How to Avoid Taking a Job You Hate

The goal is simple

To avoid taking a job you hate
To never spend a Sunday dreading a Monday
To seldom submit to an authority you don’t respect
To not feel like you’re throwing your life away

The goal is simple

To do work you love
To be around people you enjoy
To happily commit to new projects
To make your little dent in the world

The goal is simple, the path is tricky
So it’s best to start early—in your teens or twenties

Here’s the way I see it


First, explore the world
Poke your head into every nook and cranny
Indulge and expand your curiosities
Become a student of everything

Eventually, you will find something
Something that lights your mind on fire
Something you can’t turn away from
Something you can’t not do

This is your thing—for now, at least
Devote yourself, become its humble servant
Read, watch, discuss, practice, observe
Ask every question, follow every lead

Soon you’ll understand the players, the game, the rules
The philosophy, the inner workings
Soon you’ll be able to explain this thing
To communicate its essence with simple language

Now, you’ve done your homework
Now, you’re in a position to contribute
Now, you can add value
Now, you go deeper


Begin by volunteering

With any luck, you’ll become a literal volunteer
Doing simple tasks in exchange for a view inside
Watching, assisting, note-taking, chit-chatting
Separating fictions from the facts on the ground

Internships, apprenticeships, exchanges—all are wonderful
But don’t limit yourself to formal opportunities
Because if you wait for authority’s permission
Your journey will soon end

Instead, find your own way to volunteer
To add something to this little world
To become useful
To someone, anyone

Craft a video, take a photo
Contribute to a subreddit, a wikipedia, a fan page
Explain a tricky idea, tell a story, curate resources
Convene a meetup, put on a little event

When you’re unsure about where to go next
Become again the curious explorer, the humble servant
Ask again “how can I help?”
Learn, create, share, repeat

No matter which path you take,
Remember to bring yourself, your story
Your quirks, your weirdness, your joys, your sadness
Mix these into everything you do

For if you try to speak in some impartial, neutral voice
Few will listen, fewer will care

You will scream into the void, wondering what’s wrong
Forgetting that people care about people
So don’t forget to be a person with a personality

Now, you are beginning to contribute
Now, you are giving others a reason to care
Now, you begin to make friends and allies
Now, the snowball rolls downhill


Now, you can begin to look for a job
An amazing job, a dream job

The competition will be fierce
But you have a secret weapon

For you have more than a killer résumé or a clever cover letter
You have skin in the game
You have proved your dedication
You have explored this landscape, made your own map

Even if you lack formal credentials
You possess connections, conviction
You care in a way that others don’t

If those guarding the front door don’t understand
If Human Resources leaves you out in the rain
Find your way to the side door

Look for small ways to interact with people in this organization
Meet them online, find them in real life
Share what you’ve learned, seen, built

Eventually, one may say—“Hey, you should work here”
And you’ll say—“Why, what a fabulous idea!”
An introduction will be made
The snowball rolls downhill

Or perhaps they’ll show you that this dream job
Is actually not so dreamy
Saving you time, effort, grief
Propelling you toward the next opportunity

Either way, put little faith in the traditional hiring process
Sending out applications is the easy part
Learning, creating, connecting is the hard part


And what if your dream job doesn’t exist?
What if you bristle at bosses, bureaucracy, hierarchy?
Then strike out on your own

Begin again with the spirit of volunteering
Return to the question, “how can I help?”
Look for biggest small problems you can find

Seek whichever unique brand of suffering
You hardly consider suffering at all
Seek that which others call “hard”
And you call “fun”

Look for where you possess an “unfair advantage”
Because you’ve invested so much already

Eventually you’ll find something that others need
But cannot or will not provide for themselves
Thus they will pay you
To provide it for them

This is your business

Start as small as you can, as soon as you can
Make yourself useful to whoever will engage you
Charge just enough to cover your costs, or nothing at all
You will be paid in feedback and experience

Over time, you can begin to charge more
Over time, you can expand your client base
Over time, you can learn accounting, marketing, taxes
Over time, you can become “official”

For now, focus on delighting your first customers
Listen to their comments, make little tweaks
Gather their testimonials, encourage referrals
Make these people the center of your world

This is the heart of self-employment
To do what you love, but not just for yourself
To get a little better with each go round
To delight in delighting others


Self-employment, regular employment
Each can be lover or tyrant
Best to remain open and agnostic
Following any opportunity to learn, grow, contribute

By that point, anyway, your ship is at sea
You’ll know the winds better than I

So let’s finish by asking, what will sink your ship
Before it even leaves the harbor?

First is waiting for permission

Permission to start learning, creating, volunteering, associating
If you wait for permission, you’re dead in the water
You’ll wait in line for the next bullshit job
You’ll wait to win the lottery

If you picked up this nasty habit in school
Kick it now, cold turkey
Don’t wait for permission to begin
Just set sail

Second is lack of time

To explore the world, to indulge your curiosities
To play, experiment, weather setbacks and false starts
This requires time
And time requires food, shelter, internet, et cetera

So begin early, ideally when you’re still supported
If you’re in school, consider unschooling
If you’re in college, look beyond your classes
If you’re already working, find your secret space

Third is perfectionism

Following a passion is not the same as waiting for a perfect opportunity
Any attempt to contribute, to be useful, to transcend “normal”
May stutter, fail, and mildly embarrass
Accept this, now and forever

Perfectionism is fear masquerading as strength
Perfectionism is the fast track to anxiety
The ship mustn’t look perfect
All it must do is float


Also posted on Facebook.



💬 Want to leave a comment?

Please get in touch directly--I'd love to hear from you.