3 Tips for Optimistic Overplanners – Like Me!

Are you like me? If you clicked this post, then you probably are.

Confession time: as this post title suggested, I am an overly optimistic planner / goal setter / to do list writer. First, I overestimate how much energy and willpower I will have on any given weekend, and/or how much free time (and motivation—more on this later) I’ll have during the week. But I don’t want to forget all these ideas swimming in my brain, so I dump everything onto paper (and/or an app on my phone).

I always have the best of intentions when it comes to getting things done, really—I do! But I seldom get everything accomplished (and I beat myself up when I don’t check everything off. Is this just me? Based on the number of productivity books and YouTube channels out thereand that I consumeI think not). Do any of us though? I guess it depends how long your list is. And herein lies the secret (or part of it anyway).

I am not claiming to have any new ideas here when it comes to getting things done, but here are my three favorite tips to first create a more realistic list and then actually check more items off of it.

Tip 1

Get real! Track your time, then HONESTLY analyze it.

Laura Vanderkam’s 168 Hours was probably the first book I read about time management. She touts tracking time in 30 minute chunks, and to date has been doing it every day for the last 10 years. WOW! I have tried time tracking like this a couple of times over the years, and it is enlightening. She doesn’t claim you have to do it for as long as she has, but for a week every so often (she suggests seasonally) is helpful to know where your time goes. I agree that this is a good cadence, either at the beginning of a quarter or the start of a new season.

Sarra Cannon, fiction writer and creator of the HB90 system for achieving goals, bases her quarterly projects on the time she will/may have available and how long she thinks each project (and subsequently each supporting task) will take. Even if both time available and time required for your goals is just an estimate, it’s a better place to start than trying to do everything on your goals list in a given time period. Overestimate so you don’t pile too much onto your plate, because if you do, it will likely be more than you can achieve in the time you have.

These two methods, when combined, are a great starting point for creating a realistic plan. Whether it be for a weekend to do list, or your yearly goals.

Tip 2

Choose three “projects” for the week, and three tasks each day.

Based on your schedule evaluation and time estimates from Tip 1, select three “projects” you want to work on or complete this week and then three tasks (either independent of the projects or actions that support achieving them) and slot them into your calendar.

I recently heard this tip somewhere… though I cannot remember where. Nevertheless, I love it! And not just because three is my favorite number.

As stated above, I tend to be overly optimistic about what I can achieve, and that leads to me setting A LOT of goals for a given period of time. This idea of choosing just three projects for a week is a happy medium. It’s not too ambitious, but it also pushes me to do something. And something is better than nothing.

Once your projects are selected, you can break them down into smaller steps and schedule those actions for specific days throughout the week, aiming for three per day. Or if you have one off tasks on your list, you can include those in your daily three as well. I like to try to have an assortment: a task from a project breakdown, a standalone to do and something fun or something that’s been on a someday maybe list that I really want to get to at some point but I keep pushing off. This doesn’t always happen but it’s a target to aim for.

I’ve been trying to implement a Today’s Top 3 list each day for a while now and even though I don’t always set these daily goals, when I doand when I check them offI feel good about making progress toward my goals or one off to do items.

Tip 3

Do not rely on motivation, but rather momentum.

This tip comes via Plan With Laken who I follow on YouTube and Instagram (I’m sure many others tout this idea, but I heard it from Laken). We cannot rely solely on motivation because it is so fleeting. Momentum is truly the trick. All you have to do is begin and then ride the wave. This is a hard one for me though. Getting started is usually the toughest part, isn’t it?

  • Break it down – Laken is a big proponent for breaking big scary goals down into smaller steps. So if your task is big enough, break it down and then do the first step. Checking this small piece off your list will most likely propel you forward to the next task, and the next, and so on.
  • Set a timer – if you struggle with taking even that first small step, just set a timer for 5 minutes and start the task. Like Nike says, just do it! If it takes 5 minutes or less, success! If it is going to take more time, but you’ve already begun, you’re likely to continue until it’s completed or at least get a bigger chunk done.
  • Make it a date, virtually or IRL – if you set a meetup with a friend to work on goals, the commitment and your accountability to them will no doubt get you going. And then body doubling while you work side by side should keep the momentum for the duration of the date. And probably beyond! Things in motion stay in motion!

Here are some additional ways to build momentum for completing to do list tasks:

  • Use the 2-minute rule – if a task will take less than 2 minutes to complete, do it immediately rather than putting it on your list. This prevents small tasks from accumulating and gives you quick wins.
  • Task batching – group similar tasks together to minimize context switching. This creates momentum through efficiency since your brain stays in the same mode.
  • Habit stacking – attach new tasks to existing habits. For example, “After I make my morning coffee, I will spend 10 minutes on project X.”

Bonus Tip

Make it a game!

Don’t use fleeting motivation as a means to begin, but as a method to push you to the finish line.

My issue is that most of the time I would much rather spend my precious free time reading or watching a YT video than starting on a task from my to do list. Especially if it’s big and hairy, and even if I’ve broken it down to something more manageable. So I tell myself that I can have it as a reward. If I complete my three tasks, or this project, or that random thing, then I can watch that video, or read a chapter in that book. This usually works!

As with all aspects of life, this is a work in progress. Do I still make big, daunting to do lists? Absolutely. Do I think I’m going to check everything off? Maybe. But definitely less than I used to. I’m more accepting of not completing everything. I’m not overwhelmed by seeing a big list and knowing I won’t get to it all. I will highlight what I definitely need or want to get done and just focus on those. And I’ll migrate other items forward that are less critical.

Are you a chronic overplanner? I’d love to hear if any of these tips help!

Photo by Volodymyr Hryshchenko on Unsplash

Leave a Reply

Your email address will not be published. Required fields are marked *