The Ultimate Guide to Time Management (Part 1): Add Structure to Your Day

by: Matt McCormick

Advanced warning: when you get to the end of this post, you’ll find a small and helpful homework assignment. If you don’t struggle with managing your time, don’t do it. In fact, you should probably stop reading now because this blog post doesn’t apply to you. For the other 90% of the population, this first article in a three-part series on time management will get you on the track to truly being more productive.

If you’re an entrepreneur like me, you either: feel crushed right now by the mountain of tasks demanding your attention, have felt that way in the past, will be feeling that way in the near future…or all three. Accounting, marketing, meetings, payroll, hiring and managing employees, finding quality vendors, paying bills…all of this and I haven’t even started talking about the day-to-day work of building a product/service, taking care of customers, or dealing with the myriad of fires popping up all the time. And perhaps at some point you’d like to have a life outside of work?

Feeling stressed now? Don’t. Take a deep breath and listen as I tell you a little secret: You will never get through your entire to-do list and that’s okay.

The first rule of time management is understanding that it’s not about getting everything done. It’s figuring out how to get more done with the time you have, and how to get the right things done.

I had a roommate when I lived in Seattle who owned his own company and worked out of our house. He’d get up at 6 am and still be at his desk when I was going to bed at 11 pm. At any time during the day you could hear him on the phone with customers or vendors. Outside of normal business hours he’d be preparing reports for customers, pulling together quotes, reading and studying industry news, and generally working non-stop.

Then one day, he came down from his office in tears (seriously, in tears). He looked at me and said, “Matt, I can’t do this anymore. I just looked at my to-do list – I’ve got over 200 things I need to do! I don’t know how I’m going to get it all done.” He was completely and totally overwhelmed.

At the time, I was just starting out with my own business and didn’t have a good answer for him. I hadn’t experienced this yet (though I would later). We sat down and chatted about it for a while and he said something that struck me:  “In the time it takes me to get any task done, at least one or two more things crop up. That means I have an infinite number of things to do.”

The longer I’m in business the more I’ve realized the truth of that last statement. There are an infinite number of things to do and you can’t do them all. It’s impossible. That’s life. You can’t change that fact, so it’s time to stop beating yourself up about how long your to-do list is. Instead, take that energy and focus on two things:

  1. Getting more done in the future than you’re getting done now.
  2. Getting the right things done.

Baby Steps

This is going to be the first of three posts on time management. Before you begin, you need to keep the following phrase in mind: “Baby Steps.” You can’t read this post, wake up tomorrow, and magically become twice as productive. Like anything in life, it takes time and practice. That’s the reason for the homework at the end of this post. You’ll have three simple tasks to do. As you master those three things, you can start working on other aspects of your time management skills. Remember: baby steps.

Structuring Your Day

If you’re going to be productive, the first thing you have to do is create structure in your life. Routine, if you will. I know it sounds bizarre because you became an entrepreneur to break away from the mundane. You love your freedom to work when and how you choose. But, if you don’t bring structure to your work day, you’ll end up working whichever 16 hours a day you want. Wouldn’t you rather get the same amount of work done in 8 hours?

Routine

I am not going to tell you how to organize your day. I have no idea what you do or how you work best. You might be the kind of person that works better from a noisy coffee shop than a quiet home office. Maybe you have to pick the kids up from school every other afternoon. Perhaps you meet friends on Thursday afternoons at 4pm for a beer. I have no idea what your life situation is, or how or where you prefer to work. But what I can tell you is if you don’t put structure around your work day, you will be unproductive.

That said, there is one thing that is critical in establishing a routine: Get up at the same time every day. Getting out of bed is the foundation of your day – it’s where it all starts. Getting up at all sorts of random times will result in you being all sorts of randomly unproductive.

The Tools

You need tools to keep track of what you have to do. Trying to keep everything sorted in your head will result in failure and lead to massive stress. Putting a time commitment in a calendar or writing down a task frees your mind. You don’t have to stress about remembering it. It’s simultaneously effective and liberating.

Note the use of “time commitment” instead of “appointment.” An “appointment” is a time you have agreed to meet someone else. A “time commitment” is time you’ve set aside for yourself to do something.

There are tons of tools out there for managing time, and the list below is not meant to be definitive or comprehensive. These are the tools I use and they work great for me.

