Winning In Your Career As A Jack Of All Trades

What's up, everyone. This is Alex Lieberman, co-founder and Executive Chairman of Morning Brew. Welcome back to Founder’s Journal, my personal audio diary, where I give you, the business builder, the tools you need to think better in order to build better, whether that's building a business, a team, or a new product. Today, I am talking about being a generalist versus being a specialist and how you can succeed as a generalist. Let's hop into it. 

Generalist vs. specialist

So from a young age, we are taught to specialize. We're told the only way to play a sport in college is to dedicate ourselves to one single sport at a young age. And I remember growing up feeling like shit as a kid, because I told myself that I wasn't the best on the high school soccer team because I dedicated myself to three other sports. So I dedicated myself to golf, to skiing as well as to soccer, whereas everyone else was focused on just one sport. We're also told the only way to find a good job out of college is to pick a specific major like Comm Psy or Economics, or that offers a specific knowledge base that employers want. And that's why I majored in business with a focus on finance and real estate. And we’re convinced that the only way to succeed in our careers is to continue to specialize and pigeonhole ourselves and become a domain expert in whatever our area of work is.

The Tiger Woods school of thought

Basically, we've been taught our whole lives to subscribe to the Tiger Woods school of thought, which basically is: start early, go as deep as possible, and put in your 10,000 hours. Just for those of you that don't know the Tiger Woods story, I’m actually reading it from the book Range by David Epstein, which is an awesome read about the generalist and building out range. But for those of you that don't know the story, Tiger Woods had a golf club put in his hand at seven months old, and then he would drag it everywhere with him in addition to his baby walker. And by two years old, he was on national television, hitting golf balls in front of Bob Hope.

Just for context. At two years old developmentally, a child is supposed to be able to stand on their tippy toes or kick a ball. And so from the age of six months to literally today, the only sport that Tiger Woods had focus on was golf. He truly achieved mastery through putting in his 10,000 hours. Now I want to propose another option, not because the Tiger Woods method is the wrong method, but because I think there's another method that could be just as effective: an option that posits that, being a generalist and having a range of skills and knowledge can serve you just as well in life and career, because there is increasing evidence that some of the best performers of our time from musicians to executives, to athletes, subscribe more to the Roger Federer school of thought and less to the Tiger Woods school thought.

The Roger Federer method

So if Tiger Woods was about starting early, going deep, and putting in your 10,000 hours, Roger Federer’s story was completely different. Roger's mom was actually his coach, but she never actually coached him. Roger played every sport you could think of, but he didn't actually concentrate on tennis until he was in his teens. He played squash. He skateboarded. He played basketball. He played handball. He played tennis. He skiied, he wrestled, he swimmed. And to this day he believes what allowed him to develop great athleticism and great hand-eye coordination is because he didn't dive into any one sport too early, but instead became a well-rounded athlete in many different things.

And now as we reflect on it, Roger Federer is arguably the best tennis player ever, yet he was a generalist for basically the first half of his life. But Roger Federer is just one example. I think there's a formula from his experience that can be found in other top professionals and that you can apply to your own experience. So take Yo-Yo Ma, the world-renowned cellist. He focused on music in the same way that Federer focused on sports, but before even getting to the cello, he tried many instruments. He tried the piano, he tried the violin and only through exploration and seeing what worked best for him and what his skills worked best with, that's what got him to focus on the cello.

The sampling period

And there's actually a name for this. Top performers go through something that's known as a sampling period, where in the beginning, they spread their time across several things to see what they like most or that they're best at based on their skillset. And then they dive deep. Another example of this is the German national team. In the last few years, the German national team won the World Cup in soccer. And if you actually look at many of their top players, there's this pattern you can notice across them, which is many of them were late bloomers in soccer. They didn't actually go deep in soccer until their teens, rather than starting at a young age like Tiger Woods did for golf. And it makes a ton of sense when you think about it. We have seen so many stories of people who started specializing early and it led to them plateauing or burning out at a young age. Taking time to find your person-profession fit, basically the human version of product-market fit, makes so much sense, yet so few of us focus on finding it, and we're told to focus on one thing so early. But there's another piece to the benefits of generalism beyond taking the time to find this idea of your ability and your interest fitting to the right profession. And this other concept is called cognitive flexibility. The world has never been less cookie cutter and it's thanks to technology. Technology has sped things up. It's turned repeatable tasks into programs, and it has made our competitive advantage as a species, creativity and improvisation.

