Post 10: Backwards Planning from Deadlines and Realistic Ambition

In my last post, I covered the foundational elements of time management you might want to consider during your planning phase: time awareness, task estimation, processing speed, calendar systems, and energy-aligned scheduling. This post takes those foundations and puts them all to work simultaneously towards the completion of a single, concrete planning problem, namely how you can turn a project deadline into a realistic workable plan for meeting that deadline. I'm going to walk through this planning process with you one stage at a time, the same way I have previously walked through this process with clients. By the end of the walk-through you will know how you can apply the same method to planning your own projects, learning how to space out your work across time so that you can work on it continuously throughout the time you have available, rather than having all of your work tasks bunch up at the last minute as your deadline looms.

Backwards Planning from Deadlines

Meet Amanda

I worked with a client I'll call Amanda. Amanda is a writer who was diagnosed with ADHD, inattentive subtype as an adult. During one of our sessions she mentioned that she had a work project due in six weeks that she wanted my help planning. Amanda explained she was contracted to write a chapter for an edited book, where the chapter needed to run about 12,000 words, draw on two source interviews she had previously completed, and be submitted to her editor as a Word document formatted using APA-style citations. She explained she hadn't started this work yet, and could see that she was likely to put off doing so until the last minute.

Like many adults with ADHD, inattentive subtype, Amanda knew she had a difficult time maintaining her focus on work projects. Most frequently she would start her projects too late and then panic, working all night to meet her deadline. Occasionally she would get started on the work early only to become distracted, losing her focus as more immediately pressing demands piled up, and then find that she became panicked as her deadline loomed.

What follows is the step-by-step, stage-by-stage backwards planning from a deadline plan creation process that Amanda and I built together to help her overcome her procrastination and distraction difficulties. To make sense of this example, you'll need to appreciate the date Amanda brought this task to me, and the date her work was due. For the sake of walking through how we constructed this plan, let's say that Amanda brought the task to me on Monday, September 8th, and her deadline was about six weeks later, on Monday, October 20th.

As we get started, I want to highlight the most important benefit that a well-built backwards plan provides you. It's tempting to think of backwards planning from a deadline as mostly a scheduling exercise, a mere matter of mapping out and managing the logistics of getting work done, as documented in your calendar and as measured in tasks and hours worked. The backwards planning process does indeed produce those artifacts, but importantly, such artifacts are merely tools to help you gain the deeper benefit of the exercise which is enhancing your peace of mind. Constructing a backwards plan is an emotional design process that redistributes the anxious dread that would otherwise collect all at once around a distant deadline but only when it started to loom large, so that such dread can be distributed out in smaller and more manageable doses, rather continuously across the entire span of the time you have available between now and that deadline. During the process of backwards planning, you'll attach manageable-sized doses of anxious dread to milestone deadlines associated with a list of specific tasks, each of which must be completed in order, so that when all of those tasks are finally completed, your project is completed. The elegance of such backwards planning isn't found in how neatly you organize your working hours. Instead, it's found in how such a plan helps you manage your anxious dread so that you can digest it bit by bit, in bite-sizes, one at a time, so that you don't become overwhelmed as your deadline approaches.

Start By Defining Your Project

The first step in the backwards planning process involves describing exactly what "done" looks like for your project, in concrete enough terms that there's no ambiguity later about whether you've actually finished.

The first thing Amanda and I did was to nail down exactly what "done" needed to look like for her book chapter. We did this by defining the finished product's characteristics in specific-enough terms that there could be no ambiguity later when she was finished. Specifically, we determined that Amanda's finished product needed to be:

• approximately 12,000 words in length
• with both interviews integrated into the text
• with her references cited and formatted in APA style
• with the finished product formatted as a Word document with track changes turned off,
• and finally, delivered to her editor by end of day on October 20th.

Being this specific about what criteria her finished product needed to satisfy matters a great deal! Without us first defining exactly what her finished product needed to be, Amanda was at risk of forgetting to do something important, resulting in a final product that did not meet expectations.

Worse than that, any vagueness in Amanda's vision of what her finished product needed to look like might cause her to under-estimate how long it would take her to make sure everything was just right. If Amanda hadn't taken the time up front to become this precise about the final characteristics of her project, she couldn't have accurately estimated how long that work would take to complete, and she would have been left guessing as to when she could realistically expect to deliver her final product.

