I'm a huge fan of making goals.  I have monthly goals, yearly goals, five-year and ten-year goals, and "Lifetime Goals."  It's not easy to make, track, and work towards these — it's a skill that's honed over time and is slightly different for everyone.

For this post, I'll go over Five Things That I Do To Make and Achieve Goals.  Let me know if you do any of these!

One: Be Quantitative.

If your goal is "learn how to surf" or "read more" it is extremely likely you will not complete this goal.  

There is an old comedy crowd-work routine that goes something like this:

Comedian: Hey, what do you do for work?
Audience Member: (Shy, Caught-of-Guard, or Unemployed): Oh, nothing...
Comedian: Yeah?  How do you know when you're done?

The gist is that if you do something qualitative (that is, without something to measure how you're doing) then how will you know when you're finished?  How will you know if you're good enough at surfing, have read enough, or anything else that is qualitatively defined?

It is extremely important to have a metric: a number (most of the time) which tells you how to measure how well you are doing at your goal.

A goal you can measure how well you're doing (most of the time using numbers) is called a Quantitative Goal.  Here's some examples of qualitative and their associated quantitative goals:


  • Learn to surf
  • Read more books
  • Write more
  • Save money for a sweet moped


  • Go to 6 surfing classes and spend 100 hours surfing
  • Read 20 fiction and 10 nonfiction books
  • Write 500 words each day
  • Save $500 each month for a sweet moped

You'll note that with the quantitative goals there is almost a plan built in of exactly what you need to do.  Most of these can be broken down into smaller tasks and done at a reasonable pace.  For the qualitative goals there's no instructions on where to go from here: learn to surf, sure, but how do I know if I've learned?  When can I check this off my to-do list?

Tl;DR: Quantitative goals are better.

Two: Time-box.

In the last section we made quantitative goals.  Great, but say we have the reading goal to read 20 fiction and 10 nonfiction books — how long should this take us?  If we have zero urgency to get started, we might pick up one book (excited to start the goal!) and then maybe the second book we wait a bit until life is less hectic (it never is) and then the goal peters out until you've read exactly one book and half of another.  

Procrastination is easy when the thing you're doing isn't urgent.

In addition to being quantitative then, you'll want to say when should this be done by?  This is a bit trickier than making the goal quantitative and the gravest mistakes I see people making is making the time-box either much too tight or much too loose.  Let's look at the following two goals:

Read 20 fiction books and 10 nonfiction books in 2 weeks.
Read 20 fiction books and 10 nonfiction books in 2 years.

The first will never get done — the time-box is much too strict and this can discourage the goal-maker.  It might cause them to abandon the goal entirely.  The second is just as dangerous: it gives too much time, there is no urgency.  For goals like this, sometimes it is better to chunk things up into time-frames you are comfortable with.  For example,

Read two fiction and one nonfiction book per month.

This is a bit more ambitious, but it does seem more manageable.

TL;DR: Time-box your goals.

Three: Break It Up.

People have different ways of approaching their quantitative, time-boxed goals.  But if you try to eat the whole goal-sandwich all at once you might choke.  We need to break it up a bit.  This part is usually the how part of the goal: how are we going to get our goal done?

In the previous section we saw that we could break up our reading goal into monthly pieces.  This is manageable, but we might want to go a bit further: exactly what are we going to read?  Do we have a queue of books?  Should we keep track of things?  

My personal goal-making usually includes this kind of micromanagement, though it isn't necessary for all goals.  I tend to use something like Trello.  For example, here are my book and movie lists for 2020:

Book and movie list for 2020 in Trello

Note that these are part of much larger reading and movie-watching goals.  For movie-watching, for example, I am working through a large number of movies that I have in a spreadsheet — the way I chose to chop them up was, for each year, to do the top 10 longest movies I still had, and all of the movies older than a certain date (hence the "Old" tag on these; I also have a "Long" tag).  

Breaking this up allowed me to know exactly what I was going to be doing and approximately when.

As another example, if your goal is to "lose weight", we can evolve this and break it up as follows:

  1. (Original Goal) Lose weight
  2. (Quantitative Goal) Lose 15lbs.
  3. (Quant + Time-boxed Goal) Lose 1.5lbs per month.
  4. (Q+T Broken Up Goal) Lose 1.5lbs per month by going to Yoga MWF, Cardio Th, and using MyFitnessPal to eat fewer than my recommended calorie intake each day.

Seems like a lot but this is nearly a full plan already: if you stick to it, you will lose that weight.  The problem, of course, is sticking to it, which we'll get to next.

