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Are You A Generalist or a Specialist?

This Is The Only Strategy You’ll Need To Take Advantage Of Both

Some people are always jumping from one interest to another, starting new projects and finding new fields to dive into. Others choose a skill or area of study and achieve true complete mastery in it. Which one are you? I’ve always been the former. I’d start projects only to discover something else I was interested in. The problem was never finding new things to do or try but to focus long enough to become really good, let alone master, a skill.

Mastery takes time, effort, and intense discipline. Experts and thought leaders are critical to any field whether it’s trade, a field of academia, or even a sport. People like Nassim Taleb whose focus on applying concepts of randomness and risk-analysis transformed the practice of traders. And often, most people at the top of their fields in academia are experts where they serve as thought leaders. These are the specialists. Specialists have incredibly deep understanding, knowledge, and skill in their particular field/job. If the job was to build a house, a specialist would be the guy who’s worked for 20 years solely on crafting the best windows a house could have.

At the same time, some of the best innovations in history are made by those who existed at the intersection of various fields. Leonardo Da Vinci was an inventor, sculptor, and painter… but he was also interested in science, architecture, music and a handful of other subjects. Steve Jobs bridged industrial design, computers, marketing, and business to create some of the most innovative digital products of the 21st century — and he arguably could only do so because he dabbled in many different fields. These are the generalists. Generalists know more than the average person in a variety of subjects, but nowhere near a level of mastery. In building a house, they’d be the project manager — someone with a general understanding of architecture, civil engineering, business, land development, and construction.

Growing up, all my friends seemed to be specialists — they were really great at math or writing, but nothing else. On the other hand, I was taking a hodgepodge of classes that consisted of math, business, history, and political science. Thus, the debate between generalists and specialists has always been in the back of my mind. But now, more than ever before, it’s important to settle this debate once and for all.

Why?

Because the world is changing — and not in a turn-of-the-century kind of way. Technology is changing our world every single day. It’s changing the way we interact, the way we learn, even the way we buy our groceries. But most terrifying of all, it’s rendering jobs obsolete. The issue of automation is not a new one in our time period, or even throughout history. At this point, it’s inevitable that some white-collar jobs will be automated. There’s a non-zero chance that your job, whatever it may be, could be taken over by machines in your lifetime.

But don’t worry, it’s not all doom and gloom. For all the talk about technology taking away jobs, we seem to forget that it’s going to create a lot of new jobs too. When cars replaced horses, coachmen suddenly found themselves out of a job… but the auto-industry has created millions of jobs as well. New technology has always replaced humans in some areas, but it’s also always opened up new opportunities.

The problem is, we don’t know what those new opportunities or jobs will be yet. We need some level of specialization to get the jobs that exist now… but we need some level of generalization in order to protect ourselves in case our job becomes automated.

That’s why we need the T-Strategy.

The T-Strategy is how we’ll adapt to change and uncertainty in the future. Adopting the T-Strategy gives you an extreme advantage. You’ll have the depth and expertise to get jobs you want or the work you’re interested in now. But you’ll also have the breadth to adapt, switch paths, and have a bunch of starting points if anything ever changes.

In the picture above, the horizontal part of the T represents breadth. These are the skills or fields you’re a generalist in. You’ve got above average knowledge on, but you’re not an expert. The vertical part of the T represents depth. This is the field(s) you’ve got complete mastery over, both in understanding and application.

Take a minute to pull out a piece of scrap paper and draw out what your T looks like. Write down the different fields you’ve got an above average knowledge on. Those are your circles — connect them. Now draw a vertical line down depending on the level of expertise you feel you have in each area.

Here’s an example:

Is it just one big horizontal line or one deep vertical line? Maybe you’ve got huge breadth and a bit of depth in a few subjects? The T-Strategy is to turn whatever you have, into a more traditional looking T. If you’ve got huge breadth, you want to add some depth and vice-versa, if you’ve got intense depth in one field, you want to add some knowledge in other fields too.

I think everyone is naturally a specialist or a generalist. Some of us just have a tendency to dive head first into a topic we’re interested in. Others are more non-committal and enjoy learning about a variety of fields. It’s possible we’re a generalist sometimes and a specialist other times. It doesn’t matter which you are, it only matters that you take the time to apply the T-Strategy to expand the areas you’re missing.

