Tapestries-2 | A map for a shifting territory

Some thoughts on how to structure a curiosity-driven career.

The world is changing around us at an accelerating pace. To thrive and succeed within this change, we need to reassess the way we think about our skillsets and how we invest our time. We need to reassess how we value breadth vs. narrow expertise, generalists vs. specialists.

To the extent we adjust our views on the value of one approach over another, we then need to consider how this should change our behaviours and what tools we have available to support our refreshed approach.

Breadth vs. specialization: Understanding the different approaches

Specialists: Masters of their realms (for now)

We have been raised in the age of specialization, where a clear, well-understood profession (think: doctor, accountant, financial planner, marketer) was always the end-goal. There are valid reasons why we have been pushed towards specialization.

Firstly, it is a risk averse approach to ensuring stable and secure remuneration; to be paid consistently for something, the skill we are being paid for must be relatively scarce or possess some barrier to entry. By specializing we put in the work to become proficient in something that has natural barriers, in the hope that we will be paid for it.

Secondly, we specialize because others can clearly perceive the value of what we do; becoming a specialist is hard and brings with it external validation. Status and money are easier to measure for specialists and we therefore gravitate towards those things we believe others value (which we impliedly value ourselves too).

Advising somebody not to specialize is therefore inherently risky, because it realistically provides the inverse possibilities to the specialization route. The value that you may bring or possess is not as clearly identifiable, which has material implications for the size and security of your compensation, as well as undermining the potential for external validation. Today, it therefore takes a brave person to advise someone to take the route of more breadth and less specialization.

At this point, it’s important to qualify the scope of this thinking. There are no hard and fast rules for how different people should think about and approach their careers. The risk averse nature of specialization is entirely appropriate for risk averse people. Those who prioritize security, predictability and consistent results over potentially exceptional results and curiosity-driven careers, should lean into specialization to a greater degree than generalization. However, there exists a spectrum, and as we will discuss below, most people should sit at some point along the spectrum, not at the extremes.

On the basis of these qualifiers, the remainder of this piece is largely directed at those who look to excel, and those for whom curiosity forms a key part of their constitution.

For those that seek to be leaders (not necessarily in a particular field), choosing the specialist route likely does not provide the greatest prospects of success. Becoming a leader requires you to achieve true prominence in said specific field. This is because the level of competition increases as you progress higher due to greater proficiency and likely greater motivation.

As I sit here today, amongst other things I happen to be a practicing lawyer (please don’t tell anyone). Even if I wanted to become one of the best lawyers in the world, I would need to devote the rest of my life and waking hours just to give myself the chance to be in that category; even with a lifetime of work, I don’t like my odds. Don’t get me wrong, I would still become a very good lawyer and be paid handsomely for it. But I would just be another lawyer, and that doesn’t do it for me. The same logic is true of other professions.

Generalists: Investing for an uncertain future

The alternative path is that of the generalist or polymath, who follows their curiosities down multiple paths, either with or without the intent to apply their curiosities professionally.

Pursuing curiosities does not require any formal undertaking; instead, the only commitment is an intellectual commitment to exploration and learning, which is much more powerful and enduring than the financial incentives associated with learning for the purpose of further specialization. The choice therefore to become a generalist is often the natural path for the curious individual or polymath, as much as a strategic career decision.

If we find ourselves on the generalist path, we must understand the potential value we are creating, notwithstanding that we cannot be certain if, when, or how our disparate skills may converge. Becoming a generalist therefore carries a risk that the specialist has explicitly solved for: whereas a specialist’s value is clear, the generalist’s objective value is more obscure.

However, for the much smaller subset of people who do appreciate the unique value of a particular generalist — due to the unique combination of his or her skills — the generalist is significantly more valuable. We should aspire to succeed by being different or creative, not the smartest. This potentially involves investment of time to create a future and unknown skillset, to achieve yet-to-be-seen goals or fill a role we have yet to consider (or doesn’t exist yet), reinforcing the need for a generalist to have a larger risk tolerance.

Perhaps the most important imperative to become a generalist relates to the initial point about a changing world. Through applying themselves to multiple pursuits and acquiring different skillsets, the generalist becomes proficient in perhaps the most important skill of all: learning.

