How to Plan (Since Life Doesn’t Go As Planned)

Summary

The article emphasizes the importance of planning for the near future with precision while adopting a flexible approach for long-term plans, acknowledging life's unpredictability.

Abstract

The article discusses the necessity of planning in life, advocating for a balanced approach where detailed planning is applied to the immediate future, while a more adaptable mindset is taken for the distant future. It suggests that while serendipity plays a role, achieving goals such as completing a degree or organizing a family trip requires careful planning. The author introduces the concept of holding the near future tightly with concrete plans, while holding the far future lightly with intentions and desires rather than fixed plans, due to life's inherent unpredictability. The article uses examples like booking a babysitter for a night out, planning for school breaks, and setting dates for events like weddings to illustrate the predictability of the next few weeks to a year. However, it also cautions that beyond a year, plans should be considered as changeable desires, using the author's personal experience with an international choir tour that was postponed multiple times due to unforeseen circumstances. The author concludes by encouraging readers to think of plans in terms of "tight" or "light" focus, allowing for excitement about the future while recognizing its uncertainty.

Opinions

The author believes that while serendipity is valuable, it is not a reliable strategy for achieving life goals.
Planning is essential for turning desires into reality, whether it's for a weekend get-together or a significant life event.
The future is unpredictable, and plans should be adjusted according to the timeframe: detailed for the near future and flexible for the far future.
It is practical to plan for the next 6–12 months with a reasonable degree of certainty for major events and commitments.
Long-term plans beyond a year should be held lightly as intentions or desires, acknowledging the high probability of changes.
The author uses personal anecdotes to illustrate the unpredictability of life and the importance of adaptability in planning.
The article suggests that thinking in terms of probabilities can help in making informed decisions about the future.
The author encourages maintaining a balance between planning and openness to opportunity, allowing for adjustments as life unfolds.

How to Plan (Since Life Doesn’t Go As Planned)

Serendipity is wonderful. But most events and accomplishments won’t fall like fairy dust into anyone’s life.

If you want to go back to school to finish your degree, you’ll need to choose an institution, and complete the application process, and figure out what classes you’ll need to take. If you want to go to the Bahamas with your extended family, you’ll need to choose dates and make reservations and book tickets. Even something as simple as getting together with friends this weekend means texting them and seeing when they’re free.

In other words, you need to plan. You’ll need to think about the future, and what you’d like to have happen in that future. You need to plot out the logistics that will need to happen in order to make that future come to fruition.

This makes sense, but there’s a fundamental problem here, which is that the future is unknowable. A health crisis might put the degree on hold. A hurricane might pre-empt the Bahamas trip. How can we plan, and not feel like we’re wasting time, given this reality?

Some people throw up their hands, but I prefer to remember this phrase: Hold the near future tightly, hold the far future lightly. You can and should plan the next few weeks in full detail. You can have a resilient but solid action plan for the next 6–12 months. Past that, though, you’re better off thinking in terms of intentions and desires, rather than specific plans. This mindset allows you to focus your efforts on where those efforts will yield the best results, while leaving yourself open to opportunity and life as it comes.

All of life is really about probabilities, and you can see the shape of the next few weeks quite well. Not perfectly, of course, but if you and your spouse would like to go out on Friday night, it would be silly not to book a babysitter because life is unknowable. The odds are very good that you can make it happen. Most likely, if you call a longterm client and say you’d like to come talk in the next two weeks, the two of you will be able to choose a time and execute on that desire, because the odds of something completely unforeseeable pre-empting it are low.

The next 6–12 months are likewise reasonably foreseeable, at least for the big things. You can see when your kids’ schools are off for winter break. Maybe something crazy will change that, but if Christmas is on a Sunday, they are probably not going to school on Monday the 26th. You could sign up for a fall 10k knowing the race date is probably set. If you’d like to be able to say you published an article in an industry journal by the end of the year, you can get started on that process now, with a reasonable certainty that the journals you are targeting will still exist for at least the next few months. Things like weddings and school admissions processes tend to be set in motion about a year ahead of time. There is more uncertainty — but enough things are taking shape that you can make informed choices about what you’d like do.

Past that, though, “plans” need to be thought of more as desires, with the understanding that things might change. I do understand that some events need to be planned more than a year ahead of time, but the odds of circumstances changing on the ground go up a lot. I’ve been thinking of this with an international tour that my choir is planning to take this summer. I joined the choir in the fall of 2017, which was when they were taking sign-ups for this (optional) trip for the summer of 2020. I remember thinking how different life could be by then, and sure enough, in my case, I wound up having another baby in late 2019, which would have made leaving that infant for multiple weeks that summer quite challenging. Then, of course, most 2020 travel wound up canceled because of the pandemic. The organizers hoped to reschedule the tour in summer 2021, and then finally pushed it to summer 2022. It looks like they will be going now — we’re only a few weeks out, which is when odds become more clear — but a lot has changed since 2017 for sure.

With this in mind, I recently made a 5-year travel “plan” that’s really more of a limited bucket list. In the next five years, I’d like to go to Hawaii, Norway, and Japan (among other places). But I haven’t gone so far as to say that I will definitely go to Hawaii over my kids’ spring break in 2024. I’m not quite sure what those dates will be yet anyway. I know that in the next three years I’d like to write another book, but I don’t know exactly what the topic will be. I have things I’d like to do, and if I see a lovely resort in Maui or I think of a great subject, my desires will help me pay attention to those things. But it’s a little early for specifics.

When you think about plans as “tight” or “light,” then you can still think about the far future, even if the future is unknowable. You can be very focused on the details of the next few weeks. Do you have something to look forward to this weekend? Have you solved any logistical problems presented by your business trip two weeks from now? And you can daydream about that great trip you’ll take once you actively decide to pull it into the 6–12 month horizon where things happen.

Life in an uncertain world is kind of like walking on a trail in a dark woods. Shining a flashlight, we can see the next few weeks pretty well. Past that there are a lot of shadows, but it’s OK to still be excited about what’s around the bend. All of that will come into the light eventually, especially if we keep shining the flashlight forward.