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April 30, 2025
• Updated

When the system breaks down: How to reset your planning practice

A practical guide to resetting your ADHD planning system using small steps and supportive tools like Tiimo and Flown.

No items found.

Even the best planning systems sometimes break down. Especially if you're an ADHD'er or navigating executive functioning differences, or periods of low motivation, it’s normal for routines that once worked to suddenly stop feeling doable. If you’re staring at an abandoned calendar, a cluttered to-do list, or a planner gathering dust, you’re not alone and it doesn’t mean you’ve failed.

Planning systems break down, and that’s okay. You can rebuild support with the right tools, a few small steps, and a bit of flexibility. Here’s how.

Why planning systems break down

Planning isn’t a one-time thing; it’s a relationship you build with yourself. And like any relationship, it can be affected by:

  • Energy fluctuations (hello, executive dysfunction)
  • Life changes (new jobs, moving, health issues)
  • Burnout or overwhelm
  • Systems that were too rigid or complex to begin with
  • Shifting priorities or needs

When your brain or life changes, your planning system needs to change with it. But most traditional advice treats planning like a static skill you either “have” or “don’t.”

In reality, most people, especially ADHD'ers, need flexible, evolving planning systems that can handle real-life messiness, not just ideal conditions.

Signs your planning system needs a reset

Sometimes it’s obvious when a system isn’t working. Other times, it sneaks up on you. Here are common signs:

  • You dread opening your planner or app (or forget it exists entirely)
  • Your to-do list is overwhelming, pointless, or so full you don’t know where to start
  • You keep missing tasks, appointments, or deadlines
  • You’re avoiding planning altogether because it feels like another chore
  • Your system adds stress instead of offering support

If any of these feel familiar, it’s a good sign your planning setup needs adjusting; not because you’re failing, but because your system is no longer matching your reality.

How to pause and assess without spiraling

When a system fails, it can trigger shame spirals: “Why can’t I just keep up?”

Instead of blaming yourself, try this reframe:

  • Pause and notice: “My system isn’t working for me right now.”
  • Detach identity from outcome: Planning is a tool, not a test.
  • Ask curious questions:
    • What’s feeling too heavy?
    • What’s missing that I need?
    • What worked before and why did it work then?

This curiosity makes it easier to troubleshoot without slipping into all-or-nothing thinking.

How to reset your planning practice step-by-step

Resetting doesn’t have to mean overhauling everything. Here’s a simple way to reboot:

Clear the deck

  • Archive old tasks you won’t realistically tackle.
  • Create a “maybe later” list for non-urgent ideas.
  • Try using the Eisenhower Matrix to prioritize what’s truly urgent versus what can wait.

Pick one tool to restart with

  • Choose a system that adapts to you, not the other way around. A tool like Tiimo, for example, offers a visual, flexible way to plan that supports ADHD and executive functioning needs. You can customize layouts, organize tasks visually, and get reminders that help rather than overwhelm.

Struggle to start tasks or stay on track?

Tiimo helps with task initiation, time agnosia, and follow-through, with visual timers, smart checklists, and flexible planning built for ADHD brains.

Apple logo
Get Tiimo on App Store
Google logo
Get Tiimo on Google Play

Start with micro-plans

  • Plan just today or even just the next two hours.
  • Break tasks into tiny, actionable steps. Tiimo’s AI Co-pilot can help you break things down and reduce the cognitive load of getting started.
A hand holds a smartphone displaying Tiimo’s AI Co-planner interface in dark mode, with a task list including meetings, medication, and household chores.
Tiimo’s AI Co-planner helps break tasks into manageable steps, so you can start without overthinking

Add in body doubling for momentum

  • If you need a little extra accountability or support, try body doubling. It’s a simple strategy where doing a task alongside someone else, virtually or in person, can make it easier to start and stick with it. Flown, one of the best-known platforms for body doubling, offers live, guided sessions you can join from anywhere. You set your intention, do your thing, and wrap up together. No pressure, just shared structure to help you get going.
A laptop screen shows a weekly schedule on Flown’s virtual co-working platform, with session options like Deep Dive, Power Hour, and Meditation alongside instructor images.
Flown’s weekly calendar lets you join live body doubling sessions whether you’re working, tidying, or just trying to get unstuck


Prioritize “done is enough” over perfection

  • Planning works best when it feels low-friction and low-stakes. Give yourself permission to start small, skip steps, or change your mind. The aim is to stay in conversation with your plans not to execute them flawlessly. Let good-enough be a way back into momentum, not a compromise.

