The Art of Setting Personal Annual Goals

People tend to be a bit skeptical about setting a personal annual goal. Plans often don’t align with your reality and we’ve all experienced the frustration of setting a goal and giving up a few months into the year, unintentionally hurting your self-esteem.

But, if we don’t have a goal and a plan, we don’t really know whether we are headed in the right direction nor whether we’re making a progress towards a goal or not.

I deeply believe one of the core purpose of personal goal setting is not only to achieve them, but to build up your confidence and increase your self-esteem.

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For the past 14 years straight, I’ve created a ritual of setting a personal annual goal on the 1st week of January and track throughout the year whether if I’m getting close to those goals or not. It started out as a simple blog post with a list of items that I wanted to aim that year, organized into a few categories.

Then I realized the ones that were vague were not getting done or had to make a subjective judgment at the end of the year that felt kind of cheating. So, started to apply a few rules of goal setting and then fine tuning them over time.

I draft a personal annual plan into 4 categories, with 3-5 goals per category, broken down quarterly. The goals tend to be stretch goals, but not always as I’ll explain below. In hindsight, this evolved into something similar to company OKRs. But let me list some of the rules I’ve used that turned out to be pretty helpful when setting your own personal goals for the year.

Lesson 1. Make your Goals “SAM”

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There are frameworks like “SMART” goals, but I use a simpler SAM framework: Specific, Actionable, and Measurable. For someone to actually accomplish the goals and track progress throughout the year, it’s really effective making them SAM.

First, the goals need to be specific! Pretty straight forward, right? In reality, we’ve all set our new year resolutions before: “I’m going to eat healthy this year” or “I’m going to loose weight” or “I’m going to travel more” or “I’m going to cut down drinking.”

Sounds familiar? Probably after a quarter or so, these “goals” tend to feel more vague, and you feel like you’ve tried already, probably made some effort and possibly a bit of progress, but don’t really feel like you’re on the right path and eventually loose interest in them after the first few months.

Now, if we turn these goals into “I’m going to run an average of 3 hours weekly and 1 hour of weight training” or “I’m going to eat only half of whatever that comes out from a restaurant” or “I’m only going to drink 2 glasses of wine and 1 bottle of beer and no other types of alcohol in a week” makes it more interesting and doable.

Second, they need to be actionable! When you are new to annual planning, the level of goals will vary quite a bit, because we’re not yet used to breaking down the goals in to similar size chunks. This requires practice.

For example, “I want to take better care of those around me this year” or “I’m going to be a better partner” can be directionally good, but it’s highly likely to fail as a goal. What’s worse is that there’s no real way to tell whether you’ve actually succeeded or failed.

How about, “I’m going to send 3 of my close friends and 5 colleagues a hand-written cards on their birthdays and buy them 1 cup of tea per person a month” or “I’m going to go on a 3 full-day out-of-town trip a quarter with my partner” can make these goals more vivid and actionable.

Third, make them measurable! You can’t measure everything in life in the most accurate way possible, but as you can see from the previous examples, it’s easier to get the sense of the momentum and progress by making them measurable in an objective way.

Instead of setting “I want to write more this year,” changing the goal to “I will write 2 blog posts a month” makes it much better goal for you to track and raise your motivation as you make further progress. It’s also easier to track your overall pace, as you can easily track whether you are behind the annual goal or getting ahead.

Lesson 2. Minimize the Management Overhead

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When you first set goals, you immediately jump into action and make progress on your first week. Like bookkeeping or writing diaries, you do a good job in the beginning, but the progress winds down after the first few months, if not weeks. 

If you run too hard and tight at the beginning, your management overhead (e.g. effort of recording, time, attention, etc.) becomes an overbearing burden, so you will likely to drop the goal the moment you make a mistake or fail to keep up with your initial pace.

So instead of pressuring yourself to execute and record everything on a daily basis, try to make it easier for you to track with wider cadence. A simple recommendation is to track smaller items weekly and bigger items monthly or quarterly. 

For example, unless you’ve built a strong habit of reading books regularly, there are periods in a month or a quarter where you really have a good momentum of reading books, then there are periods where you simply don’t want to open a book. So set quarterly goals for this, so you’re not pressuring yourself to perform constantly everyday, and bake in enough flexibility to pick things back up when you can, and at the same time, you kind of know at the back of your head that it’s one of the goals you want to hit this quarter.

