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Do Quests, Not Goals

South Island New Zealand aka Middle-Earth

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.

Just met department revenue target for Q3

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.

Better, less cluttered stretch of time finally secured

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.

Does quests AND day job

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).

You, duly equipped

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.

“Quests are for losers! Stay home!”

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.

(You can start with something smaller)

*** 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 26th, 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.

***

{ 39 Comments }

kate August 8, 2024 at 11:03 am

read ‘the war of art’ – steven Pressfield. it’s short and calls you out on your stuff.

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David Cain August 8, 2024 at 12:12 pm

I’ve read it. It’s a good one. I still think about the “resistance” concept all the time, particularly when it comes to writing.

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Laurie August 8, 2024 at 11:05 am

Hi David, I’m super interested. What access do we get to you? Are you in the group forum? Any coaching calls?

Thank you, your work has changed my life.

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David Cain August 8, 2024 at 12:15 pm

I read/respond to all forum threads and you can email me with questions whenever you need. No coaching calls at this point but maybe in the future.

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kiwano August 8, 2024 at 11:35 am

…and now I’m wating for some HR/management type to share your observation about “goals”, and start the process of attaching the same soporific, institutional soullessness to “quests” — but at least the term still works now (and the rationale is quite good, even in the face of the relentlessness of the inspirational treadmill)

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David Cain August 8, 2024 at 12:15 pm

Haha… that may be inevitable if this catches on.

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Amy August 9, 2024 at 9:30 am

Currently feeling dragged down by the day job aspect of things. The Indiana Jones pic + caption made it feel a bit more questy. Might mess around and make some new business cards

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Pebbles August 21, 2024 at 2:37 am

What a great read! Thanks David I started my ‘quest’ in autumn ’22 as a mature student studying for a degree. I added learning a language last year. This year I’ve been decluttering and added a fitness regime. It’s been such fun feeling the joy of achievement

Oleksii August 9, 2024 at 5:48 am

I am a manager, can confirm.

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patti hirschberg August 8, 2024 at 12:23 pm

Sorry, but i’d love to see a similar list applicable for those who are not
privileged/white and want to make our suffering world a better place. Where’s the tangible goals that would make a difference, eg. recycling initiatives, joining environmental groups etc. The world’s on fire. Our unprecedented existential threats are reflected in mental health stats, ie. our mental health/anxiety crisis. If you wanna Inspire, wake up!

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David Cain August 8, 2024 at 1:27 pm

Keep the race war stuff out of my comment section please.

One project for you might be to read with a charitable mindset something that does not confirm your existing views. Definitely challenging and transformative, and most people never get around to it. The world and its people are more interesting (and diverse) than you might think.

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mehul August 9, 2024 at 9:39 am

I’m not white and I don’t come from a privileged background yet I found the post to be incredibly useful in reframing a bunch of things I’m working towards. The mental model is universal and can be applied to the initiatives you mentioned, can you not reframe them as quests? Maybe your mental health and anxiety wouldn’t be so intense if you did?

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Todd August 11, 2024 at 7:02 pm

So interesting you called out your race as if that’s a factor in goal setting. Please explain what the color of your skin and socioeconomic status has to do with trying to do better.

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Tari August 11, 2024 at 7:21 am

I would agree that quests can be multi-colored and the list shown was not representative of our world. The concept of replacing the word “goal” with quest is a fantastic approach and I will be happy to use this in my academic coaching with the diverse group of students that I work with.

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David Cain August 11, 2024 at 8:16 am

Can you please break down for us which goals are appropriate for which race?

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James August 20, 2024 at 12:45 pm

David, get off the defensive and grow up. Both of these comments are clumsily worded but have charitable interpretations that you’re choosing to ignore.

The first person (patti) was clearly just having a cranky day. She thought the goal examples had insouciant “first world” vibes and it bothered them. She could (and should) have simply offered suggestions for other goals, but instead made a snarky comment that clearly wasn’t thought-out (since I doubt she *actually* thinks non-white people are unable or unworthy of coding, gardening, etc.).

Was it an emotional, unconstructive and unkind comment? Yes. Did you need to stoop to its level? No. Instead of getting triggered and embarrassing yourself, you could have simply stated the facts: participants are free to choose whatever project they want; it’s fine to do projects in your spare time that aren’t about saving the world; feel free to join and do a project you think could improve your community.

As for Tahi… uh, they’re clearly agreeing with you. “I would agree that quests can be multi-colored” = anyone can do these quests. “the list shown was not representative of our world” = the list isn’t trying to reflect every type of concern/person. They then praise the project and say they will use it in the classroom.

In conclusion, chill the fuck out. “I’m polite, serene and open-minded unless someone triggers my white fragility” is not a good look for yourself or your business.

Kay August 8, 2024 at 2:06 pm

One Big Win is exactly what David explains so well. If you are at all attracted by it, you’ve got everything to gain if you go for it. I was one of that first group he describes. The shift from the feeling of a “goal” to the feeling of a “quest” was one of my two biggest outcomes, and the one that allowed me to start and keep going. Lots of the people in the first group tackled more tangible and/or creative projects and accomplished them–in retrospect you could say they reached goals, though they weren’t just about that. I admired them all and learned a lot from the discussions. My own quest did not exactly have an “outcome” because the things that matter most to me are always unfolding. So I used the OBW to give myself permission to focus on my own less tangible, more inner quest. Spending focussed time and being eager to do so, just to see what would happen by the end of the 8 weeks, was a grand journey! Dragon deflated, check. Sense of accomplishment, check. In a new and better place at the end, check. Ready for the next creative step, check.

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David Cain August 8, 2024 at 4:09 pm

Excellent. I’m going to send out an email about this soon, but all of the first group’s members are welcome to jump in for this one too, if you want to do another quest.

