South Island, New Zealand, a.k.a. Middle-Earth

If you were to make a list of what you want to get done this week, it would mostly consist of things you have to do. Get groceries. Book a hair appointment. Get back to so-and-so. Read that health and safety thing for work.

If you were to make a list of things you want to get done in the next two years, it would probably be more personal and more empowering. Learn to record my own music. Double my client base. Set up my dream office. Write my screenplay. The list would contain fewer things you must do –- since, by definition, those things will get done anyway — and more of what you actually want to do with your life.

We usually call these optional aspirations goals, but doing so immediately introduces a few problems that make them less likely to happen.  

The first problem is that goals are things you expect to do later, because they aren’t strictly necessary, and you’re currently busy with the to-do list stuff. You’ll do them, soon, but not quite yet. There must first be a lull in the noise and stress of normal life, in order to make goal-achieving feasible.

The other problem with goals is that, outside of sports, “goal” has become an uninspiring, institutional word. Goals are things your teachers and managers have for you. Goals are made of quotas and Key Performance Indicators. As soon as I write the word “goals” on a sheet of paper I get drowsy.

Yet the wiser part of you knows that to live a great life, you need to do goal-like things, and do them on your own initiative. You need to form your own aspirations, define their completion criteria, and work towards them systematically. And these efforts have to happen now, not in some hypothetical later-state; they must happen alongside regular, busy, workaday life, or they won’t happen. I’ve said all this before.

Still, the tendency is to wait for a better, less cluttered stretch of time to appear before you do that. You will execute your great plans as soon as life becomes a little easier and more spacious than it is now.

This is exactly backwards. Forming and achieving aspirations is how life gets easier and more spacious. It’s how people build skills, gain experience, invent things, declutter their homes and lives, start businesses, and enrich the mind with art, exploration, and creative work.

Last year I launched a pilot program for helping people do that – achieve a significant personal victory, over eight weeks, while you live your normal workaday life.

I called it One Big Win — the idea being that if you can pull off a personal win like this once, without waiting for better life conditions, you know you can do it again and again using the same method.

And the next time will be easier. Each win could add a new and empowering condition to your life: new skills, time-saving systems, organized spaces, a new income stream, more possibility in one way or another.

The Quest Mentality

The conventional term for this sort of personal campaign is a “short-term goal.” But I suggested to OBW participants that they drop the G-word in favor of something more fanciful: the quest.

If that sounds a bit whimsical, hear me out. Whereas “goal” has become a tired and bloodless descriptor for the (supposed) intention to do something great, the word quest instills the right mentality for achieving a real-life personal victory:

A quest is an adventure, and you expect it to be one. You expect a quest to take you into a new and unfamiliar landscape. You expect there to be puzzles, surprises, perils, and curious encounters. A bridge you counted on will be out. You’ll meet an interesting stranger on the path. You’ll hear wolves howling at night. This is all part of the fun. The goal mentality frames this stuff as setbacks, problems, pains – stuff in the way of the goal.

A quest changes you, not just your situation. Goals are practical attempts to change your circumstances. A quest is personally transformative – the endeavor itself shapes who you are, and what you’re capable of. It’s not only the reward that does this, it’s your inevitable encounters with the unfamiliar, and the new capabilities you gain as you handle these encounters. You don’t just get the novel started, you become a writer. You don’t just declutter the house, you get your house in order.

A quest has a dragon to slay (and it’s inside you). In all worthy quests, you (the hero) at some point will face a fearsome beast that seems at first like it will be your doom. Maybe there’s a tough conversation you have to have, or a tricky concept you have to learn. From a distance, the dragon always seems unconquerable, yet the hero finds a way. In epic fantasy tales, the dragon is always symbolic — the hero defeats it by overcoming some inner sense of limitation, which they had believed was a permanent flaw.

Also, the dragon always guards a hoard of treasure – your life-expanding reward for overcoming this particular inner limitation.

A quest can change the world. Everything great ever achieved required someone to overcome an internal obstacle. Society is built from realized human aspirations. Your project may be humble, but the way it transforms you is a big deal. It will bring more capability into the world as a whole.

This way of thinking about goals is what I call the quest mentality. In OBW, the Block method, which you may already know, is your trusty walking stick, your magic wand, the sword at your side. It also helps to have people questing alongside you (just ask Frodo).

In the first run of OBW, many people remarked that the quest mentality, and particularly the dragon, was the most powerful part of it. The goal mentality sees the dragon as bad, but in the quest mentality, it’s the key, or at least a clue, to becoming the version of you who actually achieves goals, and no longer waits for a better time.

The surprising thing about the dragon is that it doesn’t actually want to fight you. It wants to frighten you into going home, or not starting at all. Many participants chose a particular day to tackle their “dragon,” and found that it only took two or three 25-minute Blocks to properly slay the thing — it was scary to actually show up for the battle, but as long as they did, the dragon was no match for them.

The Quests People Did

Here are some of the quests people took on:

• Declutter the whole house
• Record an EP
• Prep six months’ worth of lessons for my students
• Set up an artist’s workspace
• Finish two short stories
• Gain a basic knowledge of classical music
• Fill every page in a sketchbook with drawings
• Complete a classical guitar program
• Make an “If I get hit by a bus” folder for my family
• Get rid of everything I don’t need
• Learn a new programming language
• Finalize retirement plans
• Create a mosaic wall surrounding a fireplace
• Compose two original pieces of music
• Get rid of hoarded possessions and invite people for coffee at the end
• Start a podcast and launch the first episode
• Set up a biodiverse garden on the balcony
• Build an app for a client
• Get up to speed on my financial position and make new budget
• Set up a home recording studio
• Write and submit a research proposal

You can perhaps imagine, for some of these, which part was the dragon – the crux moment, often close to the end, where you really want to delay, compromise, or wait for a better time. It was really cool to see people conquer their dragons.

Once you slay your first one, you know how the dragon operates. It still inspires fear, and the fear is real, but you know it can’t actually stop you. One person I spoke to today is on her fourth big win since last winter’s inaugural session.

*** Update (8/24) The group is full and registration is now CLOSED for this session. There will be another cohort in 2025. ***

I’m running the second One Big Win group session in just a few weeks, and registration is open as of right now.

The official group start date is August 26^th, but once you’re registered you can begin on any day you choose.

Selecting a personal quest is part of the course, so you don’t have to have one in mind already. The whole thing will be done in eight weeks, and you don’t have to wait for life to stop being busy first.

Sign up now | How does it work?

The program is still in beta so there is still a large (~$60) discount for participants this time.

The eight weeks will pass by anyway (and then another eight weeks, and so on). You can have something genuinely exciting to show for it, and a method for doing it again and again. New landscapes await.

***