The Doer and the Guesstimater

The joys of guesstimating and doing your day

Setting your day up so the doer (your Now) and the guesstimater (your Next) can both win


Many people have given up and don’t plan or guesstimate their day, even though they are aware of how much value it could add to their life. Their day ends up going catch as catch can.

Avoiding the delusional plan

Others “plan” their day, but their plan is a delusional list, rather than anything that is more fully do-able. A ten-year old could tell you that. Then, at the end of your harried day, you still have things on the list (I call these parts) that you didn’t get to, leaving you feeling discouraged and even guilty.

A part is a project, activity, routine, or task that takes up (or will take up) a portion of your scheduled day. Every minute of each scheduled day will be "occupied" by one part or another, with all the parts together consuming all the time available.


Welcome to a fresh and effective new way to guesstimate (plan) your day that provides results, satisfaction, and enjoyment, with no guilt or disappointment.

Why "guesstimating" instead of "planning"?

This link used to be called "The Doer and the Planner." But I realized that it is uncommon that a scheduled part will take the exact amount of time budgeted, not a minute over and not a minute under, that you allocated for that part. Even for a scheduled thirty-minute telephone appointment with someone, it could end up being thirty-one minutes or twenty-seven minutes. Or the other person might even cancel and it would take no time. Or consider when you allocate time for a part, like preparing food and eating a meal, or for a group of miscellaneous mini-parts, including things like going to the toilet, your allocation is likely to miss the mark by as much as fifteen minutes or more, either plus or minus.

Did you "follow your plan"?

In most world cultures, if we "follow our plan" then that's a good thing. If we "don't follow our plan," that's not so good. In a not-so-subtle sense, "planning" sets us up for failure even if we manage to do all the parts, because the times were not exact. There is an inherent implication of "we need to be perfect" in our planning and its execution implied by "making a plan and following the plan."

The joys of guesstimating

That's why I switched to using the word guesstimating. Its connotation is more playful. It also more accurately reflects what we're doing than does the word planning. It implies the valuable feedback-loop of the learning process we're engaging in. We guesstimate the time for the various parts for today. We track the time we actually spent on each part as we flow through our day. Then when we guesstimate the time for each part for the next day, we notice any interesting discrepancies between what we guesstimated the day before and what we actually did. We then make any refinements with our new set of guesstimations. 

I will also call these daily guesstimations daily projections.

Morning or evening daily projections?

First, it’s important to decide whether to guesstimate in the evening for the next day or in the morning before you start doing any parts that can vary for that day, that is before any morning activities that are not already completely standard, like your morning routine. If you’re an evening person, it might make more sense to set up your projections for the next day instead of waiting for the morning. If you're like me and you’re a morning person, an early morning projection for the current day could be more effective. I consistently finish guesstimating my tasks each day before 3.00am. I'm a super lark, usually out of bed at 2.00am.

The guesstimater's #1 guideline: 95+% do-able and likely to love the process

Okay, imagine it’s time to set up your day. Put on your guesstimater’s hat, which is also your Next's hat since you're doing this daily projection to help ensure that your future will be good. Then remind yourself of the guesstimater’s #1 guideline for creating a good set of projections for the day: “How can I set this day up so that I have at least a 95% chance of finishing all the parts in my projection, but also that my doer, who will be more in a Now mode, is likely to enjoy the process of moving through the execution of each part that I've allocated time for.


The reason this guideline says “95%” instead of “100%” is because some unforeseen circumstances may arise during your day, the best handling of which involves modifying your original projection, requiring that you either cancel/reschedule or modify one or more of the parts that you included in your day's projections. If we were able to somehow know, that is we had God's knowledge, of these circumstances at projection time, then we could ensure 100% accuracy in our projections every time. 

The guesstimater's #2 guideline: under promising and buffer


The second guideline is that, in the guesstimation process, if you have a tendency to under estimate how long the various parts will take, as do most of us, then intend to under promise. Go the other way and put in some extra buffer time for each part. In addition, allocate some time just for buffer to give yourself more flexibility and avoid blindsiding yourself by things not going quite as anticipated. If you pack too many things into a day, not only is it difficult to enjoy the process, but you’re less likely to create quality results and maybe even get less done.

