Ep. 53 : Why Your To-Do List Is Making You Feel Like a Failure
Your to-do list is lying to you, and Laura is here to prove it. This Pivot Tool episode breaks down the exact system she used to grow Lead Intact while still showing up in corporate every day.
This is a Pivot Tool episode, the first-Wednesday-of-the-month format Laura created specifically for listeners who want the how-to, not just the inspiration. Today she teaches the personal productivity system she built by adapting Agile, Scrum, and Kanban methodologies for real life. No tech background required. No jargon. Just a framework that actually works.
Laura walks through two core concepts: task specificity and task sizing. She uses a real client story to drive the point home. The client had three things on her weekly to-do list, finished two, and felt like a failure. The third task? "Move." As in, the entire act of relocating her life. Laura breaks down why that one word on a list is the reason so many high-achievers feel behind even when they are doing everything right. The problem is never your work ethic. It is how you are writing the list.
From there, she walks through exactly how to build your own board, whether on a physical wall, a whiteboard, or inside Trello, the tool she personally uses and recommends. She covers how to set your sprint cadence, how to cap your weekly task limit (she says start at three to five, and yes, she means it), and why the done column celebration at the end of the week is not optional. It is the whole point. Because if you never feel like you are winning, you will quit. And you are not here to quit.
What You'll Hear
✔️A client wrote "move" as a single to-do list item, then wondered why she could not get it done alongside two simple emails.
✔️Laura explains why capping your weekly tasks at three to five is not lowering the bar, it is how you finally start feeling like you are winning.
✔️She breaks down the four-column board system she still uses today to run both her personal life and Lead Intact.
✔️Trello tip included: Laura sets her background to a Manhattan penthouse view, and she explains exactly why that detail matters.
"Please remember to always proceed as if success is inevitable, because it is."
— Laura Dionisio
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You made the move, or maybe you're about to, or maybe you're still in it, showing up, performing, delivering, while something quiet in the background keeps saying, "This is not it." Either way, something has shifted, and you can't unknow it. Here's what nobody tells you. The landing strip is a little rocky once you come down from the high of accomplishment.
There are moments of real excitement, real clarity, like, "Yes, this is exactly where I'm supposed to be." And then night comes, and the anxiety rolls in. The what ifs, the what am I actually doing? Not because you made the wrong choice, by the way, but because you're standing in the space between who you were and who you're becoming.
Done pretending this is enough, done pushing through, done ignoring the thing that keeps pulling at you. That's exactly where this podcast lives. I'm Laura [00:01:00] Dionisio, founder of Lead Intact, and I've been exactly where you are. The corporate success that stopped feeling like success, the leap that was equal parts terrifying and necessary, the messy, non-linear process of building something that actually fits, and learning to trust yourself through all of it.
This is the pivot point. Real conversations about what's actually happening beneath the surface, and what it takes to build a life that feels as good as it looks. Not just the wins, the attempts, too. Because I'm not here to romanticize the journey. I'm here to show you what it's really like. Let's get into it.
Hello and welcome to another episode of The Pivot Point Podcast. I'm your host, Laura Dionisio, and today's solo episode is [00:02:00] gonna be a little different than the ones we've had in the past. Today's gonna be a little bit more technical, more of the how-to because this is a request from some of my listeners.
I call this type of episode The Pivot Tool, and my goal is to provide this kind of episode the first Wednesday of every month
My hope with this type of episode is that you learn something, whether it's you apply it directly or you decide this is a crock full of shit. But it gets you to start thinking about what tool might work for you, or you try it out for like a week or two and modify it in a way that suits you.
Today we're gonna talk about my favorite topic, one that I've talked to a bunch of my friends about, one that I've taught both as part of my corporate career but also to some business owners as well, and it's how I use Agile, Scrum, and Kanban to my personal life. So If you've heard of Agile, Scrum, or Kanban before and you're [00:03:00] like, "Ugh, why?"
No, I promise I, I'm not as strict about it. There's just certain components about it that I really love. Now- I'm not gonna particularly use the specific terminology that they use because they use things like user stories, story points, et cetera, and it's not the most descriptive if you're not in that space.