Set a mini check-in

  • After a few days, take a moment to reflect. What’s helping you feel more supported? What’s still feeling clunky or hard to start? Are you using your tools or avoiding them? A system that evolves with you is one you’re far more likely to stick with.

Tiny resets > giant overhauls

Big overhauls can feel exciting but they rarely stick. Especially with ADHD, they tend to burn bright, then fizzle fast. What actually works is much quieter: a small shift, a gentle restart, a tiny experiment you can build on.

Tiny resets make space for progress without the pressure.

  • A single task written down instead of a full-blown plan
  • A five-minute tidy instead of a weekend deep clean
  • A low-energy Flown session instead of powering through alone

These aren’t shortcuts, they’re strategy. Small adjustments that rebuild trust, reduce friction, and make it easier to keep going.

Rebuilding your planning relationship

Planning often unravels when it starts to feel like a performance or something to maintain rather than something that supports you. Especially for ADHD’ers and folks with executive functioning challenges, the most effective systems are the ones that offer flexibility, reduce friction, and make it easier to start again when things go off track.

Tiimo helps turn time into something visible and manageable. Flown brings gentle structure through shared focus. Together, they offer rhythm, not rigidity, a planning practice you can return to, again and again.

Ready to reset?

If you’re ready to rebuild your planning practice with tools that actually support how your brain works, Tiimo and Flown have teamed up to help.

Get 35% off new annual plans when you use code FOCUS35 and start building a system that moves with you, not against you.

About the author

Beaux Miebach

Beaux is Tiimo’s Inclusion and Belonging Lead, a queer AuDHD leader designing systems where accessibility and intersectionality come first.

Read bio
April 30, 2025
• Updated:

When the system breaks down: How to reset your planning practice

A practical guide to resetting your ADHD planning system using small steps and supportive tools like Tiimo and Flown.

No items found.

Even the best planning systems sometimes break down. Especially if you're an ADHD'er or navigating executive functioning differences, or periods of low motivation, it’s normal for routines that once worked to suddenly stop feeling doable. If you’re staring at an abandoned calendar, a cluttered to-do list, or a planner gathering dust, you’re not alone and it doesn’t mean you’ve failed.

Planning systems break down, and that’s okay. You can rebuild support with the right tools, a few small steps, and a bit of flexibility. Here’s how.

Why planning systems break down

Planning isn’t a one-time thing; it’s a relationship you build with yourself. And like any relationship, it can be affected by:

  • Energy fluctuations (hello, executive dysfunction)
  • Life changes (new jobs, moving, health issues)
  • Burnout or overwhelm
  • Systems that were too rigid or complex to begin with
  • Shifting priorities or needs

When your brain or life changes, your planning system needs to change with it. But most traditional advice treats planning like a static skill you either “have” or “don’t.”

In reality, most people, especially ADHD'ers, need flexible, evolving planning systems that can handle real-life messiness, not just ideal conditions.

Signs your planning system needs a reset

Sometimes it’s obvious when a system isn’t working. Other times, it sneaks up on you. Here are common signs:

  • You dread opening your planner or app (or forget it exists entirely)
  • Your to-do list is overwhelming, pointless, or so full you don’t know where to start
  • You keep missing tasks, appointments, or deadlines
  • You’re avoiding planning altogether because it feels like another chore
  • Your system adds stress instead of offering support

If any of these feel familiar, it’s a good sign your planning setup needs adjusting; not because you’re failing, but because your system is no longer matching your reality.

How to pause and assess without spiraling

When a system fails, it can trigger shame spirals: “Why can’t I just keep up?”

Instead of blaming yourself, try this reframe:

  • Pause and notice: “My system isn’t working for me right now.”
  • Detach identity from outcome: Planning is a tool, not a test.
  • Ask curious questions:
    • What’s feeling too heavy?
    • What’s missing that I need?
    • What worked before and why did it work then?

This curiosity makes it easier to troubleshoot without slipping into all-or-nothing thinking.

How to reset your planning practice step-by-step

Resetting doesn’t have to mean overhauling everything. Here’s a simple way to reboot:

Clear the deck

  • Archive old tasks you won’t realistically tackle.
  • Create a “maybe later” list for non-urgent ideas.
  • Try using the Eisenhower Matrix to prioritize what’s truly urgent versus what can wait.

Pick one tool to restart with

  • Choose a system that adapts to you, not the other way around. A tool like Tiimo, for example, offers a visual, flexible way to plan that supports ADHD and executive functioning needs. You can customize layouts, organize tasks visually, and get reminders that help rather than overwhelm.

Struggle to start tasks or stay on track?

