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162 | The Four Tendencies And FI With Gretchen Rubin

Although finding the path to FI can be exciting, it can be frustrating to have difficulty communicating this vision to your family and friends. Gretchen Rubin, author of The Happiness Project, sheds some light on the Four Tendencies or people and how to communicate with each tendency.

Gretchen’s Story

Gretchen is an Upholder by nature. She walked away from a Supreme Court clerk position to become a successful writer and made her dream of writing come true.

Along the way, she uncovered the Four Tendencies that can help you understand your own and other people’s outlooks on life better.

The Four Tendencies

Gretchen developed the Four Tendencies later in her writing career with her book, The Four TendenciesBefore writing this book, she had written others including Better Than Beforewhich led her into the territory of habits.

Once she started thinking about habits, she wanted to understand the reasons why different people thought about the concepts of habits differently. Some people enjoyed New Year’s resolutions, others thought they were too arbitrary. Some people could regularly exercise with a group but couldn’t get out the door by themselves.

Listen: Atomic Habits

After some careful digging, Rubin uncovered the Four Tendencies. She built this framework to help understand how people approach things differently.

The Four Tendencies, which is a personality framework that explains how people come to these situations from different perspectives, they have different challenges…If you understand how someone has a different perspective or a different kind of challenge, you can set things up in a way where it will work for both of you because a lot of times, we just assume everybody sees the world [the way] we do.

A lot of times, we assume that other people see the world in the same way that we do. When they don’t and we are baffled that they have a different perspective. You can use the framework to better understand where someone else is coming from and work towards a solution that you can both accept.

Otherwise, you’ll just “throw spaghetti at the wall” until something sticks or works. However, this trial and error approach can be a very frustrating process.

The quiz that Rubin created is very specific. Unlike a broad personality test, it is not trying to paint an entire picture of your personality. Instead, it is only trying to uncover a small slice. Even though it doesn’t show you the whole picture, it is a significant aspect.

Resource: The Four Tendencies Quiz

Uncovering The Four Tendencies

Building a way to look at people’s personalities is very difficult. In fact, Rubin claims it was the most difficult mental exercise of her life. And she served as a Supreme Court clerk!

After thinking about it in many different ways, she suddenly realized that there are two types of expectations. Inner and outer expectations.

There are two kinds of expectations people fall into or experience. Outer expectations like a work deadline or a request from a friend; and then, inner expectations, which is my own desire to keep a New Year’s resolution. My own desire to write a novel in my free time. My own desire to get back to playing guitar. As I started thinking about it, I realized that people experience outer and inner expectations differently.

When she boiled it down to inner and outer expectations, it created only four possibilities for different tendencies. After all, you can only accept or resist inner or outer expectations.

Of course, there is some grey area because the tendencies are a spectrum. Additionally, the book dives into the nuanced details to explain the concept. Once you understand the tendencies, it can be very easy to pick out other people from your circle.

Your Values

In addition to your tendencies, a lot of what you do depends on your values. For example, a Rebel might seem inconsiderate. However, if they place a high value on being good citizens or doing things out of love, then they may be very helpful.

Listen: The Why of FI

Breaking Down The Four Tendencies

Let’s take a closer look at each of the tendencies below.


An Upholder readily meets both inner and outer expectations. They typically meet work deadlines or keep New Year’s resolutions without any fuss.

Discipline is my freedom.

Brad and Gretchen both fall into this category.


This individual questions all expectations. They will do something if they think it makes sense. They will not do something if they think it is arbitrary or unjust. It needs to meet their inner standard.

I’ll comply if you convince me why.


An Obliger needs accountability. They care about outer expectations but not about inner expectations. If they want to meet inner expectations, then they need to create outer accountability. For example, if they want to read more then they should join a book club.

You can count on me and I’m counting on you to count on me.

This is the most common tendency. If you need help with accountability, then check out the Better app.


A Rebel resists all expectations, both outer and inner. They want to do what they want to do in their own way in their own time. They value the freedom to do something in their own way and they often love a challenge. Typically, they don’t want to tell themselves what to do. For example, they are unlikely to sign up for an exercise class on a Saturday.

You can’t make me and neither can I.

This is the least common tendency.

Understanding The Tendencies

Each tendency has its strengths and weaknesses. When you understand your own tendency, then you can lean into your strong points. You’ll be able to set up a system that works for you. For example, if you are a Rebel that hates doing busy work, then set up everything on autopay.

Additionally, you may find that you have more empathy for people with other tendencies.

Although we each have a dominant tendency, there is a definite overlap. It is likely that you tip one way or another on the most connected tendencies.

FI Conversations

If you want to share FI with your family but they don’t share your enthusiasm, it can be frustrating. However, you can use the tendencies to at least start a conversation about Financial Independence.


If you are working with an Obliger, then create some outer accountability. Set up an appointment with a financial advisor with the consequence of an appointment fee. Put it on the calendar and they will likely show up. Also, talk about the idea of others depending on this conversation. After all, money can be a way to help others that might be in trouble down the line. An Obliger will want to be the helping hand.


Rebels don’t like to be told what to do. However, they put a high value on freedom and choice. Financial Independence is the ultimate freedom. Show them the possibilities of breaking free from your financial chains because money will give them the ability to make decisions more freely.


A Questioner is more data-driven. If you show them the numbers of Financial Independence, they will likely get on board easily.


Finally, an Upholder is the easiest person to start talking to. Just put it on your calendar for a time when they are well-rested. They will sit down, especially if this is just to service the situation.

Start with information, surveying the situation, and getting on the same page.

How To Connect

You can find Gretchen’s content on or through her podcast, Happier with Gretchen Rubin. Check out the Four Tendencies Quiz here.

The Hot Seat

Favorite Blog, Podcast, or Book:

Podcasts: 20k Hertz, Happier in Hollywood, Dolly Parton’s America

Books: A Pattern Language, Man’s Search for Meaning, The Story of a Soul, Internal Time, The Goblet of Fire.

An Inflection Point: Switching from law to writing. Also, meeting her husband at the law school library.

Favorite Life Hack: Get enough sleep.

Biggest Financial Mistake: Not keeping a close eye on what is coming in and out. She wants to pay more attention in 2020.

The advice you would give your younger self: Be Gretchen.

Bonus! What purchase have you made in the past 12 months that has brought the most value to your life? A Bandolier Phone Case It lets her keep track of her phone easily throughout her travels.

Related Articles

New to FI? Be sure to check out Episode 100: Welcome To The FI Community!

Choose FI has partnered with CardRatings for our coverage of credit card products. Choose FI and CardRatings may receive a commission from card issuers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities. American Express is a ChooseFI advertiser. Disclosures.
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