The Best To-Do List App for the Smart Risk-Taker

Fellow Riskologist,

For the last few weeks, we’ve focused on finding and addressing fear so you can move forward with big projects in your life. Before you clear away underlying fears, getting started on a big project can feel like pushing a boulder up a hill while breathing through a straw.

But once they’re dealt with, you start see the way forward. You see the things you must to-do to succeed, and that’s where the next problem strikes: overwhelm.

If you’ve read Riskology.co for a while, you know how I feel about overwhelm: It’s a gift.

But left unchecked, it’s still a problem. And the solution is a system to organize all your to-do items—something to manage the overwhelm and keep you on track.

That’s why I felt our little series needed one last installment: How to manage your massive to-do list.

I’m not much of a productivity nut. In fact, I get a little annoyed around people who can’t seem to do anything but talk about how to do boring work even faster. But I love what I do and, I must admit, the idea of doing a better job at it is appealing. I’m always optimizing how I work to get to all the fun stuff I wouldn’t be able to otherwise.

There are dozens of productivity tools out there to help you manage your endless to-do list, but few have ever worked for me.

Over the years, I’ve learned whatever tool it is I’m using to manage my life, it absolutely must meet these requirements:

• It must be simple. If it takes more than a few seconds to input and update the system on a daily/weekly basis, it’s a waste of time I could be spending actually doing stuff.
• It must be flexible. Reality changes all the time, so it’s critical that any tool I’m using makes it easy to change the plan—reorganize tasks, change deadlines, etc.—when necessary.
• It must be able to rank tasks. Any Riskologist who’s taken on a big project knows a mile long checklist is terribly overwhelming and useless. A good project management tool allows you to easily see which tasks are most important right now and work on just those.
• It must support deadlines. Face it: If you don’t give yourself a deadline, you’re probably never going to finish. Giving yourself hard and fast dates to complete the milestones of your project is critical.

Introducing Trello: The Smart Riskologist’s To-Do List System

First thing’s first: Trello is free, and I have no relationship with the company nor am I compensated in any way for recommending it. I just think it’s great.

I’ve tested many different project management apps over the years and abandoned most of them because they didn’t work the way I wanted them to. I’d spend hours setting everything up and then get frustrated with the workflow and give up just days later when it wouldn’t accommodate the way I wanted to work.

That finally changed when I tested Trello last year as my business partner Jonathan and I started building BrewPony. It was perfect. We were able to run the entire project through the app. Any time something needed to be done, we’d just create a “Card” in Trello, and assign it to one or both of us.

The reason Trello works so well is because, at its core, it’s very simple: a series of to-do lists. But if you want, just a few clicks will allow you to use it many ways.

You can test out Trello over here.

How I Use Trello

I’ve used Trello in different ways for different projects (which is a testament to its flexibility), but the standard workflow I use for most projects looks something like this:

First, I set up a new “Board.” This is where everything for any specific project lives. Then, I set up four specific “Lists” inside that board:

• To-Do
• Doing
• Blocked
• Done

Those lists are pretty self-explanatory. When a project is beginning, I’ll load every task I can think of into a Card  what holds an individual to-do item) on the To-Do list.

Once I start a task, I’ll move it to the Doing List if it’s something that’ll take a little time to complete. Once it’s complete, I move it to the Done List. For short tasks that I can finish quickly, I don’t bother using the Doing List. I just move it straight from To-Do to Done.

If I run into a roadblock while working on a task, I’ll move the card to Blocked if I get frustrated and want to move on. This way, I never get bogged down or lose track of what I’ve done. If I need to leave things unfinished at the end of a day, I can come back to Trello any time and see exactly what I’ve already started and where I’m blocked. Then, I get to work on those things first.

How I Organize Trello Cards

The Trello Card is extremely simple, but also versatile. At it’s most basic, you can just type a task into one and call it a day. Or, you can open the card and use it’s more robust features to do a lot of organization.

Trello Labels

The first thing I’ll do when I create a new card is assign a “Label” to it. Trello allows you to assign up to 6 different color coded Labels to a card. Here’s how I typically handle this:

• Red = Urgent
• Yellow = Important But Not Urgent
• Green = I’ll Get to it “Someday”

Whenever I log into Trello and I’m in a hurry, I’ll immediately filter the cards so that I only see the urgent ones (Trello has an incredible filtering system that allows you to see only what you want at any give time). That way I don’t have to wade through a lot of stuff that’s important but I don’t have time for at the moment.

