Possible Futures of Happiness

At Automattic, we don’t have customer service or support, we have Happiness Engineers. 🙂

There’s also a #ceo Slack channel where anyone can drop in and request a meeting, which my esteemed colleague Damianne President did, and this morning we had an interesting chat that set my mind racing about how we might engineer happiness in the future.

One overriding assumption: Personal agents will trounce company agents in most cases.

Your personal agent can — or soon will — know all your history, your calendar, your email, your preferences, and your photos, and it speaks your language. So much time is wasted in traditional support trying to see through the customer’s eyes, or authenticate them. That goes away, but watch your thinking! It’s so easy to fall into the mental model trap of legacy chatbots and data models.

As a company, your website, your WordPress, documentation, tutorials, menus, manuals need to be amazing and up to date. That’s the source of truth, and an agent will read all of it!

The interface and APIs remain because that’s useful to both human visitors and the agents.

Whenever possible, make support public. More blogs and bbPress. I actually weep a little when I think of how many beautiful words are written by our Happiness Engineers that are only ever seen once in a chat box or email thread.

My goal with our products is that support is radically available, and you almost never have to use it.

If you’re in a support role, I think you can pick a lane based on where you get energy.

If you love looking at screens, I think there’s a future where customer service wizards are watching over an Iron Man-like interface, armies of chat bots talking to people, where they can see how they’re going and intervene or nudge them as needed. There’s a ton of work in tuning agents and interactions.

If people recharge you, I actually think this will be the greatest era. All of the basic, mechanical stuff will be automated, but I think human connection will be what economists call a Veblen good, more in demand even as it is more expensive.

I think Happiness Engineering in the future will look a lot more like community building. A bot can’t host a meetup or a WordCamp.

I was the biggest Waymo fanboy, but this year with lots of trips to and from hospitals with Om I found myself craving human connection and used Uber more than ever. (It also gave me a chance to practice the one repeatable way that money can buy happiness, which is keeping a couple Benjamins in your back pocket and surprising people with them.)

14 thoughts on “Possible Futures of Happiness

  1. > If you love looking at screens, I think there’s a future where customer service wizards are watching over an Iron Man-like interface, armies of chat bots talking to people, where they can see how they’re going and intervene or nudge them as needed. There’s a ton of work in tuning agents and interactions.

    > If people recharge you, I actually think this will be the greatest era. All of the basic, mechanical stuff will be automated, but I think human connection will be what economists call a Veblen good, more in demand even as it is more expensive.

    My team and I were basically having this same discussion this morning, about how exciting it is to be humans-on-the-loop, and advise agents. We as humans get to be the tastemakers, we get to set the standard of judgement, and we get to connect, human-to-human, rather than be under a pile of reports that a machine could have managed. It’s a really exciting time!

  2. Lovely communication as always. I am 82 and have been all alone for eight months and pray for human visit or call or looking forward to your visit

  3. Enjoyed reading this and appreciate you sharing these thoughts publicly.

    I’m a little biased since I lead one of our onboarding/live call teams here at WordPress.com, but this resonated:

    > If people recharge you, I actually think this will be the greatest era. All of the basic, mechanical stuff will be automated, but I think human connection will be what economists call a Veblen good, more in demand even as it is more expensive.

    People recharge me, and they recharge my team. We love spending our days talking with interesting people building interesting things on WordPress.com. A recent Trustpilot review(https://www.trustpilot.com/reviews/6a1ef989cfc2be2123032f4b) from one of our onboarding sessions summed it up: “Tutorials, AI chatbots are useful but live collaboration is much better and necessary.”

    Let AI handle the mechanical work so Happiness Engineers can spend more time building trust and connection.

    Excited for what’s ahead!

    1. We’re in a weird phase where the bots write poetry, and we still have to fold our laundry, but hopefully they’ll get better at some of these mechanical tasks, and we’ll have more time for poetry. 🙂

  4. I’ve felt for a while that tech has been moving us away from human connections, I see AI removing the distractions so we can be human again. Great post and happy to see you feel the same! Waymo is super disconcerting, not because of the tech but it’s very lonely – I enjoy the random chit chat as well as hearing about what the driver likes in the city. It’s very, for lack of a better word, real.

  5. Great post! This is something I have been pondering lately, what comes next, and this really traces a path into the possible futures.

    The bit about beautiful words that are “only ever seen once in a chat box or email thread” and about making support public is what stuck with me the most. Coming from the Woo side, it made me think about the .org forums as somewhere Happiness Engineers could take more part again.

    It could be a place worth mining. We would be engaging more with the community, those words of happiness would reach everyone instead of stopping at one email, and the agents would pick them up too.

  6. TIL: Being an Aussie, I had no idea what “keeping a couple Benjamins in your back pocket” meant.

    I used the Codex ‘Computer Use’ feature this week to direct Codex through doing specific tasks using WhisprFlow.

    I also started using Claude Voice on my morning walks to go through Slack notifications, catch up on P2’s, discuss my role and set action items to work on for the day, when I get back to my desk.

    It gave me a sense of what managing AI Agents is going to feel like. And I kinda like it. I felt like I wasn’t bogged down in the little things, but sitting above it all.

    I’m excited for this era we’re in and the one(s) we’re heading to.

  7. > I actually weep a little when I think of how many beautiful words are written by our Happiness Engineers that are only ever seen once in a chat box or email thread.

    Ikr! A part of me has always been like “what if we have a short form blog where we can publish summaries of an issue and share quick steps readers can take”. It’s not long form documentation, but digestible ones (with citations and references, of course).

    Of course, I’d like them to be available at org level. Happy to experiment publishing these posts at the personal blog level to kick things off.

  8. I have been reading this blog for a while and I really liked this post. Moving from my background playing NCAA Division I tennis into the tech and engineering space, this concept of human connection as a ‘Veblen good’ makes total sense. On the court, technique matters, but it’s real mental support that wins under pressure, and it’s the same when troubleshooting tech.

    Letting AI handle the mechanical work so we can focus on building communities and bringing genuine empathy back to the forefront is a future I’d love to see. Less robotic back-and-forth, more room for poetry.

  9. So wholesome: “I was the biggest Waymo fanboy, but this year with lots of trips to and from hospitals with Om I found myself craving human connection and used Uber more than ever.

    And relatable: (It also gave me a chance to practice the one repeatable way that money can buy happiness, which is keeping a couple Benjamins in your back pocket and surprising people with them.)”

    This post is so heartwarming and really hits home for me. Human connection really is amazing, isn’t it? Right now, I’m away from home studying abroad. I’ve been enjoying the nature and the culture, but making friends here has truly been the best part.

    Thank you so much for sharing this post!

  10. When I was in college, I was a “Tech Tutor” of a newly formed tutoring program. And my boss and mentor at the time (now my dear friend!) taught me; “Teach students with a mission that your service will no longer be needed”

    Whenever I have a customer in front of me (ticket, chat, in-person), I want to put my 100% as if that interaction might be the last chance for me to share. And I cherish every interaction I have with our customers.

    I dream of the day where technicality is handled with precision by AI and we humans simply get to connect with others. I deeply resonate with your reflection!

  11. Automated chat support works best when it handles the common 80% of questions well, and seamlessly hands off to humans for the complex 20%. The goal isn’t to replace humans but to free them for high-value conversations.

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