So if you make it easier to keep a record and also give wide enough cadence and timeline for you to perform them, your likelihood of stopping midway will decrease and your subconsciousness will eventually pick things up and steer you towards the direction you’ve set.

Lesson 3. Add Buffers to Your Goals

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Some of you may remember creating a 24-hour pie-chart schedule when you were a child, breaking down each hour and minute, placing activities in those slots. Wake up at 8am, eat breakfast for 30 minutes, exercise for 15 minutes, study for 30 minutes, go out and play with friend for 1 hour, come back, etc. You get the idea.

There are 2 problems to this approach:

  1. You’ve put too much will into the plan, but your energy, attention, and focus will fluctuate throughout the day and the week.
  2. If any one of the items fails in your plan, rest of the items get impacted physically or emotionally.

For example, some people will put into their plan “go to gym 3 times a week” or “learn 2 new musical instruments” or “learn to speak Spanish!” as their goals. Ambitious, but most of these goals come to a screeching halt after a few months, because you didn’t think about coming up to the surface to breathe a little.

Again, the goal setting is there to help you focus, create wins, and build greater confidence in yourself overtime. So don’t set yourself up for failure. Instead of starting with a high chance of demotivation from missing your goals, which leads into a vicious cycle of lower self-esteem, set up goals with good buffer to help you achieve them.

Instead of “go to the gym 3 times a week,” change them into “go to the gym on the average of 2 times a week, once a week at a minimum and only up to 4 times and not a day more.” So if you’ve went 3 times in a week, you already feel like you are ahead of the curve, so you might want to keep that streak going, but in some week when you simply don’t lack the energy to go, you can slow down a bit, but as long as you go once, you’ve still achieved your goal. Of course, there’s no material health benefit to going once a week, but you can save your morale and be able to pick it back up next week, instead of dropping your entire goal for the year and beating yourself up for it. The psychology of goal setting matters a lot.

So when you set your goals, add some buffer so that you can recover from your losses quickly and get back on track.

Lesson 4. Reward Yourself for All the Reasons

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This is a lot more important than you might think. Find all kinds of reasons to reward yourself. Not self-indulgence or spending money beyond your means, but in a way that’s meaningful to you and is kind of a fun experience.

“I’ve read 4 books this month, so I’m going to treat myself to a really nice restaurant” or “I’ve hit my sales quota by 200% for this quarter, so I’m going to get a fun watch to remind myself that 2019 was a great year for me” or “Our daughter was born this year and we’re going to plant a strong tree, so that our daughter can visit this tree when she turns 10!” 

It may feel a bit cheesy to find a reason to reward yourself, but psychologically has strong positive effects. You are creating an association between making progress through delayed gratification with hard work and something that brings you joy and creating a fond memory. These association done multiple times over many years will create and reinforce anticipation and discipline, allowing you to stay focused on your goals throughout the year.

My personal favorite has been treating myself to a nice tasting menu with a glass of good wine. Figure out what works for you and find multiple reasons throughout the year to reward yourself.

Lesson 5. Create a Portfolio of Goals

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Every annual plan should have a set of key focus goals. A key focus goal is something that you know will be quite challenging, but worthwhile, that you really want to give a full swing at. There’s even a high chance that you won’t achieve this goal this year. You do need these goals to make great progress in life.

But should you fail, it can and will hurt your morale quite a bit. Remember, the purpose of personal goal setting is to increase confidence and self-esteem. So you want to create a portfolio of goals that surrounds these key focus goals. These smaller portfolio goals can be something that are not quite as risky or big, but will be smaller, achievable, yet meaningful goals. They could be the ‘lower’ hanging fruits for you to achieve quickly and repeatedly. 

Place these goals across your categories, so that you can achieve small wins that will create momentum to boost yourself into achieving the key focus goals and bigger wins. You are optimizing for higher morale and using that to swing for the fences.

It’s an Iterative Journey 

By applying these 5 lessons on our personal annual plan, we need to iterate to build a virtuous cycle of goal setting and making meaningful progress in life.

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It’s hard to get the personal annual plans right the first time, so set your goals in a “SAM” way, execute and fine tune your methodology each quarter and every year. As you continue to iterate, you will learn something new about yourself and get better with goal setting and achieving them.

We’re just around the corner from year 2020, so may all your wishes goals come true!

* Update with 2 videos:

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