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Obviously, Winter Summer Bash is delightful and fun and rewards regulars with a little gamification. But it also seems like a fairly large effort to plan, design, and maintain. Is there a business reason for Stack Exchange as a company to do the bash each year?

Example: Your fiscal year is ending and you need a large burst of participation around certain community-improving tasks to close out the year?

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    IIRC essentially that's the reason, traditionally activity dips at the end of the year, and it keeps people engaged.
    – Journeyman Geek Mod
    Commented Dec 22, 2022 at 0:30

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In addition to rationale in other answers, the event shows, in an engaging way, some new features introduced by Stack Exchange in recent years, which users might not know about or are not used to. Moreover, during the search for Secret Hats, the users would try some features/flows they had never used before (I sure did) or get to rarely visited pages (like Cookies Settings or Legal).

For example, this year, we have several such hats for relatively new additions to the Stack Exchange network:

  • A penny saved hat that encourages saving posts (the mechanics of saves/bookmarks changed recently).
  • Lifesaver hat that demonstrates the use of custom save lists (I totally did not know about this useful feature before this Winter/Summer Bash).
  • 2cool4skool hat promotes Dark Mode (was also promoted by another hat during Winter Bash 2021).
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    If you want some supporting documentation. meta.stackexchange.com/a/384857/284336
    – Catija StaffMod
    Commented Dec 22, 2022 at 2:47
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    @Catija "CMs are the ones who come up with the ideas for the hats and their triggers." Ohh, then Winter Bash is also an act of humorous creativity by the CM team 😲 that's nice to know because you're the staff members we tend to interact most with 😊
    – bad_coder
    Commented Dec 22, 2022 at 6:36
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    @bad_coder You may think that creating Winterbash hats is fun and relaxing, but it is some of the most intense, stressful, difficult, and strenuous work Community Management has to offer. The hours spent in deep contemplation, the intense whiteboarding, for weeks - nay, sometimes months - in advance of release, all focused on the solitary goal of creating the most perfect hat, would put the work of even the most ardent scientists to shame. Truly, there is no higher honor, nor any greater challenge, in this world.
    – Slate StaffMod
    Commented Dec 22, 2022 at 18:17
  • @Slate That’s beautiful…
    – Izquierdo
    Commented Dec 26, 2022 at 2:38
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with a little gamification

It's more about entertainment than gamification since the gains end when the event.

Is there a business reason for Stack Exchange as a company to do the bash each year?

User engagement. Every commercial venture out there (online or brick&mortar) focuses on the holiday season, so to keep competitive and capture (or just retain) the level of attention the userbase has through the remainder of the year you have to do something.

But keeping a less machiavellian view of things, SE hosts an event for our leisure and to break the monotony at the end of the calendar year.

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The reason I've heard in the past is to encourage activity during a period where a lot of activity drops off due to the holidays. Additionally, this year, Winter Bash brought in a sponsorship:

splunk hat, sponsored by Splunk®

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It motivates users to engage. This may encourage them to do so through the year, thus increasing the usefulness of the site. Other actions are beneficial even if only annual: clearing out review queues, for instance.

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