Episode #24: The Four Tendencies (Personality Tests & Entrepreneurship Mini-Series, Part 2)

In today’s episode, we’re bringing you the second of our three-part mini series on personality tests! We’re going to dive a bit deeper on a framework we discuss often on the show, The Four Tendencies. Then we’ll finish the show with a weekly actionable tip.

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Cassy Joy: Start to maybe question themselves, your intention, or how your belief in a project. And I know that’s not the case for the Questioners out there. You’re like; I just want to know why so that I can really buy into this thing. So I would say; give folks a heads up. Really help manage other people’s expectations of how to work with you. And this is true of all the tendencies, but I think it’s especially true here. Because it can be such a blind spot. Because a Questioner is like; what? I’m going to get it done. I just need you to explain more to me.

Welcome to Driven; a show about business, life, and wellness from two confident, curious women who are pulling back the curtain on what it’s like being an entrepreneur. Each week, join hosts Diane Sanfilippo and Cassy Joy Garcia talk about being your best, showing up for your dreams, and kicking self-doubt to the curb.

Diane is a business whisperer, best-selling author, and plant-hobbyist based in San Francisco. Cassy Joy is the founder of www.FedandFit.com, best-selling author, and casserole enthusiast. She calls San Antonio, Texas, home.

Diane Sanfilippo: In today’s episode, we’re bringing you the second of our three-part miniseries on personality tests. We’re going to dive a bit deeper on a framework we discuss often on the show; the Four Tendencies, by Gretchen Rubin. Then we’ll finish the show with a weekly actionable tip.


  1. What’s on my plate [2:04]
  2. Shop Talk: The Four Tendencies [17:39]
  3. Shop Talk: Upholder [32:39]
  4. Shop Talk: Obliger [41:10]
  5. Shop Talk: Questioner [49:31]
  6. Shop Talk: Rebel [57:22]
  7. Tip of The Week: Take the test [1:15:13]

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1.  What’s on my plate [2:04]

Cassy Joy: What’s on My Plate. In this segment, we talk about what’s happening in our businesses, and in our lives this week. Good morning, Diane!

Diane Sanfilippo: Good morning. I’m going to ask you to kick off our What’s on My Plate today.

Cassy Joy: {laughs}

Diane Sanfilippo: Because, I don’t know, I just want to hear what’s on your plate.

Cassy Joy: Oh man. When I was making notes for this, I’m in one of those stages; I’m knee-deep in book three right now. And it’s such a weird stage. This is a totally private podcast {laughs} It’s just between us, right? {laughing} But I was going to say; I’m in that weird stage of the book project where I really can’t share a lot about it. But it’s taking up the majority of my time. So aside from just taking photos of my computer, and endless Google docs, and all of my writing; that’s what’s taking up a lot of it, so we’re knee deep in book three. We already had our cover shoot, possibly.

Diane Sanfilippo: Oh, exciting!

Cassy Joy: Yeah. I mean, maybe. Maybe a cover will come out of that. And Kristen Kilpatrick, the photographer we’re working with, she’s essentially going to be the creative director for this book is really the role that I’m giving her. And after that shoot, Diane, I walked away so thrilled with her in that role. Because she’s just; we’re going to talk about tendencies today, but she’s got the right amount of vision. The ability to share her ideas. And just the right amount of authority. And a good portion of that. I just really love really strong, authoritative women.

Diane Sanfilippo: Yeah. It’s nice to find that. It’s hard to find somebody who we feel has that kind of strength that we can trust.

Cassy Joy: Yes.

Diane Sanfilippo: And lean into that a little bit more rather than just having to do things ourselves or rely on ourselves for those big decisions. So that’s nice.

Cassy Joy: Totally. Exactly. I’m not an expert in book covers and photo composition of people. I’ve accidentally become an expert in photo composition of food. {laughs} Anyway, that was so exciting. We’re well on our way there. What we really were working on this morning; my team is here at my house today, and we’ve spent the last three hours talking about our email verticals and our lists and really our strategy there.

And it’s really not a glamorous thing to do because it doesn’t feel productive. It’s not like we have a thing to publish at the end of this. But after 8, 9 years of running Fed and Fit, we just have tens of thousands of emails. And all of these different content verticals at Fed and Fit. We have food, lifestyle, wellness, family, so on and so forth; style. And it’s like; how do we offer customized, curated content for the folks who want more of that thing without bombarding everybody with more of that thing. And then at the same time, when we create these individualized e-courses, is what I call them, miniseries within a certain vertical, how do I make sure that somebody who does want three out of the five things doesn’t get three emails a day from us?

So we are just really doing a thorough audit on all of that stuff and coming up with a strategy. When I broke to record with you, we were about two-thirds done with it. So that was good. We’re going to make progress. And that’s one of my big things I want to check off before I have this baby, and I go out for maternity leave so that’s kind of running in the background. Right?

And then, another really fun thing; my self care club, I’ve mentioned it before, is close to launching. It will essentially live on Instagram, but we’re getting closer there. And that’s going to be really a wellness avenue for people who just want to have more conversation there around self-care. We have some really fun surprises up our sleeve.

And then my last update is pretty exciting! I gave myself a little cheers at Sunday family dinner. Normally we brag on each other at Sunday family dinner; my sister won an award and I was like; oh, I want to brag about Sam. And I was like; I just want to say, Cook Once, Eat All Week sold 100,000 copies!

Diane Sanfilippo: Wohoo!

Cassy Joy: Which is so exciting! That’s just a major milestone!

Diane Sanfilippo: That’s so exciting.

Cassy Joy: And it’s been out for less than a year. I think 8 months it’s done that. Who knows what the future will look like. So I want to count my blessings while I’ve got them. But I’m really proud of that. We managed, I think, to do that in the calendar year of 2019, which was the goal I had set. So; it was a big goal! I didn’t say, it’s this or bust. But, it was exciting. I’m really proud of the whole team, because it was definitely a group effort.

Diane Sanfilippo: I love that. That is awesome.

Cassy Joy: What do you have going on?

Diane Sanfilippo: 100,000 copies; that’s huge.

Cassy Joy: Yeah!

Diane Sanfilippo: That’s a lot of people!

Cassy Joy: That’s a lot of people. I don’t know that many people. {laughs} Not even close. It’s four times what Fed and Fit sold in four years. So, it’s good. I’m really proud of it.

Diane Sanfilippo: It’s amazing.

Cassy Joy: And I hope to continue, surprising and delighting that audience.

Diane Sanfilippo: I hear that. So you mentioned email, and I’m going to give a quick note on that, too, because that is something that’s big that my team and I are also shifting. All of these things just kind of happen at the right time. We’ve known for a long time we needed to move; we currently use MailChimp, and we need to move off of MailChimp, for a variety of reasons. Not the least of which is getting way, way better at segmenting our list. Which is kind of what you’re talking about, where you have these different verticals. You have people who have signed up for different types of information.

