← Back to Winlo The weekly challenge

One challenge. Every week.

The same challenge at the same time.

Each week brings a new challenge that every player takes on together. Most take 30 to 60 minutes. Some build community. Some push your body. Some quiet your mind. All of them nudge you just past comfortable.

The challenge library

A rotating set of 52 challenges. Here's the full lineup.

1

The Encouragement Call

Call someone going through something and spend at least 30 minutes just listening—no fixing, just presence.

2

The Sunrise Moment

Wake up early and watch a full sunrise, being fully present for the experience.

3

The Life Vision Night

Spend one uninterrupted evening planning your ideal life 5 years from now.

4

The New Activity Trial

Try a completely new physical activity you've never done before.

5

The Thought Dump

Journal continuously for 30 minutes without stopping or editing your thoughts.

6

The Coffee Invite

Invite someone you don't know well to grab coffee or a meal.

7

The Deep Clean Reset

Spend at least 45 minutes deeply cleaning one space in your life.

8

The Fear Blueprint

Reflect on your biggest fear and write a clear plan to confront it.

9

The Phone-Free Walk

Walk outdoors for one hour with your phone completely off—no distractions.

10

The Skill Gift

Spend 45–60 minutes helping someone using one of your personal skills.

11

The Personal Record

Attempt a personal record in fitness (speed, distance, reps, etc.).

12

The Distraction-Free Conversation

Have a 1-hour conversation with someone with no phones or distractions.

13

The Digital Declutter

Spend 45 minutes cleaning up emails, apps, and your digital workspace.

14

The Creative Hour

Spend one hour creating something purely for the process, not the outcome.

15

The Cold Plunge

Take a cold plunge or cold shower intentionally.

16

The Reconnect Call

Call a friend you haven't talked to in over a year and catch up.

17

The Generosity Stretch

Give away something that feels slightly uncomfortable to part with.

18

The Curiosity Deep Dive

Read or watch something long-form on a topic you know nothing about.

19

The Two-a-Day

Complete two workouts in one day (planned and intentional).

20

The Unplanned Hour

Spend 60 minutes doing absolutely nothing and observe your thoughts.

21

The Thoughtful Letter

Write and send a meaningful message to someone who impacted your life.

22

The Skill Builder

Learn and practice a small, specific skill every day this week.

23

The Sunset Fast

Fast from sunup to sundown for one full day.

24

The Social Host

Organize a small gathering and invite at least two people.

25

The Exploration Hour

Explore a new place for at least 45 minutes with full curiosity.

26

The Future Letter

Write a letter to yourself one year from now and store it.

27

The Anonymous Act

Do a meaningful good deed without anyone knowing it was you.

28

The Documentary Night

Watch a full-length documentary on a completely unfamiliar subject.

29

The Sunrise Workout

Complete a workout at sunrise.

30

The Mentor Ask

Ask someone you respect for advice and apply it.

31

The Childhood Throwback

Do something you loved as a kid and fully lean into it.

32

The Half-Year Plan

Map out your next 6 months with clear, actionable steps.

33

The No-Tech Day

Take one full day completely off all technology.

34

The 60-Minute Workout

Complete at least one 60+ minute workout this week.

35

The Community Hour

Spend at least 1 hour volunteering or engaging in your community.

36

The "See Them" Challenge

Intentionally engage with someone who is often overlooked.

37

The Give-It-Away Project

Prepare and give something meaningful to someone else.

38

The Advice Letter Exchange

Write from your 80-year-old self, then respond as your present self.

39

The Phone-Free Workout

Complete a full workout with no music, phone, or distractions.

40

The Declutter & Donate

Spend 45 minutes gathering items to give away to others.

41

The Family Reconnect

Reach out and reconnect with a family member you haven't spoken to in a while.

42

The Board Game Night

Invite a friend over for a planned activity like games or a movie.

43

The Silent Sit

Sit in silence for 30 minutes with no distractions.

44

The Early Wake-Up

Wake up 30 minutes earlier each day and use it intentionally.

45

The Imperfect Art Session

Create multiple pieces of intentionally "bad" art with no pressure.

46

The Off-Route Workout

Do a workout in a completely new location or route.

47

The Cook Something New

Prepare a new recipe using unfamiliar ingredients.

48

The Reframe Exercise

Reflect on past challenges and rewrite them as lessons.

49

The Weekly Review

Leave a detailed positive review for a business or creator.

50

The Workout Buddy

Complete a workout with a friend.

51

The Unsubscribe Sweep

Clean out subscriptions and organize your digital life.

52

The Let-It-Go Cleanout

Go through your belongings and remove what no longer serves you.

Take on this week's challenge.

Start your first week with Winlo — free on the App Store.

Download on the App Store