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40 Questions To Ask Every Year (2025)

Written By: Zachary Kai » Published: | Updated:

I saw Ava answer these a little while ago. Because I love participating in IndieWeb-adjacent prompts, I thought I’d join in. There’s still time before the year’s end if you want to write yours!

All credit goes to Steph Ango, who started asking these questions, and who knew! He’s Obsidian’s current CEO. Feels appropriate, given I wrote this using that beloved software.

Questions

What Did You Do This Year You’d Never Done Before?

Visited several new countries, got interviewed live on radio, contributed to a printed directory, got published in an American print magazine, and featured at a writers’ festival.

Did You Keep Your New Year’s Resolutions?

Most! Some no. I suppose that’s always the way it goes.

Did Anyone Close To You Give Birth?

Not anyone I know well, but a few people in my wider circles. Many congratulations to the wonderful, joyous new parents!

Did Anyone Close To You Die?

No, and I count my good fortune for that.

What Cities/States/Countries Did You Visit?

I spent time in Spain, Turkey, Albania, North Macedonia, and Kosovo (where I write this.)

What’d You Like To Have Next Year You Lacked This Year?

More peace of mind, at least within the influences that are in my control. And more completed projects instead of half-finished or a-third-started ones!

What Date(s) From This Year Remain Etched Upon Your Memory, And Why?

Good question! I don’t remember the exact date, but getting snowed on for the first time while waiting to board a plane in February was extraordinary.

What Was Your Biggest Achievement Of The Year?

It’s hard to choose! I’d say hosting two events for HTML Day 2025. Nerve-wracking, but fun!

What Was Your Biggest Failure?

Not republishing The Mara Files in all the usual places, and not setting up my Ko-Fi store.

What Other Hardships Did You Face?

Apart from the usual neurodivergent and anxious person struggles, I’ve been so lucky.

Did You Suffer Illness Or Injury?

A few colds, sure, but nothing serious. Again, I’m almost terrified by how fortunate I am.

What Was The Best Thing You Bought?

Renewed my Dense Discovery membership, and a copy of Good Internet Magazine issue one.

Whose Behavior Merited Celebration?

All the wonderful folks on the IndieWeb and the adjacent quiet/slow/poetic web. Your kindness, willingness to share perspectives and knowledge never cease to amaze me.

Whose Behavior Made You Appalled?

I’m…not going to answer this in any detail because I try not to talk about others in my life in public settings. Still, one thing that riles me up is the insistence the humanities don’t matter.

Where Did Most Of Your Money Go?

Groceries, utilities, and accommodation. The building blocks of funding an existence!

What Did You Get Really, Really, Really Excited About?

Making things on the internet. Learning about programming. Learning new things!

What Song Will Always Remind You Of This Year?

Probably Welcome To The Plains by Wyatt Flores. Admitting I liked it allowed me to admit I enjoyed some country music. Just like when I allowed myself to acknowledge I like mainstream pop music, the earth didn’t fall out from beneath me, nor did the sky swallow me.

Compared To This Time Last Year, Are You: Happier Or Sadder? Richer Or Poorer? Healthier Or Unhealthier?

Overall, happier, richer, and healthier. I’ve found some purpose and enjoyment in work, had a few unexpected windfalls and freelance projects, and am feeling better. I’ve given up adding salt to my food, kept at my six-days-a-week intermittent fasting, and moved more regularly.

What Do You Wish You’d Done More Of?

Journaling. The days blur into each other as I spend most of my time working, so having something to look back on to find the bright spots and small moments would’ve been nice.

What Do You Wish You’d Done Less Of?

Chastising myself. Listening to the harsh inner critic. Overthinking the harmful trivial.

How Are You Spending The Holidays?

I made a fruitcake, which despite having toasted edges, was delicious! Also roasted veggies and made cauliflower cheese for the first time, and both turned out well.

Did You Fall In Love This Year?

In the romantic department? No, I’m solitary by nature until proven otherwise.

Do You Hate Anyone Now You Didn’t Hate This Time Last Year?

No! There are few people I detest, and I’ve never had the misfortune of knowing them.

What Was Your Favorite Show?

I watched only a little television this year: The Dragon Prince’s seventh and final season, and the limited series ‘Asterix + Obelix: The Big Fight’, so I’d say it was the latter.

What Was The Best Book You Read?

Do I have to choose? I don’t wish to play favorites!

What Was Your Greatest Musical Discovery Of The Year?

Sabrina Carpenter and Chappell Roan, and to my surprise…Taylor Swift. I blame James.

What Was Your Favorite Film?

The Electric State. No doubt a wild difference from the source material, and the outlying opinion, but I adore its humor, the narrative threads, the heartache, and the themes.

What Was Your Favorite Meal?

Trying traditional North Macedonian food at a local restaurant. It was fascinating being introduced to the different items, and it was amazing!

What Did You Want And Get?

I wanted more proof of my professional experience for my resume, and I got it (and lots of ideas for improving my work) for taking several HubSpot certifications this month.

What Did You Want And Not Get?

More mental relaxation. I’ve been stressed this year more often than not (mostly self-inflicted.)

What Did You Do On Your Birthday?

Contacted family and friends, which was lovely. Spent most of the day working on this site!

What One Thing Would Have Made Your Year Immeasurably More Satisfying?

More time for futzing on the internet. Just surfing through sites, seeing what I find, making things on my website, getting new ideas, emailing people…I don’t do it as much as I’d like.

How Would You Describe Your Personal Fashion This Year?

Personal fashion? What personal fashion? I don’t know what that even means!

What Kept You Sane?

Reading. Learning. My curiosity is endless, and while it’s overwhelming, it’s also comforting.

Which Celebrity/Public Figure Did You Admire The Most?

Thomas Sanders, for his charm, wit, and delightful videos. Brian Merchant, for his incisive writing and never-wavering focus. Kristoffer Tjalve, for everything he does for the web.

What Political Issue Stirred You The Most?

Minor, perhaps, yes, but the need now, more than ever, for libraries. Get a library card already!

Who Did You Miss?

Friends I spend lots of time with years ago, family, and friends I’ve never met in person.

Who Was The Best New Person You Met?

The lovely proprietor of mewizard.nekoweb.org.

What Valuable Life Lesson Did You Learn This Year?

I’m not an island, as much as I might try. I’m an animal, and that means I have needs. Humans aren’t machines! We’re creatures of flesh and blood, so I need to care for myself as such.

What Is A Quote That Sums Up Your Year?

‘Life is what happens to us while we are making other plans,’ as attributed to Allen Saunders. May I learn to embrace flexibility and uncertainty in the year to come.

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Zachary Kai's digital drawing: 5 stacked books (blue/teal/green/purple, black spine designs), green plant behind top book, purple heart on either side.

Zachary Kaihe/him |

Zachary Kai is a space fantasy writer, offbeat queer, traveler, zinester, and avowed generalist. The internet is his livelihood and lifeline.