A 100-day challenge with friends to finish the year walking
The last 100 days of a year begin on 23 September, which makes late September the one moment when “starting on Monday” and “finishing the year properly” are the same decision. A 100-day challenge with friends works because it is long enough to change a habit and short enough to see the end. Here is how to structure one so it survives October, November and the holidays, rather than dying in week three.
The dates, so you can stop doing the arithmetic
Counting the last day of the year as day 100, the last 100 days start on 23 September. If you are reading this later, the other useful start dates are 1 October, which gives 92 days, and 1 November, which gives 61. None of them matter more than picking one and telling people, but a round number is easier to get five friends to agree to than a vague “let's do something for the rest of the year”.
Pick a start date at least three or four days out. People need to install anything they need, grant permissions, and get their watch talking to their phone. A challenge announced and started on the same day loses everyone who was busy that evening.
- 23 September: the last 100 days of the year
- 1 October: 92 days, the cleanest month boundary
- 1 November: 61 days, still enough to build a habit
- 1 December: 31 days, better treated as a sprint
Why the rest of the year is the easiest stretch to commit to
January challenges are crowded, everybody is doing one, and the failure is so normal it barely registers. A challenge that runs to 31 December has a different shape: it ends on a date that already means something, it is bounded, and it goes through exactly the weeks when a walking habit usually collapses. Getting through the dark end of November is the whole prize.
It also sets you up. Arriving at 1 January already walking every day is a materially different position from arriving at it with a resolution.
The format that survives 100 days
Total-steps leaderboards do not survive this long. Whoever walks most in October is untouchable by November, and everyone else stops opening the app. A daily goal is better, because each day asks the same fair question, and a goal that climbs slowly is better still, because the challenge gets harder exactly when the weather is trying to make you quit.
That is how a Stepr league works: everyone clears a daily step goal, the goal rises by a fixed amount each day, and anyone under it when the day ends is out. The last one walking wins. One honest thing to know before you plan a hundred days around it: a survival league ends when one person is left, which with a normal ladder takes three to six weeks rather than a hundred days.
Two ways to make it actually last to 31 December
The first is a gentle ladder. Start at 3,000 steps and add 100 a day: by day 50 the bar is 7,900 and by day 100 it is 12,900, which is a real challenge but not an absurd one. Add free passes so illness and travel do not end someone's season in week two. A league set up this way is the closest thing to a single hundred-day run.
The second, and the one most groups enjoy more, is seasons. Run October, November and December as three separate leagues with the same friends. Each is short enough to be gripping, everyone who went out early gets back in on the first of the month, and you keep a running tally of who won each season. Stepr's You tab keeps a lifetime record of league wins, so the three seasons add up to something at the end of the year.
- One long league: 3,000 on day one, +100 a day, with a few free passes
- Three seasons: October, November and December, fresh start each month
- Duo lobbies so nobody faces November alone
- Agree the ladder before day one; changing it midway ends the arguments and the challenge
Planning around the holidays
Two weeks of the run are not normal weeks. Travel days are the single most common cause of a missed goal, usually because someone sat in a car or on a plane for nine hours, not because they were lazy. Decide what happens before you get there rather than arguing about it on 24 December.
The straightforward options: give every player two or three free passes at the start, or run December as a short sprint that finishes before people scatter, or switch to team lobbies for the final month so a travelling friend is carried by their team's combined goal. Airports, as it happens, are excellent for steps; long drives are where seasons end.
Keeping five friends in it through November
The mechanics that matter are unglamorous. Everyone needs to see the standings without asking, so a live page anyone can open beats somebody posting a screenshot. Everyone needs a warning before they lose, which is why Stepr says at 9 pm if you are short rather than telling you at midnight that you were. And nothing should be self-reported, because the moment one person's numbers look invented, the rest stop caring.
Beyond that, it is social. Name the league something stupid. Say something when a friend goes out. Take the walk after dinner with someone else rather than alone, because the friend you walk with is the actual accountability, and the app is just the thing that keeps score honestly.
Setting one up
One person creates the league, picks the start date and the ladder, chooses solo, duo or team, and drops the six-character code into the group chat. Up to 100 people join free from their own iPhone. Steps come from the motion sensor and Apple Health, so nobody types a number and an Apple Watch, Garmin or Fitbit that writes to Health counts too.
Joining is always free. Hosting is $18.99 once or $9.99 a month for unlimited leagues, and free for everyone during launch. Every player needs an iPhone for now; friends on Android can follow the standings page but cannot compete yet.
Questions people ask
When do the last 100 days of the year start?
23 September, counting 31 December as day 100. 1 October gives you 92 days and 1 November gives you 61, both of which are easier to remember and work just as well.
What is a good 100-day challenge to do with friends?
A daily step goal that climbs beats a total-steps race, because a race is decided in the first fortnight. Set a low day-one goal everyone can clear, raise it slightly each day, and agree what happens when someone misses before you start.
How do you keep a long challenge going past week three?
Make the daily target specific, make the count automatic so nothing is self-reported, give people a warning before they lose the day, and build in a few free passes for illness and travel. Most long challenges die from admin fatigue or one unverifiable score, not from lack of willpower.
Can a Stepr league run for a full 100 days?
It can, with a gentle ladder such as 3,000 steps rising 100 a day plus free passes, but a survival league ends as soon as one player is left. Many groups prefer three monthly seasons for October, November and December, keeping a tally of who won each.
Is it better to start now or wait until January?
Now. January challenges begin with everyone starting from scratch in the hardest month of the year. Arriving at 1 January with three months of daily walking behind you is a much better position than arriving with a resolution.
Start a league
Free to join. Share one code, and the last one walking wins.
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Last updated September 2026