But when we are communicating with people, very specifically, as well around transactional behaviors. So, the email system that we’re looking into is called Klaviyo, with a K. And it’s very intimately tied with Shopify, which is where both of our stores are, between Balanced Bites meals and spices. And I’m still putting it out there that hopefully one day Shopify will have the ability to split warehouses, because I can’t ship both of those things to people through one transaction because of the separate warehouses. Well; kitchen and warehouse.

But that being said, we really want to get a lot better about emailing our customers based on the behaviors that they have in a non-creepy, but very supportive and logical and nurturing way. And probably the best example initially I have of this; it’s just a very basic example. For the folks who might be getting my Balanced Bites insider’s emails, we currently send a newsletter type of email on Sunday with a resend on Monday if you didn’t open it on Sunday. And that’s the one that has recipes, and if we have a discount code that week or something going on. Lots of nutrition education, and then of course, information about our products and all of that.

We also send another email Friday with; I abbreviate it DNO resent; like, did not open, we resend it to people who didn’t open on Saturday, with a last call ordering reminder. And it’s so obvious that we should not be sending that email to someone who already ordered meals during the week. They knew, they got their order in. They don’t need the reminder. But we just have not had the ability, or perhaps we haven’t drilled in to see how to get that ability between MailChimp and Shopify, but I don’t think we have that ability. I don’t think MailChimp service is powerful enough or detailed enough in terms of pulling data from Shopify.

So, all that being said, we had a call last week, myself and two other team members to go over with one of the reps from Klaviyo on how that’s going to work. And I was like; holy cow, my brain is exploding. I see so many possibilities. But here’s the first thing we need to do; not send these people the reminder.

Cassy Joy: Yes.

Diane Sanfilippo: You know what I mean? It’s rude. I don’t want to do it. But at the same time, it is a huge bulk of our orders come Friday and Saturday. Because I behave that way, too. I don’t order it until the day of the deadline. And most of us do that. So it is really interesting. And we can’t not send those right now, because we have to make sure that people don’t miss the deadline. Because it’s also bad customer support if we don’t tell them; hey, you’re going to miss it. And you wanted to order.

So, anyway. Really interesting. So that’s kind of my little quick email follow up. A couple of notes on Balanced Bites meals and spices. I’ve been chatting with my friend Mary Shanuda, who is absolutely one of my favorite people. Such a badass. Mary is @ PaleoChef, and she owns and runs Phat Fudge. She is one of those friends who; Cassy and I have this type of relationship where we will talk shop until we’re falling asleep, talking about it.

Cassy Joy: {laughs}

Diane Sanfilippo: Mary has really specific insight on bringing products to market and all of the challenges that come with that, and bringing them to retail, and talking with accounts and vendors and all of those types of things. She also understands me really well. So we’ve been talking about personality types, and she’s also an Enneagram 8, so she understands how intensely I need to be called on my BS when it’s happening. And when I express my “fears” or reservations or hesitations, helping me very much sort out what’s real and what’s me being detail-oriented, and deliberate versus just holding back based out of fear.

The things that I talk to her about are; these are the reasons why I’m not just charging forward, because my tendency would be to just charge forward and not be concerned about the details. But then I also want to be very thoughtful and intentional about the types of decisions I make so that I don’t launch something knowing there were a few details that really could have given me a better shot had I launched with those in place. Does that make sense?

She’s just super valuable having these conversations with me and I really value that relationship. So talking about potentially bringing meals, frozen meals to retail; and/or spices, but I’ve been kind of leaning towards possibly doing the frozen meals first. It’s just something that I don’t have a ton of insight on, like the consumer behavior and the shopping patterns, and who that person is standing in the store. And that’s really interesting to me. And I actually want to go stand at the store for hours and just watch people buy frozen meals. {laughs} Talk to them, if they’ll talk to me. Because the buying patterns of that person versus somebody at home I think are really different, so I’m curious about that.

Anyway; a couple of other quick things. I’m learning a lot about how to manage inventory when it comes to a product that does have an expiration, like my spices. We have to put an expiration date on them just because of the way we need approvals for labeling and organic label and all of that. They don’t actual expire; obviously, if you have spices in your cabinet for five-plus years, they start to lose potency. But you’re not going to get sick using them. There’s no; if I don’t throw this out, something bad is going to happen.

{laughs} And of course, I think of Sex and the City; something bad happened?

Cassy Joy: {laughing} Yes.

Diane Sanfilippo: We have to establish our movies that we’re going to be quoting, you know.

Cassy Joy: Yes.

Diane Sanfilippo: Or TV shows. But it is really interesting because I don’t like to operate in a very hyper sale-oriented space. I don’t want people to rely on only shopping when there is a sale. However, I’m going to need to move through inventory at different points in time. And I also need to recognize this is just kind of me talking to myself as the entrepreneur that having a sale is an amazing way to introduce a lot of new people to the brand. There are people who are sitting on the fence for a long time, and that is a motivator. And I need to look at it from both sides and understanding that motivation as the consumer. I have those types of motivations too. But also understanding that sometimes it is beneficial for me to have a lot of orders come in where we’re not actually generating much in terms of any profit. But it does help to introduce new folks to the brand. And we have to sometimes move through that inventory because of those dates.

Cassy Joy: It grows your base.

Diane Sanfilippo: Exactly. So I have to see a lot more upsides on it. Because looking at the bottom line, I’m only typically seeing those downsides. But it’s an interesting thing. And that’s something I’m learning about, so I’d like to share that on this show specifically. Because I think it’s important for people to hear those things that we’re consistently learning. We don’t know what we’re doing with everything.

And then I guess I’ll save this other note for another day, but the fancy food show was here in San Francisco just this past weekend, and I went yesterday with my friend Jenny Castaneda. I actually don’t know how to pronounce her new name, of Cook and Savor.

Cassy Joy: {laughing}

Diane Sanfilippo: {laughs} It’s a very beautiful looking German last name. Her husband is German. But at Cook and Savor is Jenny. We’re really good Expo buddies, is what we say, because we like all the same foods. And you can’t say yes to every sample. So sometimes I’m like; you taste that, you tell me if it’s good. {laughs}

But everything I posted about being favorites from the show I did personally taste myself. And it was just a great time. I got to see some different potential vendors or folks I’m going to work with when it comes to packaging and different ideas I have around that for my products. As well as do what we love to do, right, and connect with brands. Whether it’s brands we know and love, or some new brands. Seeing what they’re bringing to market that’s new, or just kind of, you know, having a little chat.