Task Analysis: Breaking the Project into Its Component Tasks

This second step uses Task Analysis, described earlier in this series, to identify the specific tasks that need to be completed in order to deliver your finished work product.

With Amanda's deliverable first having been carefully defined, we next did a task analysis, during which we broke up Amanda's writing process down into its component tasks. It turned out that Amanda's writing project broke down into six tasks, which needed to unfold in a particular order as later tasks depended upon completion of earlier tasks:

1. Research Integration, during which task Amanda would review her interview notes, pulling relevant quotes and material, and identify any small gaps that needed more research
2. Outline Creation, during which task Amanda would create a full section-by-section outline of her chapter's argument
3. First-Half Draft, during which task Amanda would draft her chapter's opening and first main section, roughly 6,000 words
4. Second-Half Draft, during which task Amanda would draft her chapter's remaining arguments and closing section, roughly another 6,000 words
5. Revision Edit, during which task Amanda would do a full structural and content editing pass of her whole first-draft
6. Final Edit and Citation Check, during which task Amanda would carefully read over her document line by line to ensure that all required formatting was in place, preparing the file for final submission

Notice how each of these six tasks has been defined precisely enough to enable Amanda to know when each of them has been completed. It's important to do this for emotion management reasons, so that it's never unclear whether or not a task is finished.

Duration Estimation: Figuring Out How Long Each Task Should Take

This third step is about estimating how long each task you identified in your Task Analysis will actually take to complete.

Amanda had completed writing projects before, and had some appreciation for how she tended to encounter difficulty. One of the things she'd learned from past mistakes was that she almost always under-estimated how long it would take her to complete tasks. Based on a tracking exercise she had done during an earlier work project planning cycle, Amanda had learned she reliably underestimated her own writing time by about 60%, meaning it actually took her about 1.6x as long to complete a task than she initially thought it would. In this particular case, Amanda's 60% under-estimation figure wasn't a guess, but instead had been derived from a comparison of her initial work-task estimates from the previous project to her actual measurement of how long each task actually took her to complete.

If you're new to the backwards planning process, it's almost certainly the case that you will not know how much longer work actually takes you to complete. That's perfectly okay. In the beginning, you will need to make a guess. But do write down your time-estimates next to the definition of your work-tasks, and then later keep track of how long each work task actually takes you to complete, so that in the future you too will be able to more precisely estimate whether and how much you tend to over or under-estimate the time it takes you to complete work.

For each task in her plan, Amanda made an honest first guess at how long it would take her to complete, and then multiplied that guessed-at time-estimate by 1.6 (her estimated time plus another 60% more) to get her adjusted per-task time estimates:

• Task 1: Research Integration: Amanda guessed 4 hours, then adjusted her guess to about 6 hours
• Task 2: Outline Creation: Amanda guessed 3 hours, then adjusted her guess to about 5 hours
• Task 3: First-Half Draft: Amanda guessed 15 hours, then adjusted her guess to about 24 hours
• Task 4: Second-Half Draft: Amanda guessed 15 hours, then adjusted her guess to about 24 hours
• Task 5: Revision Edit: Amanda guessed 8 hours, then adjusted her guess to about 13 hours
• Task 6: Final Edit and Citation Check: Amanda guessed 5 hours, then adjusted her guess to about 8 hours

Many people get into trouble at precisely this estimation-plus-correction step while backwards planning from deadlines. The most common mistake people make is thinking "I don't need to correct my initial guesses, because this time will be different" and skipping making adjustments. My experience shows it is generally a mistake to think this way! If you do skip making adjustments and if you also do tend to under-estimate how long tasks actually take you to complete, you'll end up not scheduling enough time to complete your tasks. If that happens, your backwards planning will fail!

Amanda didn't skip adjusting her estimates. That single decision was a big part of why the rest of the process worked out well for her.

Buffer Allocation: Building in Room for What You Can't Predict

This fourth step adds additional buffer time on top of your task-duration estimates, to account for ordinary task variability.

In addition to having Amanda adjust her task-duration estimates based on her own personal knowledge of how much longer it typically takes her to complete tasks, I also instructed her to add additional "buffer" time to each of her estimates. It might seem confusing to adjust the estimates twice, so I want to make clear what each adjustment is correcting for.

