TLDR

Exploration – trying new things, even when there are safe, familiar things within reach – is hard. Risky. Stressful. It’s also essential to a rich and vibrant life well lived. Like most other hard, stressful, important things, it’s better done together than apart. With our unique mixtures of shared and unshared experiences, we can use our gifts to help each other explore the world.

I

Let's say you recently finished reading a novel, and are looking for a new book. You have many thousands of choices: classic fiction, science fiction, poetry, true crime, history, popular science, self-help, wisdom literature, politics...the list goes on and on. Authors you know, authors your friends read, authors you've never heard of that popped up while idly browsing Amazon. An impossible profusion of words, which you could dive through forever without seeing the bottom.

But you have to pick something, so let's artificially constrain your options. Your long-time favourite novelist has a new book out, which you're very excited about reading; you expect it to be much, much better than any random book you pick. At the same time, your friends have been raving about some obscure author you've never heard of, who wrote a lot of books in the 1960s, and you've been thinking of trying her out. Or you could try some poetry – you've never really gotten on with poetry, but you’ve also never read it much since you left high school. Maybe you'll like it more now you're a little older.

Which should you pick?

The simple approach is to pick the book that you expect to most enjoy. That's clearly the one from your favourite novelist: you've yet to read a book from him that you'd give less than 8/10, and you're confident this one will be another humdinger. Why gamble your precious time away on something new when you have a guaranteed win waiting on your bookshelf? Under this approach, you stick with what you know is good, unless you get a very strong recommendation from someone you trust.

Yet, this approach is clearly missing something. Most of us have had the experience of opening a book and discovering a whole new world inside: a kind of writing and a flavour of ideas you didn't really imagine could exist until you experienced them. There was a time when you didn't know your favourite author existed, yet now you've discovered him you can hardly imagine life without his books. Who knows how many other such authors are waiting out there for you to find?

What the stick-with-your-favourites approach is missing is all the other books you have ahead of you – a whole lifetime of reading, which could go very differently depending on what you discover in the meantime. Even if you expect to like the other books on your list less than your favourite author, you might be wrong – and if you are wrong, you can then read all of their other books too! The potential upside of a new discovery is huge, while the cost of being proven right is very limited – one disappointing book, or even less if you abandon it partway through.

What holds for authors holds even more strongly for genres. If you discover that you enjoy good history writing after all – or epic verse, or true crime – that unlocks a vast trove of books that had previously passed you by.

This asymmetry means that, paradoxically, the best decision can be to try an author or type of book you expect to be worse than your current favourite, if it has some realistic change of being better. How big the chance has to be before you take that bet varies based on circumstance, but the basic lesson is clear: when the cost of failure is one dull read, but the benefits of success can be reaped for the rest of your life, take risks.

Perhaps you should try that poetry collection after all.

II

Now imagine it's Christmas time, and you're looking for a gift for a friend. Let's assume your primary goal is to benefit your friend – to make her happy, to enrich her life – not just signal that you care or fulfil a social obligation.

Again, there are countless options – but this time, your task is much harder, because you almost certainly know your friend far less well than you know yourself. As a result, for any given class of things you know she likes (wine, say, or cinema) you’ll very likely do a worse job of getting her something good than she would herself: some value will be lost in the gap between your mind and hers. The safe option is to get her something you both like, where you both trust your taste and are confident in her appreciation. Perhaps a really nice bottle of red, or a great board game you know she wants, or (in years other than 2020) a standing offer to take her out for dinner at a restaurant you both like. You’re almost certainly locking in some deadweight loss that way, but if you know your friend well it will hopefully be small, and perhaps made up for by the pleasure of companionship or the satisfaction of feeling valued.

Is there some way you can buy your friend a gift that is more valuable to her than what she would spend the money on herself? On the timescale of a single gift, that’s a tall order – you’re never going to know her preferences as well as she does. But on the timescale of a life? That might be a different story.