I loved chatting with the woman who owns and runs Caulipower. So they’re the cauliflower pizza crust and all those, everything, all the new products that they’re doing. Gina is the name of the owner, I think. And she’s just a really cool, kind of badass entrepreneur. They’ve blown that business up over the last few years. Hoping to be able to continue that conversation with her, because she is in the frozen food space, and she might have some great insights. I’m not a brain picker, but I want to build that relationship in a way that, you know, if I have one question, maybe she’ll answer it for me. And I’m happy to support her brand, as well.

I tasted their new chicken tenders, and they were awesome. Like, I definitely want to keep those in my freezer.

Cassy Joy: That’s exciting.

Diane Sanfilippo: #Notsponsored. But yeah, it was exciting. I had a great time. I’m glad that I went, and I love that it was here. That was very easy.

Cassy Joy: Yeah. That’s great.

Diane Sanfilippo: And my favorite from Fancy Food, if you guys did not see, I posted on Instagram a little grid of 9 items. It was a frozen passionfruit; I don’t know if it’s a puree that they make into bite-sized pieces, there’s nothing in it. They take the seeds out. There’s no sugar, there’s nothing added to it. But you know how much I love passionfruit. Are you a passionfruit fan?

Cassy Joy: I love it. Every time I see passionfruit anything on the menu, I think to myself; aww, Diane would order that. {laughs}

Diane Sanfilippo: Well I found out that our friend Stacy Toth also loves passionfruit, so now I get to tell her when I find something passionfruit. Because she seems to be as obsessed with it as I am. So I was really excited about that.  And I’m definitely going to be buying it from this band, Pitaya Plant Power. I think they do acai and some other things like that, as well.

Cassy Joy: Very cool. 

2.  Shop Talk: The Four Tendencies [17:39]

Diane Sanfilippo: Now it’s time for Shop Talk. In this segment, we talk about topics that are on both our minds and yours. We’ll cover all sides of the issue, and hopefully land somewhere concise, actionable, and helpful. And today we’re talking about the Four Tendencies. We’ll cover an overview of the test and the framework; the Four Tendencies themselves, our favorite resources, and share our own tendencies, of course, and how we use this system in our organizations. We use this test to essentially look at recruiting, hiring, managing, motivating, etc. With not only ourselves, our teams, our larger audience, all of that.

So, should I dive in to just some of the basics? What do you think?

Cassy Joy: Yes. Yeah, will you give an overview of what the Four Tendencies are?

Diane Sanfilippo: Yeah. So the Four Tendencies; it’s a framework created by Gretchen Rubin. For those of you who don’t know, she’s written the Happiness Project. Many, many books. The Happiness Project, I think, Happiness Project maybe at home is another one? She has also written a book called Better than Before, which was sort of the initial motivator for the Four Tendencies, because she wrote all about habits and habit change, and how can we become better than before. This episode is not sponsored; I’m just a fan.

Somebody sent myself and Scott; somebody sent us mugs that say our tendencies, and I don’t know who sent them. I don’t know if they’re from Gretchen; I mean, she was on the Balanced Bites years ago, talking about this. I think actually twice.

Cassy Joy: That’s so neat!

Diane Sanfilippo: We literally received Rebel and Upholder mugs; although we’re not sure if Scott is an Upholder or an Obliger. Like, 100%, because maybe I need to have him retake the test. So she created this framework. She wrote the book, Better than Before, and then that lead into writing the Four Tendencies. Because she kind of ended up realizing that the way that we handle expectations truly does fall into these four buckets. And of course, there can be some crossover. And she talks often about how there are people who like categories of things, and like to put names on things, and people who don’t. And she’s definitely who somebody who does like to name things.

So, the Four Tendencies is a framework that helps us to best understand how we handle expectations. It’s not everything about your personality, or what drives you. But it is an extremely useful tool, both in the areas of habit change and just your life, as well as in work and entrepreneurship and working with others. So we have found it to be extremely useful. I have found it to be sort of liberating; a little upsetting {laughs} when we talk about our tendency.

But there are four types. And the first one is an Upholder. When you go through, you can go over the GretchenRubin.com/quiz, I believe is the URL. Take the quiz. If you’re thinking; I don’t want to take a quiz, these things. I don’t know if I trust it; you’re probably a Questioner, and we’ll get to that in a second. But Upholder, Obliger, Questioner, and Rebel are the Four Tendencies.

Diane Sanfilippo: Upholders readily meet outer and inner expectations. You’re somebody who; you set a New Years’ resolution, and you tend to uphold that. You do really well with creating goals and initiatives and plans for yourself as well as maintaining what other folks might expect of you. So if you’re somebody who just can’t understand why someone can’t just do something {laughs}. Why someone said they were going to do it and they didn’t. And this is not about massive integrity issues. This is like, little things that you just kind of; your husband or your spouse, your partner or your friend, they said they were going to do this thing, and they seem to keep not doing it. As an Upholder, that might be really hard for you to understand, because you’re like; I say I’m going to do this thing, and then I just do it. So, nod to Nike there. But that’s generally what an Upholder moves around the world like.

Obligers are the largest percentage of people. And Obligers readily meet outer expectations and struggle to meet inner expectations. So an Obliger does very well when they have somebody who is expecting them to deliver. Whether it’s to show up to an exercise class, whether it’s a boss who gives you a deadline. Whether it’s an accountability partner, or an accountability coach. Having some outer expectation is not only helpful, but generally required of an Obliger.

And it can’t be, again, your own expectation because that would make you an Upholder. And it can’t usually be someone like a spouse or a very close friend, because Gretchen describes thins in her book, but essentially the folks who are super close to us, they almost become us, in a way. Where we just don’t do what they say they want us to do. because they’re just too close. And it’s too intimate of a relationship. And we don’t feel the same pressure to not let them down, for whatever reason. So an Obliger needs that outside accountability. And if you’re an Obliger, you may identify this, finding that exercising on your own is challenging. But you remember back to when you showed up for a friend that you would always meet at a class. Or just even the class itself; the fact that the class is there, and the time is there. Or maybe you always ran when you were on a team. But then you don’t understand why you can’t just put your running shoes on and go by yourself. And that’s often a sign that you’re an Obliger. Not a definitive sign, because I definitely have workout Obliger tendencies, sometimes. {laughs}

So it doesn’t describe everything in your life, but it really does help you to know; why am I not getting this thing done? And what has helped me to do that in the past? Did you want to chime in on that before I keep going?

Cassy Joy: No. Dead on.

Diane Sanfilippo: Ok. So Upholder, Obliger. Questioner readily meets inner expectations and struggles to meet outer expectations. And what this looks like is; if something passes through your filter of rationale, as a Questioner. You want to know why, you want to know the context, you want to understand why this thing needs to happen. why somebody needs this of you. And if you’re in agreement with that, and it makes sense to you, you will go with it.

