we change over time. And consequently, the paths we choose to go down change, too. I was perfectly suited (literally) for a Wall Street sales role back in the early 2000s. Bright-eyed and enamored with the world of finance, I wanted to be at every happy hour, and every sports event, shaking every hand. (This was pre-COVID, remember. Let's just fist bump the next time we see each other, okay?) But over time, I've changed. I've come to place greater value on having the time to think more deeply. (File under: Most pretentious sentence I’ve ever written). Today, my job is creating content, which requires quiet time and thinking. It's more suited to who I am today. Maybe that will change again. Who knows?

Not only do we change, but the game changes. If you graduated college 20+ years ago, you had no aspirations of becoming a Youtuber, a Twitter star, or a cryptocurrency specialist. Why? Because of course, none of those things existed. Mobile telephony was nascent, as was the internet. Entire industries have been leveled (print newspapers) and others have risen to great prominence (social media) since then. How is it therefore possible to map out a 20-year plan when you quite literally don't know which industries will even exist twenty years from now?

You can't. It's impossible.

And if you've been reading my writing for a while now, you might know that I think things are about to get really crazy in this regard. The wheel of economic and technological change is spinning faster now than it's ever spun before.

I wrote about NFTs two weeks ago. Here's an innovation that seemingly came out of nowhere and within months entire industries are rising up around it. The broader crypto and blockchain spaces are even better examples. The pace of innovation is breathtaking.

All of this is enabled by real-time idea sharing from anyone around the globe who is interested. We knew cheap smartphones and internet access would lead to an explosion of ideas, but seeing it in real-time is incredible. It once took months for Albert Einstein and his peers to read and react to one another's work. Today, it takes minutes. Even seconds.

The wheel spins faster and faster.

Enter artificial intelligence. Enter the newfound ability to work from anywhere. Enter thousands of cheap or free tools available online to build products or distribute them.

What we're about to see in terms of change is going to be nothing short of shock and awe. Old industries and businesses will fall far more quickly than ever before. And new ones will rise in their place just as fast. Even the idea of a company as we know it will be re-thought as innovations like Decentralized Autonomous Organizations (DAOs) form new ways for people to organize and do business together—even without ever meeting.

If it seems impossible to keep up with all of this, it's because it is. No one has their arms completely around it.

But if we want to avoid becoming dinosaurs, it's incumbent upon us to try. Why? For the sake of our careers. For the sake of spotting new opportunities as they emerge. And for the sake of understanding what the heck our kids are actually doing on those iPads. (As long as it's not watching other people play video games on YouTube, because that's where I draw the line).

3 Ideas

Here are three ideas you might consider when it comes to staying current and managing your own career:

  1. Stay curious — World-class educations on literally any subject are available today online, for free. If you can find the time and have the motivation, there is no subject you cannot become an expert in. To make it easier, pursue the areas that naturally feel more like play than work. I'm way down crypto and life extension rabbit holes these days—and it doesn't feel like work.

  2. Control and curate your information diet — The downside of this new world of ubiquitous information is that there's too much of it. I wrote this piece on content diets a while back. I'm becoming more and more convinced that curation is going to become massively more valuable in the years ahead. One of the goals of this newsletter is to curate the best ideas on a wide variety of subjects from habits to health to Bitcoin, and to surface them to you, and tell you what conclusions I'm drawing from them. Find sources you trust to deliver you the information you want and need.

  3. Build resilience into the system — If we take as a given that our world—how we work, how we socialize, how we consume goods and services—may change more in the next 20 years than it did in the last 100, then the only thing we really know is that we don't know anything. So how do you prepare for such a world? You try to build resilience into the system. Last week, I wrote about how the greatest skill we can develop is adaptability. One way to remain adaptable is to keep learning (see above), to keep developing new skills. In the years ahead, as more industries get disrupted (including lots of cushy white-collar jobs), we're going to need to be creative about re-positioning ourselves. The concept of skill-stacking is critical here. What skills do you uniquely have that are transferrable and can be uniquely combined to create something scarce and valuable? I’ll write something on this topic another time but the more malleable our skill-set is, the more resilient we are to all of this change.

At the end of the day, it’s easy to be intimidated by the pace of change we are witnessing. And there might even be a temptation to “tune out” and assume it’s something you don’t need to know. In my opinion, that’s a mistake. It’s much more interesting, fun, and maybe even profitable to stay current. I hope this newsletter is one small part of helping you do so.

Thanks as always for reading. See you next week. — Greg


Photo credit: Marc-Olivier Jodoin

Extra credit: Speaking of content curation, here are a few things that caught my eye (and ear) this week.

Paul Graham is a well-known venture capitalist and co-founder of the start-up accelerator Y Combinator. His blog is always great, but two pieces this week jumped out in particular:
1. How People Get Rich Now — despite the somewhat crass title, this article is a great overview of how the economy has changed over the last century and why fortunes are being minted more by tech entrepreneurs today than by real estate or oil tycoons.
2. Inside PayPal — If a company ever caught lightning in a bottle, it may have been PayPal in the early-2000s. What was it about that culture that catapulted the careers of so many well-known tech/business leaders, including Elon Musk, Peter Thiel, and Reid Hoffman? This short compilation of quotes from those on the inside provides a window into the unique culture of early-days PayPal.


After his appearance on the Tim Ferriss show, Balaji Srinivasan is fully on my radar screen. If you missed that episode and are interested in things like geopolitics, media, cryptocurrencies and… well.. the future of humanity, it is 3 hours very well spent. I think I said "wow" out loud to myself multiple times while listening. Anyhow, Balaji had this tweetstorm on how companies are increasingly controlling their own narratives (vs. relying on traditional media) which is a trend I've been following for a little while with great interest. See Tesla firing their PR team and Coinbase conducting their own IPO-day interviews on YouTube as recent examples.

And two more things:

1. I’ve started to mention that I’m becoming more interested in the topic of life extension. I’ve been reading and listening to more on this topic recently. If you’re interested in this topic, too, a good place to start may be this interview with Dr. David Sinclair and Rich Roll, one of my favorite health & wellness podcasters. Pretty mind-blowing stuff on what is becoming possible in treating the ‘disease’ of aging.

2. a16z’s crypto/blockchain guru, Chris Dixon, is on the latest episode of Invest Like the Best. I’ve only listened to the first 15 minutes so far but it’s already a strong recommend.

Okay, I’ll stop there.

Hope you found a nugget or two here that’s of interest.

Thanks as always for reading and if you find Intentional Wisdom valuable, please continue to share it with whoever you think might get some value from following along - Greg