Online Task Managers Asana

One of the coolest things about being a productivity coach is that I’ve listened to thousands of people tell me their stories.

And with rare exceptions, they tell me the same story: they’re working harder than they ever have in their life, but still feel like they are “losing” their weeks. If life were a battle, they feel like they’re on the losing side. 

Often the best they can do is play good defense, keeping the enemy at bay and trying to maintain their position for as long as possible. Any victories are quickly eclipsed by the sense that they are nevertheless slowly losing the war.

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I’ve been there myself. In July of 2010, I was in the prime of my career. I had just been promoted, and was now one of the youngest senior equity analysts on Wall Street. I was doing regular television appearances on financial news networks like Fox Business, CNBC, and Bloomberg TV. 

But instead of riding high, I was flat on my back (literally) recovering in a hospital bed in New York’s Upper West Side. This was my second surgery, battling the runaway effects of an intense but mysterious autoimmune disorder. It had been negatively affecting my life for a long time, and now it was affecting my work, too. 

My doctors were puzzled how someone so young could suddenly start seeing widespread system failure. As happens so often in the case of autoimmune diseases, the doctors couldn’t agree on a diagnosis. And the treatments they had tried weren’t working.

Finally, one doctor was clever enough to ask me, How many hours are you working, by the way?

“Never less than 80 hours a week — sometimes as many as 100!” I bragged. Like many professionals in New York, I wasn’t ashamed of that fact — it was a point of personal pride!

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The work culture in New York City is brutal. They celebrate “Hustle Culture” – a euphemism for simply brute-forcing your way to success by working around the clock. And I was a true believer. I worked nights and weekends throughout my twenties. Even as I ballooned up in weight. Even as my relationships failed. I knew it would eventually all pay off, with interest. 

I was wrong. It didn’t pay off. It landed me in the hospital, facing the risk of an early death.

Within a month of my doctor telling me to work fewer hours, I was working less than 40 hours a week. I had halved my working hours in less than 30 days. My symptoms subsided completely inside of two months, and I was feeling better than ever. And it wasn’t just me who was seeing the results. A couple months after that, I got a huge promotion. My health crisis became the catalyst that forced me to discover a way to work far fewer hours, yet experience more success, happiness, and longevity. 

What I’m sharing with you in this article is a big part of how I turned my productivity around. It’s a framework for solving the biggest problem in productivity today — handling the strain of the modern lifestyle with ease… AND without ever burning out. It’s also an operating system for how to plan and execute a great week. I call it the Winning The Week Formula

To be clear — I’m not promising you that once you start using this framework, everything will start magically going your way. Instead, I’m promising you a way to move the big ball forward despite the obstacles; masterfully meet your commitments, and consistently stay on offense instead of defense.  

The Winning The Week Formula

What’s more important to winning your week — the preparation, or the execution? 

Abe Lincoln was very opinionated on this point. He thought that preparation was worth twice as much as execution:  

“Give me six hours to chop down a tree and I will spend the first four sharpening the axe.” 

~Abraham Lincoln

He wasn’t alone in this conviction. Some of the wisest leaders and thinkers in history have told us repeatedly that planning is the key to winning.

“If you fail to plan, you are planning to fail.” 

~Benjamin Franklin, Founding Father, author, statesman, postmaster general, diplomat and inventor

“The general who wins the battle makes many calculations in his temple before the battle is fought. The general who loses makes but few calculations beforehand.” 

~Sun Tzu, famous Chinese military strategist, general, and author of The Art of War

“Plans are nothing. Planning is everything.” 

~Dwight D. Eisenhower, five-star general and former United States President

“Luck is what happens when preparation meets opportunity.”

~Seneca, Stoic philosopher, statesman and orator

So here’s the least controversial statement anyone could make about productivity: planning your week ahead of time is the key to winning your week

You might be saying “duh” right now. It certainly feels like an obvious statement. When I asked over 5,000 professionals about this, 94% said they consider planning ahead to be “key” to productivity success. So it sure seems like this is common knowledge, right? 

But when I followed up and asked those same 5,000 people, “Have you conducted a planning session (ahead of time) for the past four weeks?” only 6% replied yes. When I went on to define what I consider to be adequate planning, that number then dropped to lower than 1%

So despite how obvious this statement seems, it’s extremely rare to find someone who actually plans out their week on any consistent basis. There’s a Texas-sized gap between our beliefs and our behaviors here!

How can we be aware that planning is the key to winning, and yet less than 1% of us are doing it? 