So I think for Questioners, truly understanding the context and the framework of the Four Tendencies helps to make more sense or give it more grounding or more weight other than just; oh take this test and it’s going to tell you something about yourself. That usually doesn’t work for a Questioner, and they will question the validity of the test, and they will question the outcome of the test.

I think sometimes a Questioner is a person who we can be confused about if we are not a Questioner, but we will ask for their help. We’ll ask them to do something, and they seem to be resistant or perhaps they want to say no before they say yes. And the reality is, they just need some context so that they can pass it through their filter to understand why they should say yes to something. Why they should do something.

So, we’re going to talk about some examples, but one way this might play out; and I can think of this very specifically with my parents, for example. My dad is very obviously a Questioner, and my mom is totally not. My mom will do anything anyone asks her to do. I’m pretty sure she’s an Obliger, not an Upholder. But my dad; he will do things. He’ll help out. No problem. He just obviously needs to know why. He just needs to hear; can you pick this up at the dry cleaners now? Because I won’t be able to go later, I have this other commitment. Literally, the because.

Cassy Joy: It makes all the difference.

Diane Sanfilippo: It makes all the difference. Just asking them to do something because you want them to is not going to be helpful. So giving the context as to why.

And then the Rebel; the Rebel resists both outer and inner expectations.

Cassy Joy: It’s a rough life. {laughs} Just kidding.

Diane Sanfilippo: People think it’s tough to work with Rebels. But let me tell you; being a Rebel, I don’t know how to get myself to do anything.

Cassy Joy: {laughing}

Diane Sanfilippo: And so the Rebel; I should have pulled up the taglines. I’m going to see if I can find these, Four Tendencies taglines. But I know that the tagline for the Rebel is; “I can’t make me, and neither can you.”

Cassy Joy: {laughs} I mean, fitting. Diane and I are both; fall on the Rebel tendency.

Diane Sanfilippo: You didn’t want to say we’re both Rebels? Like, you didn’t want to just 100% own it? Like, we are Rebels.

Cassy Joy: Is that a Rebel thing? {laughing}

Diane Sanfilippo: {laughing} I don’t know.

Cassy Joy: Rebelling against the system.

Diane Sanfilippo: Oh wait, I think I said it wrong. “You can’t make me, and neither can I.” Because I was like; I can’t make me and neither can you. That’s obviously not proper English. You can’t make me, and neither can I. That’s the slogan of the Rebel.

I’ll go backwards here. The slogan of the Questioner, “If I comply,” Oh my gosh you guys. Words are hard today. The slogan of the Questioner, just going backwards, “I’ll comply if you convince me why.” Right? Obliger is, “You can count on me, and I’m counting on you to count on me.” And then the Upholder is, “Discipline is my freedom.”

Cassy Joy: Oh my gosh!

Diane Sanfilippo: Mind blowing.

Cassy Joy: So many shoes fitting. {laughing}

Diane Sanfilippo: As I move through my life as a Rebel, I wish I was an Upholder. I think most of us kind of wish we were, because it feels like that would be so much easier.

Cassy Joy: Yeah.

Diane Sanfilippo: Any who.

Cassy Joy: It does.

Diane Sanfilippo: So, Rebels. The best way to really handle Rebels; I think they’re sort of a mashup of everything. Because obviously, we do get some things done. Right? And we seem somehow wildly productive, yet we can’t set these expectations necessarily for ourselves in a certain way or always answer to other people’s expectations. But the thing that Rebels respond really well to, not expectations, but consequences. And I think what’s really interesting about Rebels; and I made this note to get into later, but I’ll mention it now. Unfortunately for other types who interact with Rebels, I think Rebels are uniquely either qualified for or talented at/ok with handling consequences and potential consequences that make other people very uncomfortable. And I think we are naturally entrepreneurs for that reason. I told you, words are hard today.

I do think that other folks, when they think; well, what’s the consequence of this thing not working out, or if I don’t meet the deadline, or whatever it is. For some reason, I just think that as Rebels, we’re like; I will handle that.

Cassy Joy: That’s fascinating, Diane. Because when I think about it; was it the previous episode that I was talking; or maybe we were offline. But I was talking about how I identify as a parachute builder. Like, I jump off a cliff, and it’s in jumping off the cliff that I’m like; ok, I have X number of seconds to build myself this parachute. And that really motivates me. So this is a really; it’s a tacky example.

Diane Sanfilippo: Yeah, it’s a risk/consequence situation.

Cassy Joy: Yeah. And I really do thrive in those environments. That’s really interesting. I honestly have not; I am a Rebel for sure, but I have not identified as a consequence motivated person. But I guess I am.

Diane Sanfilippo: Well, I’ve identified it because over the years, I remember. {laughs} Let’s just get a little personal. My mom; I mean, my mom is the best. Very concerned with deadlines and consequences and perhaps late fees. So over the years; many years of being an entrepreneur, you know there were plenty of years where I didn’t actually owe more taxes to the government on April 15th. I was probably in a situation where I would get money back, or whatever.

So for those of you who are not aware, if you don’t owe money, the paperwork is not actually due in April. You have until October. I don’t think she really knew that, and I don’t think she really knew the full concept or the full scope of the fact that I wasn’t owing money, and it wasn’t a problem. The consequence did not exist, and she was putting this weird pressure on me at different points in time of being an entrepreneur. Which, my mother is also not an entrepreneur, she was a schoolteacher for a long time. But she would put this pressure on me; like, did you get your paperwork in? You know; and I’m like, mom. Simmer. I was probably in my 30s.

Cassy Joy: For six months.

Diane Sanfilippo: Yeah, and also, if I don’t, guess what? I pay the fee. And it’s ok. I have other, more important, more pressing things to deal with. I’m ok with that consequence. And she could not handle the fact that there might be a late fee. And I was like; that late fee is less important to me than the fact that I’m going to way out earn that late fee doing the thing I’m busy with right now than you telling me I need to be worried about that. I was like; I have bigger fish to fry right now.

Cassy Joy: {laughs} Diane;

Diane Sanfilippo: {laughs} are we the same person?

Cassy Joy: I’m the same person. I know we’re kind of on a tangent right now, and we’ll get into the details on all these types. But I racked up; I’m not proud to admit this. Let me start by saying that. In college, I cannot tell you how many parking tickets I got on campus.

Diane Sanfilippo: I knew you were going to say parking tickets. {laughs} I don’t know why.

Cassy Joy: Because I was like; oh my gosh, what? You’re going to charge me $30, if I get caught? But the risk/reward proposition is, I’m on time to my class. And I’m on time to my meeting afterwards. And I have the best dang parking spot, a better experience for me. And I don’t care, I’ll just pay it. Because I worked. It’s not like I just; anyways. It wasn’t worth it to me.