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Deb August 8, 2024 at 6:14 pm

I’ve been reading your site forever and have been inspired by so many posts! I love the pics and captions. They make me laugh every time.

I want to join the questing group but wanted to make sure the forum is a regular secure website not Facebook or similar correct. I’m not on Facebook and have no desire to be.

Thanks again for sharing your unique take on the world we live in.

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David Cain August 9, 2024 at 7:47 am

Hi Deb. The forum is on Discourse, which is secure, and the conversations are not indexed by search engines. You can also stay anonymous by choosing any username you like.

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Matthias Klose August 8, 2024 at 9:33 pm

Uplifting Read, proper Vehicle! Many thanks.

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Raithe August 9, 2024 at 2:40 am

To make it even more interesting, use a program that gamifies it: https://habitica.com/ :)

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Jules August 9, 2024 at 10:49 am

I’m in! I’ve been reading your posts for years and always learn something worthwhile. Looking forward to this!

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David Cain August 9, 2024 at 11:14 am

Woo!

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Daniel Ryan August 9, 2024 at 1:57 pm

Also reminds me of the excellent short book “How to Fight a Hydra”

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Miguel August 10, 2024 at 7:20 am

Love it! I can see how re-framing goals as quests gives it a whole different outlook.

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Shane August 10, 2024 at 8:40 am

l love the mindset switch from goals to quest. Very clever.

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Khürt Williams August 10, 2024 at 9:54 pm

Changing the word doesn’t change anything for me. It’s just a word change. Like calling red blue and blue green. But I’ve never had a problem with goals.

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Rose brinks August 11, 2024 at 8:16 am

This reminds me of what Father Thomas Merton wrote: “Do not depend on the hope of results, when you are doing the sort of work you have taken on. You may have to face the fact your work mat be apparently worthless and even achieve no worth at all, if not perhaps, results opposite of what you expect. As you get used to this idea, you will start more and more to concentrate not on the results, but on the value , the rightness, the truth of the work itself.”

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Stefan August 11, 2024 at 8:16 am

I’ve learned that waiting for the perfect time never works. Just start now, even if life is busy. It’s like going on an adventure—along the way, you grow and discover new strengths you didn’t know you had.

Btw, great article, tnx for sharing your thoughts!

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I hurley August 11, 2024 at 4:40 pm

I am a therapist that works with a fragile population that is homeless, exposed or victims of complex traumas, hopelessness, and life of pain. Our weekly sessions do not include discussions of setting goals to declutter or write a novel, they are more basic in need: Find safety, Obtain food & medical care, Flee abuse, Find stable /livable wage employment, manage severe mental illness & poverty. Your concept of a Quest versus Goals is beautiful and very relatable. Thank you

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Ali August 11, 2024 at 7:38 pm

You’ve hit on something I have been doing for 5+ years.

I have an LLC named Human Quest, and under it, I build products with the name “X Quest”.

For example
Handstand Quest: https://handstandquest.com

Plan Quest: https://plans.quest

I am launching 2 new quests and have 10’s in the backlog (aspirations like you mentioned)

Given what you write about, I feel like there is a large opportunity for us to combine efforts, especially on Plan Quest, which was built to help people turn their aspirations into achievements.

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Vlad August 12, 2024 at 12:45 am

Sign me up!

Still can’t believe how much you can influence my inner world via text, David; through the years this has been my favorite blog. You’ve been my meditation and mindfulness teacher, I’m very grateful.

Kinda stuck with goals, mostly also because the market doesn’t seem to respond proportional to my input, I’m learning helplessness, I fear. Thanks for putting the blocks in my focus again.

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David Cain August 12, 2024 at 8:06 am

Welcome Vlad! I’m looking forward to seeing what quest you choose. Whatever it is we will find a way.

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Rachel MacDonald August 17, 2024 at 11:07 pm

Hi David, I’ve just now discovered your work but it is really inspiring. I like this idea of a quest, not just a goal! Mindvalley also uses the term quest but they mean a course of 20 min a day…

I like your idea better because, indeed, our lives are not linear. There will be mountains and valleys and rapids with rafts and forests etc. To go through. In a quest, we expect that is part of the journey! And it’s exciting n motivational, not discouraging.

In response to the person who wrote that your list is white centred… mmm, I don’t think so. It’s not even first world centred. As long as people are fed and clothed and sheltered and have safety, we all seek fulfillment and have the same longings. I’m mixed race, by the way.

But all people can go on quests! Every culture has quests in their literature and stories. It is in large part our stories which give meaning to our lives!

So, this is good, and thank you!
Peace, Rachel in Canada.

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David Cain August 18, 2024 at 11:19 am

Thanks Rachel. I agree. Most people found that they achieved their quest in bursts, some days doing a lot more than others. One short session a day sounds good on paper, but life unfolds unevenly and when you miss one you already feel like you’ve botched the plan. Later in the course there’s a suggestion to “take a day,” where you devote a half or full day to the project, to bring the whole thing one massive step forward. Many people said this was the pivotal day of their quest.

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Chodpa August 31, 2024 at 4:35 am

Thank you for such a reflective article. I just wanted to share that sometimes the right way for some people is to rest in openness, and the letting go and ability to rest in the present allows the right path to open up for us. All without hankering after goals, or chasing tomorrow. Something profound often unfolds when we truly let go.

thanks once again.

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Anne-Sophie September 5, 2024 at 4:24 am

Thanks so much for your article – this is so inspiring!I love this way of seeing things, evolving and transforming along the way!

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sahar September 24, 2024 at 12:05 am

Download lamentation, I dreamed of tears and harem

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