Want things to go well? Plan like a defensive pessimist

So often we underestimate the time and effort required to reach our goals. You can avoid that trap with realistic planning

by Julie K Norem, professor of psychology

An overgrown garden with a blue boat surrounded by tall grass, houses in the background and a wooden fence in the foreground.

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When I needed to travel a few weeks ago, like many people, I planned to get some work done on the trip. I succeeded in arriving at the airport long before my flight to capitalise on the time. To my dismay, however, this airport (unlike others I’d flown out of) had virtually no space for work, no flat surfaces, and nothing that would allow me to set out papers around my laptop. I got very little done. In hindsight, I should have thought more carefully about how airports differ, but it just did not occur to me, and my plan didn’t include other ways to accomplish what I wanted to.

It’s easy to find other examples of plans going awry. You might plan to spend half an hour cleaning a refrigerator, a car or a room, only to discover that you have to do all sorts of scrubbing and rearranging that you didn’t anticipate. You could plan an elaborate menu for a dinner party, only to find that the main dish takes much longer than you anticipated (since you don’t have a sous chef to chop ingredients like the chefs on cooking shows). You may plan to tackle the hardest part of a project first, then realise you don’t know where to start. And, so often, we plan as if every day will be our best day. We plan as if we’re the non-procrastinating, energy-filled, mind-like-a-steel-trap people we want to be, and when the time comes, it turns out that we’re just our normal, well-intentioned but fallible selves.

‘If you fail to plan, you are planning to fail,’ the saying goes. But as the examples I described suggest, even those of us who believe that planning is important could often use some help doing it more realistically and effectively. Fortunately, psychological research has identified some of the most common planning pitfalls, as well as effective strategies for overcoming them.

Despite a common belief in the power of optimism, I and other psychologists have shown, through decades of research, that, for some people and some situations, more pessimistic approaches are effective. Defensive pessimism is a strategy that involves assuming that things will go wrong (that’s the pessimism part) and thinking through what might go wrong in concrete and specific detail (that’s the defensive part). This ‘thinking through’ process often helps anxious people prepare for what they imagine will go wrong, and they end up being able to take small, specific steps that keep them engaged in the situations that make them anxious, which helps them accomplish their goals.

What defensive pessimists do for themselves fits with what other research has shown about goal-setting and planning processes. I have learned as much as I can about that research over the years, and it helps inform the following advice about planning well.

Key points

  1. Optimistic plans often go awry. There are many planning pitfalls, but you can avoid them by being more strategic and considering how things could go wrong.
  2. Start with setting clear goals. Break abstract or vague goals into smaller, more concrete pieces.
  3. Give yourself a chance to make easy progress. Often, getting started is the hard part, so make the first steps of your plan easy to take. Then you’ll have momentum on your side.
  4. Write down your plan, if you can. Describe the steps, on your phone or on paper, to offload cognitive effort and highlight your progress.
  5. Think about how long your plan will really take. Avoid the ‘planning fallacy’ by envisioning what each step will actually require.
  6. Get feedback on your plan. Ask someone who knows you – and understands what you’re trying to do – whether your plan seems realistic.
  7. Anticipate obstacles and make backup plans. Ask yourself what could get in your way and have alternative courses of action at the ready.
  8. Remember who you are. Make plans that account for your preferences and limitations, rather than pretending they don’t exist.

Start with setting clear goals

The way you think about your goals will influence both how difficult planning is and how well it’s likely to proceed.

You can think about goals in a variety of ways. When I ask the college students I teach about their goals, their responses vary, but they are often vague: ‘I want to do well,’ or ‘I want to learn a lot.’ Abstract or broad goals can be inspiring: I feel a warm glow if I assert that my goal is ‘to be a good person’, or ‘to achieve important things’, or even ‘to clean my house today’. The problem with abstract goals is that it’s often not very clear how to accomplish them. Waking up in the morning and whispering to myself that ‘I’m going to be productive today’ may get me out of bed, but then reality kicks in and I face the question of what I’m actually going to do. Similarly, if my goal for the day is framed as ‘clean my house’, I may feel daunted by the magnitude of that goal and just pull the covers back over my head.