Diane Sanfilippo: Yeah, I think our values are really different.

Cassy Joy: Yes.

Diane Sanfilippo: I think as Rebels our values are just in a different place.

Cassy Joy: Yes. Which is, to my Upholder husband, it still, to this day, blows his mind that I had between 20 and 30 parking tickets at my career at Texas A&M University {laughing}.

Diane Sanfilippo: So Rebels truly value freedom of choice, and I think that there’s something about the Rebel tendency. I think there’s something about entrepreneurship that’s very innate to us. And I think there’s something about it that other people look at and they’re like; man, I wish I could be like that. And we’re like; but I wish I could figure out how to get myself to do anything.

Cassy Joy: Yeah. I mean, you said it. Upholder; I don’t know if this is a Rebel wish; if that’s the grass that’s greener on the other side of the fence. But dang it, that looks like a nice life, is that Upholder tendency to meet both internal and external expectations.

3.  Shop Talk: Upholder [32:39]

Diane Sanfilippo: Indeed. So do you want to go through and let’s do a quick; we’re going to look at each type, what that’s sort of like as yourself, what it’s like to be working with others who might be that tendency, and then we’ll see if we can do some examples of each.

Cassy Joy: Yeah. Let’s jump into it. Ok. So we’re going to start with the Upholder. So if you, yourself. Let’s say you’ve already taken the test, or you’re going to take the test and you’re going to listen to this again afterwards. If you identify as an Upholder, meaning you meet both internal and external expectations pretty easily, I encourage you to get yourself a mentor that you trust to help you prioritize. Because what I have found, Diane, is that Upholders, they will stay in activity no matter what. And we both have examples of Upholders in our lives. I have several; I have an Upholder that I work with, an Upholder I’m married to, and I have some friends who are Upholders.

But what I have found is that they will constantly be doing things and will stay in work, but they will not always prioritize what’s the most important thing to do on my list. So even though it’s productive, I think a Rebel can fall into this trap of busy work a little bit more easily than maybe some other types.

Diane Sanfilippo: You mean an Upholder can?

Cassy Joy: I’m sorry. I meant an Upholder. An Upholder can fall into the busywork trap a little more easily than some of the other types. And I really see that if you are an Upholder, and you can see that for yourself, I think it’s a great opportunity to bring in a mentor if you are the business owner, if you are the spearhead and the boss. I think it’s really important for everybody to have a mentor, but especially this one. because it’s one of those; you’re already sailing. You already have some great momentum. And maybe just a slight course correction would help you really pursue the path that you think that you’re on.

Rebels are; gosh, we joke, like; I wish I could be one. May you have them.

Diane Sanfilippo: Upholder. You keep saying Rebel! {laughing}

Cassy Joy: Oh my gosh!

Diane Sanfilippo: You’re fired.

Cassy Joy: I’m fired. I’m rebelling against these notes. An Upholder. I mean, may we be them. May we raise them. {laughs} It’s kind of a running joke. These are all lovely tendencies.

Diane Sanfilippo: I want to note. I truly would love to hear a lot of the downsides. Aside from what you just mentioned; I think that’s a good one. Potentially getting stuck in the busy work.

Cassy Joy: I do. And I think that also, although an Upholder can dream big, I tend to see them as, they’re your super steady-Eddies that you can always rely on to get things done and to get them done in a timely fashion. But it doesn’t mean that an Upholder cannot dream big and take big risks, which is why I think it’s so important for them to have somebody that helps them see the forest through the trees, so that while they do have their head down, and they’re doing the work, they have somebody that’s looking over their shoulder a little bit and anticipating things ahead.

And then if you are a mentor of a coach of or an employer of Upholders, what I say being in that role as I have an Upholder, for example, on my Fed and Fit team that I’m employ. I say, don’t take Upholders for granted. It’s very easy to be like; oh, so and so is on that, and she’s an Upholder so you know it will get done. You can just give them a list of things to do and you know that they will do them. But they actually thrive with reassurance and check-ins in my experience.

And it’s not necessarily to keep the productivity going as you would with an Obliger, which we’ll talk about. But checking in and reassuring an Upholder helps keep moral high and I think that you will see a difference in the work quality when you are reassuring and checking in when it comes to your Upholders. They’re going to take more joy in their work, they’re going to take more pride in it. Instead of just checking the box. I think they’re going to make sure that it is an A-plus effort. So I think that’s really important.

And then I just want to double down on this, but I have found with the Upholders in my life, is when working with them, is to help them prioritize is very important. My husband is a really good example for this; I can use him because it’s a safe space and he’d be fine with it. But when it comes to Honey-do’s for example, in the house. He will go and busy himself with anything. He’s busy all the time. He’s always doing something, and he’s always working. But he doesn’t always think about the fact that because so and so needs to take our daughter to her swim class on Monday, we really need to install that car seat right now. Right? So just because he’s busy doing other work, doesn’t negate the priorities that are set. That should be overarching over the to-do list.

So if you do have Upholders in your life, I mean, man it’s powerful, but it’s really important to help them prioritize, if they wanted. I’m not saying we need to boss them around. But offer that insight if you can.

Diane Sanfilippo: Yeah. That’s a good note. And I can think of two different women that I’ve worked with and that I continue to work with in different capacities; one of whom is an Upholder who was previously on team Balanced Bites and is still on my Beautycounter team. And I have definitely served as both kind of her boss, more directly, and now more of a mentor with things she does even outside of Beautycounter and what she’s growing. And I can see the position that were kind of indicating as a mentor.

I think there can be a tendency for; not to overuse that word tendency. But for an Upholder to not be the visionary, kind of as you said, or to need or to want a bit of reassurance of; yes, that thing that takes you outside of, for lack of a better word, the hamster wheel of productivity that kind of grows the wheel in a way, where you are now doing bigger, thinking bigger, reaching more of what your true potential is. I think having that vote of confidence from somebody else.

And these tendencies are not everything about a person. Right? So we might see some of these things have some crossover. The person I’m thinking of also happens to be a type 1; and type 1s as we talked about last week are very hard on themselves. Strong inner critic. So when you’ve got the combination of an Upholder and a type 1, that’s somebody who is extremely productive and very much going to do the right thing. But sometimes, we need to be the one to say; I think that you are the right person for this job, that’s a little bigger than what you’re doing now. And you’re going to reach more people, help more people, fix more problems. You know, the Fixers.

But I see that for sure. That mentorship, and that permission to level up. I think giving that permission is really helpful. And then in terms of another Upholder who is currently on my team, one thing I love about Upholders is; I find that they’re probably some of the best at anticipating needs, and I value that very highly. We can’t expect people to be mind readers, but I feel like an Upholder is the most likely to be that one. And I do really value that.