A big part of it is mental. Planning sounds so neutral, but in reality a good planning session is quite stress inducing, forcing you to look at things you’d really rather avoid. That generates resistance from the limbic system (also known as your “lizard brain”). This can cause a downward spiral so potent, it can cause us to self-sabotage before we even start. 

It’s just as important to realize, though, that people just don’t know how to plan properly. It’s not something we are taught in school, the workplace, or anywhere else in life. Despite how incredibly important planning is, we’re all left on our own to figure it out. And since it’s highly counterintuitive, most of us get it wrong. These planning “fails” further reinforce our negative associations with the practice. 

Allow me to introduce the Winning The Week Formula. Like the scientific method, it’s easy to understand, and it helps you move past your biases to see the world as it really is. It’s a structured method for looking at your week and gaming out all the relevant pathways to win, in thirty minutes or less. It takes the form of a simple checklist, designed to walk you through the most important components of planning your week. But there’s a lot happening underneath the surface.

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Review the past week

The Winning The Week Method starts with a five minute review of the past week. Over the course of five minutes, you’ll review what you accomplished last week, and what you did not.

This will culminate in a “lesson” you learned from the past week that you want to take into the coming week.

This is important for a couple of reasons. 

First, this simple practice creates a feedback loop – allowing you to continually return to the beginning, except with slightly better information than you had the last time you went through the loop. Done properly, your week can become an opportunity to try new things, evaluate your wins and losses, and fine tune.

This kind of strategy results in small incremental improvements—but very consistently. While that may seem too small to make a difference, just a 1% improvement each week rapidly becomes exceptional progress within a year. 

Secondly, this practice is good for your soul! We naturally tend to focus on the negative—the things that didn’t get done, or the frustrations that haunt us. But even in a bad week, one tends to get a lot of things done!

A simple five minute review will mirror back to you all of your great efforts this past week, and daylight some wins you may have overlooked. That’s going to make you feel good, offering you a small boost as you get ready to plan your coming week. 

Set your priority

With learnings in hand, you’re now ready to start planning the upcoming week. That starts with deciding your number one priority for the week. If you have a goal for the month, you’ll want to nest your weekly goal inside of that larger goal. That ensures that you stay at (or ahead of) pace to hit that big goal. 

The biggest mistake I see my clients make in their planning is choosing the wrong priority, or choosing multiple priorities instead of one. They try to work faster during the week to be more efficient, but eventually realize they’re just spinning their wheels.

    Efficiency is swimming well. Effectiveness is swimming in the right direction. I’d like both, but if I had to choose, I’d choose the latter every time. 

    Being efficient but not being effective is an absurd and sad way to live. It’s like getting swept out to sea and then swimming in the wrong direction to try to get back to land. You could be Michael Phelps, but if you’re not swimming towards land, it’s just a matter of time before your strength gives out. Efficiency is swimming well. Effectiveness is swimming in the right direction. I’d like both, but if I had to choose, I’d choose the latter every time. 

    So at the start of the Winning The Week Method you ask the question: are you swimming in the right direction? If you’re not, you run the risk of exhausting yourself and being very unhappy with the outcome. 

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      Review your time supply (AKA your calendar)

      Next, you’ll take five minutes to review your time supply. This is how much time you have available in your week to take action, and it’s represented by your calendar.

      Most folks think they know what a calendar represents, but they are only seeing a small part of the picture. Your calendar isn’t only for reminding you about dentist appointments and meetings. It’s a tool that represents your entire supply of time. As such, you have to make sure that you keep accurate track of how much inventory you have available. 

      If you owned a business selling flour, you would need to keep accurate records of how much flour you had in inventory, how much had already been purchased, and how much was still available. Similarly, your life is your business. You sell your time to others or you consume it yourself. As such, you need to keep an accurate inventory of the time that is already claimed, the time you still have available, and a little extra supply on hand for emergencies. Most people would nod their heads and agree with this approach. 

      The problem is that, in the real world, people hate looking at their calendars… because it only shows them things they don’t want to see: the places they have to be (that they don’t want to go), the things they have to do (that they don’t want to do), and the people they have to meet (who they don’t want to meet). The resulting dread means that most people will glance at their calendar only when absolutely necessary, then run away as fast as possible.

      But avoiding your calendar means your time inventory isn’t accurate, which is a disaster waiting to happen! It could be the volleyball game you have to take your kids to (that you forgot about). Or the meeting that got changed from 9 am to 12 noon, conflicting with another meeting.

