Jamie on Software

Enthusiastic amateurs: some practical tips

Yesterday, I wrote about enthusiastic amateurs, a model for how I think about the trade-off between expertise and being a generalist. The median person is unlikely to become an expert, and pursuing expertise can be very costly, so perhaps there is a better path for the median person to take. This path is, roughly, to explore more, learn broadly, and rely on the interconnections between ideas to add value.

If that discussion is at all salient for you, a natural next question is how one ought best cultivate the characteristics of an enthusiastic amateur.

With the very big caveat that I’m still figuring this out myself, here are a few ways that seem to work well for expanding my interests and developing the sorts of knowledge that are additive rather than distracting:

  • Optimise for breadth. This might seem like trivial advice given the definition of an enthusiastic amateur, but it’s amazing how much more breadth can be gained by asking at a higher-than-normal rate “does this decision expose me in a meaningful way to more interesting stuff”. Follow blogs on subjects you know nothing about. Listen to lots of podcasts from lots of experts. Get used to clicking around Wikipedia aimlessly.
  • Avoid optimising for depth. I think optimising for depth is the default pathway, in many important ways, for lots of mostly contingent cultural reasons. If you want to be an enthusiastic amateur, you should resist the urge to optimise for depth. A lot of the stuff you do will also involve developing depth in a given field, but you shouldn’t be afraid to forgo depth in service of breadth, and then let depth develop naturally across a range of subjects, rather than by sacrificing breadth on the altar of depth.
  • Cultivate enthusiastic amateur friends. Enthusiastic amateurs usually have a richer and more idiosyncratic answer to “how can you do X better?”, generally because they actually end up answering a different question: “how do I think about X differently?”. They’re also very likely to recommend books and other media sources that might stray from expert’s canon. (Interintellect is a good place to start! So is Twitter!)
  • Cultivate expert friends too, but recognise their expertise might skew their answer away from breadth. Expert friends can teach you things you will never learn otherwise. They’re extremely good at nudging you away from dead-ends in their fields. It can also be a valuable way to get personalised feedback on your projects that sit in their domains. But experts are also more likely to rank you and your work against the norms and common knowledge in their field, which can lead you to develop the same sorts of blind spots that they do. It’s difficult to see the water you swim in.
  • Quit more. Quit early, quit often. Discipline is overrated. Projects that languish can be discarded. You shouldn’t forget that the sunk cost fallacy is still a fallacy, even when you’re labouring under it. If you’re at all like me, you should give yourself more permission to halt, reverse, rework or otherwise abandon some interests and projects as others begin to take their place. You’ll float back to things as and when you’re in the mood.
  • Use Anki and take notes. Breadth means you need to build more branches on the knowledge tree. You’ve got fewer coat-hooks, as it were, upon which to hang new facts. Popular science television, for instance, even the not-so-good stuff, is usually packed full of non-obvious observations and the distilled wisdom of experts. Even more so for the really good stuff; even more so still for books. People consume this content passively, and so don’t retain it. The trick is to consume actively.
  • Talk more. Connections between ideas often rely on pragmatics – how things are said, and in what context – rather than the actual semantic content of the connection. So talking about your latest subject of interest with smart people in a variety of different contexts can help you see beyond the standard narrative and see links that others might not.
  • Write more. This is the sort of trite advice you hear often, but it can’t be repeated enough: so much of the process of writing just is thinking, and forcing yourself to write helps you retain what you’re learning and distill an argument or theory or model to its essential components.
  • Think about thinking. How can you better distill an idea to its essence? How can you better think about the content you’re consuming, and what you do with it once it’s consumed? How can you curate your inputs in a way that leans towards high-quality breadth?

None of these methods are foolproof, but they point towards an enjoyable and rich intellectual lifestyle that doesn’t involve the sort of high-risk turmoil attached to pursuing expertise.

Being an enthusiastic amateur is like giving up for smart people.

6:25pm. March 10, 2022.

Enthusiastic amateurs

In this post, I’d like to try to raise the relative status of the casual polymath, at least insofar as it motivates an individual to decide what she should work on. It seems likely to me that pursuing expertise is overrepresented in career-advice-giving contexts, and that we should try to reframe not being an expert in a more positive light. We fetishise a very specific sort of expertise – A Beautiful Mind, 100-hours-a-week, obsessional expertise – as the gold standard for living meaningful intellectual lives. I’d like to suggest that there’s an alternative approach.

So here’s my reframing: more of us should try to be enthusiastic amateurs.