And getting things done, like you said, perhaps the downfall of getting stuck in the checking the boxes. But I love that they are great at managing themselves and not always needing a deadline because it seems like they have a sense of urgency. But a pitfall of that would really be to check in on; did you just overcommit. Did you say yes to everything, and do I need to help you, as you mentioned, prioritize. Because ultimately, I do think the Upholder will, when unchecked, whether through themselves or through the person that’s their boss or working with them. I think they can burn out and overcommit and not look at things really objectively and say; this is what I can actually handle.

And we’ll talk about Obligers too, because I think they have this potential pitfall, as well. But being able to say, what’s realistic for us to expect of you today, this week, this month, etc. so that we don’t just let you fall into that; I say yes to everything and I think I can Uphold all of that. Right? Without checking in on it. So I think all of that is really powerful.

4.  Shop Talk: Obliger [41:10]

Cassy Joy: Ok, next up is Obliger. Diane, do you want to tackle self and others?

Diane Sanfilippo: Yeah, I’ll talk a little bit about this. So Obligers, again, readily meets external expectations, resists internal. So if you’re an Obliger, an accountability partner is extremely helpful. Now, that doesn’t mean that other people don’t do well with accountability partners. As a Rebel, for certain things, I find it very powerful for me, as well. But an Obliger truly, truly needs this to meet those expectations. And you want to make sure that it’s somebody that you really do not want to let down. I mean, it’s that feeling of; I’m not going to let this person down. I don’t want to disappoint them. I am obliging to what they’re asking for.

Now, as I was talking about a little bit before with Upholders, you really want to check yourself to not overcommit. Not over-obligate yourself. That can be; so, being a people-pleaser and being a yes person. You could be an Upholder or an Obliger. I would say that a lot of Rebels would not identify as being people pleasers.

Cassy Joy: Unless they chose it.

Diane Sanfilippo: Maybe a little bit now and then.

Cassy Joy: Yeah. {laughs} Which we’ll get into.

Diane Sanfilippo: Right. But I do think that because most people in the world are Obligers, I think that’s why we have so many people who struggle with people pleasing. But it’s important to, again, check in on priorities with yourself or with your outside accountability. Making sure you consistently know what the priority is. Because you will likely continue to have this long list of things that other people are expecting of you.

And I did not mention this earlier, but Obligers can fall into this rift of what’s known as Obliger rebellion. So Gretchen Rubin talks about this a lot. Where it’s the enough is enough, and you kind of look like a Rebel at a certain point where you have just met, met, met, met, met these outer expectations for so long that you just blow it all up.

Cassy Joy: You’re done.

Diane Sanfilippo: Yeah. And I feel like a great example of this would be like Glennon Doyle; I feel like her books and her life situation with Love Warrior and the types of things she was doing and the life she lived in the past, and what she does now. So if you guys don’t follow her, you can check her out. But when I heard her story, I could not relate to it at all. Because I’m not an Obliger. So I was like; why did she keep doing these things that other people expected of her. {laughs} And now it totally makes sense, right? It’s not personal. And I see her in a completely different light. And I love the work she’s doing. 100% respect.

But I couldn’t understand it. And this framework really helps those of us who are not Obligers to understand; why does that person keep saying yes if they don’t want to? It’s like, this is just their tendency. And also, for that person, it’s how they get things done. They do need to have that outside accountability. So, that’s the kind of internal side of things.

And the external side; if you are working with Obligers; it is so important to set clear expectations, to set deadlines. I don’t think it’s for nothing if you give context. They may not be a Questioner, but I do still think it’s always valuable to say why. But an Obliger may not need to hear why. Because it is in their tendency to do the thing that you expect of them, if they respect you and have decided that’s the way they’re going to move through getting things done.

So a couple of examples here. One in particular on my team; I have one Obliger who, same thing we mentioned with Upholders. Systems and priorities work really well. She can kind of get things done for a long time pretty unchecked. And then every now and then, we need to check back in and say; what’s on the top of the list. Because she will, similarly to an Upholder, kind of potentially get stuck in some busy work. Or upside, we’ll find more things to do, and that’s great. I think we just need to make sure that we’re always checking in on that. Incentives can work really well, where they have some reason to kind of go for something other than in just doing this thing for myself.

Do you have a good example of working with an Obliger as well?

Cassy Joy: I do. In my Beautycounter business, the grand majority of my team members are actually Obligers. And in that context, I have found in working with others as a Rebel, having Rebel tendencies, I have found it’s really important. Because I still want to support those folks and set them up for success and the way that they interpret it. It is very important for me to matchmake them with accountability partners, like Diane said, that will actually have some integrity when they’re thinking about; do I want to let this person down or not. Right?

So I work probably the hardest on that population of my Beautycounter consultants, my Obligers, and helping set them up with accountability, teams or partners, and then also help them set up clear expectations, like you’re saying in terms of monthly tasks to stay on top of, quarterly things to shoot for, and then just checking back in with them. Which is effort. That is a huge; I’m not just talking about the effort of doing it. But it is so against how I like to operate as a person. I am not a micromanager by nature, and I’m really resistant to micromanaging people. So it’s ironic that I have the most Obligers in my life, because I resist that type of support that they need more than any other.

Diane Sanfilippo: But that’s the largest percentage of the population, too, so it’s going to happen, no matter where we are.

Cassy Joy: It is. That’s true. It’s true. It’s honestly, at the end of the day, I see it as a great growth opportunity for me, because I’m not saying that I’ve got this whole thing figured out. I think it’s good to really stay tuned into what people want and need from me in order to really help empower them.

And then I have a very close team member on Fed and Fit who is an Obliger. And similar to what Diane just said about the gal that she works with; my team member is actually very productive in a silo. You could think she’s actually an Upholder, but she is an Obliger. She’s very productive in a silo. But when I make time to check in and review things and strategize with her on where we’re at on certain projects, it moves the needle by multiples, in terms of not just productivity, but also emotional buy in and belief in a project. Which I think are very, very important.

So for me, what I’ve found; and I, as the boss, in such a small organization cannot be the person that everybody is accountable to. Because that’s going to run its course. You cannot always; an Obliger doesn’t just attach to one person, one human, as their accountability partner. So what I’ve found is with my team members, we’re accountable now to this vision. We’re accountable to our community at large. And those are much, much bigger than me.

And it’s more respectful, right? To this person, as a professional, who can move mountains in her own right. So that’s been really powerful.