Tiimo helps with task initiation, time agnosia, and follow-through, with visual timers, smart checklists, and flexible planning built for ADHD brains.

Apple logo
Get Tiimo on App Store
Google logo
Get Tiimo on Google Play

Start with micro-plans

  • Plan just today or even just the next two hours.
  • Break tasks into tiny, actionable steps. Tiimo’s AI Co-pilot can help you break things down and reduce the cognitive load of getting started.
A hand holds a smartphone displaying Tiimo’s AI Co-planner interface in dark mode, with a task list including meetings, medication, and household chores.
Tiimo’s AI Co-planner helps break tasks into manageable steps, so you can start without overthinking

Add in body doubling for momentum

  • If you need a little extra accountability or support, try body doubling. It’s a simple strategy where doing a task alongside someone else, virtually or in person, can make it easier to start and stick with it. Flown, one of the best-known platforms for body doubling, offers live, guided sessions you can join from anywhere. You set your intention, do your thing, and wrap up together. No pressure, just shared structure to help you get going.
A laptop screen shows a weekly schedule on Flown’s virtual co-working platform, with session options like Deep Dive, Power Hour, and Meditation alongside instructor images.
Flown’s weekly calendar lets you join live body doubling sessions whether you’re working, tidying, or just trying to get unstuck


Prioritize “done is enough” over perfection

  • Planning works best when it feels low-friction and low-stakes. Give yourself permission to start small, skip steps, or change your mind. The aim is to stay in conversation with your plans not to execute them flawlessly. Let good-enough be a way back into momentum, not a compromise.

Set a mini check-in

  • After a few days, take a moment to reflect. What’s helping you feel more supported? What’s still feeling clunky or hard to start? Are you using your tools or avoiding them? A system that evolves with you is one you’re far more likely to stick with.

Tiny resets > giant overhauls

Big overhauls can feel exciting but they rarely stick. Especially with ADHD, they tend to burn bright, then fizzle fast. What actually works is much quieter: a small shift, a gentle restart, a tiny experiment you can build on.

Tiny resets make space for progress without the pressure.

  • A single task written down instead of a full-blown plan
  • A five-minute tidy instead of a weekend deep clean
  • A low-energy Flown session instead of powering through alone

These aren’t shortcuts, they’re strategy. Small adjustments that rebuild trust, reduce friction, and make it easier to keep going.

Rebuilding your planning relationship

Planning often unravels when it starts to feel like a performance or something to maintain rather than something that supports you. Especially for ADHD’ers and folks with executive functioning challenges, the most effective systems are the ones that offer flexibility, reduce friction, and make it easier to start again when things go off track.

Tiimo helps turn time into something visible and manageable. Flown brings gentle structure through shared focus. Together, they offer rhythm, not rigidity, a planning practice you can return to, again and again.

Ready to reset?

If you’re ready to rebuild your planning practice with tools that actually support how your brain works, Tiimo and Flown have teamed up to help.

Get 35% off new annual plans when you use code FOCUS35 and start building a system that moves with you, not against you.

About the author

Beaux Miebach

Beaux is Tiimo’s Inclusion and Belonging Lead, a queer AuDHD leader designing systems where accessibility and intersectionality come first.

More from the author
When the system breaks down: How to reset your planning practice
April 30, 2025

When the system breaks down: How to reset your planning practice

A practical guide to resetting your ADHD planning system using small steps and supportive tools like Tiimo and Flown.

Tiimo coach of the month icon

Georgina Shute

Gina is an ADHD coach and founder of KindTwo, helping overwhelmed leaders reclaim time and build neuroinclusive systems that actually work.

No items found.

Even the best planning systems sometimes break down. Especially if you're an ADHD'er or navigating executive functioning differences, or periods of low motivation, it’s normal for routines that once worked to suddenly stop feeling doable. If you’re staring at an abandoned calendar, a cluttered to-do list, or a planner gathering dust, you’re not alone and it doesn’t mean you’ve failed.

Planning systems break down, and that’s okay. You can rebuild support with the right tools, a few small steps, and a bit of flexibility. Here’s how.

Why planning systems break down

Planning isn’t a one-time thing; it’s a relationship you build with yourself. And like any relationship, it can be affected by:

  • Energy fluctuations (hello, executive dysfunction)
  • Life changes (new jobs, moving, health issues)
  • Burnout or overwhelm
  • Systems that were too rigid or complex to begin with
  • Shifting priorities or needs

When your brain or life changes, your planning system needs to change with it. But most traditional advice treats planning like a static skill you either “have” or “don’t.”

