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  • Writer's pictureJason R. Waller

You’re Not Going Deep Enough in Your To-Do List

A few weeks ago, I had an epiphany. I was talking to my coach about my weekly to-do list and sharing how, typically, I’m frustrated by the anxiety I wrap around it. Frustrated that it seems like I’m being run by my to-do list, not running it.

But this day was different. It was near the end of the week and I hadn’t done a single thing on my to-do list. Not even one thing was crossed off. The kicker? I felt more productive than ever, like I was kicking goals all week.

I was baffled! But, like any good paradox, I knew there would be gold inside of it, if only I could figure it out. The revelation was unsurprisingly simple: I wasn’t going deep enough in my to-do list, which meant I wasn’t focusing on what really mattered.

I Hate to Love To-Do Lists

Some people absolutely adore to-do lists. Getting to cross off a task well done brings a little dopamine hit and makes us feel productive. I admit: sometimes I’ll even add back things that I’ve done just to be able to cross them off!

I wouldn’t say, though, that I’m a to-do list disciple. Structure isn’t natural to me (I’m a “P” in the Myers-Briggs Type Indicator). I never liked writing things down or organizing my thoughts. I never took notes in class, I experimented with a daily schedule for just one day, and I never, ever had a to-do list.

To be honest, I think it was pride that was keeping me away from structure. I liked a bit of the scatterbrained, “mad professor” persona. At some level, I felt that having a to-do list made me stiff or weak.

Fast forward to now and guess what? I’ve used a to-do list. Every. Single. Day. For the last three years. I’m not exaggerating — every Monday I sit down and deliberately carve out my action items for the week, prioritize them, and check in on them daily. My to-do list is half personal and half professional, so whether I’m working or not doesn’t matter. I even wrote about it here.

It was in my conversation with my coach, though, that I realized: I’m only tapping into half the potential of my to-do list.

Focus on Progress, Not Completion

“Motion does not equal action. Busyness does not equal effectiveness.” –James Clear

When I make a to-do list, my intention is good. I want to get out, on paper, everything that needs to be done for the week or the day. So far so good, right?

The issue is twofold. One, the metric of to-do lists is completion. I complete a task, and I get to cross it off. “Completion” does not always equal “progress.” Which ties into the second issue: not all action items are created equal. I was patting myself on the back for circling four professional top priorities and three personal top priorities each week.

It was great to be focused and clear on what really mattered! I still circle the high-priority items on my to-do list. But over time I realized that I wasn’t actually doing any of them. And why I wasn’t doing any of them came back to the issues I mentioned earlier. Sometimes, the most important task was so big that it took a while to cross off as “complete.” I might make progress on that task, but there was nothing to cross off for “progress.” No dopamine hit for me.

This meant that I would naturally focus on those things that were easy, things that were simple. Easy items are seducing, I get to cross them off my list. Urgent items are shiny and distracting too, I get to feel like I’m doing something that matters.

The “aha!” moment for me came in asking: how do I make the important stuff just as interesting to me?

Do More to Do Less

“Dress me slowly, I’m in a hurry.” –Napoleon Bonaparte

There’s also a saying from my time in the military: slow is smooth, smooth is fast. This paradox is clear to most people. Rushing creates rework. Scrambling keeps us from focusing on what matters. Move slower to move faster, and do more to do less.

What I experimented with in my to-do list was, counterintuitively, making it bigger. I built my list for the week and prioritized my top four work items, as usual. I prioritize based on what I know I can impact and what has the biggest impact. Some things I know I can’t really change, at least not right away. Some things I can do, but they don’t create any real value for what matters to me. Neither are my high priority items.

From there, I built a second to-do list, expanding on those things that matter. I put the second one right below my first one, and it’s really just the next level down of action steps. So if my big level one priority is “Reach out to VC clients,” my second list under it would have:

  • Build target list of VCs

  • Prioritize by waves

  • Check through alumni database for contacts

  • Check through LinkedIn contacts

  • Reach out to wave one

  • Follow up

  • Reach out to waves two and three

When I did this, a funny thing happened. I wasn’t looking at the easy items in my first list anymore. By deliberately breaking out the high-priority items into sub-steps, they were the easiest things on my list! It was also immediately clear what progress looked like. Even if I never got around to all the second-list items and got that tick mark of “completion,” I could see compelling progress on the stuff that really mattered.

It’s Just a Tool

“Rule your mind or it will rule you” –Horace

I’d encourage you to try this approach of building a bigger to-do list. It sounds crazy, but it will make for smaller effort in the long run. And treat this like an experiment! See what works and what doesn’t. See what’s just noise in the process and what’s really helpful. Maybe you end up building a to-do list with just four, really important things on it. Maybe you need to go three levels deep, not two.

The key here is to check in on what’s working and make sure that you’re not working for your to-do list, your to-do list is working for you. This should be a source of clarity and confidence, not anxiety.

Lastly, I’d encourage you to try doing this on real, old-fashioned paper. Apps and Google Docs are great, and maybe that’s better for you in the long-run. But there’s a deliberateness to writing what really matters out by hand that’s special. And there’s a gift in being able to reflect on your to-do list over a cup of Monday-morning coffee, without having to pull out your phone or power up the laptop.

See what works for you, and share what you discover. Good luck on your journey.

Originally published in THE ASCENT


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