How to Upgrade Your To-Do List For Ultimate Productivity

I’m not a planner guy. I’ve tried all the tricks and downloaded all the apps and have never been able to stick with the any of the tools. Here’s a laundry list of the different strategies I’ve employed:

  • I’ve written all my tasks out for the week.
  • I’ve written all my tasks out for the day.
  • I’ve written none of my tasks out and followed my heart’s desires (by far the worst decision).
  • I’ve mimicked coworkers who draw little boxes down a left hand column with various tasks down the right, checking off the boxes as they go.
  • I have a Thinkboard in my office where I write my to-do list, making me overwhelmed about everything on my plate
  • I’ve tried writing down the three tasks that are most important to complete before anything else is attended to. Then, task one takes days to finish, so I move on to the next one telling myself I’ll get back to it, which I do, weeks later.
  • I’ve tried Evernote
  • I’ve tried Wunderlist
  • I’ve tried Todoist
  • I’ve tried Any.do
  • I’ve tried Don’t Forget the Milk
  • I’ve tried Errands To-Do List

I constantly searched for new methods to magically cure my stressed and anxious self, but nothing worked. Nothing helped me “be” accomplished. This was maddening. I kept asking myself, “why can’t I stick to one of the most simple productivity hacks known to man?”

I began looking at the to-do list spectrum. On this spectrum I’ve identified two endpoints. On one end I see the “my list is in my head” crowd. On the other, I see the color coordinated, sticky-note obsessed, Wunderlist promoting, every second is planned organization czar that would be aghast to find others operate in such a whimsical manner.

Then I asked myself, “where do I fit?” Well, as I have finally discovered, it really doesn’t matter.

No matter how organized I am with my tasks, it’s much ado about nothing if I don’t start from the right place.

It’s easy to “feel” accomplished when if I have 1,000 tasks lined up for the week and I’ve knocked them all out in rapid fashion. What’s not so easy is actually “being” accomplished. And, there is an enormous difference.

Feeling accomplished is easy to come by. Write a list of activities you know for a fact you will get done today, check off each one as you go, and review your success with pride at the end of the day. And then ask yourself, "So what? What did I do today that was any different than the past other than the fact I wrote stuff down?"

Unfortunately, the answer is "nothing." Writing a to-do list without anything deeper attached to it is nothing more than a waste of time.

If I looked at my morning routine and decided to write it out every single day, knowing full and well I'm not actually changing anything, I would call myself crazy. The habits I've built around this routine have never been the result of a steadfast to-do list.

I don't hear my alarm go off at four in the morning and think "what does my to-do list say? Ah, yes, I better get up and get these boxes checked off." No, when my alarm goes off, I spring to action because I know my "why."

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There is no greater force in the universe than the one eternal motivator pushing you forward until the end of days.

When you find your "why," then you can start developing a brand new relationship with that to-do list in the form of an action plan. Your action plan originates from your why, creating a to-do list that touches your heart in a whole new way.

With this action plan, you're going to work backwards. By the time you have everything in place, every action item you lay out for yourself will be dripping with significance.

1. What is the ultimate milestone you want to reach?

You can approach this question from two different angles. One is the S.M.A.R.T. approach where goals must be specific, measurable, attainable, realistic, and time-based. The other is the D.U.M.B. approach where goals are dream-driven, uplifting, method friendly, and behavior-driven.

I've used both philosophies in my practice. In general, if I have a goal that has a numerical focus, I create a S.M.A.R.T. goal. If I have a goal that is more ideological, I go with D.U.M.B. goals. Some people are team S.M.A.R.T. through and through and the same can be said for D.U.M.B. idolizers, but I like to stay open on this one. Whatever is most attractive to you, go for it full speed ahead

2. What resources are available to you or that you can easily seek out that will help you achieve your milestone?

Every single one of us needs help in achieving our dreams. Period. If you get to the top of your mountain and have nobody to bask in the glory with, you’re in for a sad and lonely celebration. Humans need connection. Don’t deny this biological reality.

So, who and what will help you achieve your milestone? Once you’ve identified these resources, you’ll be able to attach them to the actions you’ll be taking along the way.

3. Create your action steps

With your milestone and resources out in the open, it’s time to start working backwards. From the day you see yourself achieving your milestone to now, you need to take the next few hours or even days, mapping out the path you will take to get there.

The best way for me to show this in action is to share an action plan of my own, which focused on the S.M.A.R.T. philosophy.

By April 21st, 2018, I want to have 2,532 people subscribed to the Your Pen Paul newsletter (are you signed up?).

Starting today and using a 1% daily growth strategy, I've set up benchmarks throughout the year for when I should gain 10, 100, 200, 500, 750, 1,000, and 2,000 followers:

  • Day 14 = 10 followers
  • Day 92 = 100 followers
  • Day 139 = 200 followers
  • Day 214 = 500 followers
  • Day 251 = 750 followers
  • Day 278 = 1,000 followers
  • Day 337 = 2,000 followers
  • Day 365 = 2,532 followers

In between these milestones, I've created 4–5 general action items to keep me focused on reaching the milestone in front of me.

Some of these goals include social media participation, attempting one out-of-the-box idea between each milestone, and optimizing my website for maximum user engagement (i.e. increase opt-ins). Then, and only then, do I create my weekly and daily to-do lists. I keep my milestones at the beginning of all my lists to remind myself of the goal I’m pursuing.

Action plans are yet another reminder that most of the time when you’re trying to fulfill ambitious goals, you can’t take shortcuts or “hack” your way through it. By identifying your why and taking the three steps highlighted above, you will be well on your way to making the impossible happen.


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