The Specialist, the Generalist, and the Non-Conformist

This is the story of three people: Nick, Sara, and Taylor. Each faced the common challenge of deciding what to focus on for their life and work.

The challenge was complex and involved lots of variables. What was best for one person might be the wrong choice for someone else, etc. etc.

Ultimately, however, all the variables pointed to one big decision: is it better to be a specialist or a generalist?

In making this decision, Nick, Sara, and Taylor each embarked on a different path.

Nick chose early and went all-in.

The child of a surgeon and an engineer, Nick saw how his parents had thrived by picking a path and staying on it.

Growing up, he had a strong sense of self-discipline. Whether it was test scores or sports, his parents expected him to excel. Nick learned to apply this expectation to himself, and it followed him throughout life.

As a young adult, he read books like The One Thing and Focus. These books led him to believe that his best option was to find a single discipline and learn to master it. Anything else should be viewed with suspicion, because when you distribute your attention, your ability to focus becomes limited.

After going to a good school (and earning the best grades, of course), Nick worked at a fancy consulting agency before striking out on his own.

His self-discipline served him well in this transition. Ever since his first year in college, he’d been thinking about his future. A business mentor told him that the most successful people choose a narrow lane, or a niche as some liked to call it. “The riches are in the niches,” the mentor said.

So Nick dutifully followed suit. He became the world’s leading expert on ____. He was good at it, and it was good for him, at least at first.

Because everyone knew him as “the guy who did ____,” it made for easy introductions. He found a way to monetize this knowledge and did well for himself.

But this intense focus came with liabilities. Over time, he found himself slipping into pre-programmed language, saying the same things over and over. The routine became stifling.

in the end, Nick was dissatisfied. Sure, he’d enjoyed being the world’s leading expert on ____, and he made a good living—but he realized he also wanted something else that was now closed to him.

Despite his success, he wished he’d done things differently. Looking back, he would have pursued other interests instead of going all-in.

Sara rejected the idea of forced specialization.

The child of a musician and a bookstore manager, Sara saw how her parents had resisted the pressure to find “real jobs.” In addition to traveling to music festivals and sitting in the front row at author readings, she grew up with a strong sense of autonomy. Her parents didn’t hold her back or even steer her in any particular direction.

As a young adult, Sara read books like Refuse to Choose and How to Do Everything. These books felt freeing. They encouraged her to believe that the dogma of narrow focus was overrated. Instead, she should create a portfolio of interests without limits.

In other words, she should do whatever she wanted and not worry about enforcing constraints.

Sara didn’t become an expert in any particular topic, the way that Nick did. Instead, she pursued a hybrid approach to life and work. She worked a series of jobs before doing some coaching on the side, then spending time with a business idea before signing on with a non-profit.

Life was good. It wasn’t great—but it was good.

At parties, Sara had a hard time telling people “what she did.” When she was young, she didn’t worry about this, but it became more of a concern as she aged.

She told herself that she never really wanted a big success. After all, she wouldn’t have been able to do all the other things she’d dabbled in if she’d chosen only one. Besides, her parents had always been happy with their own meager achievements. Right?

Sometimes, she believed this. Other times, she knew it was only partly true. Part of her craved the big success that would only come with fixed constraints and narrow focus. What had she missed?

In the end, Sara too was dissatisfied. Looking back, she wished she’d put her head down to focus on a core area a bit more often.

Taylor saw the merits and pitfalls of both paths.

Taylor was the child of a scientist and teacher. In early adolescence, Taylor expressed a preference for non-binary pronouns (they, them). Similarly, Taylor approached the challenge of specialist vs. generalist in a non-binary fashion.

Taylor read as many books as possible, and thought about what could be gained from each one without claiming allegiance to any particular ideology.

As an adult, Taylor tried to surround themselves with intelligent, interesting people, including some with different political beliefs.

The first few career paths Taylor tried didn’t amount to much, but they provided useful information. Something else that was helpful: taking time to travel. During school breaks and annual vacations, Taylor ventured further and further afield, seeking to see parts of the world that most people only hear about.

Over time, Taylor began seeing connections between all the things they studied. Travel played a role, too. Something that Taylor saw in Morocco connected to a nascent idea that was formed in Laos. A year later, on a train from Budapest to Bucharest, the idea turned into a business model.

And then, a surprising thing happened: Taylor choose a niche. Like Nick, Taylor was now a leading expert in _____. Unlike Nick, however, Taylor didn’t have many regrets. They never would have come to Topic X were it not for all the years spent doing many other things.

It wasn’t about “splitting the difference,” a strategy mostly used to avoid making decisions. It wasn’t about life-work balance, a concept designed by corporations to prevent employees from quitting.

It was about recognizing the validity of both approaches at different times of life. These were the questions that guided the process.

What did Taylor need NOW?

How would they build a set of knowledge that could be accessed and deployed for years to come?

Ultimately, how could they find the one thing in the right time?

This journey was not without obstacles. In fact, it was more difficult than either of the other paths, since you don’t just make one big decision. You have to constantly evaluate new information. You must gain much more self-insight.

But of course, nothing worth doing is ever easy. For Taylor, and perhaps a few other special people, this was the way.

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