The Things You’ve Been Wanting to Do: When to Let Go and Move On

Summary

At various points in life, including particularly in one’s later years, it becomes desirable and perhaps necessary to review one’s list of things to do – of actual and potential enterprises, of dreams and goals – and separate the ones to cling to from the ones to let go. It may take more than one pass, revisiting the matter over a period of weeks or months, to reach a satisfactory list of retained projects, and to figure out what to do with the rest.

That sorting process may benefit from various strategies, focused for example upon what is essential or what is close to completion. One general-purpose strategy, more like a philosophy of activity, is to conceive your life as a job that you are trying to work yourself out of. In that way of seeing things, you distinguish the things that you want or need to handle personally from those that you can hand off to others. The latter include those problems for which others have already developed a good solution.

When there is an overwhelming number of possible tasks, it may help to ask whether there is a fundamental maladjustment on another level. There may be a problem-generating factor in your life – a person, place, attitude, belief, or culture – that is cranking out obligations or problems faster than you can keep up. Identification of such a factor can simplify the chore of sorting through a massive number of possible tasks. If you do still need to sort through those myriad tasks, you may then at least be able to do so with a perspective that makes it easier to decide what is important.

Discussion

If I could clone myself, I could accomplish all the things I would like to accomplish. And that’s precisely what I’m going to do when I win the lottery: hire a dozen scholars who remind me of myself (although I know there can never be a copy as good as the original), and put them to work in a research institute, where they will spend day and night suing people and writing about issues and generally being a pain in the ass for the bad guys.

In the meantime, unfortunately, it seems I face this limitation of living only so many years and having only so many hours in the day. I am not going to be able to experience, explore, study, contemplate, and discuss everything that interests me. Somewhere, sometime, the machine is going to chug to a halt. And if I don’t want that to occur at the worst possible time and in the worst possible way, I may want to do some proactive prioritizing.

Not that this is a new issue. It does gain force as I approach 60. But I have always lived as though there were going to be a loophole. Just keep on track, keep at it, and someday, as I get closer to the final barrier, I will see a path off to the side, and it will lead on and on, circumventing the wall, letting me continue to see the trees and smell the flowers forever.

That, of course, was a fantasy. And, as I say, it really wasn’t new. At any point in my life, you could have stopped me and asked me what I was hoping to accomplish, and the full reply would have betrayed an assumption that there would be time for it all. The reality, at every step along the way, has been that two or three or probably ten new ideas and obligations have popped up, for every one that I have actually achieved or worked through.

What I am describing may sound like something that would happen only to an intellectual or academic type of person. But in different words, similar experiences occur for most of us. There is always the list of things you need to fix or clean around the house, tasks that you’re supposed to have finished at work, kinds of meditation that you’ve been meaning to try, books to read, people to meet, problems to deal with. It never ends. We’re all just trying to keep the dishes and silverware arranged on the table, as the waiter keeps bringing more and more. It spills over onto the floor; it piles up around our ankles.

I don’t know that we really have a choice. You can’t sit back and work out a master plan to deal with the future, when you don’t know what the future will contain. I suppose the future will tend to contain more of what you want if you at least try to plan for it. But that doesn’t change the fact that the future will keep on bringing more of almost everything, plan or no plan.

Contingency Plans

People have developed various ways to deal with this surplusage of opportunities and obligations. One is that you just plain get old. At various points, in your teens and your fifties and your nineties, you become less willing and able to do certain things – and even if you didn’t, your parents or your employer or your younger colleagues begin to move you along or, if nothing else, graduation day or retirement day arrives, and out you go, ready or not.

In anticipation of that, people tend toward a phasing-out process. At some age, you deem yourself too old to play hopscotch or basketball. You lose interest in the music and the TV shows that your juniors consider essential; you no longer care so much about their favorite celebrities or about the events they consider world-changing. You like to think that you are looking past the trees to see the forest, the big picture, and in some regards that is undoubtedly true. Amid your self-flattering belief in your gathering wisdom, you may be becoming an old fool, but at least you will tend to be less dedicated to the project than when you were working so hard to be a young fool.

Ideally, a person would not wait until the day of the fatal car accident or the heart attack. Ideally, that is, one would be prepared, at every moment throughout life, for the possibility that all the hopes and ambitions must cease immediately. Yet how would that be possible, when a person is simultaneously planning and striving to achieve something that may take a month or a year or twenty years to come to fruition?

I suppose the solution you would arrive at, if you were trying to resolve a similar quandary for the company where you work, would be to make formal contingency plans. If Ray suddenly drops through a hole in the floor, Alice will take over. Therefore Alice must be briefed on Ray’s work, etc. In private life, this probably translates into having a will, making sure someone knows where you keep your keys, and so forth. You can chew up a lot of time on such planning if your circumstances are constantly changing, but hopefully most of your issues settle down, at some point, into patterns that you could explain to someone else, face-to-face or in writing.

