The Four Pillars of Making Habits That Stick

How important are daily habits to financial wellness? In my own financial wellness journey, they’ve been crucial. By changing my own habits, including my inner dialogue about myself and my income, how I managed my cash flow and how much I saved and invested, I altered my own trajectory. The primary reason I became a financial planner is that I believe other people can do it as well.

We’ve all heard inspiring stories like this of people who dug themselves out of debt and went on to become millionaires. The scaffolding for their success: daily habits. Conversely, consider stories of people who won the lottery and later ended up in financial distress. In part, it’s because they didn’t change their financial habits.

As I wrote last week, I recently reread Gretchen Rubin’s groundbreaking work on habit formation, Better Than Before: Mastering the Habits of Our Everyday Lives. I highlighted Rubin’s framework of four personality types for how people meet or resist inner and outer expectations. If you’ve taken her quiz, mulled over the results, and set a goal to change or create a daily habit, what’s next?

Rubin recommends infrastructure. She outlines the four “Pillars of Habits.” That’s the scaffolding for making sure a habit sticks with you. Click on the hyperlinks to watch Rubin discussing each pillar.


The principle of monitoring is paying attention. We manage what we measure. This may mean different things to each personality type.

Let’s say you were trying to find an extra $300 per month to save for a vacation and had decided to track your spending daily. An Upholder may find it very helpful to keep track on her own, using a spreadsheet or do-it-yourself online tools. An Obliger, on the other hand, could benefit from having to report back to someone, such as partners in a Financial Independence Day group or a financial planner. A Questioner might wonder if the exercise was worth his while and instead of tracking daily expenses, might track savings, putting $10 in a jar each day. The Rebel doesn’t want to do it and decides that she’ll stay in a youth hostel if she doesn’t have enough money saved for a nice hotel.


The principle of foundation is to tackle the largest, most obvious problems first. Rubin talks about the big influences on health: sleeping, diet, drinking, etc. For most people with credit debt, the biggest problem isn’t necessarily overspending, it’s underearning.

How might different people tackle this? An Upholder, once aware that this is a problem, might look for a second job to earn more money. An Obliger could benefit from working with a career coach to find a higher paying position. A Questioner might consider making a list of one hundred ways to earn money and then trying a few that make the most sense to her. A Rebel may consider starting a side gig in a completely new field, figuring that if he’s under-earning his chosen profession, he could switch professions.


If you want to accomplish a goal, you have to make time for it. Rubin, a compulsive goal maker and organizer of time, suggests that we are more likely to stick to a habit if put it on the calendar. Practically speaking, how would this work if your goal was to become a better investor?

An Upholder could block off time every month to review her portfolio statements and schedule quarterly sessions to re-balance back to a target asset allocation. The Obliger, on the other hand, needs more external accountability so he might consider meeting with a financial planner quarterly to review the portfolio and make changes. The questioner might weigh the pros and cons of a do-it-yourself or advisor-led strategy and opt for a robo-advisor to manage her portfolio. The Rebel, who doesn’t like strict goals, could rebalance his portfolio using tolerance bands.


The strategy of accountability is about finding a way to hold your feet to the fire. That’s different for everyone. Let’s say you were trying to improve your credit score.

An Upholder might consider signing up for a free credit monitoring service such as WalletHub or Credit Karma. That way she’d get clear information about where she needed to improve and could take steps on her own to repair any problems. The Obliger would thrive in a peer-to-peer financial wellness group, where the structure and relationships would help her keep the commitments to take action. A Questioner could benefit doing online research about managing credit at sites like and by searching for topics and reading articles. Our Rebel might consider re-framing the goal so that it is about buying a house and aligning her actions with achieving that goal.

Have you read Rubin’s book? How has it helped you change a financial habit? Email me at [email protected] or follow me on Twitter at @cynthiameyer_FF


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