The Cascading To-Do List (how to get BIG things done)

How do you get from point A to point B?

Bootstrapped entrepreneurs are by their very nature highly motivated.  We love to get to work and get things done.  But that hard-driving work ethic often collides with the notion that we must have patience if we’re going to achieve the BIG goals we set for ourselves.

It’s easy to come up with a big idea.  It’s easy to start sketching, wireframing, coding, and marketing.  It’s easy to hustle and skip those weekend plans to bang through our to-do list.  But keeping at it over many months, staying focused on the goal and allowing the required time for this project to mature (before calling it quits)… That’s hard.

I came up with a mental model that I think will help to actually achieve a big goal.  I call it the Cascading To-Do List.  In a nutshell, the idea is to start with the end-goal in mind, then divide it into smaller and smaller increments.  Plan all of the actions in detail beforehand, then get to work.

Now let’s break open this nutshell and get into the nitty gritty…

Your 6-Month Goal

Start by clearly defining — in detail — a specific, BIG goal you aim to achieve within six months.  I like six months because it’s long enough to achieve something big, but short enough to be able to do 2 big things in a year.  This means I can look back on the past year and feel a tremendous sense of progress in my career and life.

The goal that I chose for my next 6 months is to write and release a book, and earn $10,000 in sales within the first two weeks.  I added this sales target because I don’t want this goal to be just about writing a book (<– I’m excited about tackling this part), but marketing it too (<– I’m a bit daunted by this part, but excited for the challenge).

What’s required for this to become a reality?

OK, so you have a goal in mind.  What will it take for this to happen?  At this stage, don’t even think about how much work or how much time things will take.  Just focus on the deliverables.  What exactly needs to get done.  Scribble down a list.  Do it quickly and don’t spend too much time thinking.  Just make a list.

In my case, I came up with the following:

  • Outline & research for the book
  • Write & edit the book
  • Design the sales page & delivery system
  • Design the book and prepare extra materials to add value
  • Build a pre-launch mailing list
  • Write several high-profile guest articles every month leading up to launch
  • Publish articles, podcasts, and interviews on my own blog on a weekly basis

Now break it down into monthly actions

Create lists for each of the next 6 months.  I find Trello to be the perfect tool for this.  What you’re doing is planning exactly which things you will get done in each month.  Yes, that means planning your deliverables in December, even if we’re currently in July.

This planning ahead is crucial, because it provides a roadmap for how you will get from point A to B.  Without mentally organizing the road ahead, it will be too easy to fall back into that “hustle” mentality, trying to get too much done the first month, then get burned out and fail, get discouraged and ultimately kill the project.  That won’t happen this time, because now we have a system in place to prevent that.

Here’s what my Trello board looks like:

Screen Shot 2013-07-10 at 9.37.09 AM

Screen Shot 2013-07-10 at 9.39.28 AM

Technically, this is a 7 month plan, because I want to release the book after the holidays.

Two-week sprints

Now that we have our months planned out, it’s about time we start getting to work.  But before we do, we must break things down a bit further.

I like to plan my schedule in two week sprints.  What’s on my plate this week, and what will I get to next week.  This is basically a two-week calendar, showing which deliverables I plan to tackle on which days.  I’m only including items that were previously listed in my monthly list.  In other words, I’m keeping the focus on the deliverables that must get done in order to make progress towards the goal.

But don’t forget about “everything else”.  Customer/client support tasks… Urgent bug fixes… Inbox (967)… Holidays… Sickness… you know, life.  Key is to leave ample space in your schedule for this stuff.  You don’t need to.  It will schedule itself in.  Just make sure “everything else” doesn’t take priority over the important things you’ve listed in your two-week calendar.

For my two-week calendar, I like to use the whiteboard on my wall.  It’s good to keep it clearly visible in my office so that I’m constantly reminded what needs to get done this week.

Here’s what my two-week whiteboard looks like:


I win the award for sloppiest whiteboard handwriting.

The 24-Hour To-Do List

With my week all planned out (based on my monthly deliverables list, which is based on my 6-month plan), I’m ready to get to work today.

At the start of every day — or rather, near the end of the previous day — I make a point of listing what I’ll be working on next.   I call this my 24-hour to-do list.  I list just a couple of things that I plan to get done within the 1 working day.  This is usually 2 things, but at most 3.

It’s OK to list things that fall under “everything else” on this 24-hour to-do list.  Things like   Now that we’ve made it to our current working window (today), we can figure out how to make good use of our time.

I like to use the mornings, particularly early morning, pre-breakfast, to knock out the most important items — the deliverables that work towards my goal.  This is when my mind is at it’s peak performance and I have minimal distractions.

