The Advice I Never Asked For (But Needed to Hear)

I’ve been asked hundreds of times: “If you could go back and give your 21-year-old self one piece of advice, what would it be?” This is the question that gets us to share our wisdom with the next generation on what we have learned so far.

But this past weekend I heard something that flipped that question on its head. I was listening to Chip Conley on The Midlife Chrysalis podcast, and he posed a different challenge: instead of looking backward, what if you imagined your 80-year-old self looking back at right now? What advice would that version of you give? Not what is happening in your life at the age of 80, but what is she looking back on wishing to give you a leg-up as you embark upon this next couple of decades?

After listening to this episode, I sat outside with my coffee and just let that question marinate. No phone, no to-do list, no podcasts. Just me and my future self… having a little chat.

And here’s what came up, over and over: Make more time for the people who matter. You know friendship is important, but you stay too busy to go deeper.

Not in a vague, someday-I-should way. In a specific, scheduled, this-week kind of way.

We already know the research. The Harvard Study of Adult Development, one of the longest-running studies on human happiness ever conducted, found that close relationships, more than money or fame or career achievement, are what keep people happy and healthy as they age. The study’s director, Robert Waldinger, summarized it plainly: “The people who fared the best were the people who leaned into relationships.”

Research from Brigham Young University found that social isolation increases mortality risk by about 29%,  roughly equivalent to smoking 15 cigarettes a day. Dan Buettner’s Blue Zones research, which studied the world’s longest-lived populations, consistently found that strong social circles and a sense of belonging were among the most reliable predictors of a long, vibrant life.

We know all of this. We’ve read the articles. We’ve nodded along.

And then Monday comes and we’re back at our desks packing our calendars with everything except time to deepen those important relationships… or to even make time to begin those relationships.

Here’s what hit me sitting outside that morning: I’m surrounded by extraordinary people at The Village every single day. Members who are building things, reinventing themselves, taking big risks. People I genuinely love. And still, I don’t always make the time to actually know them more deeply. We wave in the hallway. We have great five-minute conversations between meetings. And then we both get back to our laptops.

That’s not enough.

My contractor drove this home recently in a completely different context. During our recent kitchen remodel, he mentioned that every single month, he spends one full day with his uncle, the last surviving sibling of that generation in his family. Breakfast in the morning, time together, no agenda. He said it matter-of-factly, like of course this was worth a full day every month. No question.

My 80-year-old self loved that story. She’s taking notes and seeing who I am cultivating relationships with so they will want to spend a day with me each month.

A friendship I’ve recently enjoyed investing more time in, is with Jessica Sidener, who works with Arapahoe County Libraries and brings her team into The Village regularly. What started as a professional connection has turned into something I look forward to every week. We’ve committed to working side by side for a couple of hours each week, both of us are building apps, so we sit together, figure things out, cheer each other on, and occasionally look at each other like, “Wait, does this make sense to you?” We meet for happy hour somewhere every month or two as well. It’s collaborative and it’s fun and it’s exactly the kind of relationship that sneaks up on you and becomes important.

That’s what I want more of. Not more networking. More depth.

There’s a difference between being surrounded by people and actually being connected to them. Coworking spaces can do both, but only if you’re intentional. You can spend every day in a bustling, full room and still feel completely alone, or you can use that same room as the starting point for relationships that last decades. Just today I met an incredible woman, Erica Conway. We hit it off immediately. She was full of energy, curiosity for learning, and smart as all get-out! (Not even sure what that means, but she is brilliant, and she’ll be doing a Lunch-n-Learn here soon…stay tuned).

She told me that she moved to Colorado from Wisconsin a couple of years ago and makes a point to talk to strangers, go to events to meet and learn from others, and she had used an app that was developed there, called Sit by Me. This is a fun app for those like her and me who like meeting and talking with new people. You turn it on and it finds others in your area who are looking for a connection. Not a love connection… a friend connection.

The question my future self is asking me, and maybe asking you too, isn’t “Do you know a lot of people?” or “How big is your network?” It’s “Are you investing in the ones who matter?”

This week, I’m putting some recurring coffee dates on the calendar. Not networking meetings. Just time, with people I want to know better, or people I haven’t talked to in too long. One conversation at a time.

If your 80-year-old self could whisper something in your ear today, I’d bet it wouldn’t be about the project you finished or the deal you closed. It would probably be about a person. Someone you meant to call. Someone you kept meaning to grab lunch with.

Start with coffee. Schedule it before you close this tab.

The relationships you build right now, the ones you’re intentional about in the next year, those are the ones you’ll be telling stories about at 80.

Don’t wait until then to start.