26 October 2022

On Being Reliable

For many of us, adulthood comes with new sources of responsibilities. As a kid, it didn’t take much coordination to stay on top of a handful of classes or social groups that had expectations of me. But as an adult, I quickly discovered that new responsibilities seemingly emerge daily – each with different levels of urgency. There are things that I have to do today: pick up the kids, finish up the project I told my boss I’d get done, or pay that bill that’s due. Then there’s a class of things that I really should do soon: the yard’s overgrown and needs mowing, I need to decide on a strategy for the big project at work, and I keep putting off getting my flu shot. Then there are other things that are longer-term goals that I really want to make time for: I’d like to get a better handle on our finances, exercise more regularly, or learn to play guitar.

A few years ago, I got to a point where I was not faithfully executing the tasks in any of these categories and felt behind on everything. So I decided to start investing in finding strategies that allowed me to be more consistent with the things that I needed/wanted to do. For me, this journey can all be distilled down to two things: organization and discipline.


I’m speaking here of being organized when it comes to your responsibilities – not of keeping your room clean. If someone has their responsibilities organized, we might consider that person “reliable” or “dependable.”

It turns out that it doesn’t take much effort to become above-average at organizing your responsibilities. I’ll often hear suggestions like “we should make sure we’re prepared to start that project by next summer” or “It would be fun to go camping this fall”. In most circles I’ve been in, no one in the room actually expects that someone would follow through on those suggestions. Which means that being able to actually deliver on those ideas is perceived as a super-power.

I genuinely believe that anyone is capable of achieving this. We all have ways to remember these kinds of things if we genuinely cared to (e.g. put a reminder in your calendar), we just don’t take the time to do it. Becoming a more reliable person doesn’t require sophisticated strategies; the biggest determinant here is just deciding that you want to cultivate this skill.

There are likely hundreds of different tools and systems that you can use for managing tasks. I spent countless hours shopping for different systems that would help here and ultimately my conviction is that it doesn’t really matter which tool you use. What matters is that you have something that you’re regularly paying attention to. If I were starting this adventure all over again, I think I’d start with pen and paper. I wasted a lot of time getting distracted by various software tools and how to use each effectively. What really matters is that you have a list of tasks and when they’re due. (If you’d prefer to use something digital, look at todo.txt for a simple approach.) Then once per day, review your list to see what’s due today and what’s coming up that you need to get started on.1

The one other pitfall I experienced was trying to use too many different systems to track my responsibilities. I’ve typically had a system at work where I was expected to track my assignments, then we all have email inboxes, or incoming Slack messages, etc. Wherever possible, I’d recommend consolidating all of these into one or at most two systems for tracking your responsibilities. I found it completely overwhelming to have emails marked as unread plus Slack reminders plus a todo list plus a task board at work. I was consistently inattentive to at least one of those systems. So transfer any incoming work to your “authoritative” task list as quickly as possible. If I receive an email that requires more than a few minutes of work, I write it on my task list and mark the email as read.

If you’re curious, I’m using OmniFocus these days. It’s a perfectly fine tool, but I don’t think there’s any magic in it that doesn’t exist in any of its alternatives. The magical bit is that I look at this single tool every day and use it as my primary source-of-truth for my responsibilities.

If you’re consistently willing to invest a couple of minutes a day in this practice, you’ll quickly find that you now have a mechanism for staying on top of any number of tasks and priorities.


As I attempted to get my tasks more organized, I cycled through a variety of tools and none of them stuck. They eventually became a backlog of tasks that were hopelessly overdue. So I’d start over in a new tool and repeat the process. I blamed the tools, but I eventually realized that the common problem in all of these tools was the user (me) and that the underlying issue here was one of discipline.

I’ve never considered myself a terribly disciplined person. My wife, on the other hand, is the most disciplined person I’ve ever met. She would laugh to hear that I was giving advice on being disciplined. If you’re naturally a disciplined person, you might be able to skip right over this section. For the rest of you, hopefully my learnings as I struggled to become more disciplined will be of use to you.

No matter how well I organized my todo list, I was consistently getting behind. The tasks I’d neglect usually fell into one of these categories:

  • Tedious – “Manually copy and paste 100 items from this system to that system.”
  • Anxiety-provoking – “Have a difficult conversation with Jim ahead of his performance review.”
  • Overwhelming – “Learn to play the guitar.”

No matter how organized my todo list was, or how often I reviewed it, I never got around to completing these types of tasks. The two approaches that I’ve found that help here are decomposing tasks, and having a more strict adherence to the list.

The decomposition suggestion is probably self-explanatory. Instead of a task like “learn to play the guitar,” maybe the first step is “find a guitar teacher” or “order an instructional guitar book.” Break down the larger task into steps that you can complete in a few minutes. You could also schedule a recurring task of practicing guitar for 10 minutes every Monday (or whatever duration/frequency you know you’d be able to actually complete as your first step).

And then you just have to arbitrarily stick to doing what you said you were going to do. It won’t feel comfortable or pleasant to complete some of these tasks, but try to instill in your brain that if it’s on your todo list for today, you’re just going to get it done without delay or excuse.

As an aside, I had an interaction with a friend when I was younger that stuck with me. I was dreading doing a big project for school and complaining that I didn’t want to get started on it. He asked me sincerely: “Is it going to be easier to do it tomorrow?” My answer, of course, was: “No, I guess not.” To which he replied: “Then I guess go ahead and do it today.” I find that asking myself that question is helpful when I’m facing some of these unpleasant tasks. But to be clear, I’m still far from perfect in implementing this recommendation.

You can also combine these two techniques to suit your personality. If you’re naturally quite disciplined, you may be able to power through large, unpleasant or overwhelming tasks. I find that the more unpleasant the task is, the more I need to decompose it. In taking the example of the “difficult conversation” above, I might instead break the task down into:

  • Monday: collect examples of Jim’s problematic behavior.
  • Tuesday: sketch out some talking points on how to articulate the feedback
  • Wednesday: put a meeting on the calendar with Jim
  • Thursday: rehearse giving the feedback with my boss to get their input

These are tasks that I would actually be able to complete. It may take a bit of practice for you to identify the right way to chop up tasks that suits your personality. But if you find yourself not being reliable with certain things, pause and ask yourself why you’re not willing to do this task. Is it because it frightens you? Or because you don’t know how to start? Or because you don’t actually think it’s worth doing? Once you’ve identified why you don’t want to complete a task, you’re much closer to actually completing it (or deciding that it’s not worth completing).


Many smarter and more successful people than I have written on this topic and I’m sure I haven’t uncovered any new ground here. But I hope this testimony convinces you that even those of us who aren’t naturally disciplined or organized can still develop a reliability that stands out should we choose to.

  1. Often people start by using a calendar to manage their tasks. I think this is a reasonable place to start if you’re only intending to track a handful of todos per week. In my experience, if you’re trying to track multiple deliverables per day in your calendar, things will quickly fall apart. If When you miss a deadline, your calendar won’t easily surface that overdue item for you. And you won’t be able to meaningfully review your tasks because they’re intermingled with actual events on your calendar.