Resolution Success 2019: Planning

Daniel R Greening
4 min readJan 4, 2019

How can we improve our success odds for New Year’s resolutions? It comes down to how you plan. We can use detailed upfront planning, adaptive planning, or no planning to achieve our goals. Research shows your planning style largely determines whether you persist and achieve.

My friend 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.” Let’s see how these three planning styles would tackle her yearly goal.

Barack and Malia Obama volunteering at DC Central Kitchen, 2014

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.

If my friend did detailed upfront planning, she would likely decide which obligations she would cut over the coming year, and then schedule their termination over the course of 2019. But can she really cut them without extraordinary pain? Should she really keep the others? Could she scale back some of them or delegate? There’s a lot we won’t know in advance.

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.

If my friend did adaptive planning, she might have as a more general yearly goal, “I will know my major obligations, know their priorities, spend most of my energy on the important things, and be capable of cutting less important obligations when new obligations arise.”

She can dive into more detailed for the first two months, “Reduced major obligations to 5, worked on each major obligation, and got feedback.” We don’t go into detail for the remaining 10 months; instead, we wait until the first two months are done before planning the next 2 months.

For the first week of that two-months, she can dive into even more detail, “Identify big commitments in a mobile device to-do manager [Omnifocus, Things, and Todoist are popular examples], prioritize them, and work on some of them.” Guess what, we are not going to plan the remaining 8 weeks at this level of detail, until this first week is done.

For the first day of this week, dive right down into clear detail, “Pick and purchase a to-do manager, put today’s priorities in it, get at least one thing done, and mark it done.” She can plan the remaining 6 days in the week in the morning of the second day.

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. Laying the groundwork for opportunism is a project itself. It’s a great first step to success.

How might my friend go the no planning route? Quitting a bunch of low-value obligations would be a first good step. I often advise managers and executives. One of the first things I do is look at their calendars. Executives who let others drive their agendas will have meetings every hour and no time to think. Then I spend time with them to determine which meetings are important, and which can be sacrificed. And finally, we figure out how to defend that thinking time.

What works?

Adaptive planning beats detailed upfront planning in project success, based on a lot of data. In creative teams, 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: attempting something you’ve never done before 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, you succeed, too.


A daily sequence of courageous imperfect actions (CIA) can lead to great success.

Your goals can motivate or discourage you, see Driving Purpose.



Daniel R Greening

Agile management advocate, coach, and trainer. Software entrepreneur, executive, and developer. Speaker, writer, and thinker.