If we agree that the world and its requirements will change in foreseen and unforeseen ways, then the most important thing we can do is train our adaptability. It is this ability to learn and change together with our world, that has become a fundamental and sought-after skill.

We mistakenly accept that education ends at university or college; those that acknowledge the absurdity of this position have the ability to repeatedly become ‘beginners’ and apply themselves to evermore skills and pursuits.

A path forward: The case for becoming a generalist

The formula for a generalist is therefore as laid out by Scott Adams: become ‘good’ at or ‘well-versed’ in a particular field (say, the 75th percentile) using available resources and the 80:20 rule, allowing you to combine two (or more) seemingly disparate skills at the 75th percentile level, for a truly unique 99th percentile skillset.

Michael Simmons, in a well-laid out piece that helped to progress my thinking, makes a strong case for why everyone should become a polymath in the knowledge economy:

1. Creating an atypical combination of two or more skills that you’re merely competent in can lead to a world-class skill set.

2. Most creative breakthroughs come via making atypical combinations of skills.

3. It’s easier and faster than ever to become competent in a new skill.

4. It’s easier than ever to pioneer a new field, industry, or skill set.

5. It future-proofs your career.

6. It sets you up to solve more complex problems.

7. It helps you stand out and compete in the global economy.

He goes on to state that:

Being a polymath will be the new normal, and polymaths who synthesize diverse skills to create breakthrough innovations and solve complex problems will have a huge impact…

Meanwhile, specialists risk getting trapped by their success. They build up a narrow skill set and reputation and become highly paid for it. But their careers are fragile. As their professions disappear or evolve, it becomes almost impossible to switch without having to start over.

Polymaths, on the other hand, are what Nassim Taleb calls “anti-fragile.” Changes to the environment make them stronger. As new paradigms of business emerge or their passions grow, they can quickly combine their existing skill sets in a myriad of ways.

I wholeheartedly agree with this characterization. Diversity of skills, interests and experience is now a highly-sought after trait in the modern workforce, especially in those that aspire to lead.

How to progress from here

Assuming there are elements of this piece that apply to you, I imagine there’s an element of becoming an ‘expert generalist’ (to borrow Charlie Munger’s paraphrasing) that entices you. It is a pathway that I believe many of us aspire to, without having a clear guide or framework to apply, especially in the early years of our career.

The following guiding principles have clearly been crafted in reference to my values and aspirations, but I believe they are sufficiently generic as to be applied broadly:

• It is important to focus efforts today where they can bring the best return on investment (ROI), specifically on time invested.

• Financial independence and wealth are important, but will likely be the result of time and compounding, rather than flowing directly from specific efforts today; therefore, most decisions today should prioritize development, learning and growth — not financial returns today or for the next ~3-5 years (note: I am writing this as a 29 year-old).

• Most peers — internal and external — view the world through their own lenses, based on (i) what they value (e.g. status, money, title) and (ii) their own timeframes (usually very short-term); to the extent your values and timeframes differ, keep that in mind.

• There is merit in intentionally taking a long-term view of life and career; just as an investor should focus on long-term value and ignore short-term volatility, we should also focus on continuously investing in ourselves to achieve long-term goals.

The advice we receive from contemporaries (managers, friends, mentors) is often based on our current role and opportunity set as reference points; their advice will be predicated on us remaining on our current pathways and progressing steadily along it, because it will result in us incrementally growing what they value now — status, money, title.

If the concept of a ‘pathway’ terrifies you, then you should always qualify advice and acknowledge it is given through particular lenses. Developing a unique skillset through combining otherwise unrelated skills or fields, necessary involves taking non-standard and objectively strange decisions. If you choose a non-standard route, do so with conviction.

Systems and processes

Pursuing a non-linear career path necessarily involves an element of self-directed learning. Today, we learn over a coffee, at our desks, on the train, in messaging groups and in bed: these are our modern-day classrooms. We have frictionless access to voluminous information — but volume is not necessarily an ally of the curious thinker; indeed, it can often obscure and create noise.

Today’s generalist or polymath therefore is confronted with a multi-medium wall of information, but as of yet has not been provided with the right tool(s) to pursue their varied crafts. I am not aware of a tool to accompany you or I on this journey just yet, but may have something for you in a separate post.