If you’re a generalist (wide breadth) trying to specialize (gain some depth), here’s a 3-Step Process:

1) Gather knowledge on the subject

If you’re a generalist in the subject already, you should already have the basic fundamentals down. Now it’s time for the next step: What do the experts in your field know that you don’t? Think about this question and come up with a list of 5–7 core topics or skills. Gather a pile of resources, whether it’s books, online courses, or even experts in the field you can reach out to. Now, just immerse yourself in learning everything you can and combing through the information to look for key areas to focus on.

Here’s a great list of free online resources by Business Insider.

2) Create a personal project

Knowledge is great, but application is better. The top experts in your field not only know things, but they can put that knowledge to use. A great way to get visible, related experience in your field is through personal projects. If you’re in an artistic field like graphic design, photography, or fine arts, you can create a portfolio. If you’re in a computer/tech/digital media field, you can build an app, design a product, or recreate an existing business. And even if you’re trying to become a business analyst or accountant, you can still get creative with your projects! Simply do what you would do if you were hired for your dream job. That might be analyzing the documents of businesses who recently went public to see if their IPO is in-line with their true value. Or maybe it’d be auditing the financial documents of public companies.

Here are some great examples of people using personal projects to practice their craft:

3) Apprenticeship/Internship

Now it’s time to get paid for your expertise. You’ve put in the work. This is your chance to see if you’ve hit your ultimate goal: real-life application in your field. If you have the time available, look for full-time contract internships that are focused on the skills you’ve just developed. They’ll allow you to fully immerse yourself in the new skill, but there’s an end. If you can’t dedicate all your time to it, no problem, you can always work part-time or on a per-project basis. There are sites like Fiverr which let you practice your craft and get paid for it too!

Here’s a great example: Victor Saad created a real-world MBA by lining up 12 apprenticeships in 12 months. Not only was it cheaper than a traditional MBA, it was also exponentially more effective and it gave him the skills he’d need to work in his field. Check out the full article here.

If you’re a specialist (depth) looking to generalize (breadth), here’s your 3-Step Process:

1) Look for a place to start

If there’s anything you’ve always been interested in, now’s your chance! Even if you can’t see how a field/skill might be related to the work you’re doing now, you never know how the dots may connect in the future. Plus, if you’re already interested in the subject, it’ll give you the extra boost of motivation you need to get started.

Or, you can look to your neighbours, as in, what fields/ are naturally tied to the work you’re doing now? Are there certain skills that keep coming up in your work that you’ve been avoiding because it’s not in your area of expertise? If so, that’s the next obvious step to take.

2) Learn & Apply… At The Same Time

Unlike a generalist looking to specialize, you only need a little bit of knowledge in your field so a personal project might be overboard. Instead, try interactive learning. Interactive learning incorporates traditional passive learning with application based activities. For example, instead of just watching a video or reading a chapter of a course on business development, there may be real-life case studies instead. Note that application-based activities aren’t just simple questions or quizzes at the end of each chapter — they’re activities specifically designed to mimic real-life application of your skill.

Here are a few great platforms with interactive learning:

Codeacademy: teaches users how to code while creating real examples to practice each lesson on

Other platforms: Udemy, Lynda

3) Find A Way To Tie It All Together

The most valuable part of being a generalist is that the skills you have in multiple fields serve each other. Bringing everything you know into one cohesive umbrella helps improve your mastery of all fields. Depending on the field you chose, it may be obvious. If you were a specialized front-end developer who learned a bit of back-end development, you’ve already got a clearer understanding of software development as a whole.

But what if you were a specialized front-end developer who decided to branch out and study historical wars? In this case, it’s likely there’ll be some transferable skills. Maybe the art of story-telling throughout history can help you better express the product’s user flow when you’re developing the user interface.

Whether you’re a generalist or a specialist, it’s good to start branching out — both sideways (breadth) or downwards (depth). The best part is, there’s no end! Even if you’ve got a perfect T going, there’s always room to gain knowledge in more fields or master a field you’ve dabbled in. The T-Strategy is the best way to ensure that you’ll do a great job at your work no matter what changes in the future, whether it’s technology or simply your interests. The T-Strategy gives you flexibility and adaptability — the two most important traits in a world of change.

One more thing…

If you enjoyed this post, you’re gonna love Thirty Days. It’s a place for millennials to figure life out. You’ll find daily blog posts, monthly challenges, and insanely actionable tips to create the life you want. Join 1000+ readers!

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Jess Chan

Jess Chan

Hey, I’m Jess! I’m the founder & CEO @ Longplay (retention & lifecycle marketing agency for DTC e-commerce brands), previous CMO @ Best Self Co, & entrepreneur!