But the reason I mention Agile Scrum and Kanban is because if you wanted to look more deeply into the process that I'm gonna share today, and again, my process is modified, then you can. All right. So why is this important, and how did I use this?
This is important because something I really loved and appreciated about Scrum is the idea of sizing tasks. Now, again, if you are Agile Scrum practitioner, you're like, "No, Laura, it's called user stories." Yes, I get it. I acknowledge that that's the technical correct term. And for this podcast episode, I'm gonna call it task because nobody else in day-to-day [00:04:00] life says, "Oh, I've got a user story."
So what I love about Scrum is the idea of sizing the tasks and being very specific about what the task is. And let me explain. Have you ever written, uh, something on your to-do list, and then you look at it later and you're like, "I don't even know what that means"? Yes, that's why task specificity is important.
Now, in Agile Scrum, they have a specific format to address what task specificity means, or I guess to be technical, the user story means. But for me, the way I define it is if I were to write a task on a Post-It and I handed it to somebody else, is it clear to that person what they're supposed to do?
Here's an example of a task that is specific Call dentist to make an appointment That specific, right? Like if I were to hand that to a stranger, they're gonna know exactly what they're supposed to do and how to do it. Now, here's an [00:05:00] example of a task that may seem specific to you at the time, but maybe future you is not gonna understand. Or if you try to give this task to, I don't know, like your virtual assistant or if you're doing this for your personal life to like your kids or your partner or whatever, they're like, "I don't know what this means."
Okay?
Fix kitchen sink Now, for you, that might be obvious. You're like, "Fix the kitchen sink 'cause it's broken." But if you were to hand it to a stranger, like, okay, what's broken about it? What exactly about the kitchen sink needs to be fixed? Is it because there's a leak? Is it 'cause the hot water's not working?
Is it the cold water? Is it because it makes a weird sound when you do the garbage disposal thing? So this is what I mean by task specificity. Now, I mentioned task sizing. I have a funny story. I was talking to a client, this was many years ago, and we were talking about this process that we're gonna talk about today.
And she was telling me, she's like, [00:06:00] "Oh, man, I just, I can't believe it. I only had three things on my to-do list for the week, and I just, I got two out of the three done, but, like, I just couldn't, I couldn't get it done." And she was just, like, really hard on herself. And I asked, "Okay, tell me more about the tasks."
"Okay, task number one, email lawyer And I was like, "Okay, cool. What's task number two?" "Task number two, email real estate agent." I'm like, "Okay, cool. Notice those two, specific. Maybe the details of, like, what needs to be done, not that specific, but it's, like, specific and relatively the same size in terms of how long it would take and the amount of effort it would require, right?
Okay, good. Good. Okay, so tell me about the third task, the one that, like, you felt you just didn't make any headway on." And she was like, "Third task, move," because she was moving at the time. Now, I just... I chuckled, and I reflected back to the client "Do you see how emailing real estate agent and email lawyer, is, relative same size?
But when you think about moving, there are so many components to [00:07:00] moving, right? Even if we look at the task specificity, what about the move? Is it that you're actually gonna move, like you're loading the truck? Is it that you have to rent a truck?
Maybe you actually mean hiring a moving company. Is it that you have to pack? Is it that you have to pack the kitchen or pack the bedroom or the living room? Is it that you have to look through your stuff on what to keep and what to donate?" So do you see what I mean? This is why task sizing is super important because while emailing lawyer and emailing real estate agent is a s- a task of a certain size and those two are relatively the same, the task of move actually has probably, what, 50 things under it.
Because of course it'll be easier for you to email someone than it is to have the full-on task of moving. And of course you're not gonna necessarily get it done, the moving part, right away because you look at that task, and even if you haven't written it down, you know subconsciously that it's a huge effort.
And so what [00:08:00] I love about the idea of task sizing and task specificity is it really forces you to take a look at the thing that you need to get done and break it down to manageable bite-sized chunks that then don't feel overwhelming to take on or that then you realize, oh, I don't have to be the one to do every single part of this overall task of moving.
