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When your calendar plan isn’t working, it can be hard to tell whether you need to try harder or change the plan.
I’ve been considering that question with a recurring appointment on my own calendar.
It’s a 30-minute block called “Planning Time + Text a Friend.”
The planning part is meant for big-picture thinking — not my weekly to-do list. And the text is a way to connect with a friend, colleague, referral partner, or other professional connection.
Both things matter to me. So I gave them a place on my calendar.
They may not seem to go together, but I combined them into a single recurring calendar event because big-picture planning often brought to mind people I wanted to stay in touch with. Giving both activities the same place on my calendar seems to help me stay focused on the planning.
It’s like I’ve given myself permission to send the text when I think of the person, so I do, and then can continue my thoughts on the planning.
I’m honestly not sure why it works, but it does, so I keep them together on my calendar.
And for a while, their “regular” place on my calendar was Monday at 9:00.
Then I found a Monday Motivation live stream with Dean Graziosi. I started watching it and found value in it. It wasn’t necessarily more valuable than the time I’d set aside for planning and connecting. But it happened live at that time.
I wanted to make room for it, too.
So I moved “Planning Time + Text a Friend” to Wednesday at 10:00.
And then I learned something else.
Wednesday at 10:00 was easy for me to ignore.
Sometimes I was in the flow of creative work and didn’t want to stop. Other times, if I’d started working early and needed a break, I was walking the dog.
And when I did manage to text someone during the block, the back-and-forth conversation could continue beyond the 30 minutes and eat into more of my productive time.
So now I’m looking for a new spot where the block will fit best.
I’m considering Monday afternoon or Friday afternoon. But I like to give myself Friday afternoons off, so I’m leaning toward Monday.
It’s still a work in progress.
But the thing is this …
The appointment has moved. The priorities behind it haven’t.
When your calendar plan isn’t working, identify what still matters and examine why the current arrangement gets skipped or interrupted. Consider its timing, format, surrounding commitments, and other priorities. Change one part of the plan, then choose a point to review whether the adjustment helps you follow through.
A Calendar Block Is a Plan for Honoring a Priority
Putting something on the calendar is a useful way to give it a place in your week.
We’ve talked about that this month.
A priority is more likely to receive your attention when you make room for it alongside client work, appointments, and everything else competing for your time.
But a calendar block is a plan. It’s your best decision based on what you know when you create it.
Then you live through a few weeks.
You notice what happens at that time of day. You discover another commitment. You learn that a task takes longer than expected or that the transition into it is awkward.
And the experience gives you information.
My Monday morning block made sense when I created it. Then I found something else I wanted to attend at that particular time.
My Wednesday block seemed like a reasonable adjustment. Then I noticed how often it conflicted with the way I was actually working — or with a break I needed.
Neither decision was pointless. Each helped me learn something about the next one.
The Priority and the Method Are Different Things
It helps to separate what matters from the way you’ve chosen to support it.
Big-picture planning matters to me. Staying connected with friends matters, too.
“Wednesday at 10:00 for 30 minutes” is one possible arrangement for honoring those priorities.
But if that calendar block isn’t working well, I can look at it again. Because those priorities still matter, it’s worth revisiting the arrangement and choosing what to try next.
You may have something similar on your calendar.
Perhaps you want to develop a new service, so you reserve an hour every Thursday afternoon. After several weeks, you notice that Thursday is when client questions tend to arrive and that the hour gets interrupted.
The priority is developing the service. Thursday afternoon is the method you chose to give it attention. The method may have to change if it’s not giving you the results you wanted.
Or perhaps you want to keep in touch with professional contacts. You plan to send follow-up messages at the end of the day, but you discover that you rarely have the energy to write thoughtful notes then.
The value of connection hasn’t disappeared. The timing may need another look.
The thing to remember here is this:
A calendar block is a way to honor a priority — not the priority itself.
That distinction gives you room to make a new decision without treating the original intention as a failure.
Pay Attention to What the Week Is Telling You
When a plan repeatedly gets skipped or interrupted, it can be tempting to make a quick judgment.
You may think …
“I’m not disciplined enough.”
“I need to be more consistent.”
“Maybe this just isn’t important to me.”
But before accepting one of those explanations, get curious about what’s happening. For example:
- What else is taking place at that time?
- What does the activity require?
- What happens immediately before or afterward?
For my Wednesday block, I noticed two things about the timing.
First, I was often already engaged in creative work. When I’m in that flow, stopping to shift into big-picture planning isn’t always easy.
Second, sometimes I was walking the dog. If I’d started early and needed a break, that walk served a purpose, too.
Then there was the text conversation itself. I could send a message within the 30-minute block, but a friend might respond, and we might continue the exchange. The connection I wanted could require more attention beyond the appointment.
That doesn’t make the text a bad idea. It gives me a fuller picture of what I’m planning for.
A few weeks of experience can reveal details that weren’t obvious when you first put the appointment on the calendar.
Look at the Whole Arrangement
“Planning Time + Text a Friend” combines two activities I value.
Putting them together was strategic and one way to give both a place. Keeping the two activities together has helped me.
Now I can consider whether the timing, duration, and space afterward support both purposes.
Does big-picture planning fit well with a connection that may continue beyond the block? Would another time make the transition easier? Would a different arrangement (perhaps more than 30 minutes or additional free time after the calendar event) support both purposes?
I don’t have to settle these questions all at once. But they’re useful to have in mind as I decide what to try.
The same is true for your calendar plan.
If a recurring appointment for your business priority isn’t working, consider more than the block saved on the calendar.
You might look at:
- Timing: What else usually happens before, during, or after that block?