Firstly, as should be clear to anybody who interacts with me, I am not an expert at anything. And it’s quite possible that I’m telling this story to coddle my psyche; to bolster my self-confidence as I cling tightly to µ; to sit more readily on my averagely-comfortable chair, drinking Nescafé, as I type on my mid-range laptop with my average-sized hands. I will never have the temperament or talent to be world-class at anything, and I’d still like to be able to sleep at night.

However, I think the life of an enthusiastic amateur is not only a good one, but that cultivating it is also often the rational choice for somebody to make.

At the very least, the expertise norm is overrepresented, and that there’s value to be gained by exploring an alternative.


Who are enthusiastic amateurs? Enthusiastic amateurs are people that work hard to see the world through as many lenses as possible. They care less about being great, and more about being good enough. They aspire to be polymaths, but recognise that the definition is wanting.1

How do they compare to experts? An expert is a hedgehog; an enthusiastic amateur is a fox. An expert relies on precision; an enthusiastic amateur relies on scope. An expert is tenacious; an enthusiastic amateur is mercurial. An expert toils; an enthusiastic amateur plays.

There are obvious trade-offs to chasing expertise, and the world obviously needs people willing to make those trade-offs (an enthusiastic amateur isn’t going to engineer a rocket good enough to get humans safely to Mars, although one might build a company capable of doing so). The trouble is, you don’t really know if you’ve got the capacity to be an expert at anything until you already are one. Mozart is the exception, not the rule. Unless you feel the gods have conspired to put you where you are, expertise is the sort of thing you need to work very, very hard to achieve.

From a position of uncertainty relative to one’s own abilities, then, deciding to pursue excellence in one thing seems like a risky strategy. You could chase expertise, drill, rinse, repeat. Develop slowly a garrison of discipline and knowledge and finely-honed tools for solving the more abstruse problems in your field. Learn deeply, and feel engaged in some sort of higher purpose; luxuriate in our collective teleological hangover.

That’s the success path. There’s a failure path too. You chase expertise, drill, rinse, repeat. You spend early mornings and late nights playing your scales. You run up against your natural limits, and you don’t push past them. You continue to push, because you’re told there are diminishing returns and you need to keep working. But you never actually get past that point. You learn to work around your limitations in various ways in order to make this Sisyphean effort seem worthwhile, but you’re really just fooling yourself into thinking you’re getting more competent. Or, even if you are improving, you might never close the gap between you and your nearest competitor. There are a lot of dedicated, hard-working, decidedly non-expert people. There are far fewer who will meaningfully change their field.

You’re probably not going to become an expert. And if you’re probably not going to be an expert in the one or two things you care enough about in order to try, you’re more likely than not setting yourself up to fail. Failing can be a pretty unpleasant experience, and fighting through failure is so often a pyrrhic victory. Being irredeemably bad at something isn’t fun. This is an important psychological cost to factor in before you dedicate your life to something. (Expected value theory might be useful here: what’s the cost of failure multiplied by the probability that failure will happen? If you’re honest with yourself, it’s not likely that that number will be a ringing endorsement of pursuing expertise.)

As well as the psychological cost incurred when you wrap up your identity in a métier and then fail to live up to your own expectations, the pursuit of expertise has high opportunity costs, too: the costs incurred by not doing the other things that you could be doing while you pursue expertise. What you enjoy doing often changes, so if you spend the time becoming an expert, slogging over the plateau, it’s likely that you’ll miss out on a bunch of possible fun that you could have were your focus more elastic.

Another cost: I’m not convinced that there are always diminishing X-returns for X-ing[1], but there is a subset of Xs for which there are certainly diminishing social returns. You don’t need to be a Master of Wine to impress most dining companions: even if they are Masters of Wine, most other people are so far away from even passably knowledgeable about wine that a middling level of understanding can yield the majority of the benefits – the signalling power – that you can get from knowing about wine. In other words, you don’t need to be an expert to be impressive, even in the eyes of other experts.

If there are less obvious costs to being an expert, there are also less obvious benefits to being an enthusiastic amateur. It’s easy to underrate the benefits to being competent at a lot of things, especially when they’re compared to being excellent at one thing.

The world can often seem set up to reward experts more and reward enthusiastic amateurs less: academia seems to be a 1000-year experiment to institutionalise this model. But such entrenched reward systems often offer the opportunity for arbitrage. Being good enough at lots of things means that you can often see connections between subjects that experts, siloed into their conceptual schemes, can’t.2 Phillip Tetlock argues that being a fox makes you, on average, a better predictor of the future, for much the same reasons. Academia is famously siloed, but some of the best papers I’ve read are clever precisely because they apply techniques from one field to the problems of another. There is such a thing as gestalt knowledge, and I’d wager that enthusiastic amateurs are better at finding it than experts.