Amanda's first 1.6x multiplier adjustment corrects for something specific to Amanda: her own documented, tracked pattern of underestimating how long writing takes her. I also wanted her to adjust her estimate again in order to account for something that has nothing to do with Amanda, namely that tasks themselves are variable, and because of this some tasks will take the same person longer to complete than will others just based on task difficulty. This task-difficulty variability isn't something that can be reliably known in advance of working through that task. Added "buffer" time accounts for this second, separate source of uncertainty. Task difficulty variability is a separate source of variable from personal work efficiency variability, and thus needs to be corrected separately.

We added task difficulty buffer time on top of each of Amanda's already personally-adjusted work-time estimates, adding more buffer time where the task difficulty seemed more uncertain. For instance, research and drafting tasks got a 20% buffer since we thought that part of the writing process was where we expected to encounter more suprise difficulty. Revision Edits got adjusted by 15%. Final editing, which tends to be more mechanical and predictable for Amanda, got adjusted by 10%.

Importantly, these buffer adjustments are based on your best guess of what parts of the work process are more likely to surprise you with their complexity, and what parts you think will be more predictable. You'll need to guess these task difficulty values initially. Alter them up or down as you think is most appropriate for your particular project tasks.

For Amanda's project, we adjusted her task-duration estimates as follows:

• Research: 6 hours became about 7 with buffer
• Outline: 5 hours became about 6 with buffer
• First-half draft: 24 hours became about 29 with buffer
• Second-half draft: 24 hours became about 29 with buffer
• Revision: 13 hours became about 15 with buffer
• Final edit: 8 hours became about 9 with buffer

Total buffer-adjusted estimate to complete the work: about 95 hours.

If you don't yet have a sense for how much buffer your own tasks need, assuming more uncertainty rather than applying a single adjustment number everywhere. The less confident you are that a particular task will proceed predictably, the more buffer that task should get.

Auditing the Calendar: Finding Out What Time Actually Exists

This fifth step is about identifying your pre-existing commitments between now and your deadline, so you know how much actual time you actually have available to work with. It's usually going to be less than you initially think.

This step is easy to miss, and missing it is a common way backwards planning can fail: you can't know how much writing time you actually have to devote to working on your project until you've checked out what parts of your calendar are already spoken for prior to your deadline.

Before we did this fifth step together, Amanda thought, "I have six weeks between now and my deadline, so I have six weeks of time to work with to get my writing project done." When she actually opened her calendar she immediately saw that she had less time available to work than she thought: her contract copy-editing job took up her Tuesday and Thursday mornings between 9am and 1pm. Her weekly therapy appointment occurred on Wednesday at 5pm. Her son's school pickup needed to happen every weekday at 3:15pm, which meant her afternoon writing windows had a hard stop or she would be late for pickup. And in week four of her six-week window, between Friday, October 3rd and Sunday, October 5th, Amanda realized she and her partner were going to be traveling for a family wedding, taking three days of that week entirely off the table from a work perspective.

Once all of her pre-existing commitments were blocked off on Amanda's calendar, she saw that what remained open were two-hour periods of time in the early mornings on Monday, Wednesday, and Friday, before her son woke up, a couple of afternoon slots of about ninety minutes each on days when she didn't have pickup conflicts to worry about, and weekend mornings during times when her partner was watching the kids. Adding these open work periods together, we realized Amanda had about 15 realistic writing hours available to work on her project during her normal weeks, and only about 6 hours available on the week of the wedding.

The next step in the backwards planning process involves setting "milestone" or deadline dates specific to each of your individual tasks. It's important that the "discovering what's already on your calendar" step happen before you proceed to assign the milestone dates. For instance, if Amanda had assigned milestone dates before checking her calendar for pre-existing commitments, she would have discovered too late that she didn't actually have enough time to get her work done before her deadline arrived!

Follow this order when you backwards-plan for your own project. Open your actual calendar first (not your mental model of it!), and identify your pre-existing commitments, accounting for those times not being available for project work before you set your milestone deadlines.

Milestone Due Date Identification

This sixth step assigns each task a due date, called a milestone, by working backwards from your deadline through your task list in the order the work needs to happen.

