Resolve to Succeed: Plan

When we create New Year’s resolutions, we are using project management skills to achieve a personal goal. We can use detailed upfront planning, adaptive planning, or no planning. What approach works best for happier outcomes?

How will you plan?

Your planning style will likely determine whether you persist and achieve.

The best laid schemes of Mice and Men Go oft awry.

Robert Burns

Detailed upfront planning

Most people assume detailed upfront planning works best. They optimistically plan a year or more in advance, with specific milestones delivered at specific dates. They think they will forge ahead relentlessly, achieving success or failure by a succession of deadlines.

But there are many pitfalls ahead. They face many unknowns: if they are trying to lose weight, they probably don’t know how fast they can safely lose, and whether they can maintain it. They probably don’t know whether their family will encourage or hinder their weight loss. Unpredictable events happen to all of us: they might have to move, deal with a friend’s health crisis, or find a job. If they miss a date, they have to make up the time somehow, by working harder or taking more risks. Uncertainties torpedo many well-structured plans, and they can easily waylay theirs, and yours.

Adaptive planning

Adaptive planning starts with a very general goal and then plans specific short-term sub-goals “just in time,” adapting the next goal based on experience from previous goals. Then, thoughtfully sequence sub-goals to learn more about your goal and capabilities. Don’t plan a full year of sub-goals, otherwise you are planning upfront.

For example, if you want to exercise more, consider generalizing your goal to “improve cardio health” to give yourself greater flexibility, then set a first sub-goal to “time a 1 kilometer run three times this week.” That first result informs you about running and your abilities, so you can set a realistic goal for next week. If a unexpected disruption interferes, you can substitute a different exercise, study sustainable running techniques, or measure your blood pressure, which contributes to your general goal to improve cardio health.

No planning

No planning waits for opportunities to fall out of the sky. Planning is easy: do nothing. You may have a bunch of goals, but prefer not decide between them all. You may have a goal so broad, such as “I want to be successful,” that you can’t figure out where to start. Or you might fear commitment or failure. Or you might like to drink whiskey and goof off all day. But even with no planning, you’ll get better results by preparing yourself to act rapidly when opportunities arise. We will talk about those techniques in this series. Laying the groundwork for opportunism is essentially a project. In many cases, it’s a great first step to success.

What works?

Adaptive planning beats detailed upfront planning in project success, based on a lot of data. In software projects, which combine the creative efforts of smart people, detailed upfront planning produces a 30% project failure rate, while adaptive planning produces a 9% failure rate. If you have worked with artists, architects, designers, or entrepreneurs, you can readily understand why upfront planning often fails: you are embarking on something you’ve never done before, and it isn’t very predictable. If you are trying to lose weight sustainably, previous efforts didn’t work. Something unexpected caused your plan to fail before, and some other unexpected thing will likely cause it to fail this time.

Can we succeed with no planning? On a personal level, many people (including me) believe operating in the present moment leads to greater happiness. Taken to an extreme, this philosophy might argue against college education, against taking initiative, against ambition, all in the service of happiness. A variation where we operate in the present moment most of the time, but leap into action to exploit an opportunity, could allow us to win, and win big. So don’t worry if you don’t want to plan, this series will help you succeed, too.


One of my pals shared her goals for 2019, and here’s what she wrote

What I want from 2019 is to not feel overwhelmed any more, to not have a huge cloud hanging over my head, to stop holding my breath waiting for the other shoe to drop.

What I DON’T want from 2019 is to stop giving a shit, and to leave other people responsible for what I truly wanted to accomplish.

How to get there: I need to work on identifying all the commitments, prioritize them, let go of some things, and be able to make an informed decision about whether to say yes or no to new items.

This is a great goal, probably for most of us. Achieving it means my pal will be able to direct her own future, instead of letting squeaky wheels and crises dictate her future. Colleagues have developed to handle these issues, which we will discuss in later posts.

Let’s see how we might create an adaptive plan for my friend’s goals. I created two big, somewhat vague goals for the year, but then built more specifics into three easier goals for the current two months, three more specific and easier sub-goals for this week, and very specific and super-easy sub-goals for today.

Try it

Let’s try using adaptive planning together. I promise to help you out.

Give yourself a few moments to think about the coming year. What would you like to achieve in 2019? The most common New Year’s resolutions are these:

  • lose weight
  • exercise more
  • quit smoking
  • managing debt
  • save money
  • get a better job
  • get a degree or certification
  • take a trip
  • volunteer

If you prefer no planning, let me suggest some options:

  • become happier
  • prepare to exploit unexpected opportunities
  • reduce stress
  • deepen my relationship with spouse or family

If you’re interested in feedback, which helps tremendously when you are doing adaptive planning, please add your goals as comments to this post. I will happily provide feedback to anyone who posts their goals.

If you are interested in research related to goal-setting, you might check out

4 responses to “Resolve to Succeed: Plan”

  1. Christi Herrick Avatar
    Christi Herrick

    Cool, Dan, I’m liking the concept of adaptive planning! I am not now, nor will I ever be, a detailed upfront planner. My life is always open to the most unexpected adventures that come up. Admittedly, those adventures are usually small-scale, but they’d sure mess up a detailed life plan and I’m unwilling to give them up.

    Although my husband will tell you that I’m a big fan of lists, I’m really the type of person who leans more toward no planning at all, with the unchangeable dates, meetings and happenings fixed in my head, and even – occasionally – popping up on an electronic calendar. I remember sitting at my mother’s house for family dinner…she and my sister would try to plan the next possible night for getting together, while I pretended to look through my phone and study my schedule as I frantically went through the coming week in my head….what’s happening? School board meeting? Out of town for a conference? Cooking for the entire school staff? Dentist appointment 180 miles away? Dinner with a friend? Generally it all worked out, although I can tell you from experience that it’s exhausting trying to be in two places at once.

