10 Things I Wish I’d Known About Adventuring Before I Left the Shire

Charles Lance
6 min readSep 21, 2021

by B. and F. Baggins

One of the authors relaxing outside his home.

1Don’t read the fine print. If you do, you’ll never sign. When dwarves come knocking on your door at supper time, let them in. Yes, it’ll cost you! But you’re reading this because you want to be an adventurer, right? You can’t just sit in your cosy hole, safe and bored. You gotta spend something to make something. Risk is not only inherent, it’s essential — in fact, the bigger your sense of risk, the more likely you are to succeed (because you will be driven to!) So when chain-smoking wizards try to pull you into their dubious political schemes, say “Yes!” every time. They may never ask again.

When chain-smoking wizards try to pull you into their dubious political schemes, say “Yes!” every time.

2 Get a bigger pony. Start getting your adventuring kit in order 3–4 months ahead of when you will actually be out slaying monsters, and check that your pony can actually carry it. In my case, I brought on an inventory management intern (free — found him outside trimming the hedges) who spent weeks working part time at organizing all of my weapons, armor, magical trinkets, lembas bread, etc. into a handy spreadsheet. That saved us a lot of work when we ran into our first proper adventure arc and had to gear up post-haste.

3Stick a horn on your pony’s head. There I said it. I don’t know if unicorns exist, but wargs, dragons, giant spiders, oliphants and all manner of other weird and wonderful creatures most certainly do, so who knows? In the meantime, make do with what you’ve got. People will think you’re baller and hey, it probably makes the pony feel good, too.

If you don’t look like this, you should.

4Meet with elves. There comes a point in any adventure where you need to stop and think about what’s coming next. I spent six weeks just checking in with the advisory board at Rivendell, and chatting with fellow adventurers who had registered with the Fellowship. They offered good, free and surprisingly consistent advice about how to attract the right kind of patrons, the intricacies of dwarven security protocols, and the latest meta on stoning trolls — wish I’d known that earlier! Another advantage of these meetings is that I got a good sense of who was actually successful and which adventuring markets were already saturated; a great way to quickly identify blue ocean kingdoms rich with treasure for the taking!

The advisory board and fellow adventurers offered good, free and surprisingly consistent advice.

5 Kiss a lot of frogs. I prepared my family and staff for the fact I would be putting myself out there and would need their support. It can be demoralizing to get so many “no”s. Whether they’re tied up in a war to the north or scheming to prop up your competitors, a lot of potential allies are gonna give you the evil eye. Keep your chin up! Every conversation or meeting may not lead to a hoard of gold and jewels, but each one is a great opportunity to practice your sword stab, hone your riddles, and refine how you are pitching your mission. Even if they don’t turn into a prince, your frog may be able to make introductions, or sneak you through a swamp — so get into a positive mental space where you can give your best on each call or meeting.

6 Get ready to grow. No, I’m not talking about ent booze! You may think you are experienced, but trust me — the world out there is much bigger than you can imagine. You’re gonna learn a lot, or fail trying. Even though I raised over 4 million castar in early funding and put together a crack team of experienced adventurers, I needed new training for liaising with human kingdoms. When I discovered I’d be pitching to 6,000 horsemen over Doom with a strict 10-minute limit and only one chance to get it right, I decided to hire a public speaking coach. This made a huge difference in my confidence level and delivery, and it went great. Shaken spears, splintered shields — they love that shit!

Never do the hard work of adventuring if you can get others to do it for you.

7 Learn to speak Sindar. Elves use a specific set of vocabulary you will need to understand and be able to use comfortably. The Adventurer’s Guide to the Third Age (2nd Ed.) will teach you most of what you need to know (I read it toward the end of my 4th round and wish I had read it earlier). Do not think your wizard will handle all of this; you need to be well versed in these terms to negotiate and understand your term sheet. These need to all roll off your tongue: celeb, drego, elear, esgal, estellio, thalias — and most important of all — mellon.

8 Keep your deep plans to yourself. You’ll need to speak with conviction about your margins, run rate, total adventuring potential and EBITDA, both today and three years from now — but don’t go dropping plot hooks for other adventurers in dingy roadside pubs, or spilling your guts to easily-tempted men! I can’t stress this enough. By all means talk up the treasure you expect to pillage from grave-mounds, but be careful about sharing the where-for and the how-to. Also beware false would-be patrons, especially if they come bearing gifts. Make sure you have a solid market advantage or IP protections in place before peering into any so-called crystal balls.

9 Be a hero. Own your protagonism. Leave your insecurities at the door. This is no time for humility. Do what you need to do to get over any hang-ups you may have about your ability to achieve extreme fame and success (or at least table them for a while). Everyone is an imposter in this game — until they are not. Pitched as a professional burglar? Then burgle. Vaunted as a sneaky smuggler? Get to smuggling! But assert yourself as the center of the story. Remember that people will default to the first model they built for you in their brains — make that model heroic, and half your job will already be done.

Everyone is an imposter in this game — until they are not.

There’s no such thing as too much bling.

10 Look like a hero. If you don’t have a talented adventuring outfit designer on hand, consider hiring someone to make you look the part. It doesn’t need a lot of bells and whistles but it needs to be sharp. Quality over quantity. Shiny mithril, glowing swords, vials of light. Not too much leather and not too many pouches. You’ll be showing it off dozens of times so make sure it’s telling your story in the best possible way. We revised our gear set over 20 times before we came up with a final version. Get user feedback — from your friends if no-one else. Wear it every day so it becomes part of you (you never know who you’ll meet or when). Practice using an enchanted clicker and avoid looking directly at the mirror-pool. Oh and yes — wear shoes!

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