How to Set Goals and Achieve Them - The Optimal Goal System

How to Set Goals and Achieve Them - The Optimal Goal System

Starting the goal setting journey

A few months ago my roommate was complaining about how he wasn’t being as productive as he would have liked in his personal life. We both have busy jobs so he felt like he wasn’t spending enough time drawing/painting/doing all the miscellaneous things that misunderstood artists like him work on in their spare time.

I jokingly suggested that he should give me some money to keep himself motivated. He could set goals for himself and I would only return the money if he achieved those goals.

This commitment device system had been something I’ve wanted to try for a while but have never been able to set up. Surprisingly, convincing most people to willingly hand over money with absolutely nothing in return is more difficult than it seems.

Luckily, my roommate isn’t “most people” and he immediately agreed to the idea. He assumed that nothing is as powerful a motivator to getting stuff done as the threat of losing money.

And that’s how we started our journey of experimenting with different goal systems.


Experiment One: Month One

After getting the general agreement in place, the next step was to figure out the details: what goals, how to track those goals, how much money to put at stake, how long I get to make fun of my roommate once he loses his money, etc.

With lack of experience and naiveté on our side, we came to an agreement pretty quickly. My roommate listed out projects he wanted to set as goals for that month (X number of drawings, Y 3D models, Z design projects) and I would not only review my roommate’s output on a weekly basis, but would also determine whether he achieved his goals at the end of the month.

When it came to a discussion about how much money was at stake, the conversation went like this:


Like the RMS Titanic’s maiden voyage, the first month would not go down in history books as a rousing success. Near the end of the month, it was clear that my roommate wasn’t going to come close to achieving everything he initially laid out.

The biggest problem was that my roommate underestimated how much work he would have from his job and overestimated how productive he was going to be.

Also, while my roommate initially said he had a timeline in his head, he later admitted they were closer to “time suggestions,” so he quickly fell behind what he actually needed to get done.

I didn’t really want to take my roommate's money, so I looked for a way to extend the experiment...


Experiment One: Month Two

I offered my roommate another proposition: double or nothing. He would give me another $500 for a new set of goals for the following month. If he achieved the new set of goals he would get $1,000 back, otherwise, the entire $1,000 would be donated to the NRA to defend our God-given right to keep bunkers full of AK-47’s.

My roommate was a little bit skeptical at first. $500 was already a decent chunk of money and the prospect of losing another $500 was not the most appealing. However, I was finally able to convince my roommate to channel his inner gambling addict and double down on his “investment”.

Because of how the first month went, we were more careful about setting, tracking, and measuring the goals for month two.

Rather than arbitrarily setting goals, my roommate used the “SMART” system.

The SMART system is a framework to make sure your goals are as achievable as possible by ensuring each goal fits the following criteria:

S – Specific

M – Measurable

A – Achievable

R – Relevant

T – Time Bound

Read more here

My roommate also estimated how many free hours he had on a weekly basis and the number of hours each of his goals required. This ensured he was setting goals he had enough time to achieve.



Month two was better, but not perfect. My roommate hit his goals and his output from a quantity standpoint was significantly higher compared to previous months. My roommate said that the SMART system helped because he was more realistic about what he could accomplish every day.

By the end of the month he had gotten into the habit of blocking off time for himself to work on his personal projects.

However, the month was not without its problems.

Near the end of the month, the quality of my roommate’s work rapidly deteriorated because money became the primary driver of his output.

The number of free hours he originally had calculated didn’t factor in all the miscellaneous distractions that have a habit of inserting themselves into one’s life (e.g. work happy hours, friend birthday parties, late night froyo runs, etc.).

While my roommate was proud of his work, his desperate urge not to lose $1,000 took a lot of the fun out of what he was actually working on.

As the month ended, we agreed that although we gained some valuable insight from my roommate’s experience with this commitment device system, it was time to move onto a new system that didn’t involve him giving me more money.


Experiment Two: Month One

I didn’t participate in the first two months because the egotistical side of me was convinced that I was already good at setting and achieving my goals.

As 2016 came to a close and I saw how, despite some quality issues, my roommate’s output increased, I wondered if there wasn’t something to the idea of a formal goal setting system.

I was also influenced by just having finished Smarter, Faster, Better, by Charles Duhigg which talked about the trap of setting easy SMART goals that don’t impact our lives but make us feel good by allowing us to check things off our to-do list.

This is probably why I feel such a sense of accomplishment when I managed to put on pants today.

