Steph Ango reviews his year with 40 questions every December.
At the end of 2024, I tried it myself. One of the questions was: “What new friend did you make this year?”
I couldn’t answer it.
Looking back, I hadn’t really made any new friends since quitting Meta. It was frustrating, especially since I’d finally become an extrovert.
They say you’re the average of the five people closest to you. I couldn’t even find five. When I counted, it was mostly my wife and two kids, ages one and two. Pretty sad. I was relying on podcasts to fill my remaining slots.
Starting to change
Derek Sivers once said his goal when traveling isn’t to see places, but to meet people. I don’t care much about checking off tourist spots or hunting for restaurants, but I’m very interested in interesting people. That resonated deeply with me.
So I decided to start reaching out to people I admire. Compliment them. Then ask if they’d be up for a chat.
Was I afraid of rejection? Of course.
But trying won’t kill me. Think about it from the other side: if someone complimented you and asked to meet, even if you turned them down because you were busy or lazy, you’d still feel good about it.
Plus, this blog turned out to be the perfect business card. When reaching out, I don’t have to explain who I am. I just drop a link, and they can see what I do, what I think, and what kind of person I am.
And as the saying goes, “in any group of three, there’s always something to learn from someone.” But flip that around: I’m also someone else’s teacher. I can’t just take. I need to bring value through my own ideas.
So in 2025, I made some changes. I started joining communities of podcasts and YouTubers I follow. I started chatting with strangers online. And I started turning online compliments into offline meetups.
Going on the offensive
Last December in Taiwan, I tried this at scale for the first time. I contacted everyone I wanted to meet in advance, casting a wide net like sending out resumes.
In just one week, I met a roommate I hadn’t talked to in years, a college senior I hadn’t seen since graduation, friends from online communities, a YouTuber I look up to, an author I admire, and a cool fellow blogger.
7 days, 11 people I don’t normally get to see. 7-Eleven, literally.
Exhausting. But it opened up side quests I never saw coming.
For example, I spent an afternoon chatting with fellow blogger Wiwi and floated the idea of running an IndieWeb Carnival in Taiwan. He went home and made BlogBlog Party happen almost instantly. Six months later, it’s still going, now on its fifth edition. Adults who blog are worth knowing!
For example, Ray told me he now shoots everything with just an iPhone and a DJI Mic. Hearing that a YouTuber with 500K subscribers had ditched his Sony A7 instantly killed a lot of my gear anxiety. That’s what pushed me to shoot my first YouTube video with my crappy camera (a DJI Pocket 3).
For example, just the other day I asked Paul Millerd and Angie for advice on writing and self-publishing a book.
None of these would have crossed my mind before. I’m sure other seeds are sprouting too, ones I can’t even see yet.
Ask that one extra question
90% of people never reach out. 9% stop at a compliment. Only 1% ask that one extra question.
Doing nothing is the easiest. Spending less than a minute to write “I love your work” already puts you ahead of 90% of people. But adding “would you be up for a chat sometime?” is ten times harder, and ten times more rare.
That one question is where the side quests begin.
By the end of 2025, when I answered “what new friend did you make this year” again, I finally had an answer.