With her task list set, her adjusted-task-durations decided, and her computation of how many real and available hours she has to work with having occurred, we proceeded to assign each of Amanda's tasks a milestone due date, working backwards from her deadline of October 20th, and moving backwards through her task list as we did this, in the order that the work actually needed to occur. Continue reading to see how we did this.

Recall that Amanda had identified the following tasks:

• Task 1: Research Integration, estimated to take about 7 hours
• Task 2: Outline Creation: estimated to take about 6 hours
• Task 3: First-Half Draft: estimated to take about 29 hours
• Task 4: Second-Half Draft: estimated to take about 29 hours
• Task 5: Revision Edit: estimated to take about 15 hours
• Task 6: Final Edit and Citation Check: estimated to take about 9 hours

We took that list and then re-listed the tasks in backwards order. We did this re-listing on on paper, as trying to hold the reversal in your working memory can be difficult. It's easier to write it down reversed first and then proceed to set the dates. Separating these steps lets you give your full attention to doing only one operation at a time.

Here is Amanda's reversed list:

• Task 6: Final Edit and Citation Check: estimated to take about 9 hours
• Task 5: Revision Edit: estimated to take about 15 hours
• Task 4: Second-Half Draft: estimated to take about 29 hours
• Task 3: First-Half Draft: estimated to take about 29 hours
• Task 2: Outline Creation: estimated to take about 6 hours
• Task 1: Research Integration, estimated to take about 7 hours

From here, we started moving backwards from Amanda's October 20th deadline to determine the milestone dates when each of her tasks should be due:

• Since the Final Edit and Citations task was estimated to take about 9 hours, Amanda assigned it to be due Sunday, October 19th, one day before her deadline.
• Since the Revision Edit task was estimated to take about 15 hours, Amanda assigned it to be due Friday, October 17th.
• Since the Second-Half Draft task was estimated to take about 29 hours, Amanda assigned its milestone to be due Friday, October 10, spanning the lighter wedding week.
• Since the First-Half Draft task was estimated to take about 29 hours, Amanda assigned it to be due on Friday, September 26th
• Since the Outline-Creation task was estimated to take about 6 hours, Amanda assigned it to be due Monday, September 15th.
• Since the Research-Integration task was estimated to take about 7 hours, Amanda assigned it to be due Wednesday, September 10th.

Since in our example today is Monday, September 8th, that means that Amanda has to get started very quickly if she is to have a good chance of completing her work in a timely fashion without overwhelming herself in the process.

One caveat belongs here before we go any further. The six dates above are a first pass, arrived at purely by working backward through the task list. Nobody has checked them yet against Amanda's actual calendar, hour by hour. That check is a distinct step, and it's important enough that I want to walk through it on its own, once the rest of Amanda's plan, her energy alignment, her recovery blocks, her visual timeline, is fully built. For now, treat these six dates as provisional. Write them into your own calendar as a working draft, keep moving through the remaining steps, and we'll come back to test whether they actually hold up.

Recording Milestone Dates and Deadline Anxiety Investment

This seventh step is about recording each milestone alongside a specific statement of what's at stake if it slips, so your anxious energy has a concrete target to attach to instead of building up around the deadline as a whole.

Having identified her milestone dates, Amanda next needed to write them down into her calendar. Importantly, I encouraged her to not just write down each milestone date, but rather to pause as she recorded each one, reflecting on what would happen if she let that date go by without completing the milestone, and then writing this down in her calendar as well, placing this imagined negative outcome information at the start of each milestone period so that she would be able to read it again as she starting that milestone. Most backwards planning guidance you might find won't include this instruction, but I believe it is important to do this, as this is how you spread your anxious dread out across your tasks, preventing that dread from accumulating in any one moment which would cause you to feel overwhelmed.

Reading the negative things you understand will happen if you miss a milestone at the start of working on each milestone is a way of investing your anxious dread into that milestone at exactly the best motivational moment, deliberately aiming it towards a specific, near-term, actionable target, where it can actually help motivate you to do something useful. By taking care to do this step, Amanda helped give herself six small, specific, well-timed nudges to work on her tasks in a timely fashion, with each of these written nudges pointed at work she could start on immediately.

