I’m now entering the sixth month of my year-long Foundations project. This month’s focus is on outreach. One of three socially-oriented foundations, outreach focuses on meeting new people and sustaining friendships with people you don’t see every day.
Two related foundations, connection and service, will focus on improving close connections and finding ways to help others in my day-to-day life, respectively.
Here are some links to the previous months’ notes, in case you missed it:
1. Fitness: Start, End, Books.
2. Productivity: Start, End, Books.
3. Money: Start, End, Books.
4. Food: Start, End, Books.
5. Reading: Start, End and Books.
Why Outreach?

I don’t think I need to spell out how important relationships are to a good life. Pretty much all our great joys in life (as well as our deepest miseries) are built upon our connection to other people.
I chose to focus on outreach first because it is a logical antecedent to deeper connection. If you don’t have a lot of close friends or a romantic partner, then there simply might not be a lot of relationships in your life you have the opportunity to deepen. Therefore, meeting new people or strengthening “weak ties” comes first.
The logical necessity of needing first to meet people before you can be close friends with them isn’t a practical concern in my life now. I’m happily married with two kids. I have good relationships with my family, and I have a number of close friends, both personally and professionally.
However, I’ve definitely had times where this sequencing would have mattered. I moved around a fair bit in my early twenties, and I’ve had to rebuild a social world for myself from scratch several times. Thus, I know firsthand how important a foundation of outreach is in terms of social success.
I think it also makes sense to think of outreach as distinct from connection for another reason: the behaviors and skills that support each tend to be different. Deepening connection is largely a matter of spending quality time, being empathetic and being generous, but outreach relies on extraversion, self-confidence and openness to trying new things. From a practical perspective, it makes sense to consider outreach a separate foundation from the work of sustaining your existing close connections.
Reflecting on My Current Outreach
My foundation of outreach is weaker than I would like, although part of that is a comparison against previous eras of my life when it was relatively strong.
In my twenties, I had a social event almost every day. During the early days of my business, I spent a lot of time reaching out to other writers and entrepreneurs. And after moving to a new place, socializing to help me establish new friends (often in a language I didn’t speak very well) was often my main priority.
Today, however, my level of socializing with people I don’t already know is much lower. A big part of that is simply the current phase of my life. With two small kids at home, I have less time, and frankly less motivation, to seek out new friends. I often feel like I don’t have enough time to maintain a lot of the friendships I already have, never mind doing social activities with the express purpose of meeting new people.
However, it’s too easy to dismiss the need for outreach out of simple busyness. The same argument could apply to lots of other foundations. I don’t play sports and the need to maintain a certain physique is less prominent when you’re a busy parent—but that doesn’t make fitness unimportant as you get older. Similarly, I think a total neglect of outreach could easily lead to a situation where, emerging from the isolated cocoon of early parenthood, I find myself with fewer friends and activities than I would like. An analogy might be a person who was an athlete in college, didn’t notice they were getting out of shape in their thirties and forties, and find they now have preventable health problems in old age. Better to fix a foundation before the weaknesses cause problems.
Still, given my life constraints and my currently ample supply of friends and family, I want to strike the right balance between an appropriate amount of time spent on outreach and maintaining my existing relationships and commitments.
Keystone Habit: Weekly Social Activity
Given the need for some amount of outreach, and my existing commitments, I think aiming for a habit of attending a social activity roughly once-per-week is probably ideal. Unlike my fitness habit, in which I aim for near total consistency, given the irregular nature of social events, I’m less concerned about the strictness of this habit. I think if I hit the ~1x/week average, that would be good.
My criteria for a social activity is that there is an opportunity to meet new people. This could be Meetups, classes or group activities where I don’t know anyone already. Or it could be activities I attend with my existing friends where I don’t already know all the people in attendance.
Once per week sounds like a pretty good minimal commitment. It’s hard to imagine a person for whom one outing weekly would be excessive, but I can definitely consider some people for whom a single weekly social activity would be too little. It definitely would have been too little when I was new to a city, was single, was trying to get a foothold professionally or was simply lacking friends in my life. So I don’t think this is a universal benchmark, although it might function as a reasonable minimum threshold for most people.
To reach this goal, I’m doing what I’ve always done: finding Meetups based on some of my interests, asking friends for activities they’re part of, and keeping my eyes open for opportunities. Since I’ve been running more lately, I may drop in on a running club or two and kill two birds with one stone by getting my daily exercise in, too.
I’m also keen to restart some language practice. This was something I enjoyed pre-kids, but with the pandemic cancelling all in-person meetings and the increased demands of having two babies, I dropped it almost entirely. So I’ll keep an eye on this as well.
Other Outreach Metrics
I’m prioritizing simply attending some social events on a roughly weekly basis for my outreach activity. This is partly because my needs in this foundation are pretty non-specific. As mentioned, I’m happily married, so the dating angle that motivates a lot of social activity isn’t there for me.
Similarly, while I can always do better in professional networking, this isn’t an area I’m prioritizing either. I’m always happy to meet people professionally, but I feel like I get enough opportunities organically at this point in my career that this doesn’t require a lot of extra work.
However, in addition to the weekly habit of socializing, I’d like to be more organized about keeping up and scheduling time with more distant friends. I’m not naturally good at this, and not being on social media makes it worse. While setting up CRM software for friends seems a little dehumanizing, I think I do need some system of reminders to at least check-in on those people so I don’t lose touch.
I haven’t decided exactly what system I want to use. In the past, I’ve experimented with recurring reminders and spreadsheets to try to solve this problem, but I always bristled a bit at their formality. Instead, I might try a more regular practice of checking in on people once a quarter or year to make up for my lack of awareness of people’s updates on social media.
As always, toward the end of the month, I’ll share some insights from my reading for the month as well as how my planned habit changes went.