329 meetings might seem like a lot of meetings, but out of all the meetings that land on my calendar throughout the year (I had over 1,000 meetings on my calendar last year alone, not including the 329), these are the most important 329 meetings I have and I do whatever I can not to miss them. These 329 meetings are with myself.

Some of these 329 meetings are short and very focused. Others are longer in length and require deep thinking and planning. But what all of them have in common is that they are all important parts of my productivity system.

Below I will highlight the different meetings I have with myself and the purpose they serve. But first, it is important to understand how I structure my year.

How I Structure My Year

For starters, while most people start their year on January 1st, my year starts on September 1st and runs through August 31st of the following calendar year. So my year will be September 1, 2023 to August 31, 2024. I have structured my year this way since about 2008, when I started my productivity journey after reading David Allen’s Getting Things Done, and was strengthened after reading Mike Vardy’s The Front Nine in 2013. For me personally, September is a logical starting point. First, it is my birthday month, which always feels like a good time for a fresh start. Secondly, it is usually when things get back to “normal” personally and professionally. The kids go back to school and business starts to pick back up after a slow summer. Plus, July and August are good months of reflection for me, so it makes sense to use that as the time I think about a previous 12 month period.

As you will read below, I don’t think about planning on a yearly basis, but instead more in quarters. Some of this was just habit for me over the last decade or so, after learning that yearly planning just doesn’t ever work. Things change to fast and Murphy’s Law is too powerful to fight against. But my quarterly focus also was influenced by Brian Moran’s book The 12 Week Year, which I highly recommend.

So my year is broken down into four quarters consisting of 13 weeks each. 12 weeks are for execution of projects and the 13th week is for some of the meetings highlighted below and for reflection and planning. The year is more centered around overarching goals and metrics… the quarters are where the real work gets done.

So now that you have a sense for how my year is structured, let me tell you about those 329 meetings…

The Different Types of Meetings I Have Each Year

Annual Review and Planning (1 day a year, 8 hours in length)

Once a year I hold a full day meeting with myself that has two main objectives. First, I spend a couple of hours reflecting and wrapping up that year that is just finishing. After this meeting, I really don't want to look back at all, so I try to make sure I put a bow on the year, whether good or bad, and move forward. I wrap up all of my metrics and I archive all of the project folders accordingly.

For the rest of the day, I focus on the year to come. I don't believe in doing super concrete annual planning, meaning, I am not setting rigid goals or "have to do" plans. I like taking a more agile approach and focus on quarterly planning (which I will touch on next), so this time is more focused on higher level directional planning. What are some of the big initiatives I would like to tackle in the year to come, with the understanding that things may get derailed, but at least walking away from the meeting with a general direction. I will set metric goals (revenue, web traffic, etc.) for the year, which help inform my quarterly planning.

This meeting typically takes place in the last couple of days of the 13th week of the last quarter of the year (or in other words, Week 52).

Quarterly Reviews and Planning (1 day each quarter, 4x a year, 4 hours in length)

My entire workflow cycle is based on quarterly timing, so these four half day sessions are arguably the most important meetings I have each year. During these four, 4-hour sessions, I am thoroughly defining my plan for the next 12 weeks. The plan comes from a combination of what was set as goals at the annual planning session, as well as what opportunities may have developed since then that I want to capitalize on.

My goal with these quarterly meetings is to walk out with a clear work plan that I can put my head down and drive towards without question for the next 12 weeks.

These meetings typically occur during the 13th week of each quarter.

Monthly Checkpoints (1 day a month, 12x a year, 2 hours in length)

These monthly meetings are checkpoints throughout the quarter to make sure I am still on track with the execution plan. The meetings consist of a lot of administrative work (catching up on project notes, making sure my external communications are up to date, etc.), but also to make sure I am pacing towards my goals okay, and if not, make sure I find a way to catch up so I can meet all my deadlines by the end of the quarter.

That makes it worth mentioning one more thing about the quarterly execution… when I set a plan for a quarter, it is imperative that I only set as much work as I can get done. I don’t want to carry work over from quarter to quarter, instead focusing on starting new work. This ensures that I am delivering output on a regular basis and not getting too caught up in thinking I always “have more time to work on that later”.

The monthly checkpoint meetings happen at the very end of each month.

Weekly Review (1 hour every week, 52x a year, 1 hour in length)

Every week I take one hour to catch up from the week that has passed and prep for the week ahead. This is a very tactical meeting, spent mostly in my calendar system, moving meetings around, setting up performance time blocks in my calendar, and making sure I am prepared for any presentations I have to give. Generally I look back one week in my calendar and ahead two weeks.

The weekly review meeting and process is heavily promoted by David Allen in the GTD methodology and I can honestly say that since I started performing weekly reviews, my life has never been better.

I have held my weekly reviews on different days of the week over the past 15 years, depending on what works best in my schedule that year. In the coming year, I will be having my weekly reviews on Wednesdays, which will be new for me. I will keep you posted on how a mid-week weekly review goes.

Daily Check In (30 minutes every day, Monday through Friday, 52x weeks a year)

No matter how well my Weekly Reviews are, things are always changing on a daily basis! Therefore, I find it important to have a quick daily meeting every morning, just to get sight on the day ahead. I check on my calendar to see if anything has changed and what my top 3-5 big tasks are for the day.

These Daily Check In meetings used to be 15 minutes, but I have found that as my career has progressed and I have taken on more responsibilities not just for myself but for my team members, 30 minutes is required.

These meetings are Monday through Friday (no weekends), and usually happen around 7:00 AM.

Are the 329 meetings worth the time?

From the jump, I understand how 329 meetings seems like overkill, but like I said earlier, I find lots of value in staying connected with, well, myself (and my work). But as we all know, time is a valuable resource that is finite. So are all these meetings worth the time invested?

Here is the breakdown of time over the course of 12 months by meeting type:

• Daily Check In - 130 hours

• Weekly Review - 52 hours

• Monthly Checkpoint - 24 hours

• Quarterly Review and Planning - 16 hours

• Yearly Review and Planning - 8 hours

Adding all of those up comes to 230 hours a year. When you consider there are 8,760 hours in a year, that 230 is really only 2.6% of your time with these meetings. And even if we take out sleep (let’s use 8 hours a night of sleep), leaving you with 5,840 hours a year of awake hours, you are still only looking at all those 329 meetings only taking up just under 4% of your time. Are your goals and best work worth 4% of your time? Mine is.

Final Thoughts

329 meetings, and the way I organize and conduct them, might not be for everyone. And if 329 meetings seem overwhelming but you still want to start somewhere, I do recommend at the very least the Weekly Review meeting as a great starting point. You just have to find what works for you and your productivity system. I will just say that sometimes, from what I have found personally, the meetings that provide the best return are the ones you have with yourself.