Making Friends at Fifty is Time Well Spent

I’m almost fifty years old, and I think I need more friends.

But is it even possible to develop deep, meaningful friendships later in life when we have so many things pulling at us?

Claire’s asked me several times, point blank: “If not me, who would you talk with about something really important?” I do have friends, and we have fun together. But I couldn’t give her a good answer. I’ve realized I just deal with things myself. It’s been okay, but I’m missing out should anything really serious ever arise.

I suspect my experience is common. As we age, we become wiser. But by the time we recognize the importance of having someone to talk to about life, our struggles, and our feelings, we find out that our options are slim.

I’ve listened to more than a few podcasts discussing today’s loneliness epidemic, especially among men. When I listen, I learn that we are the sex that doesn’t communicate well. We let relationships from earlier in life—our childhood friendships and college buddies—atrophy. Our focus turns to work, family, and health. Nowhere on the priority list is “invest in friendships.”

Social media is often touted as the reason we’re lonely. It’s made us more distant, less connected. We sit in isolation and scroll. We laugh about whatever we’re fed on TikTok. We envy the perfect family portraits placed on Instagram.

I don’t spend much time on these platforms, but I’m still lonely.

I think an equally important explanation for our loneliness is that we are busy; we need more time to invest in friendships. Luckily, I have time. I simply have to make an effort, and I’ve begun to do just that.

First, I’m paying more attention to those people I want to become friendlier with, those in my orbit who’d be worth my time. This isn’t me being elitist. I only want to deepen my friendships with the right people. For me it’s about absolute kindness, connection, and ease. Who wants a relationship to be difficult? (I need to be the same in reverse.)

Then, when I find someone who aligns with my ideals (and you’ll have yours), I must be the one to put in the work. Here’s why: We’re not in the university dorms any longer where proximity breeds friendship. We live in our respective communities. We’re no longer bored with nothing to do on a Friday night. Instead, we have too many commitments. And today’s world is full of distractions. Everyone and everything are competing for our time, so we have to be the ones to push through.

My new friend Trevor made a point to visit me at my cabin this summer. He lives in Kentucky and helps his parents in Canada. But he made time to visit me for a weekend in Northern Wisconsin. That’s a friend. (Trevor, I’m sorry you strained your rotator cuff trying that slalom waterski start.)

I took a lesson from Trevor and invited another new friend, Veena, to a book signing by Oliver Burkeman, who we both love. Next, we might attend a Christmas drag show in San Francisco. (Veena and her husband Jesh are more than ten years younger than Claire and me. It’s great to have “fun friends” willing to do crazy things like this.)

Both Trevor and Veena pass my “kindness, connection, and ease” test. And they’ve been uber-supportive of my book project. I invited both to join me on an episode of The Time Freedom Podcast! If you want to meet these genuinely wonderful human beings, you’ve got to give the show a listen.

We tell ourselves we don’t have time to develop new friendships this late in life.

But I say: what could possibly matter more?

I’m choosing to make time for the people who matter, and it’s never too late to start.

Brian is a speaker, author, financial advisor, and entrepreneur. As the leading voice on time freedom, he has written the definitive book on the subject and delivers keynote talks that challenge how we think about work and money. He believes passionately that freedom isn’t just about financial independence someday, but rather about creating a life of flexibility, choice, and purpose right now.