For her Outline task, which she had decided would be due on September 15th, Amanda wrote down the following: "I need to have this outline done by Monday, or I'll be starting my first-half draft without a real map, and I'll lose days I don't have figuring out how to structure the work when I'm supposed to be writing."

For the First-Half Draft, which Amanda had decided would be due September 26th (right before the wedding week), she wrote down the following: "If this draft isn't done by Friday, it's going to haunt me all through my wedding weekend, and that weekend doesn't have the hours to give. I either finish by Friday, or I start the second half of the draft already behind."

And so on.

This is where the emotional-design I referred to earlier actually shows up in practice. A plan like Amanda's isn't impressive because the hours reconcile. Plenty of unhelpful plans will have hours that reconcile. It's impressive because of how deliberately it manages how Amanda feels and when she feels it, so that no single moment between now and October 20th has to carry the full emotional weight of her project deadline by itself.

You can build the same sort of motivational statements into your calendar when you record your own milestones. As the start of each of your milestone periods, write out specifically what will happen if you fail to close out the milestone on the assigned date. Doing this helps you aim the dread you are already experiencing at the specific work task you need to complete to move your project forward.

Energy Alignment: Matching Task Type to Your Best Hours

Once your milestones are on the calendar, it's also worth thinking about what time of day you schedule yourself to do each kind of work, rather than treating each open working hour in your calendar as interchangeable.

Using the energy-mapping principles described in the previous post, we had Amanda schedule her drafting sessions, First-Half and Second-Half, to occur during her early morning work periods, which were for her the time of day when her thinking felt clearest. In contrast, she chose to schedule her Revision and Final Editing tasks to occur during her afternoon and weekend working time-slots instead, because those less creative tasks required her to be in a detail-oriented mode and could occur when she felt less energetic.

These same energy-mapping principles apply to how you might schedule yourself to work on different kinds of tasks. When you know which times of your day tend to be better for creative versus detail-oriented tasks, you can assign your work schedule accordingly: creative tasks occurring during your most energetic hours, and the detail-oriented tasks occurring at other times of day when you are more predictably less energetic.

Recovery Planning: Building in Rest on Purpose

Optionally, and if time allows, you can schedule additional rest and recovery activities to occur for those times after you plan to work on particularly difficult stretches of your project. In Amanda's case, we explicitly scheduled recovery time activities for her to occur after each of her longer writing sessions. For example, she planned to take a short walk after completing each drafting session. She also built a full mental-health day-off into her schedule to occur after she completed her First-Half Draft milestone, in order to allow herself to rest before starting her Second-Half Draft work.

As you engage in your own planning, I recommend that you not leave recovery time to chance. Decide in advance what your rest and recovery periods should look like after you complete demanding work blocks, and schedule time when such activities can occur. Do this with the same seriousness you give to scheduling your work periods. If you don't know when you will rest, and for how long, you might not end up resting, or you might rest for too long, with either of these outcomes capable of harming your plan by pushing you off track.

Visualization: Seeing the Whole Path

This eighth step creates a visual timeline so you can see your entire project at a glance and where you currently stand within it.

Though at this point in the process your plan will be largely complete, there is one more thing you can do to make it even more useful. You can create a visual timeline that helps you to see the whole project at a glance, including what stage within the project you are currently working on, how much more work there is to complete and how much time you have left. Having this visual representation available helps you to know at a glance whether you are on track to meet your deadline or not.

Amanda agreed having such a visual timeline was a good idea. She built a simple visual timeline, six weeks across, with each of her milestone due-dates marked and also making visually clear that she had less available time to work during the wedding week. Seeing the whole shape of her project at once, rather than holding it piece by piece in her head, made her plan feel real in a way that the list of dates she had created did not.

You don't need to be an artist to create a useful visual timeline. A simple horizontal line with your own milestones and motivational statements marked on it is often enough.

What the Finished Timeline Revealed

Recall that Amanda's six milestone dates were provisional. They'd been set by working backward through her task list, but nobody had checked them against her actual calendar yet. Here's how she ran that check.

She built a second table, this one organized by week rather than by task. Starting from Monday, September 8th, she listed how many working hours each of her six weeks would actually give her, using the same real-hours figures from the calendar audit: two-hour weekday mornings, ninety-minute afternoon slots, weekend mornings, and the reduced hours during her wedding week. Then she added a running total.