TL;DR: Make a plan that breaks up your goal into bite-sized pieces that you can do.  It should give you an explicit idea of what needs to be done, and approximately when.

Four: Don't Break the Chain.

This method, popularized but not created by Jerry Seinfeld, is simple:

  1. Pick the goal.
  2. Mark the days off that you work towards the goal.
  3. Use the chain of marked off days as a motivator.

This is surprisingly effective; it's the reason that apps have "You've logged your XYZ for seven days straight!" or "You've got a 20 day crossword streak!"  You don't want to break that chain and lose that.  The same psychology is applied to goals.

There are days (sick days?  tired days?  stress days?  etc.) where you might not want to work on your goal.  That's fine.  If you've time-boxed correctly and you aren't too ambitious in your breaking-it-up, you should be able to take a break sometimes — but this is also dangerous territory for goals.

There are some goal-makers who don't recommend taking sick days or break days or mental health days; this is fairly strict and I don't recommend it.  Having said that, there is a less conservative approach here: even on sick days or break days, do something related to the goal so that you don't break the chain.

  • Can't work out because you're sick?  Do a bit of stretching at home for a few minutes.
  • Can't write 500 words because you're too tired?  Write a paragraph, at least.
  • Can't go running because it's too cold?  Jog in place for 10 minutes.

Doing this "goal-lite" activity will be good for two reasons: in some cases, you will be able to do more than you think you can (this is the same reason that people getting into running will be told "if you're not going to run, at least put your shoes on" as this will often be the foot-in-the-door they need to get moving), and, in addition, you will not be breaking the chain.  You may not have written 500 words each day, but you have written each day.

TL;DR, don't break the chain.

Five: Keep yourself accountable.

Okay, this one is tough.  

  • Some of us can keep ourselves accountable without anyone else: we want to do something, so we do it.
  • Some of us need our friends to keep us accountable — and the less likely the friend is to give you a break, the better!
  • Some of us need to post things on social media to keep us accountable.

Ultimately, this comes down to the person.  I've tried all of these (and a few others) and there are some that work better for me but work much worse for my friends.  I can't give much advise except to try them out.  If you do, be serious about it: don't let your friend give you much slack and get social media reminders to work at your goal.

TL;DR, find a way to make yourself accountable.

That's it.  That's how I do my goals.  I've got a pretty good track record but sometimes I don't quite make it — and that's okay, so long as I know I've tried.  I'll write at some point about waterfalling (or abandoning!) goals but just know that if you know you've tried your best at it and it just didn't work, that's okay.

Let's do two examples to solidify these ideas.

Example 1: Learn Improv.

  1. (Original) Learn Improv.
  2. (Quant) Take eight improv classes and perform at two student shows.
  3. (Quant + Time-box) Take these specific eight improv classes (look up the course online and sign up, which is automatically time-boxed) and perform in two student shows: one no later than a week after four classes, one no later than a week from the last class.
  4. (Q+T Broken Up) (The one above is fairly broken up.)
  5. (Q+T+BU Accountable) Take these specific eight improv classes and perform in two student shows: one no later than a week after four classes, one no later than a week from the last class. Invite my friends Billy-Joe and Carly-Anne to the two student shows.

Notice that the first goal is a nice "oh, wouldn't it be cool if I learned improv?" but the final iteration is almost a grocery list of what exactly needs to be done.

Example 2: Learn Guitar.

  1. (Original) Learn guitar.
  2. (Quant) Learn four full songs on guitar.
  3. (Quant + Time-box) Learn one song per month on guitar.
  4. (Q+T Broken Up) Learn one song per month on guitar.  Make sure that each month adds at least one new chord.  (The goal-maker could, at this point, look up and list songs here.)
  5. (Q+T+BU Accountable) Learn one song per month on guitar.  Make sure that each month adds at least one new chord.  Play the song at that Bagel Shop Open Mic Night (making sure to tell everyone you're learning guitar!) no later than one week after I learn it.

Learning guitar is a fairly common goal that I've seen a number of people start and almost all of them fail.  I'm guilty of this for piano (which I'll talk about in another post...).  The first goal is vague and a "wouldn't it be nice?" goal.  The last goal is a checklist that will get you learning and performing.

Notice also that, as we went through these goals, sometimes we increased the amount of work we needed to do.  For example, we went from four songs to twelve songs in the learn guitar part.  This is because we realized that one song every three months is too loose a time-box: we took on more work accidentally, but because it will make us better we don't mind it too much.

What are some goals you've had that you've had great success with?  Could you refine them more?  Do you have any tricks you use for goal-making?  Let me know!