In January, I sent an email to a guy I’d worked with about a decade ago. We worked on adjacent teams back then, so we’d cross paths and had loosely kept track of each other since. I had a few questions as I worked out my own next adventure, so I asked to meet for a coffee.
That coffee turned into a couple of introductions. I pointed him toward someone he should meet. He did the same for me. A few months later, he was deep in interviews for a large new role and working on some things he wanted to get better at. So we connected again. Today we’re working together—he’s one of my coaching clients. In January over a coffee, we were just catching up on life.
Since I left my company job last winter, I’ve been building an exec coaching practice while doing more catching up on life. So I now spend more time doing work with no immediate, obvious payoff: reading, reconnecting with people, writing. Just being a beginner again and learning.
In earlier career contexts, slower payoff work often felt necessary, but non-productive. Now, I’m viewing slower payoff “work” as an engine of growth and creativity. It helps generate luck, and it’s a new feedback loop for me.
The neurologist James Austin wrote about types of luck, including one you influence through your own activity. Later, the entrepreneur Jason Roberts framed the same idea as increasing your surface area for luck, viewing it as a formula:
Luck = Doing x Telling (i.e. building or trying something you’re interested in and then speaking about it with people)
Roberts’ formula is the sending half. What I’d add is the other half: some of it comes back — and whether you notice that is what closes the loop.
Here’s how it’s working for me: You send small emissaries—carriers of a message—out into the world, and some of them work their way back to you in interesting ways. This doesn’t happen linearly and is unpredictable, so sending more emissaries vs. fewer increases what comes back. What do emissaries look like?
When I look at what’s opened the most interesting doors for me so far this year, my emissaries usually take three shapes:
1. Something I create. A post, a note sent, a small thing I make and release into the world. (This post is an example). Ideas travel on their own timeline.
2. A new conversation I have. This is a coffee, reconnecting with someone, or just a question I ask a person I’m meeting. (The former-colleague now coaching-client example I shared)
3. A new place I go. My wife and I recently spent some time in Paris and Amsterdam, and we both fell for their coffee cultures. We’ve now turned into coffee nerds. Will this lead somewhere? No idea. The trip became a thread we’re still pulling.
For all three types, the magic is in the stretch, where the thing I do feels slightly hard as I do it. Like building something or being creative. That feels difficult at first. Or reaching out to a person I haven’t chatted with in a while, or maybe a place I’ve never been before. Something new.
The further outside my normal a new emissary idea travels, the more new ground it can touch. Exploring new things creates a different effect than the same people, same rooms, and same paths you’re used to. Same can be familiar and comfortable, but not as expansive. I’m learning a mix of both works best for me.
But sending out emissaries is only part one of the loop. The other half is noticing when something comes back. That’s closing the loop.
This can be non-obvious or take time. It’s like the butterfly effect. The wingbeat happens, but it’s not always easy to see a downstream effect. If you do notice it, it can change how you think. Seeing a completed loop encourages more experimentation. I see what’s possible and that it can work, so then I send more emissaries out.
So here’s an experiment for the week. Send out one or two emissaries that stretch you past your usual. Publish the draft you’ve been sitting on, reach out to the person you keep meaning to, walk into the room where you’re the newest one there. Then watch. Notice what comes back, even faintly.
You’re not waiting for luck. You’re sending for it.
👋 Hi, I’m Jeff. I coach senior product leaders through the moments their playbook stops working — drawing on 25+ years building at LinkedIn, Facebook, Headspace, and Included Health. If that’s you or someone you know, ping me.
If you made it this far, here’s a recent image from Juniper Cafe. Yum!
