A Wildly Inefficient Man’s Guide to Networking After 50

A Wildly Inefficient Man’s Guide to Networking After 50

My first full-time writing job was as a town reporter with the now-defunct Tab newspapers. The gig had low pay and long hours, but the company compensated for it with little constructive feedback or career guidance.

Or maybe I wasn’t open to any suggestions. I was 27 years old, and my brain wasn’t yet fully formed. I was underwater for the first four months (rough underestimate), trying to figure out what I was actually doing. Still, I’m going with the first one, the thing about the non-constructive feedback, because, well, it was true.

But for all the minuses, it wasn’t a bad time. I worked with a bunch of good people. We talked friendly trash, read each other’s stories, and bet on presidential elections, the Super Bowl, and Olympic figure skating—which I might have possibly organized.

The best thing was that we were all pretty much the same, i.e., young and dumb. We didn’t exactly know what we were doing, but we were getting better. And, as it turned out, some of us were going to leave journalism and become really accomplished, landing big positions in big companies. One day, those people might also need stuff written, and they might need writers to do the writing, and they might pay a decent rate. As journalism shrinks, I’ve realized it sure would be sweet to have an in on some of that writing work that doesn’t require getting subscribers. Those former colleagues sure would be good contacts to have right now, if only that concept of building and maintaining contacts had existed back in 1996.

But it didn’t. There was no platform. There were no helpful hints. There was no guru whispering in my ear, “Play the long game, son. You won’t all stay paid interns.” Now, I didn’t totally whiff. I’ve stayed in regular touch with a bunch of folks, and my life is way better for it. But some I let drift or never connected with in the first place.

Part of it was the business. We were all trying to stand out by finding good stories, beating the other paper in our town—we were owned by the same company—and possibly breaking some news big enough that the Boston Globe weekend suburban section would “borrow” it. We were in competition with each other, and being more insecure than I am now, I wasn’t prone to cheer for someone else’s success. Add to that, I can be skeptical and sarcastic, also more than now. It wasn’t a recipe for reaching out and/or staying in touch.

I feel I might have effed things up. No, I’m pretty sure I did. It’s one of my top strengths, right along with minimizing what I do because I’m the one who’s doing it.

But I think I’m pretty good at putting words together, and that’s the most I’ll say about myself. I wish I were more brash, more cocky, more able to say, “Just some shameless self-promotion”—and feel less shameless. But I’m not.

So am I screwed? Should I just quit trying to connect with people? No, says Elizabeth Gross, a career coach in Boston. She assures me that there’s still a chance that I can stop being such a crappy networker. I just have to actually do some networking.

The problem is, I don’t have any foundation. It’s like trying to learn Spanish as an adult—starting from nothing, decades late. The one thing I had going for me, back when I was coming up, was that cluelessness was an acceptable excuse. Now? “These days, no one has an excuse,” Gross says. “Young and dumb doesn’t cut it.”

Well, I’m no longer young. Maybe work on the being-less-dumb part. Gross again says that there’s hope for that, although I don’t initially believe her. I’m 58 and a writer. I feel like a fax-machine repairman in 2002. But Gross reminds me of my advantage. I might not have come from the era of social media, but I did come from the era of talking, like on the phone and in real time—and as she says, networking is all about talking.

I’m 58 and a writer. I feel like a fax-machine repairman in 2002.

I can talk. I even look up when I talk.

It’s also about being curious, she says.

Man, I get paid to be curious.

And networking, she adds, is not a quick process. It’s actually wildly inefficient.

Oh my God, I’m so wildly inefficient. I rewrite email subject lines, and you should see me buying a replacement pair of shoes that I know already fit. It’s, it’s, it’s, well…hypnotic how I can spin a five-minute transaction into the need to buy an hour’s worth of parking.

I should crush at networking. All I have to do is put myself out there and be clear with what I want—and that right there may be what’s been holding me back. I’m not always good at asking. I want people to guess what I want. I also want people to reach out to me. I don’t want to be the one who always has to initiate. Is that too much to ask?

Yes, actually it is. We all want to be considered and pursued, but someone has to be first on the dance floor. Screw it. I hate heights, but I’ve gotten up on a ladder leaning against a building. I’ve put sealant down in my shower all by myself. I decided to manage a baseball team of 10- and 11-year-olds—manage, not third-assistant coach. I can grow up. I can act like an adult. I can push through big fears.

And I can be a not-crappy networker. (Rising trumpets are playing in my head.)

And so I did. I reached out to people from various points in my life—former editors, fellow writers, a “head of people” at a startup, to add to the jargon mix. Going in, I was a touch nervous. I was relatively sure I’d get some to agree to talk—six did—but I didn’t know what would happen. I have conversations for a living, and I still wonder how they’ll turn out. Most often, they go well. Maybe one day, I’ll start to trust it.

The conversations did, in fact, go well. I would have loved to be in person, but with people in Colorado, North Carolina, and Washington, along with school pickups and that baseball team I took on, the phone and video calls had to do. We caught up, did minimal reminiscing, didn’t do much AI praising, and wondered whether and where words still mattered. On the former, we hope so. On the latter, the closest we came was Substack.

The platform would keep me busy, and maybe I could attract mid-three-digit subscribers (rough overestimate). But then I think about how many writers are actually out there producing decent copy, and wonder why anyone would pick my stuff, so what would be the point…and there I go again with another one of my great skills: talking myself out of seeing where something goes because it might not go anywhere.

Then a former editor and regular contact of mine told me that the fundamental goal of networking and self-promotion isn’t asking for work or even getting people to read the post you just put up. It’s to let people know you exist—not because they’ve forgotten about you, but because no one’s first thought during a day is, “I wonder what Steve’s been noodling around with.” They need a little nudge.

It was good to commiserate, vent, and hear how other people feel as though they don’t measure up. It was good to hear some praise for my work. (I’m not immune to words. Others probably aren’t as well. Hint, hint going forward, Calechman.) It was good to just reconnect, and I did that with six people, so those are six people who, for the next three years, I don’t have to preface an email with, “It’s been too long.” That sounds like I hit a swish at the buzzer.

So I guess I’m all set on networking, right?

Disregard and procrastination might be perfectly acceptable approaches for my yard. They’re less productive with people and my career.

Ahh, even I know I’m not done, and this is where I’ve fallen. Disregard and procrastination might be perfectly acceptable approaches for my yard. They’re less productive with people and my career. But where do I find the time for the tending of relationships with quick texts and five-word emails letting people know they’ve been thought about? My schedule is already jam-packed, what with my playing of Spelling Bee and Daily Walkoff. (This list has been condensed to hide ridicule.)

I suppose I could carve out some time, because if networking is what I just did, I was pretty not crappy at it. I actually was kind of on fire by my second call with Jon Tapper, my former colleague with the Boston Lobsters professional tennis team. Strong start? Check. Flow? Totally there. Listening? Couldn’t do enough of it. Even the wind down was solid, nothing too drastic, nothing too awkward. I was feeling the hope of being a bona fide networking man.

Then Tapper reminded me that I didn’t ask one more important question.

Do you want to get coffee or a beer sometime?

Eff me. Still taking baby steps in size 11 shoes.

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