But when you think about it, that's the opposite of pure specialization, which is what we've been taught to do for our whole lives. Specialization, meaning the focus on one thing and going deep in that one thing, it works best when you're doing something that has clear constraints and recognizing patterns is a really important part of the task. So think of golf or being an electrician or being a doctor that just does hip replacements. In these types of activities, memorization, muscle memory, and recognizing patterns pays huge dividends. But so much of knowledge work in today's day and age is less predictable than that. Managing people who have different ways of working, ideating totally new products at a company that find-product market fit, or negotiating a new higher salary and benefits, specialization doesn't help with any of these things because in a world filled with ambiguity, nuance, and emotion, your ability to memorize processes and pattern match only goes so far.

And that's why some of the greatest performers of modern society also have the greatest range. Here's an amazing stat for you: Nobel laureates, so people who won the Nobel Prize, they are at least 22 times more likely to partake as an amateur actor, a dancer, a magician, or another type of performer compared to other scientists that didn't win the prize. But let's get practical for a second. We live in a world where specialization is still what is rewarded, even if it's not necessarily where the world is going and what we should be doing as professionals. Employers value transferable skills and being a specialist is really important, especially in bigger companies where every specific need has a specific employee tied to it.And especially if you're in the middle of your career. 

Exceptional professionals have 3 kinds of knowledge

Said differently, how do you welcome range and being a generalist if you get paid to specialize further? Here's how I think about it. I believe exceptional professionals possess three kinds of knowledge. First is work-agnostic knowledge, second is context-agnostic knowledge, and third is context-specific knowledge. I think we are taught to focus most of our energy on the last one, context specific. So if you work in sales, you're expected to focus your time working on your sales pitch, on understanding funnels, and understanding the product you're selling. This is the specific language, processes, and concepts that you need to know in that job of sales. If you're an engineer, you're expected to focus your time understanding your company's tech stack, the product roadmap, and doing heads down engineering work to push the product forward. And don't get me wrong. You need context-specific knowledge. You need to know these concepts, processes, and language specific to your job to do your job well. But to me, that's par for the course. That's where specialization is helpful because all of this is based on recall and memory. My suggestion for you would be spend as much time front-loading your context-specific knowledge, so then you can accumulate work- and context-agnostic knowledge to stand out.

Those are where you stand out, work- and context-agnostic knowledge. And so context-agnostic knowledge doesn't mean, do random things for the purpose of having them help you professionally. It means do things you think you could like or be good at for the purpose of growth. So for Roger Federer, that was playing many sports and then focusing in on tennis. For Yo-Yo Ma, that was playing violin, piano, ultimately to find out that he liked cello best. And if you do these things without expectation, it will inevitably have an impact on your professional ability. So it could be joining a debate club because you're just into the idea of debate and improving how you articulate. It could be volunteering at the local soup kitchen because you want to help the homeless. For me, it was running a magazine on campus at the University of Michigan to get more exposure to writers and artists. For Federer, it was playing six different sports, for Yo-Yo Ma it was playing four different instruments. The most famous example of this is Steve Jobs who took a calligraphy class, which inspired the original fonts that were used on the original Mac. Give yourself the time to explore and sample and it becomes a win-win: You spend time growing and being interested and without trying, it makes you the best professional version of yourself. 

Tell me: Are you team generalist or team specialist? 

Now, I want to hear your thoughts on this. It's always been a contentious issue of, should you generalize? Should you specialize? And also depending on where you are in your career, one can matter more than the other. But I'd love to hear your thoughts on if you buy into the idea of generalizing, even if you are a specialist and if you're a generalist, how you continue to add value in a world where we are rewarded for specializing. Shoot me thoughts on this topic to alex@morningbrew.com or DM me on Twitter @businessbarista. Also make sure to pound the subscribe button for Founder’s Journal on Apple, Spotify, or the podcast player of your choice. It is the number one way we grow the show, and it's also how you find out about new content when it drops. And if you already subscribe, make sure to check out Founder’s Journal content on Morning Brew’s YouTube channel. Go to YouTube, search Morning Brew, and click on our channel. There, you'll see an entire playlist of Founder’s Journal videos, from why Ethereum matters to how to deal with imposter syndrome. Thanks again for listening and I'll catch you next episode.