When I ask my students how exactly they will ‘learn a lot’ in my class, they often sputter a bit before they come up with something like: ‘I’ll do all of the readings and attend every class.’ That’s a good next step, because those responses actually represent more specific goals. When you can take more abstract, vague or general goals and break them into smaller, more concrete and specific pieces, it often becomes easier to plan.

So, start with the abstract goal, and think of that as your ultimate destination. Then, plan your trip to that destination. What supplies, preparations and action steps are necessary to get you there? Each answer to that question becomes a subgoal on the way to your final goal.

Try to get as specific as you reasonably can when setting goals and subgoals. If, instead of saying that I will ‘attend every class’, I say that I will ‘wake up at 7 am in order to have time to get ready and grab breakfast before my 8 am class’, then the steps necessary to achieve the goal of attending one class (and the associated subgoals of getting ready and grabbing breakfast) become easier to see. I need to set my alarm (and maybe a backup alarm), and try to get to bed early enough the night before to decrease the trauma of an 8 am class. I can lay out my clothes and plug in my laptop so that it’s charged and ready to go, and put a protein bar in my backpack just in case.

The more specific and concrete your goals are, the easier planning for those goals tends to be. As a bonus, smaller steps taken repeatedly are also more likely to become habits – and once that happens, we no longer have to plan, we just do.

Give yourself a chance to make easy progress

Many of us get a boost from succeeding at a small, initial step on the way to a goal, and that motivates us to continue. Conversely, one of the things that can get in the way of effective planning is the difficulty of motivating yourself to actually start and persist on a plan. That’s why it’s a good idea to make the first steps of your plan especially specific and easy. If your ultimate goal is to clean your house, start by just cleaning the sink in the bathroom. While you’re unlikely to be inspired by the thought of cleaning that sink, looking at the sparkling results when you’re finished is likely to feel good. You’re then more likely to be inspired (or at least, less depressed) by the thought of moving on to the next task.

This approach can also help you leverage what psychologists call the ‘Ovsiankina effect’, named for the Russian-born psychologist who studied the troublesome feeling people have when they start something but don’t finish it. It’s a vague, unpleasant sense that something is wrong – and the way to alleviate that feeling is to finish what you’ve started. This effect happens automatically. That means you can make use of it by starting your plan with small steps that are easy to take and, once you’ve completed them, the Ovsiankina effect can help you keep going.

Write down your plan, if you can

Creating a written ‘map’ of each step makes them even more concrete, and it can help you anticipate potential obstacles. It also offloads the cognitive effort of continually trying to remember your steps along the way. Plus, it allows you to experience the delicious satisfaction of checking things off as you move through the plan.

The most important thing about a written plan is that it works for you. A straightforward list of goals and the steps necessary to reach them can work perfectly well. I have also been playing around with creating plans that look like simple game boards (think Snakes and Ladders ) that map out paths to my goals, just to introduce a bit of whimsy. Some people like having plans on their digital devices (it’s easy to carry them across locations); others prefer paper, whiteboards or other media. Some people find that arrays of sticky notes that can be re-arranged or colour-coded work well for them. It may take some practice to find what best fits you and your goals.

Though some people find it tedious to write out plans, I think the benefits tend to outweigh the costs. Nevertheless, there are potential pitfalls. If you develop a plan so elaborate that it takes a lot of effort to maintain, you may feel overwhelmed. It is important to remain flexible. If the prospect of writing out each step feels like too much, you could just write down the first step. Do that step, and cross it off. Then write down the second step, and so on.

Think about how long your plan will really take

A well-studied tendency that hampers effective planning is called the ‘planning fallacy’. This is a general tendency to underestimate the time and effort it will take to do what we are planning to do. Research suggests that most of us, most of the time, will be overly optimistic about what it will take – and, especially, how long it will take – to follow the steps of a plan. This might mean, for example, ignoring the time required to gather cleaning supplies before you can start on the bathroom, or planning as if you will always be at peak energy levels, overlooking the fact that you might need to rest a bit in between subgoals. It’s a kind of overconfidence that can get you into trouble, whether because you spend more time on a plan than you wanted to or you simply run out of time to get it done.

