Gretchen Rubin: Think about milestones, not finish lines

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Gretchen Rubin is the author of several blockbuster NYT bestsellers (Better Than Before, The Happiness Project and Happier At Home) which have sold millions of copies worldwide. If you notice a common theme of “happiness,” that’s because Gretchen is one of the world’s foremost “happiness experts.” I love this term because it says something very important yet rarely said, which is that happiness is largely a choice – that it’s not random but the product of a series of deliberate decisions that happen within a proven framework and lead to a happier life.

Today on the podcast,

  • Gretchen talks about her concept of “drift.” Drift is what happens when we take the path of least resistance, which avoids friction in the short term but often leads to unhappiness in the long term
  • She also gets into several of her “personality frameworks” like obliger, upholder, rebel, questioner. You’ll likely recognize yourself in some of these and learn from what she says about each of them
  • We talk about accountability, which is a super, super powerful (and often underutilized) tool for getting results out of yourself. Gretchen says something really insightful on this: “A lot of people who are frustrated with themselves just need accountability.” Boom.


Don’t think about finish lines, think about milestones

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Gretchen’s episode was featured in the 30 Days of Genius series of Chase Jarvis Live on CreativeLive. If you like this, join 50,000+ people who are receiving one of these videos everyday.

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Some Questions I Ask:

  • How did you go from being a clerk for Sandra Day O’Connor to being a writer? And were you running from something or to something? [1:44]
  • Is there a cultural problem that’s telling us to be things we don’t want to be? [3:10]
  • What was the drift in your case? [4:43]
  • Was there a shift in mindset from when you were going from 0 to 1 and then from 1 to 10? [7:05]
  • When will I know when it’s time to take the leap? [10:05]
  • How did you go about writing your first book? [10:26]
  • What’s the first step to knowing yourself well enough to take action? [14:40]
  • So knowing thyself is step one? [17:27]
  • How do you know yourself and what’s the mechanism for referencing that? [17:47]
  • Is there a problem with people misidentifying themselves on purpose because they want to be different from what they are? [26:27]
  • Did you know that you were an upholder when you were creating these frameworks? [28:00]
  • What are some characteristically strong limitations and strengths of each of the personality types? [31:26]
  • Am I normal in my realization that focusing on habits is stronger than focusing on goals? [42:09]
  • Is it fair to say that you should be trying to adopt other people’s habits just to figure out if it’s useful for you or not? [46:55]
  • What kinds of trends do you see in creativity that everyone could tap into? [50:15]
  • Are we still bound to know thyself to be more creative? [53:48]
  • What about the conflict of wishing you were more visual? [54:05]
  • What’s something people don’t know about you that they’d be surprised to learn? [56:27]
  • Do you have a list of habits that you look at every day or are they engrained? [56:58]
  • What’s a struggle that you’ve had making something creatively? [57:08]
  • Can you name some of your favorite books? [58:11]
  • Where are you most passionate online? [59:07]

In This Episode, You Will Learn:

  • What drift is and why you should be asking yourself the hard questions to fight it. [3:32]
  • Why it’s important and uncomfortable to ask yourself “what do I want?” [5:50]
  • How one of Gretchen’s fun pastimes, obsessive researching, inspired her to write a book. [7:30]
  • You don’t have to do all of the steps, Just focus on doing the NEXT step. [9:49]
  • Why you should do what you do when you’re left to your own devices. [11:32]
  • Why you should put yourself out there in low stakes environments. [13:00]
  • Why the best habits of others might not be the best habits for you. Find out what’s right for you. [14:57]
  • The differences between simplicity lovers and abundance lovers and how to set up your life to be most productive to your own style. [16:00]
  • Check out the book Daily Rituals by Mason Currey to learn more about different habits. [16:30]
  • Why you should be asking yourself “Whom do you envy?” [18:45]
  • Why you should ask yourself “What do I hide?” [19:37]
  • The differences between being a marathoner or a sprinter and why both methods are the right method, as long as it works for you. [20:25]
  • The four personality types and how to maximize your type. [22:45]
  • The answer to all obligors out there; set up a system for outer accountability. [24:55]
  • “There can be an element of sadness in self knowledge, because to say who you are is admitting everything that you’re not.” [27:02]
  • There’s no reason for feeling bad about who you are. [30:00]
  • Go to to find out what personality type you are. [32:00]
  • All about upholders. You might need to loosen up a bit. [32:20]
  • All about questioners. You might need to give yourself some deadlines before you start a project. [33:29]
  • All about obligors, the largest tendency type. It’s all about accountability. Set up your system of accountability. [34:56]
  • All about rebels. You have to want it or you aren’t going to do it. [38:19]
  • How to communicate with rebels; use information, consequences, choices. Listen up parents! [38:33]
  • Goals are a great way to meet a goal, but are not good ways to build a habit. [41:00]
  • How I learned to fight goal setting, and replace it with habit forming. [40:20]
  • “When it comes to habits, you don’t want to think about finish lines. You want to think about milestones.” [42:26]
  • About 40% of life is shaped by habits. [43:21]
  • Why you should be spotting your own internal loopholes of letting yourself off the hook. [44:30]
  • Two questions to ask yourself when forming your own habits: when have I succeeded in the past and when do I feel my best? [45:54]
  • The difference between abstainers and moderates. It’s worth the experiment. [47:54]
  • What creativity means for Gretchen and how it’s so different from visual creatives like me. [51:21]
  • How Andy Warhol’s writing and visual art has inspired me and Gretchen. [52:15]
  • JFK’s thoughts on the matter of leaning into your strengths vs compensating for your weaknesses; “People do best what comes naturally.” [55:50]
  • Go to to sign up for Gretchen’s book club. [58:32]


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Dustin Gurley is an Designer, Developer, Artist, Instructor, Critical Theorist and Systems Engineer. He has an extensive background working professionally with 2D/2.5D/3D Motion Graphics, Compositing, Film, Video, Photography and client-side performance techniques as it pertains to web development. Dustin recently completed work on his Master of Fine Art degree in Motion Media Design (Motion Graphics) from the Savannah College of Art and Design. Prior to beginning his graduate work, Dustin obtained a Bachelor of Art degree in Communication Studies with a concentration in Broadcast and Emerging Media from the University of North Carolina at Wilmington. In addition to design and modeling, Dustin enjoys toying with his view camera, working with scratch film, authoring media related material and contributing to various industry conferences. When not in front of a computer, Dustin can be found with his wife, Regina Everett Gurley. The couple enjoys dividing their time between their home just outside of Raleigh, North Carolina and the beautiful North Carolina coast. Currently, Dustin serves as the Lead Instructor of Internet Technologies for Wake Technical Community College in Raleigh, North Carolina.