I use Clear for my 24-hour to-do list.  I like how it’s compact and can sit in the corner of my desktop, staring me in the face, reminding me to stop checking Twitter and get back these to-dos!  Here’s what my day looks like right now:

Screen Shot 2013-07-10 at 12.17.24 PM

The Key Ingredient

While setting goals and breaking them down into smaller actionable steps isn’t a groundbreaking new concept, there is one key ingredient that often gets lost when thinking about achieving BIG goals you set for yourself.

That key ingredient is to plan everything out in detail before you get started.  Establish your mental roadmap for what exactly you will be working on today, the rest of this week, next week, this month, next month, and for the next 6 months.  When you know where you’ll be going, it will be much easier to focus your energy on execution.

Your thoughts?

  • Sean Hodge

    Great post, I’ve struggled with setting the long view first and then putting together an actionable plan, then sprints, then weekly, then daily.

    I tend to have big goals in place, but skip planning it all out, then just have rough weekly, though specific daily goals.

    You’ve really put together an actionable system here. I’ll give it a try and I think it will fill in some gaps in the way I plan and work. Thanks.

    • Good to hear you find this helpful Sean!

      I was the same way for a long time. I had a tendency to get ahead of myself and try to tackle everything RIGHT NOW. This system helps me get things off my mind and stay focused on one task at a time, knowing the rest is scheduled for later.

      • Sean Hodge

        I just downloaded Clear. It seems like a great replacement for Paper-based lists and so easy to get rolling with right away. It feels fun to use.

        I was using Wunderslist and just not digging it for daily tasks. it’s not bad for weekly agenda though. I’ll have to give Trello a look for setting those long term goals. It’s an interesting idea to use different apps for these various goal/task planning. I always tried to find one system for everything without much luck. Thanks.

        • Clear is great. Super simple, perfect for short daily to-dos. Nice syncing via iCloud too (if you use iOS). And the sound effects remind me of old-school Nintendo games for some reason 😛

          Trello’s “boards” system really works well for multiple, separate to-dos like a series of months.

          • Sean Hodge

            I do use IOS, though need to review iCloud syncing. Looks like I can get Clear on my phone. Yah, the old-school FX must be what makes it feel fun.

            I’ll give Trello a swing for organizing months of planning, as that’s something I have in docs right now, which aren’t the best view for that sort of thing. Thanks.

  • Hey Brian. Luv the blog and everything you’re doing here! Thanks for pointing out Trello and Clear plus a practical approach to applying these principles.


    • Hey Blair – thanks for reading! Glad to you find these helpful.

  • lesc1aypool

    Hey great article! I think the same way and have been trying to put together a process just like this. Thanks!

    • Glad it helped, thanks!

  • David Horn

    Great post. Love how you can take the top-level view and get really granular – down to the 24 hour list. Nice.

    • Thanks for reading David! That’s the idea 🙂

  • kitsonian

    It’s often overlook that if you can change — personally or professionally — over a the course of a year or a decade then you change atomically every single day. Making positive changes incrementally every day means we’re lessening our chance of failure in any walk of life over a sustained period.

    Great post. I wish you the best of luck!

    • Excellent point. Progress is amount forming habits that keep us productive every day.

  • jeffvlahos

    Thanks for sharing this. I’m already feeling the positive impact of implementing some of these ideas . Naturally, I adapted some of the details for me —I’ve found Trello to work well down to the sprint level for me, and don’t want to introduce a third system to my workflow. I use Trello for 1 week sprints and project-long (1-3 month) planning, just in separate boards. But your top-down approach is overall a really nice way to structure it all — work downwards from goals and aspirations, to weekly and daily action and implementation.

    • Awesome Jeff. Ya, Trello is great for so many different things. Lately I’ve been relying heavily on my hand-written notebook for daily, weekly, and monthly lists.

  • Hey Brian, thanks for taking the time to write this stuff out. I was just debating between using Things, Wunderlist, or Asana to organize some lofty goals I have for the next 6 months (which, ironically, is basically writing a book and marketing it while maintaining a SaaS app).

    Anyway, I recalled someone in a podcast recently mentioning that you had some thoughts about cascading to-do lists, and that phrase kept on in my head so I had to Google it and find this article 🙂

    I’m glad I did, what you have shared makes a lot of sense. I think I’ll give it a go with Trello and Clear. Thanks again!

  • A Jaron Middleton

    I love the article. I was so impressed with the content, I shared it with certain, specific people, whom I know of could benefits from it. You really reached into my head and formed with words what has been working for me for years… now I can share the thoughts with friends and family. You took my ideology to the next level, and in fact broke it down into such minute detail, anyone can apply this methodology to nearly ANY application they choose. Thanks again.

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  • Celiryn Noble

    Thanks a lot Brian! I’ll be applying this to my goals to be achieved this year! 🙂 I’ll be sharing this to my friends as well 🙂

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