The guesstimater's #3 guideline: your Now has to be on board

The third guideline is review each part that you've included in your day's projections. Your Next thinks each one is needed. But do you also have good reason to believe that your Now is going to be okay with and hopefully even eager to engage in doing each part when the time comes? Think about each of the parts that you've allocated time for. To ensure Now-Next Integrity, it's the job of your Next to consult with your Now so that Now's wants and needs are included in what your Next wants to do for the day. If you can't imagine that your Now is going to be at least okay with, which means Now will not be tolerating any specific part that you have included in your day's projection, you need to stop and, using the NNI toolkit if necessary, either figure out a way for Now to be happy with doing that part or remove it from your projected day. Otherwise you are planning to be out of integrity.

The guesstimater's #4 guideline: the facts are that your life is a buffet and happiness is your purpose

You can never do it all. For everything thing you choose to do there are thousands things you cannot do. Consequently, let go of the idea of "more accomplishment is better." Yes, we can have great satisfaction in accomplishment and playing the game of seeing what we can make different. To have a life that works, that flows, to love the journey and your lifestyle, you must prioritize designing processes that work and work together, not prioritizing for the most accomplishment. See What's the full idea of process first?


Secondly, ultimately everything you do is guided by the purpose of moving toward happiness and away from unhappiness. The only choice you have is whether or not you accept that fact and focus on getting good at fulfilling that purpose.

See Happiness as your ultimate purpose

Step by step planning

Okay! We’re now ready to get into the process details.

Calculate the minutes you've got in your day that you'll divvy up for the parts you want in your day

Select the starting time for the day's setup. This would typically be right after any standard items, like a morning routine, are finished. For me this might be 3.00am. 

Next select the ending time for the day. Generally this will not be bed time, but sometime before that when you want your variably scheduled day to end. For me this typically is 4.30pm when it's Dwight-Now "spontaneous" time for the rest of the day, where I might get into bed for sleeping as early as 6pm.

Calculate the minutes between those two times. I suggest using minutes instead of hours. This allows for  higher resolution guesstimating, if needed from time to time. For example with me, between 3.00am and 4.30pm there would be 810 minutes that I have to play with when I consider what my Next and my Now would like to engage in for the day.

Selecting the parts that you'd like to "spend" your time on for the day

Special note: the Doer and the Guesstimater, or D&G, is not about deciding what time of day you're going to engage in and finish doing any specific part. It's about ensuring that you've got a prudent budget of what you can get done in the day and that you can enjoy the flow and doingness of all those parts. This does not replace an appointment scheduler like Microsoft's Outlook, which I use.

Allocate time for the everyday standard parts first

You could do this by hand. I use Microsoft's Excel with a few simple formulas to set up my day, first entering the total number of minutes available to allocate for the day's time budget.

Most people have up to three standard items that apply to almost anyone's day.

Miscellaneous mini-parts

"Miscellaneous" will include all those small parts that you do every day, sometimes our of necessity, but each one of which generally takes up less than five minutes. And you often would not even be able to think of what all of them would be or whether you might end up doing a specific miscellaneous part or not.

Examples include parts like:

  • going to the toilet

  • entering a note on a special list of things you want to remember later

  • chatting for two minutes when a colleague drops by your desk

  • sending a text message to your lover

  • sitting down and closing your eyes for three minutes

I usually allocate 60 to 90 minutes a day to "miscellaneous."


Eating and snacking time could be part of your scheduled day. Ensure that you include any additional time needed for eating like:

  • preparing the food

  • cleaning up after eating

  • ordering the food

  • traveling to the restaurant

I budget 30 to 60 minutes a day to "eating."


Many of us have already calendared appointments with others on many days. These could be on the telephone, on Skype, on Zoom, in meetings, or face-to-face and one-on-one. They could include travel time or setup time. 

I usually have 210 to 300 minutes a day for "appointments."

Enter the allocated time for miscellaneous, eating, and appointments first. Then you will know the time left you can budget for other parts.