On the other hand, there’s definitely some class of problems which require deep expertise to see and understand and solve. Some problems need smart people to sit and think very hard about for a long time. But I think we generally over-index on this sort of expertise, both institutionally (via the peer-review process) and in a more broad sense, culturally.

Being good enough has another interesting corollary: being good enough at a range of things creates interesting intersections at which you can be an expert. I might not be an expert programmer, or the world’s best philosopher, or the world’s foremost authority on wine or US politics or any of my other interests. But I’m probably in the top 1% of the general population at the intersection of those things, simply by virtue of the rarity of that intersection and my enthusiasm in pursuing them. By cultivating wider interests, and by getting good enough at a broad range of things, you can carve out interesting niches which give you both the ability to be world-leading in that niche and also emerge naturally from the explorations you make, rather than because of your dogged pursuit of decisions made a priori. In other words: being an enthusiastic amateur doesn’t mean you need to give up your edge. (As long as there are only a few enthusiastic amateurs, being an enthusiastic amateur might itself be an edge.) And, nowadays, niches can pay.

One of my smartest friends pointed out that the pursuit of enthusiastic amateurness is a very Theory of Action-driven thing. That is, it suggests answers to the question “what should I do next?” rather than “what should I do in order to achieve XYZ?”. He’s right, of course, but a priorly-formed want to achieve XYZ is the hallmark of a wannabe-expert, and therefore not per se the sort of thing that enthusiastic amateurs will be concerned with. The sort of long-term goals that Theories of Change point toward are often, at least at the subject-level3, underspecified or weighed inappropriately in the more general calculation about how one should live one’s life.

The same friend also pointed out that advice is often written for the wrong people, that being an enthusiastic amateur might also incur costs. One potential cost here: it might make it more challenging to signal your commitment to a group, and therefore make it more difficult to be embedded in a community of peers. He suggested for this reason that to the extent that one can choose their community, it’s better to be more specialised (and therefore expertise is rewarded proportionally). I don’t disagree. It might be. But presumably groups of enthusiastic amateurs – LessWrong? Interintellect? – interested in how best they can be enthusiastic amateurs, exhibit the same sorts of dynamics. If you’re looking to signal your commitment to a group, “enthusiastic amateurs” might not be a bad group to join.


Enthusiastic amateurs aren’t sloppy, or dismissive of expertise. The point is not to be bad at lots of things. It’s to recognise that expertise isn’t the end of the story, and that being good enough at a lot of stuff is often so much more rewarding than being really good at one thing. For many people, expertise is just out of acceptable reach. Whatever you’re good at, there is likely a Chinese toddler doing it better than you could ever hope to. Some people are born with the requisite interest and determination and tenacity to pursue excellence at one big thing. Many, many people are not. I’m pretty sure that a lot of what becoming an expert in something and sustaining that expertise is a slog, and that a lot of people don’t enjoy it as much as they think they should, and that their response to being uninspired is to accept being mediocre, and that this shouldn’t be where careers advice leads. As a result, I don’t think that traditional expertise-oriented career advice is especially good advice for the median person.

Being ‘good enough at X’ for many Xs is completely attainable and, I think, can often set you up to be rewarded socially and commercially. There are lots of people who should know, be emboldened by the fact that expertise is one way amongst several to slice the pie. You can have a rich and rewarding intellectual life without demanding of yourself that you know what you’re destined to do from an early age, or even be destined to do anything. That you can indulge your broader interests without it immediately being written off as procrastination. It’s also playful, in an earnest sense. For many, the life of an enthusiastic amateur is, I really, truly, believe, a lot more fun.

  1. I don’t, for instance, think that the piano-benefits to becoming an expert pianist diminish with more practice. As far as I can tell, being able to play a complicated piece marginally better does unlock new modes of expression and new value in the piece, and, moreover, that seems to happen proportionally to the amount of work you put in. Once you’re an expert, small variations can produce outsized results. This seems especially true in competitive zero-sum games that get repeated over time, like two tennis players facing off regularly. Relative to me, Federer’s marginal training session likely won’t change the outcome of our match. Relative to Nadal, it seems, that extra practice might make all the difference. 

  2. For some examples, see David Epstein’s Range

  3. I’m not quite sure about the meta-level. It might still make sense to pursue expertise at goal formation, or productivity, or something. Enthusiastic amateurs tend to be quite productive, relative to the mean. But maybe that’s because a lot of what they do is amongst the lower-hanging fruit, rather than because they’re productivity experts or aiming to be such. 

9:23pm. March 9, 2022.