Surprisingly, knowing about the planning fallacy is not always enough to prevent it. So what does help? Here again, planning small, specific steps can be useful, because you may become aware that you are falling behind while you’re still early in the process and have time to make course corrections.

It can also be helpful to imagine yourself going through each step of your plan. Don’t do the sped-up, montage version of this mental simulation – that’s likely to exacerbate the problem by making everything seem easier and faster than it will be in reality. Instead, as best you can, roll through the mental movie scene by scene to clarify what’s involved in each step you plan to take. If you have to complete a report at work, for example, that movie should include collecting the files and other information you need, not just an image of you typing away at your desk. After you picture the steps of your plan, you may benefit from jotting down how much time you think each segment or ‘scene’ in your movie is likely to take.

Get feedback on your plan

Interestingly, people don’t tend to exhibit the planning fallacy when they think about someone else’s plans. So a simple tip for planning more effectively is to show your plan to another person, who might be less biased in evaluating it than you would be. Ask for their feedback on whether the time and effort you’ve estimated for each step seems realistic. Then pay attention to the feedback they give you and adjust accordingly. The better this person knows you and the kind of tasks you plan to do, the more helpful their feedback is likely to be, and the less likely you are to wind up short of the time, energy or other resources that you need to follow your plan.

Anticipate obstacles and make backup plans

In our optimism, many of us make only one version of a plan, without considering potential obstacles and contingencies. But effective planning includes anticipating where and how you might be derailed – and finding alternative pathways if that happens.

Ask yourself: ‘What could go wrong?’ or ‘What could get in my way?’ Think about your real life, not the version you wish were true. What are the chances that co-workers or family members will suddenly demand your attention, or that you’ll get distracted, or that another urgent task will come up? Ideally, a Plan B will include alternative courses of action for every step of your main plan. Your mental movie can help you here too: while imagining writing your report at work, for instance, you can anticipate that, if Sammy is around, he’ll drop by your desk to chat, so you can rehearse what you need to say to deal with the interruption politely, or find a conference room to work in.

The more important your goal is, the more you should consider having backup plans – variations that you can pivot to if one or more key steps can’t be carried out. When you have alternative steps already planned, you can respond more flexibly to what the world might throw at you.

Remember who you are

Truly effective planning requires knowing yourself, and this is perhaps the hardest part. If your plan for getting fit involves running every day of the week, and you hate running, then the most detailed, finely crafted plan is likely to crash into the huge obstacle of your own resistance. This does not mean that it’s impossible for you to achieve your goal that way; only that the cards are stacked against you from the outset.

The most effective plans take into account our own strengths and weaknesses, personality traits, likes and dislikes, resources and interests. If your plan requires time that you haven’t set aside, calls for skills you haven’t acquired yet or conflicts with other goals that you’re pursuing at the same time, it is unlikely to survive the first obstacle you encounter.

Knowing ourselves isn’t easy: we are often unrealistic about our own habits and tendencies. But here, too, talking to others as you develop plans can compensate for potential blind spots. Friends, family members or co-workers who know you well can help you calibrate both the goals you set for yourself and the plans you develop to pursue them. When asking other people for feedback, give them permission to mention your weaknesses without worrying about insulting you – otherwise they might not respond honestly. Just as importantly, remind yourself not to be defensive. If someone points out that you have a tendency to get distracted, questions whether you have the energy to do everything you’re planning in the time you’ve allotted, or raises any other limitations, that might be what you needed to hear in order to adjust your plan accordingly.

Final notes

In sum, effective and realistic planning requires being specific about what you’re trying to accomplish, determining not just what you’re going to do, but how you’ll get there. Plan in small steps, and use your imagination to help yourself account for the time and effort they will require, and to anticipate potential obstacles. Make backup plans. Ask people who know you and know what you’re trying to accomplish to keep you realistic. Try to be honest about your own tendencies. All of this will help you create a more realistic plan – and then, you’re on your way.

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