  • Google Calendar. There are a ton of calendar programs out there (iCal, Outlook, etc). It really doesn’t matter which one you use, as long as it syncs in the cloud and is accessible from your phone. All appointments should be entered in your calendar as well as any recurring tasks you need to do (like paying bills, reviewing your analytics, etc).
  • Email. My company uses Google Apps hosted email, but any cloud based email will do. Email can be a time suck but it’s also a great tool to track to-do items. Anything in your inbox should be acted on, delegated, or put in a to-do list immediately. You shouldn’t let your inbox get over 20 items, or else you will start forgetting things and become overwhelmed.
  • followupthen.com. I discovered this website 3 months ago and it has changed my life. I used to manage my inbox by moving emails into separate folders. But out-of-site, out-of-mind. Now I forward an email to [specific-time]@followupthen.com and it emails me back at the specific time. For example, if I email one of my store managers to investigate a new cleaning solution, I also forward the email to 1week@followupthen.com. Exactly one week later I get that email sent back to me as a reminder to follow-up with my store manager to see how things went. Very slick, and a great way to keep your inbox empty without having to worry about forgetting something.
  • Basecamp from 37signals. It’s the most intuitive and user-friendly listing software I’ve ever used. (It does cost $20/month but has a free 60-day trial that doesn’t require a credit card.) Previously, I used a Google Docs spreadsheet and it was okay, but it was a pain to move items between lists or reorder things. Plus, the Google Docs mobile version was horrible. I’ve also tried Trello. It’s pretty cool, but each task and list just takes up too much screen real estate, so it’s hard to efficiently manage my longer lists. I’ve also tried iPhone Notes, Evernote, and at least 4 or 5 other task management softwares. None of them were nearly as good as Basecamp for creating, tracking, and editing lists on multiple devices.

One really quick note about all of the above tools:  I get no compensation of any kind from any of the companies listed in this post except JCD Repair – the company I own.

Lists

Keeping track of everything you have to do or want to do is important, even if you know you may never get some of those things done. It wil give you peace of mind, and if you want your productivity to increase, you must have everything written down on a list.

But not just one list.

One giant list of everything will end up looking like my old Seattle roommate’s list with hundreds of to-do items. This will not help you. It will only serve as a daily reminder of how you’ll never get it all done. It’s also impossible to efficiently manage a list like that.

Like structuring your day, it’s hard to say exactly which lists you’ll need. A contract software developer is going to have different lists than a PR professional or the CEO of a fast growing startup. I recommend having one list for each of your major responsibilities, a “quick list” to add things on the fly, a list for tasks to accomplish this week, and another for tasks to do today.

Here’s an example using my Basecamp lists:

  • Stuff to do today
  • Stuff to do this week
  • Marketing tasks
  • Blog post ideas
  • Website features to add
  • Website bugs
  • Things to discuss with my biz partner
  • Requests from Employees
  • Miscellaneous

Here’s a simple example of the lists at work. A few days ago, one of our employees suggested that we get a really fine artist’s paint brush for clearing glass off of iPad screens (fixing a broken iPad screen results in tiny shards of glass everywhere). It was a great idea, but I was in the midst of five other things when he said it. So, I popped over to the Basecamp tab on my browser, and entered “fine paint brush for iPad cleaning” at the end of the miscellaneous list. That took 10 seconds. Two days later I was looking at the list and moved that item to my “Stuff to do today” list. Later that day, I picked one up at a local hardware store.

Plan Your Day

No matter who you are or what you do, there are two lists you should have: “Stuff to Do This Week” and “Stuff to Do Today”. I’ve been using the “Stuff to Do Today” list for about a year, but it never quite clicked until about two months ago when I added the “Stuff to Do This Week” list. I’m not exaggerating when I say this one additional list increased my productivity by about 30%, and my peace of mind by 100%.

One of the biggest problems with being self-employed and having a growing business is paralysis of choice. Where to start? What to do next?

Many people end up sort of starting one task before sort of starting another, and then they get an email, and then something urgent happens, and then they start a third task only to realize they need to get back to the first task, but then a customer calls… You get the picture. It’s so easy for the other 200 tasks you have to distract you from the top one you’re trying to get done.

So at the start of every day, I list the things I want to accomplish that day. There are three rules to this “Stuff to Do Today” list:

  1. You can only list three items.
  2. At least one item must be a significant task. The other two can be anything.
  3. You must realistically believe you can get all three items done in a day.

Does this mean you should only do three things a day? No. What it means is there are three tasks you have committed to doing today. You should almost certainly do other things as well. The point of the daily list is to keep you focused and help you to refocus when you get off track. I’ve learned from experience that if you put more than three things on this list, you’ll routinely fall short because of those other tasks that pop up during the day.

Rule #2 exists to keep you from cheating. I could easily put 3 10-minute tasks on my list but then I wouldn’t be accomplishing something significant every day. And if you can accomplish just one significant thing every day, you will be well on your way to great success.

Lastly, it’s important to make sure you can get through your list every day. If you routinely fail to do this, the list itself becomes irrelevant. Do you have a task on your list that is probably going to take a week (like a major coding task)? Break it into five separate tasks where each one can be accomplished in a single day. Then for five days in a row, you’ll have one of those tasks on your list.

Plan Your Week

This has been a breakthrough discovery for me. Until a couple months ago, I struggled to be consistently productive. I would have a great day followed by a horrible day. But then, I started spending 30 minutes on Sunday night or Monday morning listing what I wanted to accomplish for the week. This rid me of my paralysis of choice. It’s been amazing!

Why?

Because right there, every day of the week, I can start out by looking at what I still have left to do this week. I take the most important thing from that list and put it as the number one item on my daily to-do list. Then, I might grab another item from the weekly list,  something off one of my other to-do lists, or maybe something completely new that popped up in the past day or two.

Whatever I do, I know for a fact that every morning I’m going to have one important item on my daily to-do list and that is going to get done. It provides so much focus and satisfaction that I can no longer imagine managing my work time without it.

