There is a concept in engineering that made its way into the broader startup and business world.

Popularized by Martin Fowler back in 1999 this concept is called Re-Factoring.

In essence, refactoring is about continuous improvement of the code with goal to make it better, and more maintainable over time. You can think of it like an ongoing cleaning of your apartment, or like an artist iteratively improving a painting or a sculpture.

This concept of iterative improvement is important in many aspects of our lives because it helps us fight chaos or entropy.

In this post I want to talk about applying re-factoring to calendaring, so I will call this concept Re-Calendaring.

Before we get into the concept let’s talk about why having a schedule and managing your calendar is so important. Many of you read my post on how to calendar to help gain control over your personal, and professional life. If you didn’t read it yet, please go read it now.

Why Re-Calendar

Our lives are not static, nor is what we need to accomplish in our personal and professional lives. Even if we have a perfect calendar, as time goes by, small changes, activities, and tasks creep in and, suddenly – WE FEEL STRESSED !

Stress is caused by having too many tasks, and not enough time to do them.

The solution to the stress is not to just reduce your todos, but to become more efficient, and to be able to handle what you need to handle.

Re-calendar to make sure you are giving yourself a break, and a support system that all of us need – smart and disciplined allocation of time.

When to Re-Calendar

Obviously as soon as you are feeling stressed, you should think about Re-Calendaring.

  • Don’t have enough time for yourself ?
  • Not spending enough with your friends and family ?
  • A new recurring meeting popped up ?
  • Need more time for reading or writing ?

For all of these and many other things in your life you can Re-Calendar to reduce stress.

The beginning of the year is a perfect time to reflect, to plan ahead and to Re-Calendar.

Think about all things that didn’t work last year, think about all things you want to accomplish in the new year, and then change your schedule, and change your calendar.

The biggest gift you can give yourself is not yet another new year resolution that you won’t have time for. The biggest gift you can give yourself is a GIFT OF TIME.

How to Re-Calendar

We covered a lot of the strategies in the calendar post.

Think about which of these and other things are important to you and block the time for them.

  • Book time to exercise
  • Plan your time off
  • Schedule time with your family
  • Schedule time with friends
  • Think about how to best organize your week
  • Set aside time every week for Deep Work
  • Program in times to do emails
  • Create clarity around your weekly meetings
  • Plan your business travel
  • Figure out your weekly routines

Figuring out the priorities and fitting them all into a calendar is easier said than done.

Even for a productivity and calendar but like me this task is NOT easy.

It takes me 1/2 day or more to do, and for some of you this can take longer.

That is OKAY!

The good news is any planning is better than no planning, and whatever you will fit will make you less stressed.

Here is a system that worked for me.

Get all things you absolutely have to do on the calendar first – exercise, family time, meetings you can’t move.

Next plan time for Deep Work. This is critical, long blocks for getting your todos that require thinking and focus done.

Next, block the time for emails. Do it.

If it is not on the calendar it will be a cause of stress.

Lastly, work to fit everything else.

Can’t fit it all ? No problem. Decide what you can’t do or how you can move things around.

Your goal is to fit as much as you can of things you really need to do, and then to decide what you won’t fit in.

Iterate on your Re-Calendering

Once you are done, realize that you can never be done.

Keep iterating, and improving your calendar.

Treat your calendar like alive, ongoing canvas. Just like your life is not static, nor should be your calendar.

And for extra nerd points put a reminder on your calendar to Re-Calendar at least once a quarter.

I believe that Re-Calendaring and managing your calendar, is the single most important thing you can do to be productive, free of stress, and most importantly – to have a chance to be a happy human being.

Go ahead and do it, and see for yourself. And after you do, please come back here and comment on your best Re-Calendaring tips and scheduling hacks.

Productivity Startup Advice

Alex Iskold View All →

Engineer, Immigrant. Vegan. 3x Founder, Managing Partner @2048vc. Previously ran @techstars in NYC. I write #startuphacks: .

2 Comments Leave a comment

  1. Just Re-Calendored…Great idea Alex! Thank you. I also added lunch to my calendar. I can’t remember how many times I forgot to eat lunch because I was to busy…not a good way to stay healthy and sharp 🙂

    Liked by 1 person

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