While keeping the four guidelines above in mind, you can begin to budget the time for the rest of your day for fun and accomplishment.


Buffet list

After you've subtracted for time needed for miscellaneous and any eating or appointments, then you're ready to choose parts on which to "spend" the rest of the time available in your day.

Again, in my example, I had 810 minutes total. Then I allocate 90 minutes miscellaneous, 45 minutes eating, and 240 minutes appointments. This now leaves me with 435 minutes for other parts. Since I almost always have an hour's nap each day, after subtracting that, it will leave 375 minutes to allocate in order to have my plate "leisurely" full.

If you don't already have something that you might call an "buffet list," I recommend you create one that you keep updated with projects, tasks, or event possibilities that you could be wanting, needing, or valuable to do. For the purposes of using it with D&G, keep it prioritized in some way, which would be a periodic task that you take care of at other times, so that you can choose rather quickly from it when guesstimating your day. Of course, you may not need to refer to it if it's already clear to you what parts you want to engage in for the rest of your remaining minutes.

Next must check in with Now for each part that Next wants to include in your day

As you are considering which part you might include next in the day's design, your Now and your Next will work together, ensuring that it is satisfactory for both. See the NNI toolkit. Next will be concerned with issues of the importance or urgency of each potential part. Now will be concerned with ensuring that a given part can be enjoyable and that, as a group, they can all flow together without a lot of pressure, also giving some space for spontaneity and flexibility. Now may also want some time allocated just for himself or herself to use however he or she wants at the time. Allocating time for a nap may be something to consider. 

Inserting your choices into the day

When you select a part to add to your plate for the day, just as you would add something to your plate at a food buffet, underpromise when you create an estimate of how much time that part will take, say 45 minutes. Then subtract that amount of time from the total still available, using a calculator or Excel to make it easier and more likely accurate. 


If the part is either too big to get finished in that day, given what else you do or will put on your plate, or you’re not sure how long it might take or you need to break it up to satisfy your Now, then allocate a limited time on it, like 30 minutes, even though you may not be able to finish it in 30 minutes. If later you don't finish it in the time allotted, you'll declare it complete for the day and make a note to allocate time for it on another day. With this approach you ensure that your day’s plan is prudent and can be finished at least 95% of the time. See Finished or complete? to fully understand the power of this life approach.

Filling up your plate with goodies to do

Continue selecting the next part from your buffet of life, using the same criteria. The calculator or Excel sheet will show you how much time you have left to allocate for day as well as ensure that you don't go into the land of delusion that many of us have habitually spent time in before.  

Choosing courage to say "no"

As you begin to use this method, you may notice worry, fear, or stress. “There are just too many things that I should do, that I need to do, that I have to do that I can’t fit on the schedule for the day!” Previously, when making a plan, you lived in a delusional world and didn’t face the un-do-ability of your plan until the end of the day when you were exhausted, discouraged, and even guilty by how much you didn’t get done from your “plan.” Your Next may need to choose courage to say what you will not allocate time for in your day. Use undoing fear to turn the fear into energy and confidence. Speak the sentence, “Holy cats and jeepers creepers, I am so scared of what might happen if I don’t get this done today!” Speak it loudly. Speak it slowly. Speak it sillyly. Eleven times. Also, you can check out:


Are you like I was?

When I first started getting real about what I could do and what I could not do, it was a major confrontation to my ego and sense of identity that was insisting against reality, "I should be able to get more done than that!"

Need to change your projections?

Throughout the day, as the doer is happily completing each part, something may occur where it makes sense to modify/add/eliminate one or more parts in your daily projections. Even with the best projections, this will happen sometimes. Many of us are attached to the idea that we should always be able to follow our plan, like "plan you work, and work your plan." Yes, if we use D&G, that could happen, maybe as much at 95% of the time. But, on occasion, God has different ideas than ours and wants to present us with an adventure and a gift, even though it might, at first glance, seem more like a goft.

Is my Now just trying to dominate or should I re-allocate time for what I was not aware of before?

If it occurs that it might be good to modify your projections, ask yourself this question, "If I had somehow known these current circumstances when I had set up my day, would I have allocated time for my parts differently than I did?