The principle is the same as before: the best choice on the scale of a single decision is often not the best choice on the scale of all future decisions, because choices that are risky now might open up whole new vistas of better choices in the future. What goes for choosing for yourself also goes for choosing for others. Except now you have a crucial advantage: a lifetime of unshared choices, of things-in-the-world that you have sampled and considered and judged about which your friend knows little or nothing.

You can use that unshared experience to help your friend explore, to pick out promising pieces of the Universe for her attention that she would otherwise have rejected on sight, or not considered at all. By distilling your experience, you can pick a gift with the potential to widen your friend’s horizons, to unlock years of potential choices she could not otherwise have made.

Let’s make this concrete. Suppose you and your friend are both avid readers. There are some genres you both read a lot of – say, historical fiction – and there are genres you read that she does not – say, science fiction. You recently finished both a Booker-winning historical novel, and a Nebula-winning sci-fi novel, and loved them both. You’re pretty confident your friend hasn’t read (or bought) either. Which should you get her?

The Booker winner is the safe choice. You’re confident she’ll love it, it’s very much in her wheelhouse. But you’re also confident she’s heard of it, and will get around to reading it sooner or later without you. Maybe she'll love reading it even more if it comes from you, and that's not nothing. But this isn't a gift that will expand her horizons.

The Nebula winner, though – that’s a different story. That’s a risky gift. There might well be a good reason she doesn’t read sci-fi – maybe she tried several of the classics as a teenager and hated them all. There’s a much higher chance that your gift falls completely flat than if you bought her the Booker winner, or a fancy bottle of gin. But if it doesn’t fall flat, if she tries it and loves it against her own expectations, you might just unlock a whole new world of art and literature that had previously passed her by.

If you're thinking only about which gift will most benefit your friend in itself, you should probably get her the Booker. But if you're thinking about what gift might most benefit your friend over a lifetime, you might want to get her the sci-fi.

III

Exploration is hard. Striking out into new territory is risky, stressful and often unrewarding – it’s so much easier to retread familiar ground. But without exploring, we are doomed to miss out on countless opportunities to live richer, happier lives.

Luckily, we are surrounded by people who have lived different lives from ours, who have explored parts of the world we have never seen. If we can access even a fraction more of that unshared experience, our own exploration becomes easier, more rewarding – and more fun. Like most difficult things, exploration is better done together than apart.

Treating gifts as an opportunity for free exploration has several benefits. Firstly, it can be an essential prompt to explore at all, when our habits and routines and the demands of everyday life act to pull us ever deeper into placid, unvarying orbits. Secondly, it makes that exploration easier, more effective, and more enjoyable: how much better to start your exploration of some new place with a thoughtful guide, than to dive sightless into an unknown sea? Finally, it might just help us make better gifts: gifts that are more alive, more interesting, that communicate more about ourselves and our hopes for each other.

Treating gifts as exploration can, admittedly, be dangerous: good exploration must be risky, and risky things often fail. A pile of gifts-as-exploration will contain many interesting things, but also many things that their recipients definitely do not want. Failed exploration, especially when imposed by others, often does not feel like a noble venture sadly thwarted, but like a slap in the face: how could you possibly think I would like…?

On the other hand, it’s not as though our existing gifting habits don’t frequently lead to abject failure: we’re all well-trained from childhood when it comes to graciously receiving gifts we dislike. This can actually frustrate attempts to treat gifts as exploration: you can’t get someone a better explore-gift next time if you don’t know how flat your last one fell. But it does mean that we give each other some degree of cover to take more risks.

Exploration might not always be the right theme in one’s gifts for others: that depends on the tenor of your relationship with your giftee, your mutual tolerance for risk, your pre-existing norms of giving and getting. But even if you don’t feel comfortable getting your friends and loved ones really out-there exploration gifts (“Here, grandma, try this Deadpool comic”), you can probably push the envelope a little, shift the locus of your giving a little more in that direction. You can raise the topic in advance, suggest moving your mutual giving in a more exploratory direction. See what they say.

Above all, you can tell your friends and loved ones that what you would most like for Christmas this year is the chance to share some part of their life that you haven’t seen before.