Like the daily to-do list, there are rules:

  1. You need to create this list at the beginning of the week. I recommend Sunday night or Monday morning.
  2. A minimum of 7 – but no more than 10 – significant items should be on the list.
  3. Again, be realistic.

A quick note about rule #2. Your weekly list shouldonly contain significant items. Something like, “fax employee info to accountant” is not significant. Something like, “setup interviews with 4 possible new hires” is significant.

On the flip side, your weekly items should be individual tasks and not massive projects. “Redesign and implement a new website” is most likely a major project. “Do an initial rough draft of a new home page” would be an example of a significant task.

Should I only do what’s on my daily/weekly lists?

No.

The lists are road maps and not mandates. Sometimes detours pop-up and have to be taken. For example, if I get an email saying that our website has gone down, everything else I’m doing gets dropped immediately and I investigate and fix the problem; having a working website is more important than any other work I could be doing. I didn’t plan for it, but it needs to be done.

In addition, you will get emails or phone calls that require attention. I’m going to talk at length about this in Part 2, but know that sometimes you have to deal with legitimate and important interruptions.

What the daily and weekly lists do is get you back on track quickly. They keep you from running down a rabbit hole because you can always ask, “Is this other thing I’m being asked to do more important than what’s on my list? Does this other thing have to be done right now?” If the answer to either of those questions is “No,” then you shouldn’t be doing the other thing. You should be sticking to your list.

In addition, your daily to-do list does not and should not contain three items from your weekly list. You’ll notice I said your daily to-do list should be three items long and your weekly to-do list should be about 7-10 items per week. Assuming you work 5 days a week, your daily list would get you through 15 items per week. Your weekly list represents about 60% of that work. In other words, you should get 40% more tasks done than what’s on your weekly list.

This is important to realize because it gives you a chance to proactively get the most important tasks done in any given week, but still save time to take care of random things that pop up or, more importantly, spend some time on tasks that you really enjoy doing.

Be Realistic and Forgiving

I keep saying “Be realistic” because it’s so important. If you aren’t realistic in your expectations, you will not only drive yourself to an early grave with stress, but you’ll be more unproductive while doing it. Here is why biting off more than you can chew is bad:

  1. You’ll feel like crap for not getting more done.
  2. This horrible feeling will turn into mild depression, which will make you even more unproductive.
  3. You will get discouraged and start to give up.
  4. It’s important that you have a life outside of work, and setting unreasonably high standards will prohibit that.

Consider this. You wake up Monday morning and feel ambitious. You add five tasks to your daily to-do list. At the end of the day, you completed four of them. You fell short. You might feel like a failure, and you shouldn’t. Getting four real things done in a day is an accomplishment. Had you put three items on your list and gotten four done, you’d feel like a hero. Remember that you don’t have to stop your work day after finishing three items. It means the rest of your day is gravy and you can work on whatever you want. How awesome is that?

You also need to be forgiving of yourself when you don’t accomplish your goals for a day or week. It happens to all of us. I got married this past summer, and I can tell you that I routinely fell short on some days and weeks because of commitments outside of work. When that happens, tell yourself it’s okay and that it happens to everyone (because it does). Then wake up the next morning, make your list of the three most important things, and go after them with extra gusto.

Homework

One week. That’s all you’ll need to see whether I’m full of BS or actually know what I’m talking about. There are three things I’d like to ask you to do right now (yes, right now). I promise these will be quick to do. The catch is you have to follow-through for one entire week. At the end of a week, you’ll either find yourself more productive or you can save time by not reading my next two posts.

Do these things right now. Not the never realized “later”. Right now:

  1. Pick a time you’ll get up every work day for the next week. Set your phone alarm to that time. Get up every day when it goes off. No snoozing.
  2. Go to Basecamp and sign up for a free, 60-day trial. This only takes a minute, won’t cost you anything, and you don’t need a credit card. (I get nothing from 37signals for this – I just think it’s the best tool for the job.)
  3. Create a Basecamp project called “My To-do Lists”. Then create two lists: “Stuff to Do Today” and “Stuff to Do This Week.” Fill in the weekly list with 7-10 things you’ll accomplish in the next week and fill in the daily to-do list with the three things you’ll do on your next full workday.

I would never ask anyone to do something I’m not willing to do, so I’m going to do these three things as well. The last two are easy for me – I already have the lists. But item #1 is going to be hard. I am not a morning person. I hate getting out of bed, and often snooze for 30-40 minutes. But for this next week, I will be right there with all of you getting up as soon as my alarm goes off.

Start now! It’ll pay off in dividends down the road.

About the author Matt McCormick @Technori
Matt McCormick is founder and owner of JCD Repair - an iPhone, iPod, & iPad repair store with locations in Chicago, Seattle, and Madison, WI. In previous lives, he's run a one-man company building websites for small businesses, been a developer at Microsoft, lectured on operating systems at the University of Wisconsin-Madison, and spent three years selling robotics equipment. He has a Bachelor's in Mechanical Engineering and a Master's in Computer Science. He also reads too many business books and is frequently up for a beer.

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