How to Plan Your Month in 5 Steps
Before the travel, parties, and gift lists pile up.
TL;DR
Monthly planning moves dates, deadlines, and goals out of your head and onto a calendar.
You can do it in about 20 minutes and 5 steps.
Start with fixed events, then pick 1 to 3 goals and break them into small milestones.
Build in downtime, especially during busy months.
I’m Eric, an executive function coach and co-founder of UpSkill Specialists. I also have ADHD. The monthly planning system below is the one I use myself and teach my clients.
And it started after another late credit card fee… The sinking guilt of wasting money I didn’t have.
Constantly wondering, how am I going to get all of this done? My chest felt tight, my thoughts spinning as I stared at an endless to-do list.
Her birthday is tomorrow?! The panic and shame of realizing I’d forgotten, again, and the scramble to find a last-minute gift.
Before I understood how my brain worked, I lived week by week. I didn’t think I needed to plan any further ahead.
I was living in crisis mode. It was exhausting. I was on the verge of burnout and resented myself for not being on top of things.
As I learned more about how my brain works, I slowly built a system. Now, once a month, I spend 20 minutes mapping out what’s ahead.
Do I love doing it in the moment? Nope. I have to force myself every time. But afterward, and throughout the entire month, I’m thanking myself for those 20 minutes.
Why Monthly Planning Matters
When I plan my month:
I rarely miss appointments.
My bills are paid on time (yay, student loans 🫠).
I remember birthdays and buy thoughtful gifts in advance.
I know when I’m busy and can block off downtime for my introverted self.
Here’s why planning ahead works:
Your working memory is like a mental sticky note. It only holds a few things at a time. When you try to keep every appointment, bill, and birthday there, things fall off. Planning your month moves all of it onto a calendar, so your brain can stop holding it.
Why Planning Feels So Hard
Monthly planning is boring, and it can feel overwhelming. For many of us with ADHD, starting a task that isn’t interesting is one of the hardest parts.
Most people were also never taught a clear, simple process to follow. The five steps below take about 20 minutes.
3 Common Monthly Planning Mistakes
Picking too many goals. Ten goals in one month usually means none of them get done. One to three gives each goal the attention it needs.
Forgetting downtime. A plan with no rest is hard to stick with past the second week. Schedule recovery time like any other appointment.
Planning once and never looking again. A plan only helps if you see it. Set a quick weekly reminder to check your calendar and adjust.
How to Plan Your Month in 5 Steps
1. Start with time-bound events
Open Google Calendar or your planner. Next, add all appointments, events, birthdays, and deadlines, including bills. These go first because they can’t move.
Then set reminders on your phone or calendar for each one. I set double reminders: one 24 hours before, another 10 minutes before.
2. Brainstorm your micro goals
Micro goals are goals sized to fit within one month. Take five minutes to write down everything you’d like to accomplish this month, big or small.
Don’t filter yourself. Get it all out.
3. Choose 1 to 3 goals
Review your brainstorm and pick up to three goals that truly matter. If you’re stuck, ask yourself: “Will this matter to me at the end of the month?”
4. Break each goal into milestones
Milestones are smaller, actionable steps. Some goals need just one. Others need two or three. For example, “get my finances organized” might become “list all my bills,” “set up autopay,” and “review my budget.”
5. Add personal deadlines
Look at your calendar and pencil in a deadline for each milestone. Be realistic about your time and energy, especially during busier weeks.
Pro tip: block off downtime now. Your future self will thank you.
Planning a Busy Month
Some months carry extra weight: holidays, travel, a move, a new job, or a big work deadline. The steps stay the same, with a few adjustments:
Add more to step 1. Include travel dates, shipping deadlines, and prep tasks that come before big events.
Lower the bar in step 3. One goal is plenty. Rest can be a goal.
Add buffer time. Leave time before big events to prepare and after them to recover.
Plan earlier. For a busy month, plan a week or two before it starts.
Why Your Future Self Will Thank You
Here’s a quick recap:
Add all time-bound events, deadlines, and reminders to your calendar.
Brainstorm a list of micro goals.
Pick 1 to 3 goals that truly matter.
Break each goal into small, actionable milestones.
Schedule milestones and personal deadlines based on your time and energy.
Planning your month takes 20 minutes and rarely feels fun. In return, it clears your working memory, keeps you organized, and gives you space to live with intention. Your future self will thank you every month.
If you’d like support building a planning system that fits the way your brain works, you’ll love your monthly planning sessions. You can learn more and apply to work with me here.
In service,
Eric
FAQs
How long does monthly planning take?
About 20 minutes once you know the steps. Your first time may take a little longer.
How do you plan your month with ADHD?
Keep it short and simple. Start with fixed events so nothing gets missed, choose only 1 to 3 goals, break them into small milestones, and put everything on a calendar with reminders. A short process is easier to start, which matters when planning feels boring.
When should I plan my month?
A few days before the month begins, or on the first day. For busy months like the holidays, plan a week or two earlier.
About the Author
Eric Kaufmann is an Educational Therapist, Certified Executive Function Coach, and speaker. He is the Co-founder of UpSkill Specialists, an executive function coaching company that helps adults and workplace teams overcome disorganization, procrastination, and productivity roadblocks.
Want to learn more about 1:1 coaching? Click here.
Interested in hosting a workshop for your team or company on how to improve executive function skills in the workplace? Click here.
Looking for guidance on how to become an adult executive function coach? Click here.