Then, once a week, I’ll spend a few minutes reviewing tasks with all Labels. If something in the Important But Not Urgent Label needs attention—or if I have more time available to work on it—I’ll move it to Urgent so I can start making it a priority. I’ll do the same moving Someday cards to Important.

And just as important is taking a second to archive any cards I’ve created but realized I’m just never going to get to. This keeps the list clean and focused. I can always pull them out of the archive later if I decide I want to work on it.

How I Use Trello Due Dates

Deadlines are a critical part of actually getting anything done in life, but I admit I haven’t been the best about setting them for myself. Trello has helped me with this a lot, and the way I use them is simple and flexible.

First, only cards marked Urgent or Important get due dates. Sometimes, a due date is very clear and can easily be assigned. Other times, it’s nebulous. When this is the case, it’s easy to just ignore it or avoid giving it a deadline, but this is when it’s most important to have a deadline lest you end up with an urgent and important task that never gets done.

In these cases, I just make up a deadline that sounds good. There’s no science to it. I just pick one out of thin air.

This works because of the way I filter cards when looking at Trello. I can show myself only the cards that are “urgent and due within the next week.”

That’s my hot list that I know I need to kick it into gear on. If a task with a made up deadline  works its way into this filter that I know I don’t need to get to, I’ll simply change its deadline. Not the best, but it at least keeps me—for the most part—focused on tasks that are important and need to be done.

Due dates get the same scrutiny and adjustments during my weekly review.

How I Use Trello Checklists

The Trello Card is very versatile. It can be as simple or complex as you want it. Inside of each Card, you can also set up a Checklist. This basically allows you to create another to-do list inside of a to-do item. Very meta, I know.

I find it useful for keeping my board organized. Rather than creating a whole slew of Cards for one specific task, I’ll create one overall “to-do” Card and then set up a Checklist of tasks to complete inside of the Card that I can check off as I make progress. Trello keeps track of each Card as you make progress so you can quickly see which Checklists need to be worked on at any given time.

This is mostly a personal preference. If you’re the type of person who likes to have every task out in the open, you might opt to create a Card for every single task and not build a hierarchy using Checklists. Or, if you wanted to go all out, you might take your biggest to-dos and create a new Board just to manage that one piece of your project. The options are endless.

If at any time you realize a Checklist item needs its own card, Trello thought of that, too. With the click of a button you can convert one to the other.

How I use Trello Comments

The comments section of Trello is the most useful part of the system for me. This is especially true if you’re sharing a board with another person like a business partner or a few team members.

Each Card has its own comments thread, and you can add a note and tag other members in it (so that they’re notified) at any time. You can also attach files directly to a Card so that important assets like pdfs, images, etc. are right there for you to look at when you open a Card.

I like to use the comments system for each Card when working with other people because it’s better than email. When you work this way, conversations stay organized and on topic because there is a specific comment thread for each Card. This eliminates the frustrating headache of searching your email archive for “that one email with the thing mixed with the seven other things.”

For some reason, most people feel comfortable mixing tasks together in one email (very frustrating and difficult to track), but commenting inside Trello keeps conversations nice and organized.

I’ll also use the comments section to leave notes to myself. This is particularly useful for Cards on my Blocked list. I can leave a note explaining exactly what’s blocking me and what I’ve tried so far. When I come back to it, I have a history there so I can pick up right where I left off.

The Real Magic Behind Trello

All of Trello’s features are great but, at the end of the day, there’s one specific thing about Trello that keeps me attached to it and makes it a great project management app—the ability to move Cards from place to place.

This very simple feature—clicking and dragging a Card from one list to another—went mostly unrecognized by me at first, but when I think about why I enjoy using Trello so much it’s because I get some type of satisfaction each time I drag a card from the To-Do list to Doing or Done. It’s like a little mind trick that makes you feel like you’re getting even more done.

That bit of satisfaction is important! Staying motivated to work on your goal is what’s going to make or break everything, and Trello actively helps me stay motivated.

Now, I’d caution any smart Riskologist to never rely on a project management system as a source of motivation, but it’s good to know that Trello will never get in the way of my progress. It works just the way I want it to, when I want it to—never a source of friction.

Your To-Do List Should Actually Help You Get Things Done

At the end of the day, it doesn’t really matter what system you use or how you organize yourself so long as you have something that works. It should help you get things done and never feel like a burden.

Trello works for me, and I’m happy to recommend it with no compensation because I think a lot of Riskologists here probably have similar projects that would be a great fit for it.

Trello is completely free, and you can try it out here.

If you have a system that works for you, tell us about it in the comments because I’m sure my way won’t work for everyone. We’re all a little different!