To-Do Lists Suck

To-Do Lists suck.

Some of you might be so married to your to-do list that you feel personally attacked by those words. This used to be me.

In fact, I was so attached to my to-do list that if all my boxes weren’t checked by the end of the day, I’d be consumed by immense feelings of guilt.

I don’t do this anymore; but honestly, it’s not about avoiding feeling guilty.

The to-do list is simply a poor work and life management system.

I’m not saying that it’s not important to set daily goals and leverage action-inducing systems to progress your life.

In fact, to-do lists are built on fundamentally sound principles. They set you up to be proactive and deliberate, ultimately forcing you to take actionable steps toward goals.

But there’s a huge flaw that no one talks about.

Back when I used to-do lists religiously, regardless of how much I’d done at the end of a day, I’d be evaluating my performance based on a list of things that ambitious post-coffee me jotted down.

The huge issue with this is that to-do lists are output-based.

As you start your day, you arbitrarily set a random set of things to go out and do.

And when you’re an over-caffeinated person with high aspirations, you undoubtedly set out to do more than is possible in a given day.

Now, there’s nothing wrong with this at its core. In fact, I still think it’s important to push the bounds of what you think you can accomplish day to day.

The problem arises when we subconsciously view the state of our to-do list as a reflection of ourselves, our day, and our productivity.

And let’s be honest, it’s impossible not to do this to some extent.

The other core problem with to-do lists is that they encourage “fake work”.

What do I mean by this?

As humans, we get a dopamine hit by checking off tasks on our to-do lists.

Unfortunately, it doesn’t matter whether or not that task made significant progress toward any of your ultimate goals.

In the past, when I used to-do lists religiously, I found myself throwing half a dozen unimportant and non-urgent tasks on the list just to feel like I was being productive.

If you use to-do lists, you’re probably guilty of this whether you realize it or not. Acknowledging this reality is empowering.

Sam Altman (OpenAI CEO, ex-Y Combinator president) has a fantastic article about fake work. It’s primarily geared towards VC-backed startups but the takeaways are applicable to everyone. I highly recommend checking it out if any of this resonates with you.

You don’t have complete control over your outputs. Especially when they’re stacked up against unrealistic expectations.

What you do have full control over, however, is your time and deliberate effort.

This is where all your focus needs to go.

Timeboxing

Timeboxing is a time management system where you set predetermined intervals to focus on specific tasks or activities.

It’s incredibly effective for two reasons.

First, it sets boundaries for how you use your time and puts you in full control over your most valuable resource.

Second, it forces you to be deliberate about how you invest your time.

Remember, when you decide on a specific task, you’re trading the most valuable currency—time—for engaging with that thing.

Timeboxing a task pushes you to ask yourself how important is this thing? Is it worth 30 minutes of my time? 2 hours?

It ultimately materializes the temporal transaction you’re making and makes you aware of whether or not that thing is a good use of your time.

If my tech startup is primarily fueled by product-led growth, my timeboxed schedule should reflect this. I should be allocating the majority of my time to product and effective marketing.

If growth is primarily a sales-led motion, I should be investing the majority of my time into outbound sales.

Seems obvious, right?

Well, it is and it isn’t.

To get to this conclusion, you have to become aware of how your time is being spent. But in order to be aware of this, you need a system that makes this inherently obvious in your day to day.

Otherwise, you’ll never evaluate how your time is actually being spent. This is why timeboxing is so effective.

While I haven’t found a solid timeboxing solution out there, the good news is that you can just use your calendar as a timeboxing system.

Instead of using it for just meetings and work, start viewing it as a balance sheet for how you’re investing your time.

It does the job and will be easy to transition to since you’re likely already using google calendar or something similar.

If you prefer smooth, purpose-built apps, I actually decided to scratch my own itch and build a timeboxing app myself (I just opened up 15 completely free early access spots for anyone interested).

But remember, it’s not about the tool. And this is coming from a guy that loves software tools.

It’s about the mindset and workflow that the tool enables.

It’s true that apps can help us do things more effectively. But in reality, you can achieve the same result using a good ole notepad.

So whether it’s using an app, google calendar, or something more analog, just find what works for you, and make sure it sticks.

Box your time. Take control of your day. Invest—don’t spend—your time on things that bring you meaning and set you up for success.

Your day-to-day happiness and productivity will thank you.