You can build this same table for your own project. Lay your own weekly hours onto it, one week at a time, starting from today, keeping a running total as you go. It turns "I have six weeks" into an actual number you can hold your plan up against, rather than a rough feeling about how much time is left.

With the table built, Amanda went back through her six provisional due dates and asked the same question of each one: by this date, how many hours will my calendar have actually given me, and does that cover what my task list says I need by this point?

Her first two milestones held up fine. By September 10th, Research Integration's due date, her calendar had produced about six hours against the seven the task called for, close enough to absorb without much trouble. By September 15th, Outline Creation's due date, she'd banked seventeen hours against a thirteen-hour requirement, well ahead of schedule.

The next two milestones told a different story. By September 26th, First-Half Draft's due date, her plan called for 42 cumulative hours of work. Her calendar had given her about 39, a small gap, still absorbable. But by October 10th, Second-Half Draft's due date, the picture changed sharply. Her task list called for 71 cumulative hours. Her calendar had produced only 60. Eleven hours short, a full week's worth of writing time, and this showed up well before her actual deadline, not at the last minute.

The gap didn't close from there. By October 17th, Revision Edit's due date, she needed 86 hours and had 75. By her final deadline of October 20th, with Final Edit due the day before, her plan called for the full 95 hours, and her calendar had given her 81.

Amanda realized she didn't have enough time to complete her work before her deadline would arrive! More specifically, she recognized she needed about 14 more hours to complete her project than she actually had available, and that shortfall hadn't appeared out of nowhere at the end. A small gap had already opened by First-Half Draft, and it widened sharply at Second-Half Draft, right in the middle of her plan, which is exactly where a week-by-week check like this one is meant to catch it.

This is a new variety problem we haven't addressed before. It's a different kind of problem than the one backwards planning is designed to solve. A different tool is needed to address this problem, a companion method you can use along side backwards planning when you realize you don't have enough time to complete your work. I call this tool Ambition Analysis.

Ambition Analysis: When the Plan Reveals the Problem

Task analysis breaks a project down into smaller, sequenced, executable tasks you can work on without becoming overwhelmed. Ambition analysis does something structurally similar, but operates at a different level of analysis. Instead of breaking down a project into tasks, it breaks down the project goal itself. This is what needs to happen when your goal, as currently sized, doesn't fit the constraints you're working within.

Here's the four-step version of Task Analysis, applied to Amanda's issue.

Identify the Gap

The first step is simply computing and naming the size of the shortfall, nothing more yet. Amanda's honestly-estimated, properly-buffered plan called for about 95 hours of work. Once every fixed commitment had been subtracted from her calendar she recognized she only had about 81 hours before her deadline would occur. Recognizing that this gap exists is all this step entails.

Assess the Constraints

With the size of the gap identified, the second step involves going back through your calendar and seeing if you can find any flexible wiggle-room there. This step exists in order to prevent you from rushing to conclusions about what needs to change. It may be that the design of the entire project needs to be changed. In fact, this will likely be the case if you can't identify any other places where you can recover time to devote to working on the project as designed. However, if you can make changes to your pre-existing commitments and constraints and would prefer to do that rather than adjust your project goals, you can figure out how your calendar needs to change to enable this to happen.

In deciding whether your pre-existing commitments might change to accommodate the work you need to complete, you are faced with a values decision. On the one hand you have important work to complete, and on the other hand you probably would not have agreed to those pre-existing commitments if they weren't also important to you. I am not recommending that you sacrifice pre-existing commitments that are important to you on the altar of getting work done. I am suggesting that you conduct genuine, good-faith review of your calendar to see how you feel about making such changes so that you might continue with your work plan unaltered. In Amanda's case she checked her calendared constraints and found she had no wiggle room.

First Amanda considered whether her wedding weekend could be shortened, freeing up a day of travel time for writing instead. She and her partner talked about it and decided no, the time spent with family was too important to both of them and neither of them wanted to give that up.

Next, Amanda thought to ask her editor for a short deadline-extension, which would have let her keep her original work plan intact. She communicated with her editor to ask directly; a reasonable request to make since editors are known to sometimes extend deadlines. In Amanda's case however, the answer was no, the book she was contributing to was on a tight production schedule which could not be adjusted.

