top of page


This article was based on episode 029 of The Modern Manager podcast. To hear this episode, and many more like it, you can subscribe to The Modern Manager Podcast on iTunes, Google Play, Spotify, iHeart Radio and Stitcher. Get the mini-guide here or the full guide at Patreon.

Using a new app requires you to build new habits. The app can be for almost anything: a new meditation app, a new fitness app, a new note-taking tool or a new task manager.

Sadly, in my experience, it’s true that old habits die hard. Despite proclamations by various experts and researchers, there is no magical number of days to build a new habit. Different habits take different amounts of time to develop. There are many factors that go into how easy or how hard it is too truly form a new habit.

For some of us, the first few days or weeks of having a new technology tool is full of enthusiasm. Since it is fun and new, we are invested in gaining whatever benefit the app promises. But then, maybe you have a change in your routine or schedule, or you get too busy, so you don’t use it for a day. Then you forget to use it the next day. Finally, after a few more days have passed, you remember to use it, but you are not as motivated because it feels more like a chore than a habit. The honeymoon phase has ended. Using the app feels a lot like work since it’s not yet a natural part of your workflow. It hasn’t become that unconscious action that feels almost effortless.

Not everyone goes through that exact experience. Some people are less than enthusiastic during the beginning phase of using a new tool. For some of us, we feel the challenge right from the start. It feels like a chore, taking up mental energy to remember and motivate to use the app.

But whatever the first experience feels like for you, you are likely to end up facing this common series of challenges.


If you only sometimes use your task manager, not only will you’ll get significantly less value than if you fully use and trust the system, but you’ll likely end up negating the positive benefits you hoped for.

One of the most significant benefits of keeping your tasks in one place is better mental capacity and less stress. You can stop worrying about forgetting something if you know it’s in your to-do app with the proper reminders. Instead, the system does the hard work for you. You can relax and free up brain space for more important work.

But, if you only occasionally put content into your app, you can’t trust its accuracy. As your system becomes less reliable, you start that negative downward spiral. Why put more in when you don’t trust the system to begin with? You still have to look in your notebook or hold onto that task at the back of your mind.


Whether you’re using the app on your own or with a team, the integrity of the content is critical. If you aren’t marking when tasks are done or deleting unnecessary tasks, they become clutter, making it harder for you to find what you need.

If a colleague isn’t keeping their tasks current, it’s impossible for team members to have accurate information on a task’s status. Maybe the issue is that no ones is responsible for adding tasks from meetings, so those start slipping through the cracks again.

In any case, when the content becomes out of date, the tool becomes less valuable.


Many people really like paper. Writing notes on paper is often more practical. It helps you remember what you’ve written, is faster, and generally feels more appropriate than using your phone or computer during meetings.

Finding a solution that combines your digital app and paper is critical to achieve long term sustainability. Both paper and task apps have their own unique benefits and drawbacks.

Personally, I love using paper for the reasons mentioned earlier. I also enjoy drawing and making my notes beautiful. However, I lose track of tasks when only dealing with paper. I end up with a long running list and a task gets buried in it. I can’t search for something nor set a due date. There are no reminders. I can’t view my tasks by project or activity or due date. So while I love using paper for many reasons, it fails me when it comes to enabling me to reduce my mental stress on task management.


Why can’t technology just work the way I need it to? Why can’t the app have every feature or capability or integration that I need (and none of the ones I don’t!) to make my work easier?

No matter how well you research and explore an app prior to using it, you’ll still discover a feature that it’s missing or a need you didn’t know it had. No tool is going to be perfect. So whether you discover a need along the way or realize the tool doesn’t work the way you expected, or perhaps even know ahead of time it’s missing a particular capability, you’ll most definitely have a moment where your frustration with the tool comes out in full force.

So what can you do if you’ve found yourself or your colleagues struggling with any of these challenges?


Using a new app is no different from eating healthier or going to the gym. You have to put in lots of sustained effort until eventually (hopefully) it becomes second nature.

Here are a few approaches to help you avoid or overcome the common challenges:

  1. Make a plan for managing both paper and digital. Look at it as a symbiotic relationship where paper and your app are working together harmoniously to keep you more organized. For example, if you’re going to take notes by hands all day, then at the end of the day or first thing the next morning, input any written tasks into your app.

  2. Integrate using the app into your existing routines. New habits are formed by having a hook or trigger that causes you to initiate the behavior. Consider what existing routines you have, such as checking your email, that you can associate with also checking your task manager.

  3. Make reminders visible. Post a 30-day chart on your wall or desk to visually encourage you to use the app every day. Set a goal to use the app every day for a week and check off each day that you do. You may find that once you have a few checks in a row, you will not want to miss a day, leaving an empty box! If you work with a team, make it a collective game. Introduce the concept during your team meeting and agree to the terms. Then see if you can all use your collaborative task tool for a full week, or two, or four. Celebrate when you’ve hit a milestone as a team to make it more fun and exciting.

  4. Explore automations, integrations and new features. Can you simplify or re-energize using your tool? Look for ways to connect the apps you use using Zapier or IFTTT. Explore the help site to find new features and creative ways work-arounds. Go to the user forum for ideas and submit a feature request if there is something specific you need.

  5. Regularly reflect on how you’re doing. Hold a weekly reflection of how you’re doing with the app and how you could do better. Take 5 to 10 minutes and ask yourself or your team the following questions: a. What’s working well with the app? What benefits are we experiencing? b. What’s feeling hard about using it? What’s in the way? What’s not working? d. Are we getting the full value we desire? If yes, celebrate. If not, why not? c. How can we solve these challenges? What could we do differently? By incorporating a regular check-in, you are acknowledging the journey and giving yourself (and your team) a chance to intentionally improve.


Now that you know to expect some ups and downs when using task manager app, make a plan on how to interrupt that natural rhythm.

At the end of the day, one of the coolest things about task managers is that the more you use them, trust them, and input content into them, the more valuable they become. It’s the positive, virtuous cycle that keeps building on itself. Your goal early on is to be diligent about using your tool so that some day, you won’t be able to imagine how you’d survive without it.

Now all that being said, if you find it increasingly hard to stick with using a digital task app, consider if it’s the right tool for your needs and even whether an app is what you need at all. There are dozens of task managers each with different features and design. If your current app isn’t meeting your needs, carefully examine if it’s worth transitioning to a more appropriate tool.

There are also dozens of paper planners and note-taking methods which might be better suited for your needs. It’s okay if a digital tool is not for you, as long as you find a system that works.

Get the mini-guide here or the full guide at Patreon to help you implement the learnings and continue to enhance your rockstar manager skills.

This article was based on episode 029 of The Modern Manager podcast. To hear this episode, and many more like it, you can subscribe to The Modern Manager Podcast on iTunes, Google Play, Spotify, iHeart Radio and Stitcher. Never miss a worksheet, episode or article: subscribe to Mamie’s newsletter.




When you subscribe to my email list, you'll be notified when new blog posts are released.

bottom of page