How to think about recommendations

I make a lot of recommendations for restaurants. I also receive a fair few.

Unless the facts change from out under my feet – one day I’ll tell you a story about The Marksman – I think my recommendations are generally pretty good. But I would, wouldn’t I? Unless I don’t like you, I’m not going to recommend things I don’t think are good recommendations.

It’s very important to be careful when recommending. If you eat out often, say ~3 times / week, you can expect to have ~9,300 meals over a 60-year adulthood of eating. That isn’t many meals! I read roughly a book per week. That’s ~3,120 books in the same adulthood. That isn’t many books! So each meal and each book has to count. & many people eat out many fewer times per month and read much less. Centrally: you should respect the time and money that people will spend based on your recommendations.

It’s also easier to recommend things in the indirect-objectless sense, as I do in the restaurant list above. But recommendations are often recommendations to somebody, in some context, for some purpose.

In these cases, how should we tell which recommendations to listen to, and which to ignore? How reliable is the average recommendation? How can you reliably make good recommendations to others?

Off the top of my head, there are obvious heuristics we can use:

  • Prior experience of the recommender’s recommendations. Have you been to restaurants with this person before? Did you like the last movie she recommended?
  • The recommender’s knowledge of the subject matter. Is he an expert? Are they at least an enthusiastic amateur? Are you confident they know a lot about this?
  • The recommender’s knowledge of the recommendee’s tastes. Does this person know you? Do you have confidence in her model of your preferences? Does he buy you good novels at Christmas?
  • Consensus amongst more than one recommender. Have you heard from multiple people that this restaurant is good? Have each of them been consistent in their reasons for recommending it, or have the different reasons been intriguing and appealing?

These each seem non-controversially true: if these conditions are met, it seems more likely that you’ll get a good recommendation. But it’s not at all obvious to me that you’ll reliably (i.e. >50% of the time) get a good recommendation.

For one thing, the facts can change from out under the feet of the recommender. In a large city like London, you’re not likely to revisit the same restaurant more than a few times a month (unless it’s provenly reliable and local). Staff turns over, the great old chef moves to her new place, your friend goes on a busy night, has horrible service, and it’s game over.

For another, it’s only semi-plausible that good taste clusters. So if the recommender’s taste in novels is good, that doesn’t on the face of it seem to suggest his taste in restaurants will necessarily be good; or art, or music, or whatever else. Some people seem blessed with good taste across the board, but that’s far from true universally.

For a third – and this is my central point here – contexts which involve taste exhibit huge interpersonal variation no matter how persuasive the a priori justification happens to be.

So what are some things we can do to ensure we receive better recommendations, and can filter out the bad ones that slip through?

  • Surround yourself by people with good taste. This seems like an easy one, but something I think not enough people act on meaningfully. It’s worth selecting good taste into your friendship group, not just because the quality of the recommendations you’ll receive will increase, but because you’ll develop a better appreciation for what sorts of people are the sorts of people who make good recommendations, which of course generalises.
  • Cultivate better taste yourself; learn more. Another easy one too easily forgotten. Do you reflect on your aesthetic experiences, note what you enjoyed and what you didn’t? Do you move outside of your comfort zone frequently, and take the hits (so your recommendees don’t have to?) Do you make an active and regular effort to learn more?1
  • Select for order-of-magnitude differences. You should aim to find recommenders who have at least an order-of-magnitude more experience than you, and try to tailor your recommendations to people with at least an order-of-magnitude less. There’s enough noise so that the marginal next % of exposure seems much less important. I wouldn’t, for instance, trust the judgement of somebody who had been to strictly one more opera than me. (This perhaps isn’t the case if I’ve never been to an opera.) Another reason why a little learning is a dangerous thing.
  • Go wide then deep then wide again. A good way to think about taste is effective pattern-matching. For this you first need a broad range of knowledge to anchor novel experiences, and then enough depth of understanding to discriminate between the great and merely good. But it’s important to back out of the rabbit hole and dig yourself another one. Eat fifteen different cuisines, then pick a few and learn the regional variances within them, then eat fifteen more.2
  • Consider the incentives. Tyler Cowen’s famous piece on restaurant recommendations makes this point well. If a restaurant is full of good-looking people, it will attract more people, holding fixed the quality of the food, which reduces the incentive for the restaurant to care about the food as much. (The restaurant, in effect, stops competing on quality of food and thus stops caring about it.) These sorts of incentives are everywhere, and it’s both fun and useful to be a little cynical and consider how they might affect your experience, and the recommendations you receive and make on the basis of it.

