I Schedule Stuff in My Calendar and I Don’t Stick to It…Help!

Stephanie Wasylyk
7 min readApr 25, 2023

You’re trying to get “back on track” and “get organized” so you start putting all your appointments and tasks in your calendar. You “time block” like people (including me) suggest. Monday morning comes and before 10am you’re already off the rails and behind schedule. Or maybe you followed some of the things you planned, but by Thursday you’ve ignored a bunch of the things you wanted to do (exercise, anyone?). You say you’ll try again next week, then the week after, but it just doesn’t seem to work for you.

The first thing you likely did was blame yourself. Maybe you think you should have more willpower, or that you’re bad “at this”, or some other variety of negative self-talk.

The second thing you likely did, and the reason I’m writing this today, was you think you need a new or better system. Just this month alone I’ve had 3 or 4 clients bring this up in our call, which tells me it’s time to write about it. They come thinking they’re doing something wrong, and they want me to help them come up with a task management system and calendar that will work for them.

Here’s the news you probably don’t want to hear…replacing your current system with a new one probably won’t fix the problem. We have to dig a little (or a lot) deeper first.

I’ve come up with 14 reasons why your calendar might not be working for you that you might want to explore before you go sign up for a new tool that promises miracles. I’ll admit, this is an incomplete list. I’ve hardly scratched the surface of cultural expectations, bias, discriminatory practices, personal history, and much more, which you’re welcome to add to the list. So much comes up in a coaching session that I can’t anticipate because everyone has nuanced and unique experiences. This should be enough to get you thinking, though.

It may be helpful to read my other article about time management first since I won’t be repeating the “how” to do it here.

14 Reasons Why You Aren’t Sticking to Your Calendar

1. You have too many things on your calendar. Maybe you’re overlapping tasks or double-booking yourself. It sounds obvious, but it’s very easy to do. You might also be scheduling things too early in the morning or too late in the evening, in times you don’t intend to work.

2. You scheduled too little time for each thing. This is extremely common because it’s easy to underestimate how long something will take to do. Over time you’ll start to learn how long tasks take, and you’ll need to schedule differently for them. In the meantime, make sure to give yourself buffer times. And don’t forget to schedule lunch and breaks!

3. You’re adding things in even after you’ve scheduled the week. This happens when a request comes your way, and instead of looking at your calendar or telling them a time you can do it, you say yes and assume you’ll figure it out later. This could come from a place of scarcity or also from a place of people-pleasing, both of which you’ll need to dive deeper into if this is your default.

4. The tasks you’re scheduling aren’t at the right time of day for your energy. We aren’t machines and our energy changes throughout the day/week/month/year. It’s your job as a business owner to learn when you do certain types of work best, and plan accordingly. For example, if I don’t write on Monday mornings I find it very hard to write at any other time in the week.

5. You’re immune to seeing it in your calendar. Maybe you’ve had a task on repeat for so long you don’t even notice it’s in there anymore. I find it helpful to revisit my recurring tasks on a regular basis, and if I want to keep them sometimes I rename them to give them a fresh feel. It might also need a different time slot or length of time for it to be more effective. Or, if it isn’t relevant anymore, delete it!

6. There are too many distractions or interruptions in your day. Of course tasks will take longer if you’re constantly being interrupted! You can do your best to minimize them (turn off notifications, close browser windows, put a sign on your door…whatever you need) and if getting interrupted is part of your job, then you need to plan around it. Know what times of day you will be interrupted, and what times are scheduled without interruptions. Set boundaries and stick to them.

7. The things you’re putting off just aren’t that important. Maybe they’re things you want to do, sure, but you could be putting them off because you have more important things to get done. This could be because you aren’t clear on your strategy or goals, but it could also be that you aren’t planning time to work on things that matter in the long-term. Clients and putting out urgent fires might make other things seem less important.

8. The task is too complicated or you don’t know how to do it. This happens especially when we put giant things in our schedule without breaking them down. Something like “hire an assistant” or “launch a new product” are huge and undefined. They often have many steps ahead of them as well, like revisiting your vision and goals to make sure it’s aligned strategically. If you’re sure the project is something you want to take on, then break it down and schedule the smaller bits instead. Notice where you need help with doing it and schedule time to reach out.

9. You’re tired or burnt out. When you’re working from this lack of energy everything takes longer and feels exhausting. You’ll do the bare minimum to get through the day. If you keep working from this place instead of addressing the root cause, you’ll always feel behind and no organization system will work.

10. You’re trying to fit into a cultural expectation that just doesn’t make sense. We are all living in a capitalist economy designed to have us work harder, be more productive, and squeeze every last ounce of energy out of us. We’re always “on the clock” and needing to make more money to afford our ever-expanding lifestyles (not to mention keeping up with inflation). We’re taught to ignore the realities of life and put work above all else. This just doesn’t work for most people. All I can really speak to on this is to pay attention to what’s happening and experiment with a different way of being. I try to model the possibilities for you by writing about taking more time off, normalizing finances, and prioritising living your values.

11. The tasks or projects don’t align with your values or vision. It’s very easy to get off track and do things because they sound good or because someone else suggested you do it. When this happens, it can be hard to recognize because your logical brain is telling you it could work but your heart is resisting (procrastinating, among other things). Just because it’s right for someone else doesn’t mean it’s right for you. It may take some time to unravel what you got yourself into, but it will be worth it. I find mind-mapping extremely helpful for this.

12. You’re not honouring yourself, and you’re putting yourself last. This is especially true for caregivers, people-pleasers, obligers, martyrs, women…all the roles we’ve been trained where we don’t matter as much as someone else. Usually it’s self-care that gets cut first (lunch breaks, exercise, and sleep, among other things) but it could also be saying yes to someone else when you’d like to be working on a different project. The unlearning process for this needs to start small and we must be kind with ourselves. Self-belief coaching can really help with this.

13. Something about the task is scary, risky, or confronting. It makes perfect sense that you’d put off a task that carries some sort of risk, even if it isn’t rational. You may be criticized, you may be judged, you may be successful — all these and more can be reason enough to put off something even if it’s important to you. Self-doubt plays a big role here, so getting to the bottom of it can be liberating.

14. Maybe the system isn’t right for you. Yup, it could be that after all. Maybe you don’t really use your calendar in the first place. Maybe you don’t like to be on screens. Maybe you’re neurodivergent and there’s something else that would work better. Maybe you have some other reason it isn’t working for you practically. You get to decide if you want to troubleshoot the system or move to something else. But I will say, remembering to use the system is probably the biggest hurdle for most people. Since I use Google Calendar, I have it open up as my startup page every time I open my internet browser so it’s always top of mind. Just a little tip for you there!

See, there are TONS of reasons why your calendar might not be working for you! If you went through this list and none of it resonated or you feel totally overwhelmed, then likely it would be helpful to get another perspective. Coaching is great for getting to the bottom of WHY you’re not sticking to things you say you’re going to do.

If you’d like to try out coaching, no strings attached, my gift to you, you’re welcome to book a gift coaching session with me. You can read about what they are and how to book one here. We can get to the bottom of why your system isn’t working for you, and what might be getting in the way.

Takeaways and Next Steps:

1. There are MANY different reasons why you calendar isn’t working for you.

2. There is no one “right way” to manage your tasks or time, there’s just the ways that work for you

3. Look beyond the tool to see if the tasks are even things you want to be doing — you have permission to adjust them!

4. Go through this list and check off the ones that seem true to you to gain deeper insight