Comfort zone challenges you do alone

Most lists of comfort zone challenges are made of cold showers, waking up at five, and speaking up in meetings. Two of those are discipline rather than nerve, and the third needs a meeting. These are all things you do on your own, in public, graded from one to five so you can find the rung you are actually on.

What counts as a comfort zone challenge here

Three rules, which between them rule out most of what usually appears on these lists.

It is one discrete act with an end. Not a thirty-day habit. A challenge you can fail at four in the afternoon and be finished with by five is a different kind of thing from a month of journalling, and it is the kind that moves nerve rather than discipline.

You do it alone. This is the filter the rest of the internet does not apply. Going to a comedy night with three friends is a nice evening. Going on your own is the challenge. Almost every published list quietly assumes company, which is why they are full of things that are not frightening.

It is uncomfortable, not risky. Nothing here involves alcohol, driving, remote places after dark, or anybody else's boundaries. Discomfort you chose is the point; risk is a different thing wearing the same jacket.

The five levels

Difficulty is not duration. A thirty-day gratitude list is easier than one dinner. What makes something hard is how visible you are, for how long, and whether you have to speak:

1Ten minutes, and nobody is looking.
2Visibly alone, briefly.
3Visibly alone, for a while.
4An unfamiliar setting, plus talking to strangers.
5Several days, and your own logistics.

Level 1: ten minutes, and nobody is looking

These take less time than deciding whether to do them. That is deliberate — the first rung exists to be cleared today, not to be admired.

Difficulty 1 of 5 Order a coffee and drink it in the cafe, alone. Sitting in counts. A takeaway cup on the way to work does not.

Difficulty 1 of 5 Walk for twenty minutes with your phone in your pocket. No music, no podcast, no screen. Just the walk and whatever is around you.

Difficulty 1 of 5 Ask a stranger for directions even if you know the way. One question, a thank you, and off you go.

Difficulty 1 of 5 Spend one hour with no phone and no music. Put it in another room. Sit, walk, or do nothing at all for the full hour.

Level 2: visibly alone, briefly

The step up is being seen. Not for long, and with a clear exit, but seen — and by strangers who can tell you came on your own.

Difficulty 2 of 5 Take the window seat in a cafe and eat lunch facing the street. The seat everyone walking past can see, a proper plate rather than a snack, and you stay until it is finished with your phone in your bag.

Difficulty 2 of 5 See a matinee at the cinema, alone. Buy one ticket, sit in the middle, stay until the credits finish.

Difficulty 2 of 5 Get your hair cut somewhere you have never been. New place, new person, and you say out loud what you want.

Difficulty 2 of 5 Tell a stranger you like what they are wearing, and say what exactly. Name the thing, the jacket, the shoes, the scarf, in one sentence, then leave them to their day.

Level 3: visibly alone, for a while

Now there is no quick exit. You are in a room, on your own, for an hour or two, and the discomfort has time to arrive and then time to fade — which is the actual lesson of this rung.

Difficulty 3 of 5 Eat dinner somewhere with tablecloths, alone. A proper restaurant, a proper table, and you stay for the whole meal.

Difficulty 3 of 5 Take a gym class where you know nobody. The back row is fine. Staying until the end is the mission.

Difficulty 3 of 5 Work or study in a busy cafe for two hours, alone. A table in the middle of the room, not the one facing the wall.

Difficulty 3 of 5 Start a conversation with the person next to you in a queue. Ask what they are hoping to get and keep talking until one of you reaches the front.

Level 4: somewhere new, and you have to speak

Two things at once: a place you do not know, and a conversation you cannot avoid. This is where most people's actual comfort zone edge sits, and it is the rung worth aiming at rather than the fives.

Everything from here up carries the same note, and it is not decoration: tell one person where you are going and when you will be back.

Difficulty 4 of 5 Turn up to the first meeting of a club or group alone. Introduce yourself to two people before you leave.

Difficulty 4 of 5 Go to a gig by a band you love, alone, and dance. Stand in the crowd rather than at the back wall, and move to at least three songs the way you would if nobody could see you.

Difficulty 4 of 5 Spend one night away on your own. One night, one bag, somewhere you booked yourself.

Difficulty 4 of 5 Take a partner-dance class alone and dance with whoever you are paired with. Salsa, tango, swing or similar, a beginners class you booked alone, and you rotate partners the way the class does rather than sitting a round out.

Level 5: several days, and your own logistics

These are not harder in the moment than a level 4. They are harder because there is no going home at nine, and because everything that goes wrong is yours to fix.

Difficulty 5 of 5 Go to a country where you know nobody. Arrive, work it out on the ground, come home with a story.

Difficulty 5 of 5 Go to a multi-day festival by yourself. Two nights or more, your own tent or room, your own schedule.

Difficulty 5 of 5 Spend a weekend alone in a rented cabin. Two nights, booked by you, with your own food and no visitors, and at least one full day where you speak to nobody at all.

Difficulty 5 of 5 Book a weekend group trip where you know nobody. A guided walk, a hobby weekend or an organised excursion with two nights away; talk to everyone in the group by the end of it.

Why the category matters as much as the level

If you only ever pick from one kind of thing, you get good at that thing and no further. Somebody who does four level 2s in cafes has learned about cafes.

So the challenges are drawn from seven kinds of activity — food, culture, movement, travel, everyday errands, deliberate solitude, and speaking to people. Doing a level 2 in three different categories teaches you more than doing a level 4 in the one you already like. Speaking to people, in particular, is a separate nerve from being alone in public, and it is the one people skip; keeping it as its own category is what stops a whole month passing without a word said to a stranger. The full spread across the seven is on its own page.

How to tell whether it is working

The problem with every list like this, including this one, is that a list can only record what you did. It cannot tell you whether it changed anything, and "get out of your comfort zone" is a slogan until something moves.

The fix is two numbers. Before the challenge, write down how nervous it makes you, one to ten. Afterwards, write it down again. Keep both.

What you get after a couple of months is a line rather than a checklist, and the line does something a checklist cannot: it distinguishes practising from collecting. If you have done nine challenges and the before-number is where it was in week one, you have been picking things that were never uncomfortable. That is useful to know, and it is not something you would notice from a list of ticks.

It also makes repeats worth something. The second and third time you do the same level 3 is where the number actually falls, which is why a good run is not thirty different challenges but ten challenges done three times each.

Solo Era does the picking

One challenge a week, assigned from the seven categories on the same five levels, with both numbers recorded and the line drawn for you. Missions stay ticked off permanently, so the list only ever goes one way. An iPhone app.

Questions about comfort zone challenges

What is a good first comfort zone challenge?

A level 1 in the category that already suits you, done this week at a quiet hour. Not the one that would make the best story. The dull one you can definitely finish, because finishing is what makes the second one happen.

How often should I do one?

Once a week is enough and is better than once a day. Daily challenges turn into a streak you are protecting, and protecting a streak makes you pick easy ones. A week is long enough that the next one has to be chosen on purpose.

What if I bail halfway through?

Write both numbers down anyway and try the same one again. A challenge you abandoned is more informative than one you skipped, and the level below it is not a demotion — it is the rung you were actually on.

Are 30-day comfort zone challenges any good?

For habits, yes. For nerve, less so: thirty days of small daily acts builds discipline, and the thing that makes a restaurant easier is doing the restaurant. If you want a short structured run to begin with, the seven-day version escalates properly over a week and then hands you back to a weekly pace.

Not sure which level fits you? Take the free comfort zone quiz and get your level with three first steps.