Diane Sanfilippo: Yeah, I think that’s such a great point. And I think along those lines, what we’ve developed amongst team Balanced Bites is just enter team expectations. Three people are touching a project, and it’s not about me that they’re answering to. It’s about not wanting to let down their next team member who is supposed to jump in after they’ve done something. After they’ve edited, etc. So I like when that whole process is happening. And I may be involved at the end, and maybe not. Maybe I just see it launch, and I’m like; great. Gold star. Good job everyone.

Cassy Joy: {laughs} Gold star.

Diane Sanfilippo: Didn’t know that was happening; glad to see it.

Cassy Joy: {laughing}

Diane Sanfilippo: Things work best when I don’t even know that they’re happening, and they just kind of get it done.

Cassy Joy: Heck yeah!

Diane Sanfilippo: And I’m like; that sounds good. Good job guys!

5.  Shop Talk: Questioner [49:31]

Cassy Joy: That does sound good. Ok, let’s jump into Questioner real quick. So Questioner, just to recap, resists external expectations, but will meet internal expectations you lucky dogs. Ok, so a Questioner. If you identify as a Questioner, my little piece of advice for Questioners are to give folks a heads up as to your need for a lot of data and information and manage other expectations. Questioners; all the tendencies. All the tendencies are very powerful and can be very productive and move mountains and be visionaries.

I have found that Questioners are especially powerful, but often misunderstood. I think when working with others, the need for more data, and the need to know why when not explained or if you don’t precipitate a conversation of asking for more information with; this is the way I make decisions. I’m going to ask you 400 questions until I thoroughly understand this. If you don’t really explain that, you could lose buy in from the folks that you’re working with. And they will start to maybe question themselves, your intention, or your belief in a project. And I know that’s not the case for the Questioners out there. You’re like; I just want to know why so that I can really buy into this thing.

So I would say; give folks a heads up. Really help manage other people’s expectations of how to work with you. And this is true of all the tendencies; but I think it’s especially true here, because it can be such a blind spot. Because a Questioner is like; what? I’m going to get it done. I just need you to explain more to me.

Diane Sanfilippo: Mm-hmm.

Cassy Joy: And then if you are working with others who are Questioners, remember, whether you coach them, employ them, or are married to them or whatnot, know that they will need to know why. And try to be as patient as possible through the process. And remember; there is a critical mass. There is a point where a toddler; we were kind of joking. Where a toddler will ask why 400 times; you know, a 4-year-old will ask why, why, why, why, why. There’s a point; a critical mass where a Questioner gets the information they need, and they’re done. They move on, right? So know that is an end in sight when you’re working with somebody like this. It’s not like you’re going to be in this perpetual question and answering phase. They will get what they need to know, and they will move on and make a decision from there as an intelligent, empowered adult human being. Until maybe the next project.

So, don’t take their need for more information to mean anything more than that. It doesn’t mean that they don’t trust you and don’t value your insights. It means that they just need more information. It’s just how they process. That’s why I feel like this tendency tends to be misunderstood. Right?

Diane Sanfilippo: It can come off as untrusting.

Cassy Joy: Yes.

Diane Sanfilippo: And because you will be one tendency, but as Gretchen Rubin says, you can kind of tip. She has a Venn diagram where it shows what you can tip to if you’re a Rebel, Questioner, etc., etc. So because I can tip to Questioner a bit, and that can get kind of gnarly for people around me. I understand that.

And one thing I want to throw in; if you are a Questioner, I think the self-awareness is really valuable. Because one thing that I have worked on is making sure that I find a way to ask, not question. because I think the word Questioner inherently has weight in terms of a distrust. When someone is questioning you, it’s like they’re questioning your ability. They’re questioning your integrity. They’re questioning this. And I think, if we hold onto that identity too strongly and we don’t understand how that lands with other people. I understand very keenly how my line of questioning lands with other people, and I know the type A, all of these things together. It ends up being like steamroller effect. But in the last couple of years, knowing that so well has helped me. And I’ve often said these words; I’m asking, I’m not questioning. Like I trust you, I just need to understand a little bit more.

So not being a Questioner doesn’t mean you will never want or need a little context. I think sometimes think; well, Obligers do everything they’re asked to do without ever asking why. And that’s not going to be the case. You might sometimes ask why. And a Questioner might do something without. But if they’re not doing it, this is where the power is. If you’re a Questioner, and you can’t figure out why you’re not doing something, if you work with a Questioner and you’re like; why aren’t they following up with this thing. They probably have not passed it through their internal filter well enough to understand the real value of why to have it make sense to them to go ahead and say yes and get it done.

Cassy Joy: Yes. That makes perfect sense.

Diane Sanfilippo: So ask, don’t question is my tip for the Questioner. Does that make sense?

Cassy Joy: It does.

Diane Sanfilippo: It gives a generous assumption that the other person has good intentions, or that this goal you’re trying to get to is something you want to do. You’re just asking for a little more information.

Cassy Joy: I can use him as an example because he would also be happy for this. But my dad is a type 8 Questioner. Enneagram type 8. And he does that, what you just described, exceptionally well. Which is why, when he took the Four Tendencies, I actually didn’t realize at all that he was a Questioner. I was shocked. Because he is so gentle in how he asks, without me, being a very sensitive type 3. Also he’s my father, so there’s that part of the element of the relationship. But he’s very careful in conversation to make sure that how he’s talking is received the way he wants it to be received. And I see that now, through the lens of these personality tools, right, that he’s really done some reflection. And I don’t know that necessarily he was born that way. He’s been through several gauntlets of work and relationships over the years.

Diane Sanfilippo: {laughs} If he’s an 8, he learned how to get what he wanted by being more gentle.

Cassy Joy: {laughing} I bet you’re right. He would probably giggle.

Diane Sanfilippo: Yeah. He learned that other way wasn’t working.

Cassy Joy: Yeah. Oops, reroute. Orange barrel.

Diane Sanfilippo: Yeah. That’s how it is. Orange barrel, that’s amazing.

Cassy Joy: OK, so this last example I want to give for Questioners before we close this section out is; in thinking about real life examples and working with Questioners, I would just say that what I have found is you can’t just rely on the proof in the pudding being good enough to convince or answer the questions of a Questioner. Which is a little bit of my tendency. Maybe my tendency is just lazy leadership; that’s what I want to fall back on {laughing}. Is just; well obviously it’s working because there you go. It worked; there you go. The results should speak for themselves. And that’s not going to really translate when you’re working with a Questioner.

You actually have to either conversationally or carefully with data driven results offer insights as to why something is the right course of action. And at the end of the day, it’s just a really respectful way to do business. It’s a respectful way to show up for your partner, for your friend, is to just conversationally explain things versus just assume that the proof of something having been run its course and been successful being enough. It’s not enough for that person to have buy-in.