And then, okay, so I mentioned another agile methodology called Kanban. And again, I won't go too deep into what that is. I'm just letting you know what it's called so that you can do more research on it if you'd prefer. So Kanban is a process that's primarily used for things like IT, where there's just a s- like
You got a ticket, you gotta resolve it. You know, that kind of thing. And what I like about Kanban is in this workflow, and by workflow I mean If you think of each task as having a status where if it's on your to-do list, it's not yet done, [00:09:00] and then you decide to do it, now it's in progress. And then when it's done, then it's done.
So that's the workflow. It goes from to do to in progress to done. And what I like about Kanban is that within that workflow, there is a specified maximum of the number of tasks allowed within that workflow. So for example, if I decided for me, as I'm doing this, that I can only have 10 things within that workflow of to do, in progress, and done Then once I hit 10, I'm done, right?
It's not like I have an expectation for myself to do 20 or 100 because I'm like, "Nope, these are the 10 tasks that I'm planning to do, and that's it." And so with a combination of those two, I still use this process today, but it was especially helpful for me when I was still in corporate and Lead Intact was still a side business, and I was looking to grow my [00:10:00] business.
Because I have heard over the years a lot of my clients saying, I'm in corporate, but I have this really great idea," or, "I have this side business at the same time, and I just wanna grow it, but I can't seem to find the time." And so with this process, it allows you to find the time because you are defining how much time you actually want to dedicate for this thing.
So I am gonna go through how it works, but first you might be asking, "Okay, but how do I actually do it? Like, where does it live?" There are multiple ways to do it, but I'm gonna recommend two. One, you can do the traditional way that Agile Scrum started, which is with Post-Its or if you want a giant whiteboard.
So if you have a blank wall where you wanna dedicate space for this or a giant whiteboard, what you need to do is break it down, this is again my suggestion, into four columns. Now, these columns represent the workflow. [00:11:00] You may be saying, "Wait, Laura, you just said there were three before." Let me explain.
The first column to the leftmost is basically your never-ending to-do list because a lot of complaints I heard when first introducing this process to my clients is, " The reason why I have a never-ending to-do list is because I don't wanna forget things."
Okay, fine. In Scrum, they call this the backlog. You don't have to use that term. I personally just use the term to-do. So name it whatever you want. Leftmost column, your never-ending to-do list. You can even call it never-ending to-do list if you want. And then to the right of that is just to-do. Now, here's what I would love for you to decide if you choose to use this process.
What is a good working cadence for you? In Scrum, they call this sprint, okay? It's basically like what is a period of time that you'd like to have like a bounded container where you Take the time to [00:12:00] really think about what are the tasks I need to get done for this time period and so that you can also celebrate at the end.
When I did it, I did a weekly cadence. Now that I have a virtual assistant for my business, we have a biweekly cadence. But it's up to you. For the purposes of this episode, I'm just gonna call it a weekly cadence. So going back to the workflow. So again, leftmost column, never ending to-do list.
To the right of that, the column is To do for this week. And then to the right of that is in progress, and then rightmost column is done. Now, remember what I said about Kanban, limiting the number of tasks per sprint, or in this case, per week Decide how many tasks that you wanna sign up for the week.
I recommend starting three to five. And you might be thinking I can definitely do, like, 10." Cool. Start three to five. Here's why. The reason this will work so well, is if you feel accomplished and like you're winning, [00:13:00] okay, at the end of every sprint or every...
at the end of every week. That's why we're starting low. Because w- what have you noticed happening? For me, what I've noticed happening is my to-do list grows, like before I, I did this, and I just feel, even if I just started with, let's say three things on my to-do list, and then by the end of the day there's, like, 10 things, and I got the original three done, I feel bad about myself, right?
And then I'm like, "Well, fuck this list. I don't wanna do it anymore." So that's why I suggest starting three to five because you want, at the end of that week, to feel like, "Hell yeah, I'm amazing." Okay? So here's the process. First, create your board. Again, you can create the board on your wall or whatever. Oh, the second...
