How To Turn Your Biggest Goals Into Monthly, Weekly, And Daily To-Dos

You’ve heard the cliché that achieving a long-term goal is kind of like eating an elephant: You’ve got to do it one bite at a time. But most of us were never taught how to actually hack up an elephant into digestible bits. Instead, we spot an elephant, lick our chops, maybe even grab a bib–and then we haphazardly dive in with nothing but a fork, attempting to swallow everything we can in one sitting.

(Too gruesome? . . . Sorry.)

The point is that it’s easy to get frustrated early when you’re trying to make headway on any long-term goal–no matter how confident and ambitious you feel when you get started. That’s a recipe for defeatism, and avoiding it requires a system for patiently breaking down your biggest objectives into daily, weekly, and monthly tasks. In other words, you need to plan tomorrow’s to-do list backwards–by thinking about your yearlong goals first. Here’s how.

Your Yearly To-Dos

Switching careers, starting your own business, getting six-pack fit, learning a new language: Your yearlong goals can fall in any category, but they need to be big. Big enough to make you uncomfortable–to scare you, even. That’s when you’ll know they’re worth tackling.

Long-term goals generally fall into a few common categories:

• career
• health/fitness
• fun/self-care
• relationships
• giving

So instead of writing up tomorrow’s to-do list, sit down for 30 minutes to an hour and think hard about the biggest things you’d like to accomplish by this time next year. Just be as specific as you can. Maybe it’s changing jobs or launching a sustainable side hustle. Perhaps it’s paying down a certain chunk of your student-loan debt. You just need to figure out the “what” at this stage, not the “how.”

Your Monthly To-Dos

When you’re pursuing an elephantine goal, the only way to avoid getting full early and pushing your chair away from the table is to be able to see the progress you’re making. That’s why you’ve got to focus all your energy in one spot. If you dance around your goal, picking at it here, nibbling there, you could consume a metric ton and still not see any progress.

So pick out one aspect of your yearly goal that you can realistically accomplish in a month. To do this, schedule a recurring appointment with yourself for one Saturday or Sunday each month to sit down for a half hour or less, reflect on your long-term vision, the progress you made last month, and which chunk you can tackle in the next 30 days. Write this down.

I’ll use a firsthand example: Say you want to make a living as a writer. That won’t happen in a month. But you can make sure that happens by this time next year if you devote this month to:

• identifying a theme and mission for your blog
• learning all you can about the craft of writing
• writing 12 high-quality blog posts related to your theme
• drafting the copy your future website’s pages

Do this in four weeks and you’ll have knocked out a whole elephant-leg. That’s progress!

Then you can set your sights on landing your first writing assignments for publications, building out your site, and pitching clients–all monthly goals in their own right.

Your Weekly To-Dos

But don’t get ahead of yourself. You’ve still got to break your month down into a weekly action plan. Set another recurring reminder to sit down each Sunday, for just 10–20 minutes, to sketch out a few weekly action steps you can accomplish in seven-day intervals–and write this down, too. For the first leg of our imaginary writing goal, those might include:

• Week 1: Brainstorming the mission and theme of your blogging and outlining the first six posts you’re going to tackle.
• Week 2: Getting halfway through that writing-instruction book you grabbed from the library, taking solid notes on it, and drafting copy for your “About Me” and “Contact” pages.
• Week 3: Editing (and re-editing) the six posts you wrote over the first two weeks and drafting the next three.
• Week 4: Finishing the book, reviewing and summarizing your reader’s notes, and editing the last six posts you’ve written.

You don’t have a fully functional site yet, but that’s cool. You’re already becoming a better deadline-driven writer, and you’re figuring out how to find multiple angles on a clearly defined subject area. Anything you weren’t able to accomplish this month you can shift over to the first week of the following month–having some flexibility here is key.

The main thing is make sure you’ve got a few definitive action steps to focus on each week. As you move from week to week, month to month, you’ll get a feel for what’s overly ambitious vs. realistic.

Your Daily To-Dos

Now you’re ready for the “one bite at a time” part. By now you’ve done so much preparation that your daily to-do list practically writes itself. But you still need to set aside time for it. So every morning (or evening, as you wind down your workday), spend a few minutes drafting up your top goals for the day ahead.

Let’s say it’s Friday of Week 3 above, and you’re still polishing up a few items from the week before. Maybe today you’re going to:

• edit one of the posts you drafted on Tuesday
• draft a new post
• take notes for half an hour on the writing book you’ve been reading
• draft your future website’s “About Me” page
• purchase your domain

It’s easy to see how your work today is connected to your weekly goals, which are connected to your monthly goals, which are connected to your yearly goals. This means that you don’t have to worry that you aren’t spending your time well. You’re doing everything you need to, when you need to. Confidence in the bank.

A Healthy Appetite For Holistic Planning

I call this “holistic planning” (no relation to the wealth-management strategy) and when my coaching clients–who pretty much across the board describe themselves as “non-planners” when I first meet them–get the hang of it, they often fall in love with the planning process itself.

The reason, as I see it, is because funneling your big-picture goals into daily action steps simply feels good. It’s gratifying to know that you’re a human being who is capable of making real, measurable headway on really ambitious projects despite whatever setbacks may befall you.

But you have to practice it to perfect it. To keep this planning system running efficiently, make sure to reflect on your overall accomplishment rate during your weekly and monthly check-ins. If there’s anything that recently held you back from making headway, you can adjust your pace. After all, you’ll need to stay hungry over the long haul–rather than get full before you’ve finished what’s on your plate.