      These small errors are buried all over your calendar, like landmines waiting to explode at the worst possible time

      The goal in this stage of the Winning The Week Formula is to take an accurate inventory of all of your existing time commitments, so that you can trust your calendar more than you trust your own intuition.

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      Review your time demand (AKA your to-do list)

      Next, you’ll take five minutes to review your time demand, also known as your to-do list. This is the opposite side of the ledger from your time supply.

      In this step, you’re scrubbing your to-do list and reviewing your work and life commitments to make sure you have an accurate picture of the demands on your time for the coming week.

      Most folks think they know what a to-do list represents, but again, they are only seeing part of the picture. Your to-do list isn’t just for dumping and storing tasks. It’s a tool that captures (and reflects back to you) all of the things you want to do with your time, as well as the things other people would like you to do for them. And since your time is highly limited, the demand for time always outstrips the supply. 

      In the flour business example, I talked about keeping accurate inventory. But you would also need to keep track of all your potential buyers and bids for your inventory. Otherwise, you couldn’t possibly get the best price for your flour.

      In your real life, each task on your to-do list is a bid for your time. Since your time is incredibly finite, and not everyone’s bid can be accepted, it’s vitally important that you allocate your time carefully.  

      The problem is that people hate looking at their to-do list even more than they hate looking at their calendar! Because looking at the mountain of demands on your time and sensing how little time you actually have makes you feel overwhelmed.  The resulting dread means that most people avoid opening their to-do list, and when they do, they gravitate towards the easiest, least overwhelming tasks while ignoring the rest.

      But that means the demands on your time quickly become overgrown and overcrowded. And the more overgrown it becomes, the more resistance you have to facing it.

      Most people opt for the easy way out: just doing the tasks blowing up right in front of their face. That’s fine for playing defense, but that strategy will never get you back on offense. You can’t consistently win the week that way. 

      The goal in this stage of the Winning The Week Formula is to whittle down your to-do list, so that you’re only considering the highest-yielding bids for your time.

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        Match your time demand to time supply

        Now that both sides of your ledger are trustworthy, you can match time supply and time demand together. In this step, you’ll take 10 minutes to “calendarize” your to-do list, meaning that you’ll mark off time in your calendar to get each task done. 

        This step is both extremely easy to understand, and insanely difficult to do!

        Easy, because all you have to do is simply take a task, and mark off time on your calendar to do that task. So if you have a task called, “Write draft of Chapter 2,” then on your calendar you would create a 4 hour block titled, “Write draft of Chapter 2.” Easy enough to understand.

        But this is also quite difficult, because it feels like a heart-wrenching emotional negotiation while it’s happening! It’s easy for me to say, “Ok, now choose what will happen this week… and what won’t happen.”

        But we both know it’s not that simple. It can feel like Sophie’s Choice…being presented with impossible and heart-wrenching tradeoffs. 

        News flash: people hate making choices! 

        Like the children’s game, this is when the music stops and there aren’t enough seats for everyone. Your wishful thinking hits the hard wall of reality at full speed. Most people avoid this step for that reason; they may check their calendar, and they may check their to-do list, but they never reconcile the two.

        That means you did an excellent job planning, but it’s all for nothing. Reconciling time supply and time demand is where the rubber meets the road. It’s where you get traction and forward movement. A Ferrari hovering two inches off the ground could have a lot of horsepower, but it will be going nowhere, spinning its wheels in mid-air, until its tires actually make contact with the pavement. Only then will it zoom forward.

        The goal in this final stage of the Winning The Week Formula is to make the real choices so that your time supply and time demand match.

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        To win your week, you need to develop a habit of planning your week in advance. This is something everyone knows they should be doing, but almost no one does. And it’s something our predecessors have been trying to tell us to do for at least a millenia. 

        Although it doesn’t come naturally, it can be quickly cultivated with the right approach, and the right methodology. 

        Five simple elements are all you need for a fast and tremendously successful pre-planning process: 

        1. Review your past week for lessons learned
        2. Get clarity on what’s really important (versus what seems important)
        3. Take accurate inventory of your supply of time
        4. Get an accurate picture of the demands (bids) for your time
        5. Match time supply to time demand 

        Once you’ve completed these, you will have done a better weekly preplanning than 99% of people.

        Demir & Carey Bentley

        Demir and Carey Bentley are the founders of Lifehack Method, WSJ & USA Today bestselling authors, and executive productivity coaches. They've helped thousands of people avoid burnout and soar to their highest level of productivity. Read more about them here.