How to handle unstructured time (when you finally get it)

Busy.  That’s one word that seems to always follow us around.  How are you doing?  “Busy.”  What have you been up to?  “Man, I’ve been really busy.”  How come I don’t hear from you anymore?  “Sorry, I’ve just been really busy.”

If you are in a standard full-time job, being busy is pretty much a guarantee.  If you factor an hour each way for your commute, getting there early or staying late (which let’s say adds another hour), getting ready in the morning (one more hour) and let’s assume you get something approximating seven hours of sleep a night, this leaves a maximum of five hours in your weekday to do things like, you know, eat.  This time goes by quickly.

Weekends can be a different story.  While it’s possible to find yourself with so many errands to do that the weekends fly by, it’s just as possible that you may be left feeling oddly unsure of what to do with yourself.  And while being too busy can be stressful, not being busy enough can cause just as much stress.

Withdrawal symptoms

Having your schedule dictated to you can be habit forming.  Your capacity for dictating your own life’s path becomes slightly atrophied, and you’re left not knowing what to do, aimless in the lack of direction.  It can feel like you’re going through withdrawal.  I’ve often find myself getting to the weekend and wondering what to do with myself.  Spending all week waiting to get some much-desired time off, and then finding it and not knowing what to do with myself is almost painful, like a dull ache.

And yet dealing with this feeling is vital if we are to ever take control of our own income, which I believe is a necessary component of rejecting a system that keeps you from achieving your dreams.  When you are self-employed, there aren’t two days of empty space ahead of you; there’s a whole life of self-direction.  That’s a lot of afternoons to fill.

Self-employment makes it harder

As someone who has spent his entire working life under the direction of others, I think that lack of structure is surprisingly one of the most terrifying aspects of self-employment.  It might even be more terrifying than not having enough money to survive (maybe).  Because when you have a whole day spread out in front of you and no clear idea what to do with it, the minutes become like hours, and the anxiety can eventually rise like a panic or sink into a depression.  (I recently wrote about how someone else handled this situation, with some similar observations.)

But I’ve been doing more work for myself recently, and thus I spent at least one day a week focused on my own work as if it was “my real job”.  I’m still working on getting better at this, so I’d really appreciate any advice you have in the comments below.  But here are some things I’ve learned that have worked for me.

• Plan out a “todo” list in advance.  I can’t stress this enough.  When Saturday rolls around, don’t sit down and go “now what should I do?”  Instead, keeping a rolling tally of things that you want to accomplish.  I use Evernote for this, although there are many other tools that work just as well (I’m quite partial to a small notepad and pen).  As I think of something that I want to do, I record it immediately.  I’m quite serious about this; after a few mishaps where I’ve forgotten something after only a few minutes, I’ve actually run over to my computer to prevent a future mishap.
• Curate a todo list that’s just a bit too large to accomplish in the timeframe.  When I have a day to plan out, I usually come up with approximately two days worth of work.  This is not a desire to push my productivity to the max, or even a perverse need to feel unaccomplished, but more that there are some things that I’m just not going to feel like doing in the moment.  Having a larger list enables me to pick and choose, while at the same time, not getting me so overwhelmed by my overarching todo list (which is actually quite massive)
• Get things done in the morning.  I’m personally on the fence about whether we’re more able to accomplish things when we first wake up or not.  I’ve done some of my greatest work at 1AM.  That said, I’m a firm believer in business before pleasure.  Once you get the work done, your reward can be to do all those other things that are enjoyable, not just productive.  Besides, who wants to be hanging out and doing something awesome, only to have to cut it short and head out to get work done?
• It’s not all about productivity.  Having a little extra time in your day is actually a blessing.  Don’t substitute being busy for being busy.  Go walk up a hill and admire the view.  Get back in touch with someone you haven’t talked with.  Get the right amount of sleep you need for once.  Slow down.

Know what you’re working toward

In order to make any of the above tips meaningful, a prerequisite is to have something you’re working toward.  I skipped over this at first, but it’s actually the most important item on this list.  It is super important to have something in mind that you’re excited about.  I’m partial to creative projects (composing songs, writing letters, drawing pictures) but any projects will do (even cleaning the house, which believe it or not some people do get excited about).

Here is a (highly abbreviated) list of some relevant things I’m working on:

• Short-term:  Write two blog posts a week for this site (Monday and Thursday are my target publish dates, with none missed so far).
• Medium-term:  Develop more client relationships for my financial coaching business, write an e-book for readers of this site.
• Long-term:  Write a (physical) book, speak at a TED/TEDx conference, tour.

Having a good idea of some small-, medium-, and long-term projects that you would like to work on is key, but if you don’t have this, that’s okay.  After all, you’re probably used to spending most of your time doing what other people tell you to.  It’s understandable that your needs might get pushed aside.  I recommend spending a good deal of time brainstorming on this spread out over a period of time.  Don’t sit at your table with a blank page for three hours and think, “what do I want to accomplish?”  That’s inviting anxiety.  Instead, take a little bit of time here and there to sit down (all electronics off!) and just think.  Short bits of time determining your own work will help ensure that when the next unstructured time comes to you, you’ll be ready for it.

But enough about me.  How do you handle your unstructured time?  I’m especially interested to hear from those who are self-employed to hear how you tackle this.