    It’s not hard for me to see that adaptive planning would be a huge help to me. I plan so carefully for some things…extensive lists of things to pack and take with me, whether I’m taking snacks for a school board meeting or going on a nine-day trip. And I tend to put quick notes into my phone at night time, grab this and this in the morning, because I can go to bed with some urgent thought in my head and completely forget about it by morning.

    And yet, most of the week I’m just pulled along by events. When the second week of the month comes, I start with good intentions, then there are usually meetings three nights in a row and it’s all I can do to get out of bed and wander into work by 8:00 the next morning…and suddenly it’s Friday night and there are still things to be done, but dang, I need a little downtime…these are the times when goals that have not been written down are completely out of sight and out of mind. And obviously, those days turn into weeks and the weeks into months and the months into years, and I think there are some song lyrics in there somewhere…

    I totally get how squeaky wheels and crises can decide what’s going to happen on any given day. I have no doubt that some adaptive planning would not only keep my goals at the forefront, it would also allow me to make better use of my time and give me some breathing room in the middle of a busy week. I not only need some big goals for the year, whether well-defined or more nebulous, and I really need a way to break those down into some monthly, weekly and daily accomplishments that will give me more than just a semblance of control over those days, months, and weeks that become years.

  2. Wiley Wang Avatar
    Wiley Wang

    It’s a thought provoking writing. I totally believe that we can learn from software project based life management. Here are some of my random thoughts:
    1. “Most people think detailed upfront planning works best.” I noticed that it means people think it works the best, rather than actually do the planning. Still, this seems a rather strong assumption. “Planners” as a type of personality is rare. Most people are not planners. Most people don’t stick to the original New Year’s resolutions though. There is a Chinese word: “虎头蛇尾”, “tiger head, snake tail.” To describe the way people fail at persisting in their pursuits. When I think of goals, I think of this kind of struggle.
    2. Adaptive planning sounds like a good solution to get us there. I personally interested in how we can keep getting motivated. By week three, I may quit or I may find myself busy with work along with other distractions.
    Here are also some of my weird plans:
    1. Learn about black culture in the US. Why? Being a gay Asian immigrant, my culture understanding of the US is completely learnt, mostly during my adult time. And it’s extremely “white”. In the age of diversity, or fighting the force of anti-diversity, I want to learn more about black culture. Let it be music, history, literature, humor or entertainment. I don’t want to be embarrassed about this anymore
    2. Pursuit romance on the other side of the world. Is it a fantasy or is it real? My goal is to reveal it.
    3. Build a better rationship with money. Money is evil, right? That’s what I thought. I have a hard time respecting money, but maybe it’s time to take a second look at our love hate relationship.

  3. Naveed Ashraf Avatar
    Naveed Ashraf

    I’ve used the following in software delivery and to help people with personal goals, to start getting them to abstract estimating as opposed to absolute and accurate estimating (because some estimation is what planning is about)
    Estimate Duration = risk + complexity + duration.
    People only focus on the duration but when they have never installed a shelf after two days(me btw) they realize – Complexity – and that they may not have all the tools – RISK – the duration may be longer than what they think of how long it should take.
    2. I like the adaptive planning section, it needs a diagram. I like the idea of high level goals or themes for the longest duration of planning – whether that is a month two, three or four. This made me think I like and I may play with the largest sections being triplets – then it made me think about breaking the year into triplets (four month theme or high level goals) and then fill in the sub goals at the start of the triplet. I like the triplet more than the quarter for personal goals. Jan to April, May to August, September to December.
    3. Every four months I’m evaluating my sub goals as I learn but this applying the learning doesn’t have to wait till the end of the triplet. Change the sub goals on the fly. The most important part of this would be that learning is being applied. Some of our goals may or may not be repeated – getting down to X weight is a goal then the goal might change to maintaining it.
    4. How do I stop myself from having unattainable goals that I fail at, my biggest demotivator. I’m like a kid , I like my rewards thru accomplishments. I crumble under personal failure, I want to avoid setting goals that I may not achieve. I don’t have a solution for this ,I’ll come back to it.
    5. I LOVED your pals goals,you should think about how to bring that closer to start of the article , it’s powerful. And that made me wonder if sharing themes or triplet goals or high level goals , whatever you want to call them, helps people get off the starting block what if you published an ever growing list of high-level goals or wrote more examples like your pals.
    6. And I think Russell Brand does a similar less instructive job to you and adds inviting mentorship into your life.
    7. Im thinking its important to move away from the fact that Jan 1st is some magical date or milestone. In fact take it a step further , does offsetting the planning increments from the year actually help you be more conscious about re-planning? Jan 1st is in fact arbitrary anyway
    8. You’ve picked up on what is quoted here as an atomic habit. In your case it might be an atomic next step
    How to Crush Your Habits in the New Year With the Help of Science

  4. Alexander Coward Avatar
    Alexander Coward

    You’re really onto something with your article. In fact it has been very well researched in education, but sadly rarely well implemented. What you’re calling “adaptive planning” in education is called “formative assessment”. In robotics it’s closed loop control. The strange thing is how difficult people find it to grasp given how obvious it is. If you’re landing a SpaceX booster, you have a long term goal of landing on the pad, and make continuous real time measurements to track progress and adjust accordingly, obviously. People often think it means no planning.

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