I was talking to a friend the other day who was trying to get out of a slump. He felt emotionally flat and bored. I suggested he try something new —something he hadn’t done in a while, or maybe even something he’d never done before—a quest, so to speak.
My friend isn’t alone.
We’ve all been there before, myself included. In the modern world, we are all too prone to sleepwalking through life, perpetually going through the motions in a kind of half-dead, half-alive trance.
In trying to eliminate all friction and discomfort from our lives, we’ve made our lives boring. But this need not be the case.
Humans aren’t machines. We are meant to care. We are meant to struggle. We are meant to feel doubt and apprehension and resistance and fear—and we are meant to overcome it. All of which is to say we are meant to exert effort, and we are meant to go on quests.
Here are 33 to try in October.
These quests are simple and practical for a reason: there is a powerful inertia to action. A fundamental truth of the universe is that the little things add up, sometimes in surprisingly big ways.
Go on a day hike somewhere new.
Watch the sunrise from your porch with coffee or tea.
Host a dinner party.
Send a handwritten note to a mentor thanking them for their guidance.
Read an entire book—or two, or three—before the month ends.
Plant something in your yard: flowers, a tree, tomatoes— anything goes, so long as it’s alive.
Take a digital sabbath: one full day without your phone or computer.
Attend a live concert (it doesn’t have to be big or someone famous)
Have a difficult conversation you’ve been putting off.
Take a long walk without your phone.
Watch a serious documentary: my recent favorites include RAFA, Come See Me In the Good Light, and Untold: The Testimony of Vince Young.
Work out of a new coffee shop.
Cook something you never have before.
Sign up for a lesson or course to develop a skill.
Donate blood at your local Red Cross.
Clean out your closet: give away anything you haven’t worn in the last six months and wouldn’t think to wear in the next.
Do one really hard workout, where the whole point is testing yourself.
Listen to an album straight through with no distractions.
Eat at a restaurant you’ve never been; ask the waiter or waitress what to order and then order that, no questions asked.
Write down 3 goals for the next month, the next year, and the next decade.
Take an inventory of the apps on your phone that zap your energy. Delete them. Just do it.
Try a new morning routine for 3 consecutive days: keep it simple.
Watch the sunset. You may want to do it again, and again, and again.
Sign up to volunteer-coach or teach in your community.
Take one week where you don’t use any digital devices after 8 PM, including Netflix. See how you feel.
Learn how to deadlift.
Buy a small notebook, carry it around, and jot down interesting observations and thoughts.
Do not use AI for creative work.
Keep your phone out of the dining room at least three nights each week.
Pick an activity you do regularly and ask yourself how you could make it more fun; then do that.
Label the emotions you feel so you can respond to them instead of reacting.
Give yourself permission to care deeply and try your hardest on something where you’ve been holding back.
Reflect on what you found most valuable and make a plan to stick with it next month.
Choose at least three to five to try. And share with your friends!
Hi Brad,
I like the framing of a quest because it gives effort a direction without requiring us to pretend we have discovered some singular, preordained purpose.
A good one creates uncertainty, resistance, and movement; in the process, it can reveal capacities that comfort rarely ever does.
I’m increasingly interested in what happens when one quest ends, though. We can get very good at pursuing what is measurable and difficult, then mistake the ability to complete quests for knowing what deserves our devotion next.
I think part of a well-lived life is learning to recognize when an old one has finished and allowing the next one to emerge from a different part of us.
One I am trying out is squash. I haven't played since I learned in high school in the early 90s. It goes for about 5 months..and is a box league...If I drop to the bottom box and never make it out....at least I played a bunch of squash games and met new people.