Amanda next considered whether she could find hours elsewhere in her week that she hadn't already accounted for, for instance by trading some of her commitments, for instance arranging for someone else to do her pickups so she could continue writing. She looked, but unfortunately did not find such substitutions were possible.

Having diligently checked all of her constraints and learning that none of them could be changed, Amanda realized that there was no way for her to meet her deadline except by adjusting her project goals.

It's only after pre-existing constraints have actually been tested in this manner and have held firm that it will become clear that the project goal must change. If you find that your project goals must change, you should go on to the next step. Otherwise you can stop here if you end up solving the problem by adjusting your constraints.

Break the Aspiration Into an Achievable Milestone

If none of your pre-existing constraints can be adjusted, then it becomes necessary to adjust your project goals. With this need confirmed, Amanda and I looked specifically at where the extra 14 hours in her original plan were concentrated. She identified that her original plan had her working on a comparative case study in addition to integrating the interviews she had already completed. This comparative case study contributed to the amount of time she needed to complete three tasks within her plan: her Second-Half Draft, her Revision pass, and her Research stage. She realized that cutting out the comparative case study from her project would bring her Second-Half drafting time estimate down from 29 hours to about 20, her Research estimate down from 7 hours to about 6, her Revision estimate down from 15 hours to about 12, and her Final Editing estimate down slightly from 9 hours to about 8. She realized dropping the case study from her project would save her 14 hours, which was exactly the size of the gap she had identified in step one of her Ambition Analysis that she needed to address, and decided dropping the case study was how she would proceed. Accordingly, she rebuilt her plan with the case study removed. Her recalibrated chapter plan, designed to lean on her two already existing interviews but with a sharper closing section instead of a third comparative example, now fit inside the 81 hours actually available to her.

Refocus Energy Toward the Milestone

This fourth and final step occurs after your project has been recalibrated to be smaller and more modest than originally conceived. It consists of accepting the changes you've made as necessary and moving on without regrets for what you realize you can't accommodate.

This step may sound trivial, but I ask you to consider its true importance. People can and do experience shame when they realize they can't realize their ambitions. I have known some people to get stuck at this stage, experiencing shame and continuing to obsess over their original project design and the gap that has shown them they can't make that original design work. These people are effectively haunted by that original design, which makes it harder for them to get on with the work they need to accomplish.

Rather than having every drafting session haunted by the ghost of the case-study chapter she'd originally imagined, Amanda thought about her situation in practical terms, accepting that the revised chapter design was as good as she could manage given her constraints. Consequently, she abandoned her original design as an artifact of history, and moved directly towards executing on her revised design. Her energy flowed into execution of the tighter, achievable version of her project.

With her goal recalibrated, Amanda didn't have to redo her whole planning process from scratch. She adjusted the affected milestones, updated her calendar, and kept everything else, her energy alignment, her recovery blocks, her deadline anxiety statements attached to each due date, exactly as built. And then she got down to starting the work.

A Word About Shame

I mentioned just above that some people end up feeling ashamed about needing to make changes to their plan. This observation will benefit from some further unpacking so that in the event you end up experiencing any such feeling of shame you can know what to do with it, whether to apply Ambition Analysis and move on, or whether an entirely different approach is needed.

Shame can be thought of as the emotion that occurs when you experience a gap between where you are (the actual) and where you want to be (the ideal). But not all shame experiences are identical. Sometimes your experience of shame will be what I'll call "workable", meaning that it doesn't overwhelm you, and because you're able to keep your wits about you as you experience that shame, you can utilize it as a motivating energy; something you can escape from by doing the work you need to accomplish. At other times your experience of shame will feel overwhelming and would be better named as debilitating or destabilizing.

I didn't come up with the distinction between workable and destabilizing shame on my own. This idea draws on clinical work distinguishing types of shame based on their regulatory functions, with this most directly formulated in Ken Benau's book Shame, Pride, and Relational Trauma, which offers a framework that separates out shame experiences that can motivate (good-enough-me shame) from overwhelming shame (not-me shame) that fundamentally collapses a person's self-esteem and self-efficacy.

