This article is an old favorite from 2013. Catch up on my latest stuff here.
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…
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).
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:
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:
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:
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:
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.