I forgot to mention, the second way you can create this, and this is what I did, is I used this tool called Trello. And what I love about Trello is that you can use it on your desktop, but you can also have an app on your phone. Now, if you use Trello, just create your own board with the four columns that I just talked [00:14:00] about.
Don't get distracted by the templates, because simplicity is the name of the game. All right. So you have your board, right? That's step number one. Just, step number two, decide what your sprint is. Again, for the purpose of this discussion, I'm just saying a week. So maybe for you, you want it every other week, maybe you want a month.
Doesn't matter, but decide. Three, g- go ahead and write your shit down on the never-ending to-do list. Everything. You can categorize if you want in terms of, like... Like for me, I had categories for work and then I had for personal. It's up to you, but let's just keep it simple for now. List everything in your, that to-do column, and then decide what your task limit is for the duration of your sprint, right?
So , let's say my sprint is a week. Again, start with three to five for the week, right? So that's your task limit. What that means is in that second column, the second from the left column that's to do for this week, you are not allowed to have more than five. Okay? Once you start getting [00:15:00] into it and you notice you're consistently doing five, okay, maybe you bump it up to seven, but just start three to five.
Now, next step, if you're starting this process on, like, a Sunday, choose your tasks for that week. So now you're gonna look at your never-ending to-do list, and you're gonna pick three from that, and you're gonna move it to the to-do for this week column. Now, when you look at those three to five tasks in the to-do for this week column, this is very important, make sure to assess each task for specificity.
Again, like, if you just say, "Fix kitchen sink," what does that mean? And for sizing, make sure that they are relatively the same size. Because if you're just like, "Oh, well, I only have three tasks," email real estate agent, email lawyer, and then move, well, move was really, like, 20 freaking tasks. So no, you actually had 22, right?
So you may notice, and this was for sure me too, you may have to break down some of the tasks, right? [00:16:00] And if so, then you go back and you make sure that the to-do for this week only has three to five tasks. If you, when you go through the exercise of breaking down, like, making sure they're the same number of tasks, you end up with 10, then move five back to the never-ending to-do list, okay?
This is very important And then the next step is to just go and do it. So now every day, this is why I love the in progress, so every day you look at the to-do for this week and you decide, "This task is what I'm gonna work on today." You move that task to the in progress.
And maybe later on you're like, "Actually, I wanna do this task as well," and then you move that to in progress. Why is this important? So that you can see which of the tasks you are already actively doing, and so that you get motivated to complete them instead of like, I don't know, doing half of the five tasks, right?
And then this is super, super important, maybe the most important step. At the end of the week, you look at [00:17:00] everything in your done column and you freaking celebrate. And you just go, "Yay, look at me. I'm amazing." And then that's it. You start over again. One thing to note too about Trello and why I love it so much is such a minor detail, but I like things that are motivational. You can choose a background photo for Trello, and I recommend choosing something that motivates you. So for me, I've always had this dream to live in a penthouse here in New York City.
So my background photo is as if I am in my penthouse and you can see the view of the Manhattan skyline. And so a friend of mine when we talked about it, he changed his to a picture of his family, 'cause that's his motivation. So that's something to keep in mind as well. All right, that's it for today's Pivot Tool episode.
I hope you found this useful. If you did, please subscribe if you haven't already. Leave a review, share this with your friends. [00:18:00] And with that, I will see you next time.
And please remember to always proceed as if success is inevitable because it is
If this episode hits something in you, good. That's not an accident. The discomfort you're feeling isn't a sign that something's wrong with you. It's a sign that you're done. Done living in the eh, done waiting for it to magically feel better, done being really good at a life that doesn't actually fit you anymore.
And if good enough stopped being good enough a long time ago, that's exactly who I work with. I'm Laura DiNisio. I'm a coach for high achievers who are done pretending that checking the boxes is enough, and are ready to do something about it. If that's you, let's talk. Book a free clarity call at leadandtact.com/booking.
We'll figure out together what's actually going on and what your next aligned step looks [00:19:00] like. And if you're not quite there yet, that's okay too. Subscribe so you don't miss the next episode. Share this with a friend who needs to hear it. You probably already know exactly who that is. And with that, I'll see you next time