If you have made it your goal to be a millionaire by the time you are 25, you might know that the secret is to make every choice based on that sole criteria. But at first, you might not have any good skills for making those choices. Will buying this stock be the better choice, or investing in this real estate? So at first, you make choices a little bit blindly until you get better at the process.

I’m finding a similar thing to be true about choosing happiness. It turns out there’s an extensive learning curve in figuring out how to make the choice that makes me more happy. I’m better at it now than I used to be. I’m picturing one particular night in my first year of college when I was pretty sure that “drinking this whole bottle of tequila” would totally make me happy. But then I tried it and got some pretty immediate feedback about that choice. Conclusion: Drinking a whole bottle of tequila will not make me happy. Important life lesson.

So I’ve come quite a way since then. I’ve experimented with the answer to the happiness question in millions of ways since the tequila experiment when I was 19 years old. But embarking on this new more conscious experiment, I find that I struggle with it a lot more than I expected. It seems like I hardly EVER know which of the available options will bring me more happiness.

I was talking with a friend lately about goal-setting, and what qualifies as a goal. He pointed out that a goal needs to have a specific end – a date on which it will be (or not be) accomplished. And it needs to be measurable, or you won’t have any way of assessing whether it was accomplished or not. If I am going to take on this year-long process in a serious way, I need to be able to measure whether I am actually happier at the end of the year than I was at the beginning.

I was thinking I could make this really easy by just drinking a whole bottle of tequila on New Year’s Eve, so that I would start the day on January 1st quantifiably unhappy. That would make it really easy to tell that I’m happier at the end of the year. But I decided against that route (yay for better decision-making abilities!) and decided to figure out how to check in daily about my level of happiness. I’m going to keep this really simple.

Every day, I’m just going to rate my overall happiness for that day on a scale of 1 to 10. A simple line graph at that end of the year should give me a clear picture of my progress. And in the meantime, it should help me assess feedback about my choices even if they are less obvious than the results of drinking a bottle of tequila. If choices I make increase or decrease my overall daily happiness, I’ll be able to see that in a more actionable way.