Two final points to consider. Firstly, perhaps try to elicit and make anti-recommendations rather than positive recommendations. It can often be more helpful to know where to avoid rather than where to go. This seems a little counterintuitive, since we’re optimising for the positive case – i.e. the case in which we in fact do go to the restaurant – but it’s useful because it provides useful information and still ‘frees up’ the higher end of the recommendation spectrum to float more independently. Similar concerns apply to groups of positive recommendations (“eat in Shoreditch”, “read novels from feminist authors in the 1920s”). You can then use your good taste to narrow it down further.

Finally, and most importantly, try to keep an open mind, and give others as many opportunities to be open-minded as possible. (If that means hiding certain things from your recommendees, so be it.) This can be very high-leverage, because the best sort of recommendation (at least in an information-theoretic sense) is the recommendation somebody is unlikely to receive from anybody else. For instance, many people miss out on amazing food because they dislike the idea of offal, while at the same time are fine with a chicken liver pâté. It’s not that they won’t like offal, it’s that they’re unlikely to follow a recommendation that mentions it, and therefore people are unlikely to make these recommendations in the first place. Sometimes it takes a bit of energy to get past the inertial resistance.

My mother hates the idea of lardo, but couldn’t stop eating the lardo-fried rice at Smoking Goat. I may have forgotten to tell her what it was.

  1. There are some interesting questions about the dynamics of taste. Tastes appear to ossify as you get older, which is a shame since your knowledge accumulates (generally) monotonically. I need to think about this more. 

  2. This approach also helps counter Gell-Mann amnesia, because you interlace the development of expertise with novelty and force yourself to consider whether and in which ways the experiences cross-cut. 

9:31am. January 3, 2022.

The trade-offs are worth it

I’m very prone to greener-grass thinking.

Sometimes it’s important to acknowledge that the grass is greener, because, well it is. Sometimes you’re not in the best possible timeline, and bringing it to your own attention is the first step toward changing it.

But it’s often unhelpful, too, and can trap you into a cycle of distraction and dissatisfaction. You change something, because the grass over there is greener, and you reinforce the preferences you have for novelty. The less you develop the ability to stick with something, focus, persevere, the more difficult it becomes the next time you must.

The more vulnerable you become to your own whims.

The more often you throw away something valuable, because you’re suffering under some sort of novelty bias and what appears to be objectively better is simply fresher.

So it can be useful to reframe how you view your current situation. When I regret some decision because the alternative looks easier, or if I suspect I have made a mistake, I can find solace in the knowledge that:

  1. It can be easy to forget you’re making trade-offs explicitly and knowingly;
  2. and, the tradeoffs are generally worth it.

The beginning of anything requires a first step. A new job, a new purchase, a new skill or hobby, a new relationship. If you’re a thoughtful and goal-oriented person, you will consider whether this the right step for you. Something that might appear to be obvious at the time might be a mistake later, and you know this, so you take your time, weigh up your options. Consider the pros and cons and decide to act.

The next day, you’re in the honeymoon phase. The cons are irrelevant. The pros are even better than you expected. You enjoy the present. You look forward to the future with anticipation, with giddiness, with glee.

Some days later, the pros and cons look evenly balanced. You’re less interested than you once were, but stasis is a powerful force, so you do nothing about it.

Some days further, the cons are now what is salient. What began as small pet peeves or niggling doubts have blossomed. The cons are so overwhelming, so frustrating, that you cannot imagine why you could ever have thought the pros might outweigh them (or, hell, even counterbalance them!)

What seemed like a good idea now looks like a set of inappropriate, naïve preferences borne from the brain of somebody who knew less than what you do now.

But here’s the thing. You made those tradeoffs. You considered the pros, you considered the cons.

You might have missed some of the cons initially; not everybody gets it right first time. But this also applies to the pros. Are there not things about your role, your club, your partner, your commitment, whatever it is, that are unexpectedly pleasant, as well as unexpectedly not-so?

If it appears not, then consider this: even if you were able to predict everything a priori, do you think you’d be weighing the cons and pros appropriately after the cons have become so aggravating that you felt the need to reweigh them in the first place?

People only really reflect on whether their decisions were correct when they have reason to suspect that they weren’t.

People don’t look to upend the boat when they’re enjoying the journey.

So your re-evaluation may be happening from a place of more intimate knowledge, but it’s also happening from a place of discomfort.

There are definitely times when you should re-evaluate. When you are being harmed. When you have good reason to suspect you misjudged it all initially. Or when your preferences have changed significantly since then.

But there are lots of times when you shouldn’t. When, were you to reflect in a pro-dominant phase, you’d conclude quite differently.

The grass is always greener, Jamie.

The tradeoffs are usually worth it.