The Serendipity Paradox — or How to Plan to Make More Luck Possible
Magic can happen when we are at the right place at the right time. I met my husband in a bar in New York City almost 20 years ago — which is random enough, but it was also my second stop of the evening. I had almost gone home instead! The Best of Both Worlds podcast, which is almost five years old, came to be because I responded to a favorite blogger’s casual comment on her blog that she was thinking of starting a podcast. What if she hadn’t decided to mention that thought that morning? What if I hadn’t been reading? But she did and I was and here we are.
“Serendipity” means chance events that turn out in a happy or beneficial way. Most people would love more serendipity in their lives. It’s how we meet cool people, start projects we wouldn’t have otherwise, and just have adventures in general.
You can’t plan serendipity. The definition requires chance. But there’s a paradox here, because I really do believe that in busy lives, planning is what allows for serendipity to happen. We need to put ourselves in interesting places (rather than sitting at home) and we need to have enough space in our schedules that we can seize opportunities. Humdrum work and the administrative details of daily existence can easily consume all space. But with a few smart strategies, serendipity becomes far more likely. Here’s how to plan to create more luck in your life.
Plan your weeks on Fridays. To be open to opportunity, you need to feel like your life is under control. So take a few minutes on Friday afternoons to think about your upcoming week. Think about what you need to do professionally and personally, and any intermediate steps required to fulfill those obligations. Figure out when you will do these things. Enlist any assistance you need. When you’re not overwhelmed, you’ll be more likely to say yes to coffee with that intriguing friend of a friend…who two years later starts a company which will then hire you to head a major division.
Plan in one big adventure and one little adventure each week. Routines make good choices automatic, but sometimes routines can become boring. Days and weeks blend into each other until whole years disappear into memory sinkholes. To combat this, I suggest planning one big adventure and one little adventure each week. A big adventure is something out-of-the-ordinary taking 3–4 hours (think half a weekend day). A little adventure might take an hour, and be doable on a lunch break or a weekday evening. When you plan to go to that botanical garden on a Saturday afternoon, instead of sitting at home watching Netflix, you might hear a local band that turns out to be amazing. You start listening to their music, going to their performances, and just generally finding a whole new source of joy in your life.
Reach out. Other people bring more possibilities. If you’d like more invitations, ideas, and opportunities, get in the habit of reaching out to at least one person a day. Each week, spend a few minutes planning who you will contact and why. Options could include old friends, former classmates, prior colleagues, or just someone doing something cool in the world. Some of these notes will be ignored. Some won’t lead to anything but a polite exchange. But some might result in the person telling you she’s actually in town two weeks from now and has an extra ticket to a musical and would you like to go?
Build in open space. When you build in open space, you give your schedule more flexibility. If a friend does ask to meet for lunch last minute, and you’ve got something big due on Thursday, you’ll be more likely to say yes if you know you’ve planned in a buffer of a few extra hours before your deadline. Open space means you can linger in something, like stopping by that cute little stationery shop with your daughter after her dentist appointment, because you’re not racing to something else that you’re already late for. The two of you discover a brand of journals you both adore and you find a new subject to bond over — all thanks to your open space. In a busy life, alas, the only way to have more open space is to plan it in. If you don’t, it will be consumed by low-value meetings, email, and just general puttering around the house.
Plan to be “the kind of person who does fun stuff.” It is always easier not to do things that require effort, or are a bit outside your comfort zone. If you want more serendipity in your life, though, try changing your default answer from “no” to “maybe.” The reason I went to the second bar of the night two decades ago, and was willing to chat with the charming gentleman who struck up a conversation with me, is that I had made a conscious decision to be open to meeting more people. The definition of a “plan” is “an intention or decision about what one is going to do.” In other words, I had planned to change my mindset, and someone who is open to meeting more people is happy to respond to a friend’s text that she’s at a nearby bar and do I want to stop by? To be open to serendipity, plan to act with the identity of “a person who does fun stuff.” If you’re weighing options, what would a person who does fun stuff do? Odds are, that action will bring more wonderful chance things into your life.