If the answer is "no," it probably either means that you weren't fully including Now in the set-up process or Now changed her or his mind anyway. Regardless, stop and do a Now-Next renegotiation where both are happy.

If the answer is "yes," it probably means that it will serve both your Next and your Now (that means you), given the new information, to redesign your day from where you are now.


Examples of things that could come up that call for redesigning the rest of your day

  • you unexpectedly need to take a nap,

  • you have a more accurate perspective on something that involves your previous projections,

  • or your boss calls with an urgent request.

When redesigning your day, perhaps choosing some courage, then declare a guilt-free change in plans, make sure that you're complete in doing so, and put any displaced parts back on your buffet list for another day. This would then be one of those 5% days when you didn’t complete the original plan. And it’s no problem.


Staying out of God's business

I often think, “I have my plans for my day and then God has Her plans for my day. Sometimes, God doesn’t let me know in advance when Her plans are different from mine. Therefore, when I find out that there’s a difference after I have made my plan for the day, I re-plan to cooperate with God.”


Are you leisurely busy?

People often ask me, maybe just politely, “Are you busy?” My reply is, “I am leisurely busy.” I am busy in a quite enjoyable way. I am busy with buffer. I am busy in a way that allows for flexibility, spontaneity, and creativity. If something unexpected happens, I can easily and happily make the necessary adjustments.

Step by step out of your handcuffs

The Doer and the Guesstimater is an important tool in you breaking out of your lifecuffs.

Less than 15 minutes

Important note: with just a little practice, setting up your day with this process should take less than 15 minutes each day. If it's taking more, go to undoing perfectionism.

Reasons your Next may object to D&G

You would think that Next would love everything about D&G, right? Making plans and having structures are key to your Next being able to take care of your future. Yet, at least two factors could contribute to your Next wanting to avoid doing D&G:

Next's ego and identity are attached to "should be able to get more done"

Next often wants to avoid looking closely at the limitations of what you're able to do. His or her ego is attached to getting more done. Related to this, your Next can have the habit of believing thoughts like, "I have to do this," "I must do that," "I can't take anything off my plate," and "I should be able to get more done." If your Next did D&G daily, he or she would have to question these beliefs. Having to calculate clearly each day of how much time is available and under-promising on parts can be quite confronting.

Next doesn't like the restrictions of including Now in the process for the day's set up

Next has a deeply ingrained belief that Now should just do whatever Next thinks is right, regardless of what Now wants and needs. Next feels shackled by the requirement to consider Now's needs. It's like a slave owner of former times who was no longer able to ignore the needs and wants of the person who was formerly their slave, but now they have to pay them and negotiate the working conditions with that former bondservant if they want their cooperation.

Reasons your Now may object to D&G

It's more obvious why your Now would object to D&G. Whereas planning, scheduling, promising, and creating structures are essentials "tools" in supporting Next in fulfilling on his or her needs, Now often uses the "tools" of spontaneity and "going with whatever the feelings are" for getting what he or she wants.

Now doesn't trust that Next will really partner with Now in following the D&G guidelines

Next's history of showing disrespect for Now, especially when initiating new structures to support what Next wants, leaves Now wary of Next using yet again another tool to dominate Now with. Consequently, Now doesn't want to allow Next to get a toe in the door by Now agreeing to experiment with D&G.

Now doesn't trust himself or herself to stand up for his or her needs in the face direct negotiations with Next, and even with Others

For some, their Now had indulged in a kind of learned helplessness when it comes to openly speaking up and asserting his or her needs and wants in the face of Next's demands, which could also include the demands and needs of Others. Now has reverted to a more passive-aggressive approach.

Now doesn't believe that any fundamental rapprochement is possible with Next and D&G

To agree to any regular structuring process occurs as at odds with a fundamental sense of freedom that Now wants to feel and have. As such, Now is going to be very reluctant even to consider doing D&G with Next, especially regularly.

A new habit for a lifetime...

Welcome to the new world of planning where your Now and your Next can be on the same page. Happy days are here again! Happy days are here to stay!