Poor planning will kill your success in an instant

September 30, 2019

Next to Interruptions, I can't think of another Time Thief that will undermine your success more than poor planning OR no planning.

I'm all for spontaneity and don't think you need to be scheduled to the second, although I'm also not opposed to that degree of granularity IF it serves you.

But basing your success on a wing and a prayer may only be useful if you're an actual angel. For the rest of us, a concise and clear plan of action is probably a better bet if you want to get something done, on time and on budget.


So much of good time management and enhanced productivity is based on simple math. So if you have a story that says you're creative and suck at math, I'm calling bullsh*t.

If you can buy a pack of gum at 7-11, you can do the kind of math I'm talking about.

Let's start with the biggest number you'll be dealing with168 hours.

That's the total number of hours we all get in a week.

No one gets 172 because they’re extra good and no one gets only 160 because they are bad.

Math is an equal opportunity employer.

HOW you spend those 168 hours determines how and what you'll get done in that week.


Do you know about Vilfredo Pareto? He was a 19th C. economist. He discovered that 20% of the population in Italy owned 80% of the land there. He then started to see this 80/20 split play itself out in other occurrences. Kind of like the VW Bug or Volvo driving game once you are looking for something, you start to see it everywhere.

Imagine how much more you could get done if you simply doubled the work that is creating 80% of your revenue? It would be a game changer. Click To Tweet

So while you may not know Pareto by name, you probably have heard of the 80/20 rule. That's his.

This is so important when it comes to planning because we want to be focused on the work that yields the greatest result with the least effort.

Imagine how much more you could get done if you simply doubled the work that is creating 80% of your revenue? It would be a game changer.


The first 20 years of my professional life were spent in the theater. I understood a few metrics (like butts in seats) but the idea of measuring things intimidated me.

1) I didn't know what to include in a budget because

2) There didn't seem to ever be enough consistent money to bother with a budget

and when it came to time, I worked until I was finished whatever that meant. Or exhausted. Which was easier to define than finished.

Can you relate?

On the money side, I spent what I could when I could and relied on credit to close any gaps. And there were a lot of gaps.

My method of managing money as a nonprofit administrator was similar to cry poverty, spend as little as possible and then try to do the math after everything was over.

As I mentioned above, one metric that was easy to evaluate was butts in seats but only as far as how many people bought a ticket, how many were comped, and how much we grossed. Beyond that, it was hard to figure out if a show was actually profitable.

When I started running a business and working with other professionals who have worked for real companies, they started asking me questions about ROI and KPI's and it all just sounded like gibberish to me.

I was also a bit skeptical that THEY knew how to measure these things, because even though they threw around these terms, there wasn't a lot of data they were sharing and nothing sets off my bullshit meter more than vagueness when dealing with numbers.

Vagueness around narrative is not my favorite but its understandable. Words have various interpretations and context is important.

2+2 consistently equals four. There is no narrative you can slap on that to fudge the corners and make 2+2 = 3.75 or 4.5.

Since bringing on a COO and getting better colleagues meaning colleagues who:

A) Know how to do their work

B) Know how to measure their work

C) Know how to report on their measurements

its become easier to track things.

And because I want to grow my business, we've got to be looking at measurements.

When I was working by myself, it was easy to just put my head down and do what I know how to do which is network, hustle for clients, and service clients.

Then rinse and repeat.

That is not a model for growth. The only option there is work more and charge more.

But you're still in the dollars for hours game.

The metrics of that are super easy to track how many hours did I work, how much money did I make, how much money did I spend making that much money.

Once we started to measure things, especially time, it became clear where I need to be spending mine and what I need to be delegating.

And then the fun begins. I'm being facetious.

What you learn when you start to measure your time is what you do well and quickly, what you don't do well and don't do quickly, what you like doing even though you don't do it quickly, and what you don't like doing even if you can do it quickly.

This was tremendously eye-opening and still frustrates me today. I want to be completely honest about that.

There are still things that I love to do that I should not be doing.

And even though I can tell myself a story, or perhaps one of my 200 Lies, about the intangible benefits of doing it and how that improves the quality of my life, there ought to be a way to measure that improvement or impact as well, or its just bullshit.


To-Do Lists are to your tasks what your closet is to your clothes you don't get up each morning and put on all of your garments, so you have no business dragging your to-do list around with you either.

Your best practice should be going to your to-do list and looking for tasks that you will take on during the day and by extension, the week and the month then scheduling discrete appointments with yourself to accomplish those tasks. At that point, you can put the list away again until you need it.

If you have the bad habit of scribbling notes to yourself all day on random pieces of paper or Post-its but never transferring them anywhere, Id like to break you of that.

You're creating clutter and distracting yourself and these notes can become potential landmines that will completely blow up any ability you have to get things done in a timely and efficient way.