Strategies

Contingency planning is fine, as far as it goes. But it doesn’t really answer the question. Yes, you hope that Alice, or whoever takes over, will share your priorities, and that your work or your love for your kids (or whatever you are planning for) will carry on. But in the meantime, while you are still alive, you’ve got this neverending stack of things to deal with. Chances are, you’re going to be around for a long time yet. Your interests and desires are going to persist even if your opportunities (i.e., what you are able to do, and what you are permitted to do) shrink, for reasons anticipated or not. There is going to be this ongoing question of how to triage among an embarrassment of possible pursuits.

On one extreme, you can try to do everything. On the other extreme, you can give up. Some phrase it in terms of “having it all” versus “letting go.” And sometimes those terms can seem to describe your actual situation. Mostly, though, those phrases just mean that you have a good ability to forget what you once dreamed about, or to overlook the ways in which you continue to be involved in the details of life. Most likely, the person who has everything has already decided what “everything” means, and the person who has given it all away has merely mentalized his/her obligations and possessions. These can still count as achievements. But they probably represent the feasible end, not the uncertain beginning, of the process of sorting and prioritizing among your possible activities.

The question here is, where do you begin? At any random moment in your life, what should you be doing to manage your vast flood of possibilities? You could stand still; you could walk forward or back, left or right, and you could turn again, or around, at every turning point – and along the way, you could be singing or talking or silent, thinking about A or B or Z. How to choose?

It seems to be a question of strategies. One strategy would be to start with the full set of possibilities and pare away the nonessentials; another would be to start with nothing and identify the essentials. Where possibilities multiply like bunnies, it seems obvious that paring away nonessentials would be a losing approach. You would no sooner eliminate one option than another would spring up in its place; moreover, the one that you thought you had eliminated could come back to life in new forms, perpetually offering alternative ways of achieving what you weren’t really sure you wanted to achieve in the first place. Then again, how can you even decide what’s not essential – how can you be sure that you want to eliminate a line of endeavor if you haven’t rolled up your sleeves and dug into the squirming mass of possibilities embodied within it?

Instead of seeking to distinguish essentials from nonessentials, a different strategy would focus on tying up loose ends. If you can wrap up a project or an area of concern, put a nice bow on it, and present it to the world as a completed achievement, then maybe that’s a logical stopping point. Yes, you could choose (or be dragged) into extending the achievement – enlarging the business you have created, for example, or going on to earn a more advanced degree in your field – but at least you might have a sense of control.

In a sense, “tying up loose ends” is what much of life is about. We are forever looking to get rid of the old car, get the kids through college, put together a credible dinner, and otherwise consolidate assorted achievements, large and small. Far from “having it all,” we often find ourselves struggling to stay afloat in the day-to-day torrent. This state of affairs seems to argue in favor of a strategy of simplification. In other words, if you want so much as a moment to breathe and clear your head, you might begin with a focus on time: identify what is consuming the most of yours, and resolve that first.

No doubt there are other possible strategies. But let us regroup. These brief remarks have tended toward the sense that an effort to relinquish one’s aspirations, later in life, is really just a continuation of the lifelong need to prioritize within one’s resources and abilities. Pending further exploration, it tentatively seems that one might appropriately begin by simplifying – by trying to wrap up those loose ends that are especially complicating and time-consuming. Get the kids out of the house; look for timewasting tasks that you could minimize; sell off the business; move to a smaller space that requires less cleaning and that accommodates fewer distractions.

An Umbrella Concept:
Working Yourself Out of a Job

Perhaps the foregoing strategies and priorities could be subsumed under the concept of “working yourself out of a job.” As developed in another post, working yourself out of a job includes a variety of perspectives. It can mean teaching people (e.g., your children) to stand on their own feet, rather than depending upon you. It can mean eliminating unnecessary and duplicative tasks. It can mean finding others within the family, church, team, or company (or, indeed, within the world at large) who could do what you do just as well – who would grow if they were expected and trusted to take over. It can mean clearing the decks so that you have time and energy for your own growth into more important or worthwhile activities.

So described, working yourself out of a job can operate as a shorthand expression incorporating several strategies (e.g., simplifying, identifying essentials, tying up loose ends). Its core idea is not that you will stop working; it is that you will work less on some things, freeing you up to concentrate, as you wish, on other tasks of greater importance. It is not a philosophy of simply letting go, which could mean allowing things to fall apart; it is, rather, a matter of arranging a responsible conclusion or transfer of obligations and objectives that should be eliminated or placed into the hands of others. Working yourself out of a job can be a plausible objective at any point in life, as you strive to translate your present situation into new or more refined opportunities.

An effort to work oneself out of one’s job could have a particularly large impact for people like me, who may indulge a sprawling assortment of projects in various stages of completion. Suddenly there is this notion that I should be examining each of those projects, along with a host of ideas that have not yet achieved project status, and asking myself whether and how I could make myself unnecessary for each of them. The answer, mentioned above, is simply to win the lottery and hire scholars to complete them for me.