In reality, most people, especially ADHD'ers, need flexible, evolving planning systems that can handle real-life messiness, not just ideal conditions.

Signs your planning system needs a reset

Sometimes it’s obvious when a system isn’t working. Other times, it sneaks up on you. Here are common signs:

  • You dread opening your planner or app (or forget it exists entirely)
  • Your to-do list is overwhelming, pointless, or so full you don’t know where to start
  • You keep missing tasks, appointments, or deadlines
  • You’re avoiding planning altogether because it feels like another chore
  • Your system adds stress instead of offering support

If any of these feel familiar, it’s a good sign your planning setup needs adjusting; not because you’re failing, but because your system is no longer matching your reality.

How to pause and assess without spiraling

When a system fails, it can trigger shame spirals: “Why can’t I just keep up?”

Instead of blaming yourself, try this reframe:

  • Pause and notice: “My system isn’t working for me right now.”
  • Detach identity from outcome: Planning is a tool, not a test.
  • Ask curious questions:
    • What’s feeling too heavy?
    • What’s missing that I need?
    • What worked before and why did it work then?

This curiosity makes it easier to troubleshoot without slipping into all-or-nothing thinking.

How to reset your planning practice step-by-step

Resetting doesn’t have to mean overhauling everything. Here’s a simple way to reboot:

Clear the deck

  • Archive old tasks you won’t realistically tackle.
  • Create a “maybe later” list for non-urgent ideas.
  • Try using the Eisenhower Matrix to prioritize what’s truly urgent versus what can wait.

Pick one tool to restart with

  • Choose a system that adapts to you, not the other way around. A tool like Tiimo, for example, offers a visual, flexible way to plan that supports ADHD and executive functioning needs. You can customize layouts, organize tasks visually, and get reminders that help rather than overwhelm.

Start with micro-plans

  • Plan just today or even just the next two hours.
  • Break tasks into tiny, actionable steps. Tiimo’s AI Co-pilot can help you break things down and reduce the cognitive load of getting started.
A hand holds a smartphone displaying Tiimo’s AI Co-planner interface in dark mode, with a task list including meetings, medication, and household chores.
Tiimo’s AI Co-planner helps break tasks into manageable steps, so you can start without overthinking

Add in body doubling for momentum

  • If you need a little extra accountability or support, try body doubling. It’s a simple strategy where doing a task alongside someone else, virtually or in person, can make it easier to start and stick with it. Flown, one of the best-known platforms for body doubling, offers live, guided sessions you can join from anywhere. You set your intention, do your thing, and wrap up together. No pressure, just shared structure to help you get going.
A laptop screen shows a weekly schedule on Flown’s virtual co-working platform, with session options like Deep Dive, Power Hour, and Meditation alongside instructor images.
Flown’s weekly calendar lets you join live body doubling sessions whether you’re working, tidying, or just trying to get unstuck


Prioritize “done is enough” over perfection

  • Planning works best when it feels low-friction and low-stakes. Give yourself permission to start small, skip steps, or change your mind. The aim is to stay in conversation with your plans not to execute them flawlessly. Let good-enough be a way back into momentum, not a compromise.

Set a mini check-in

  • After a few days, take a moment to reflect. What’s helping you feel more supported? What’s still feeling clunky or hard to start? Are you using your tools or avoiding them? A system that evolves with you is one you’re far more likely to stick with.

Tiny resets > giant overhauls

Big overhauls can feel exciting but they rarely stick. Especially with ADHD, they tend to burn bright, then fizzle fast. What actually works is much quieter: a small shift, a gentle restart, a tiny experiment you can build on.

Tiny resets make space for progress without the pressure.

  • A single task written down instead of a full-blown plan
  • A five-minute tidy instead of a weekend deep clean
  • A low-energy Flown session instead of powering through alone

These aren’t shortcuts, they’re strategy. Small adjustments that rebuild trust, reduce friction, and make it easier to keep going.

Rebuilding your planning relationship

Planning often unravels when it starts to feel like a performance or something to maintain rather than something that supports you. Especially for ADHD’ers and folks with executive functioning challenges, the most effective systems are the ones that offer flexibility, reduce friction, and make it easier to start again when things go off track.

Tiimo helps turn time into something visible and manageable. Flown brings gentle structure through shared focus. Together, they offer rhythm, not rigidity, a planning practice you can return to, again and again.

Ready to reset?

If you’re ready to rebuild your planning practice with tools that actually support how your brain works, Tiimo and Flown have teamed up to help.

Get 35% off new annual plans when you use code FOCUS35 and start building a system that moves with you, not against you.

Illustration of two hands coming together to form a heart shape.

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