The first kind of gap between ideal and actual feels workable. You look at the distance between your current draft and how your finished project needs to be, and even though more work is required before your draft is ready to be handed in, you expect to be able to get that work done. This gap generates a shame that's uncomfortable but usefully motivating: it tells you where to put your effort, and it responds to that effort by becoming smaller and less bothersome as you move your work towards its ideal state. Ambition Analysis can usefully address this kind of gap.

When Ambition Analysis Fails

The other kind of gap between ideal and actual is fundamentally different and far more maladaptive. It doesn't say "you're not there yet, but you can get there and here's the path." Instead, it says "you will never get there because you are a fundamentally inadequate person". This kind of destabilizing shame usually isn't rooted in a single project or deadline, but instead will trace back further into your accumulated past experiences, often finding its roots in your early relational experiences. This maladaptive shame experience doesn't respond easily to methods like Ambition Analysis. If you experience this variety of shame, my advice would be, "do the best you can do with your project, including using Ambition Analysis if needed, but more to the point, recognize that the deeper issue plaguing you may best be addressed through you seeking trauma psychotherapy to help you work through the underlying relational trauma driving your shame experience.

Appreciating The Wider Utility of Ambition Analysis

You might have noticed that all of the above discussion has illustrated the application of Ambition Analysis to a single project: one chapter, one deadline, and one recalibration if that becomes necessary. Usefully, the same planning and recalibration process can also be applied at larger scales.

You don't usually discover your goal is oversized through quiet reflection. Instead, you more often discover this is the case the way Amanda did: by trying to concretely plan against a real deadline and realizing there isn't enough time.

Importantly, this is true whether the goal you're referencing is a single small book chapter project or something much larger: for instance, a new career direction, a relationship you're trying to build or a new and better version of your daily life you've been aiming to realize.

When any such goals feel crushing rather than motivating, when the gap between where you are currently and where you pictured yourself being starts to feel less like a path that guides you forward and more like a brick wall that blocks your progress, you can apply the same four step Ambition Analysis process. Determine what is the nature of the gap you face and what are the real constraints, then decide if constraints can be adjusted (allowing you to keep your original goal intact) or if you need to adjust your goal in order to close the gap. If you do need to shrink your goal in order to close the gap, pay attention to any shame experience you might have. If you can, accept the need for the adjustment and move on. If you can't, consider seeking professional help in becoming more able to accept and make such adjustments.

Integration with What You've Already Learned

Backwards Planning and Ambition Analysis aren't separate systems competing for your attention. They're sequential tools that feed into each other. Backwards Planning is how you discover whether your goal fits your available time and capacity. Ambition Analysis is what you reach for when it doesn't. And having used Ambition Analysis to downsize your project, you can return to Backwards Planning with your right-sized goal, adjusting only those milestones that will have changed, rather than needing to start the planning process over from scratch.

Both tools function in service of the same underlying aim, which is to help you plan out and manage your emotional experience associated with working. At its best, your work plan will enable you to take deliberate charge of your emotional experience throughout the entire time you are working so as to make that period as pleasant and peaceful as possible.

Both tools also interconnect deeply with the Daily Aiming Ritual and your Backlog system, which I'll cover extensively in the next post. Backlogs are containers in which you preserve the elements of your various work plans so that they are safely stored and you can focus only on those elements of your plan that are relevant now. You populate and repopulate your Backlogs each time you formulate (or recalibrate) your work plan. You scan your Backlogs each time you perform the Daily Aiming Ritual in order to survey where you are in the progress of your various projects, identifing the tasks you need to work on today, which you should record into some variety of Daily Todo List. How and when you go about executing the tasks in your Daily Todo List benefits from thought to the energy-aligned scheduling I covered in the previous post.

Continuing Your Journey

Forward to Post 11: Building Your System: Backlogs and Daily Todos, where you'll learn about the containers that hold your projects and tasks between planning sessions, including where a recalibrated goal and its milestones actually live day to day.

Back to Post 9: Time Management for Planning, which covers the foundational time-awareness, estimation, and energy-alignment skills this post builds directly on top of.

Work with Dr. Dombeck

If you're facing a goal that keeps not fitting the time you have for it, and you'd like support figuring out whether that's a planning problem or a sizing problem, I offer individual coaching in executive function. Learn more at psychtools.com.