While I wait for that winning lottery ticket to materialize, it seems I might entertain myself by seeing what I can do about the problem. I suppose a first question is, what kind of timeframe are we talking about? If I am required to arrive at a refined definition of my “job” – my avocation of writing, my collection of ideas and writings waiting to be converted to books and articles – and to hand off major chunks of it within the next 24 hours, I will probably take very different steps from an alternate scenario in which I would have several years to think about and manage things.

The short answer to the timeframe question is, I think, that this is to be a departure from business as usual. We are not anticipating that someone in my position will complete all of those many projects. The imaginary boss inside yourself, the one who is asking you to get things moving, will not keep you around for additional months just to fiddle with details. You need to wrap it up. There are other, more important things that you should be doing with your time. That, anyway, is the underlying mindset of working yourself out of a job.

Where to Begin

Viewed that way, there is at least a tinge of crisis planning in the air, when one begins to work oneself out of a job. No time to dilly-dally. One had better start from the top down, with the key tasks that you would really not want to be forgotten or mishandled. Decide what needs to be done, and either figure out how to get it done or find someone else who can. The ones you keep for yourself will probably be the key activities on which you will be spending significant time for weeks, months, or years to come.

Researchers and writers often face the question of whether they really need to research or write some particular thing. The question has many parts: will you buckle down and get it done? will the resulting product be of good quality? will you enjoy researching or writing it? is it important that you do it? will anyone buy or read what you have written? has it already been done, or is it likely to be done, by someone at least as able as you? and so forth. Similar questions arise in other kinds of vocations and avocations. They are questions of why you think this, or that, is one of your most important projects.

Answering such questions can become a major project in itself. For many of the things that a person might want to write or do, there may be someone else out there, somewhere, who has already written or done it, or who has invented a method or tool or philosophy that does it better or that explains why it should be done differently or perhaps should not be done after all. For that matter, you may not be aware of others who would be interested in taking that load from you. But how can you find this unknown person or tool or philosophy? Maybe the best one can say is that, the more you become familiar with what you are planning to do, and with what others have said and done (or are trying or willing to do) in that area, the more likely you will be to make an informed decision on whether you need to spend the time to invent a solution.

If there is nothing in particular that you have been meaning to do, you are probably not reading this post. If, on the other hand, you find yourself groaning under more expectations (from yourself or others) than you can handle, it may be helpful to consider whether you are burdening yourself unnecessarily and perhaps even counterproductively. For instance, if you expect yourself to complete numerous projects, and yet are unable to answer the kinds of questions just posed (e.g., has it already been done?), it may be that your real project – the one filling your days or complicating your list of things to do – exists on a different level.

What is “a different level”? Here’s an example: people can become agitated about huge political or psychosocial topics when the problem is really just that nobody seems to love them, or that they were pushed too far by one experience with a zoning board or a divorce court. Conversely, people can become highly preoccupied with some seemingly minor thing – a neighbor’s fence, say, or a bank’s overdraft fees – when the real problem is that they have run out of patience and are in need of a major change (e.g., a few years living in the countryside or on another continent). Or they may simply have transitioned into another phase of life, without fully recognizing it. Such realizations may not take care of the inevitable task of sorting through and thinking about a pile of projects that you have been holding onto. But they may equip you with attitudes or priorities that make it easier to know what you really want to do about those projects.

Some people, facing a mountain of potential tasks, may have no choice but to chip away at it piecemeal over a long period of time. In some cases, one might treat the exploration, consolidation, and reduction of that mountain itself as the task that one retains, farming out or otherwise eliminating pieces of it along the way. This would still be a task amenable to the philosophy of working yourself out of a job; it’s just that it may take months or years to shed this particular job, as some portions of the heap prove amenable to swift disposition while others demand detailed attention. It may sometimes develop that a bit of poking around will suggest ways to chop up the mountain more rapidly than expected.

These are just examples. The general idea is to get your thinking focused on the level of analysis where you can identify a manageable number of key projects that you are going to triage, perhaps keeping one or more for your own long-term attention and releasing the rest into the hands of some other person or group, near or far. If the very attempt to sort things out is itself going to become a bottomless chore, you might try to make a first pass, doing a rough sort; eliminate what you can; and then come back for one or more passes. Without denying the demands of your inner boss (above), sometimes those multiple passes might best unfold at a rate of one pass per week or month, so as to allow time for your thoughts to gel and for some aspects of the situation to settle down. But in some cases it could be unwise to drag out the process too long: the opportunity to set things in order may pass, or you might become impatient or burned out, and wind up just dumping half of it.

Conclusion

This post has offered a few thoughts on the topic of prioritizing among multiple tasks that a person might have been wanting or meaning to complete. There is no doubt an endless number of situations and strategies that could be added to the several discussed here.

Somewhere in or beyond this post, there may be a way of thinking, or of seeing things, that can make one’s list of tasks manageable. It may take some tinkering, some exploring, some openminded consideration of possibilities previously ignored or rejected. In the terms suggested here, however, such a process of thinking and sorting might be viewed as a commitment to work oneself out of a life – distinguishing, at any age, the things that one must do from those that one can hand off to others, so as to free oneself for other priorities.

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