We use Asana in our office as task management software. So rather than writing a bunch of to-do items and THEN transferring them into an app, we enter them directly into Asana and assign them to a team member and add a due date all at the same time whenever we’re in a team meeting or even working 1 to 1, we have Asana open and will be posting new tasks and projects online in real time.

I can’t tell you how much of a game changer this has been for us well, I guess I just did.

If I am in a meeting away from my computer or phone, since Asana has a mobile app as well, and I do write a note on a piece of paper, the next thing I do when I get back to the office is to either dictate it or type it into Asana and then recycle the piece of paper.


1) Change Your Expectations.

The first thing you should do regarding your to-do lists a mindset adjustment. If you have any thoughts or intentions around crossing everything off your to-do list, you got a faulty mindset. You will never get to to-do list zero. Not going to happen.

There will always be new things to do and it is likely that you will die with recycling in the bin to take to the curb and dry cleaning needing to be picked up from the cleaners.

So my best advice is to surrender this notion because it’s only going to make you upset and you’re never going to win.

2) Be Thorough.

I'm all for a thorough mind dump. Set yourself up someplace quiet and dictate or write down all of the things that are on your mind that are needing to be done.

Don’t censor yourself or discount anything by saying it’s too small or inconsequential the purpose is to get everything out of your head and onto a piece of paper whether that paper is analog or digital.

Then you can take these tasks or items and start to group them into similar or like categories.

I call these Time Buckets.

The visual just helps me to think of a container I’m dropping similar items into. It works for me. If it doesn’t work for you, you can call them categories.

Here is a list of Time Buckets that you can download and use to create your own categories.

The key here is for them to be specific enough to segregate your tasks from each other, but not so specific that you would only ever have one item in a bucket.

You may end up with only one item in a bucket after you've completed some tasks, but when you’re beginning this process, it’s not a good idea to be so hyper-specific that only one task would belong in a specific bucket.

3) Be Singular.

If you are someone who is constantly writing to-do lists and starting lists over and over and over again, please stop now.

You are creating your own clutter and confusion.

There’s something wrong with your system if it requires you to keep writing the same things over and over again, under the guise of not forgetting something important.

The way to not forget something that is important is to write it down once and then schedule an appointment with yourself to complete it. Scribbling it over and over again on anything that you can find to write on is not going to get you any closer to getting it finished.

If you currently have many versions of the same list, I suggest you set a timer for 30 to 45 minutes, and then merge your lists together eliminating all duplicates.

This will do two things for you.

It will give you a sense of accomplishment as you merge the list together and eliminate the duplicates, you will get the satisfaction of crossing things off your list sometimes multiple times.

The other thing this will do for you is quiet your mind if you’ve been at all anxious or agitated when you think of the many many things you have to do.

This exercise will demonstrate to you that you probably have fewer things to do than you imagined, or clarify for you that you do have a ton of things to do and at least now you can begin to methodically attack them.

4) Be Specific.

By putting your tasks into your various time buckets, you are now able to more accurately prioritize.

If you have struggled in the past to successfully prioritize, it could be that you were pitting two competing tasks against each other that were both high priorities but in completely different categories or buckets.

For example, getting your annual physical and reviewing your blood work with your doctor may be a #1 top priority in your medical time bucket.

Finishing the second quarter report on the Jones project may be a #1 top priority in your work bucket.

If you have these two tasks sitting next to each other on the same to-do list, it could be easy to get overwhelmed or confused about which one you should do first and when.

If they are in their own discrete buckets, it becomes much easier to prioritize them when comparing them to less important but similar tasks.


When it comes to planning, by all means keep a to-do listjust don’t confuse it with an actual time management tool like a calendar or a timer.

Remember also to just keep one list per time bucket or category.

If you are not using task management software like Asana, which we use (or Trello, etc.), you should be scheduling regular appointments with yourself to harvest tasks from your to-do list and scheduling them manually on your calendar.

Hopefully you can see how the digital version of this process saves a ton of time, but if youre old school and like paper and pen, I’m not going to try to take that away from you.

Beyond tasks, when it comes to planning, you want to be able to measure these things:

1) How long it takes you to do something consistently

2) What your time is worth to the company

3) How long it would take anyone with a comparable skill set to do something consistently

4) What the minimum and maximum charge for doing that Task would be by someone else

5) What do you do better than anyone else in the company that adds quantifiable value to the business

6) What tasks only you can do and are those tasks directly or indirectly tied to revenue

7) What tasks are you performing that are scalable, meaning:

A) Either you can batch them so you do multiple similar tasks at the same time which reduces the overall cost in time and probably materials to complete similar tasks


B) What can you do once and either service multiple clients simultaneously or get multiple uses out of the completed task

These are the two primary ways to grow and scale.

And you can only do this if you are measuring time and money. If this sounds like something you're ready to take on or improve upon, check out our Your Next Big Thing Coaching Program. We have an entire module built to teach you HOW to plan and stick with it.

Declutter Your Life Podcast by Andrew Mellen. Available on iTunes!