- Format: Is the activity designed in a way you can reasonably begin and complete within the designated block?
- The whole commitment: Does it involve preparation, follow-up, or an exchange that may continue afterward?
- Other priorities: Is the plan competing with work, rest, relationships, or another commitment you also value?
You may discover that a different time would help. You may find that a shorter starting step, a different format, or clearer expectations would make the plan more workable.
You may also realize that the current plan is asking more of your week than the calendar block shows.
That’s useful information for CEO You.
Revising a Plan Is Different From Quietly Letting It Disappear
There’s a difference between noticing that an arrangement isn’t working and continuing to skip it without deciding what happens next.
I know my Wednesday block is easy to ignore. That tells me it deserves another look.
If I keep moving past it without revisiting the arrangement, I may gradually lose the big-picture planning and connection time I wanted to protect.
Revising the plan gives me a chance to ask whether those priorities still matter — and if they do, how I want to support them now.
Of course, there may be seasons when you don’t have the time or capacity to revisit every plan right away. Sometimes simply noticing that something keeps getting missed is the first useful step.
You can return to it when you’re able and ask:
“Do I still want this to have a place in my week? If so, what have I learned about the place I gave it?”
That question keeps you connected to the reason behind the appointment.
It also allows for an honest answer. Perhaps the priority has changed. Perhaps it still matters, but not in the form you first imagined. Or perhaps the goal is the same, and the timing needs to change.
Make the Next Version an Experiment
I’m considering Monday afternoon for my planning and connection block.
I’m also considering Friday afternoon, although I like to give myself that time off. That’s part of the decision. Protecting time away from work matters, too.
Right now, Monday is the option I’m leaning toward. I haven’t yet settled the plan or discovered whether it will work.
Whatever new calendar plan I choose, I’ll pay attention to what happens.
Is Monday afternoon a good time for big-picture thinking? Does the text conversation fit comfortably into the rest of the day? Does the block support the connection I want?
I can use those observations to decide what comes next.
You can treat your own adjustment the same way.
Choose one change based on what you know now. Give it a reasonable opportunity to work, then check in.
You don’t need to make a promise that this will be the perfect arrangement forever. You’re making a decision for the current conditions and staying open to what experience teaches you.
Changing the plan can be leadership, too.
Ask What Future You Will Need
As October comes to a close and the season grows fuller, you may notice more demands arriving on the calendar.
That makes this a useful time to distinguish between what you want to protect and the particular arrangement you’ve been using to protect it.
A priority might still deserve attention, even if its current time block no longer fits.
A commitment might still be worthwhile, even if it needs a different scope.
A connection might still matter, even if the way you’ve been trying to maintain it needs adjustment.
CEO You can consider those possibilities before Employee You is left repeatedly trying to make an awkward plan work.
Ask:
“What have I learned that would help me support this priority more realistically?”
Then use that information to make one thoughtful change.
For Tenacious WFH Entrepreneur Insiders and VIPs: October’s CEO Decision Bridge can help you revisit a priority, identify a practical adjustment, and consider a pressure point that might interfere. Use it to record what you want to try next. Your membership includes the monthly Mini Power Tools and their archive.
Your Action Step This Week
Choose one priority that still matters to you but has an arrangement on your calendar that isn’t working as well as you hoped.
Then answer three questions:
- What still matters?
- What has the current plan taught me?
- What is one part of the arrangement I can change?
Make one specific adjustment based on what you’ve learned. You might choose a different time, revise the format, or account for something the original plan left out.
Then give yourself a chance to notice how the new version works. Perhaps even choose a specific point when you’ll evaluate it ─ after the next two or three occurrences, for example.
My “Planning Time + Text a Friend” block is still a work in progress. I know why I created it. I’ve learned something from the times I’ve tried. And I’m considering what to do next.
You can do the same, friend.
Keep the priority in view. Let your experience inform the plan. And give yourself room to lead the week you’re actually living.
FAQs
Frequently Asked Questions About Adjusting Your Calendar Plan
Choose one recurring block that gets skipped, interrupted, or extended beyond its allotted time. Identify the priority it was meant to support, then examine what happens when that appointment arrives. Adjust one part of the arrangement — such as timing, duration, or format — and choose a point to review whether the change helps.
Moving a calendar block can be a way to keep supporting a priority. The appointment is an arrangement you chose, while the priority is the reason behind it. If that reason still matters, use what you have learned to choose a more workable arrangement and give it a specific place in your week.
Look at where the difficulty occurs. If the block regularly conflicts with focused work, needed breaks, or other commitments, timing may need attention. If the activity requires more preparation, follow-up, or decisions than expected, examine its duration or format. Start with the adjustment that addresses the difficulty you have actually observed.
Consider what usually happens before, during, and after the proposed time. Account for preparation, transitions, follow-up, and conversations that may continue beyond the block. Also consider other priorities, including rest and relationships. An apparently open space may already serve a purpose that deserves consideration.
Choose a review point that gives you a useful chance to observe the new arrangement. For a weekly appointment, the next two or three occurrences may provide an initial picture. Notice whether you begin the activity, have enough time, and can accommodate what follows. Use those observations to decide what to keep or revise.
Revisit why you created the appointment and whether that purpose still deserves a place in your week. You may decide to continue it, change its form, or release it. Make the decision deliberately so the recurring block reflects your current priorities rather than continuing simply because it is already on the calendar.
Yes. Use your calendar or a notebook to answer three questions: What still matters? What has the current plan taught me? What is one part of the arrangement I can change? October’s CEO Decision Bridge gives Insiders and VIPs a structured place to record an adjustment and consider what might interfere.