The author’s solution was to combine SMART goals with “stretch goals” - long-terms goals tied to what you want to accomplish in life. You first come up with a stretch goal that is not only deeply meaningful but also inherently challenging. You then create a plan around how to achieve that goal by setting SMART sub-goals that are tied to the overarching stretch goal.

This idea resonated with me, and my roommate was open to trying anything that didn’t involve either handing me more cash or supporting guns.

We both wrote down six to seven stretch goals we wanted to accomplish this year such as “build on my social life,” “improve my Chinese,” and “land on Mars” (one of these is a joke - I have no social life to build on). Afterwards we took those goals and broke them down into SMART sub-goals. This meant setting milestones for ourselves to achieve on a weekly/monthly basis such as “talk to X people at bars,” “watch Y Chinese movies,” or “build Z spaceships”.



At the end of month one, my roommate and I had made significant progress on some of our goals and no progress on other goals. When we reviewed our progress, however, we noticed that the goals we had made no progress were the ones most important to us. We had naturally gravitated toward the stretch goals that were easier and “fun-ner” to accomplish.

When faced with the decision on a typical Friday night to either work towards my “build on my social life” goal by going out to a bar to meet new people or work on my “start a company goal” by staring at a wall and sinking into a pit of frustration and despair, of course I was going to choose the option that allowed me to drown my inadequacies in alcohol and loud music.

The problem was that the “start a company” goal and all the important goals were the more difficult and frustrating to work on.


Experiment Two: Month Two

Realizing that as long as we had multiple goals, our attention would always be divided, my roommate and I took a closer look at our goals for the second month. We imagined ourselves in December and asked ourselves which goals we actually cared about completing.

I narrowed my 2017 goals down to two: start Late Night Froyo and start a business.



By focusing my efforts, I knew what I should be working on at all times. Although many of my previous stretch goals would not be accomplished, I was now only working on what was actually important to me.

It has now been another month and I have made real progress on my two goals. Late Night Froyo is finally live (aka what you are reading), and I have begun actual work on my business (more to come in a later article).


What We Learned

So what did we learn from our four-month experiments with goal systems and how to set goals? What should you take away if you skipped the first 2500+ words of this article?


1. Use a commitment device when starting a habit/project

Net, net, we would recommend that giving money to someone else to hold you accountable is a good way to start a project or habit. If you set concrete goals and create an actionable plan, the additional motivator of not wanting to lose money can ensure you stick to that plan.

However, money as a motivator is not a long-term solution and you should prepare yourself for the consequences of relying on money to influence your behavior such as decreased quality, more stress, and, of course, the fact that you may actually lose the money.


2. Setting stretch goals keeps yourself motivated for the long-term

After starting a project or habit (perhaps with a commitment device), stretch goals are necessary to keep you motivated for the long-term. Set goals that are not only challenging, but also tied to what you want to achieve in life.

However, don’t spend so much time trying to pick the perfect goal that you don’t actually get any work done. It's fine to change your stretch goal later on if you discover it isn’t as fulfilling or as linked to your life goals as you would like.

While you shouldn’t plan to fail at your stretch goals, you should still be prepared to do so. True stretch goals are audacious which means there is a chance they won’t be completed. After getting over feeling like an Asian child bringing home a B on his report card, you will discover that you still made tremendous progress that wouldn’t have been possible without the stretch goal in place.


3. Set Concrete/SMART Goals

Setting stretch goals is good and all, but you also need a plan to achieve them. Create sub-goals that follow the SMART system and a timeline for when to achieve each sub-goal.

Map out how many hours you think each sub-goal will take to make sure that achieving every sub-goal is possible.


4. Reduce your number of stretch goals

Every additional stretch goal takes time away from all the other stretch goals that you have set. Imagine yourself at the end of the year– if you could accomplish one goal from your list, which one would it be? Is it writing that book you’ve always wanted? Is it running that marathon? Is it learning that new skill?

You might discover that there are only a few goals that are actually worth pursuing and that watching all 10 seasons of Friends back-to-back while only consuming cold pizza isn't one of them.


Closing Thoughts

My roommate and I are far from having everything figured out. I’m sure things will change as we continue to try different goal systems. Hopefully this article will at least help you set your own goals and avoid the mistakes we made.

I generally think it’s too easy to fall in the trap of researching productivity hacks (goal setting systems, motivational articles, productivity systems) without actually doing the necessary work. I understand the irony in writing this article.

Thus, if there is one takeaway from this article or any article I write about how to be more productive/creative/motivated, it’s this:

Spend less time thinking/reading about how to be productive and actually BE productive.


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