6.  Shop Talk: Rebel [57:22]

Diane Sanfilippo: Indeed. Ok. So Rebel. And we did this last so that we wouldn’t let it run over all the time, because I know we’re coming up on our; we try to keep these episodes to around an hour, but sometimes we’ve got more to say. It’s just going to happen. So the Rebels, resisting external and internal expectations. So the thing I didn’t’ say earlier about Rebels is; we are driven by choice and consequences. But we are also very much driven by identity and who we believe we are in any situation. So we have to identify with who we are in a given task or situation. Whether that’s just what we think. Whether that’s what the situation is that we’re walking into. And we have to decide that that is what we’re choosing. And it’s not about the project, or the rules, or any of those expectations. It’s just about our identity.

And I think; it’s really interesting to me, because I do wonder how many type 8s are not Rebels. Because I do think that those have a strong correlation. Because as an Enneagram 8, my identity and who I think I am is of the utmost importance. So a lot of people will ask those questions; how do you become more confident, or not care what other people think? I’m like, I don’t know how to care what anyone else thinks more than I care what I think myself.

Cassy Joy: {laughs}

Diane Sanfilippo: {laughs} That’s just; reading more in the Wisdom of the Enneagram. It’s a situation where the folks who developed; and I’m curious to hear what the crossover is on Rebels who are other Enneagram types; so you’re a type 3. But type 8s have gone through, according to the Wisdom of the Enneagram, a time in their lives where they had to “grow up fast.” And I really didn’t identify that in my childhood until more recently looking back at it. And seeing those years when that was the situation. There was a period of time where, when I look at it, I was kind of fending for myself. And I had a very, what I consider, stable, loving family situation. But you know; we just experience the situation differently. And at the time, it was very much; well, I’m just going to need to figure this out for myself and take care of myself. Because we’re in a moment here where people can’t really pay attention to what I need.

Cassy Joy: Mm-hmm.

Diane Sanfilippo: So I needed to just do it. So here’s the part where I identify with this whole thing as a Rebel, where it’s like; well, I think of myself as an entrepreneur, I always have. So the way I make decisions and what I chose to do and how I move through things; it doesn’t mean I won’t answer to timelines and deadlines. But I need to feel like I’m kind of in charge. So that’s kind of the self side of things. We need to know who am I, why am I choosing this. And that will help us get something done.

And a lot of times, there are, as you mentioned, those outside accountabilities of; well, as a person, I deliver what I say I’m going to deliver. If we say there’s a newsletter every Monday, there’s a newsletter every Monday. That’s part of just integrity and I am who I say I am. We deliver. If I decide this book is going to come out this date, and I know that I’ve got to deliver drafts and edits, etc., backing up so that the book releases on that date, well first of all it’s what I’m choosing that I really want. I don’t want the book to not come out on that date. So backing that up, and I also don’t want to force other people into too tight of a turnaround based on my behavior.

So those are all; I think with Enneagram we talk about health and unhealthy. The same can be true of these types, as well. And I don’t know if; I forget. I have the Four Tendencies book, but I think my cat literally ate the book. I mean, he shreds paper, and we must have left it somewhere too low one day. So I may have gotten rid of the one copy that I had, because he shredded it apart. But I’m curious about the sort of healthy/unhealthy sides. Right; an unhealthy Obliger becomes that people pleaser too much. The martyr. The, nobody loves me and appreciates me for all that I do.

Whereas an unhealthy Rebel is just not delivering on anything. And I think we’ve got to make sure that we’re aligning with our choices in the right way. Because we don’t want to be not getting things done, and then it puts additional pressure on those people around us. And I think that’s something that Rebels, we can slip into pretty easily. Where if you needed three days to edit, but I delivered a little bit late, now that pressure falls on you and that’s not fair. So, as a Rebel yourself, you’ve got to find the way to click in to who am I in this situation, as you’ve kind of noted. I know we both have notes on this as Rebels. And how do I show up? Because that’s what I’m going to answer to. What I see myself as.

So if others are working with Rebels, this is the advice that I have. And I actually gave my mom this advice, because I think my sister and I are both Rebels. I know we are, because watching my sister’s behavior, I’m like; she’s obviously a Rebel. Like, mom, you need to give her the options. Then give her deadlines that are meaningful and note the consequences of her lack of response to that deadline.

Cassy Joy: Amen.

Diane Sanfilippo: Right? So, this is a constant situation we’re in. My mom is trying to book flights. Bless her heart.

Cassy Joy: {laughing}

Diane Sanfilippo: She’s booking flights for like, July. I’m like; it is January. The world doesn’t work how it did 30 years ago. Prices of flights are not quite as volatile these days. People book flights much more closely. And, our lives change. You know, in a short amount of time sometimes. Especially as entrepreneurs, right? We can be called on for something. So for me to commit to something in 7 months; I’m like. Mom. What?

But I need her; she does this to me, too, but also with my sister I had to explain what’s happening. I was like; you need to tell her that if she wants you to be at this graduation ceremony, you found XYZ flight. You have until this time to book it. If you don’t get to book it by then; you know, what are the consequences? And she needs to identify with those. And don’t make them arbitrary. They’ve got to be real. Because if they’re not real, I will see right through you, and so will she. So they’ve got to be real.

And you have to be pretty self-assured and confident when you’re working with a Rebel to present them with; here’s what the options are, and here are the consequences of staying with it, or not. And then you’ve got to be ready; and I think this was a note you had. You have to be ready to walk away. I was like; mom, you have to be ready to not go if she doesn’t answer you when you said to answer by. I mean, this is like real parenting stuff. Right? This is the; if you say we’re leaving, we leave. You know. One more outburst and we leave.

And I think you and I were joking about how, sometimes I think being a Rebel people think we’re just like a toddler who never grew out of it. Although, toddlers might ask why a lot.

Cassy Joy: Yes.

Diane Sanfilippo: Or they might be super, what we consider, “well behaved and just do what you say.” Which, maybe people think that’s always the best. But I’m like; well, I don’t know, I think we turned out ok.

Cassy Joy: Yeah.

Diane Sanfilippo: But you do really have to stick to those consequences if you’re trying to build a relationship with a Rebel where you don’t consistently feel taken advantage of. Because a Rebel will push boundaries consistently. We will; especially a less healthy Rebel. So looking back at maybe who I was not that long ago, not delivering by a certain deadline, but then expecting someone to pick up the slack because they’re on my team and I’m paying them to. Years ago I may have lived in that space. Now, I’m identifying; you know what? I’m not delivering this feedback for you fast enough.

This just happened this weekend. We have drafts that I accept on Thursday, and in a perfect world I would give feedback on Friday, that could be edited and made before the weekend for an email to send on Sunday. That’s a really tight turn around. And with just a few weeks under our belts of that tight turnaround timeline. Say that three times fast. I realize, I’m not delivering. So rather than consistently push that responsibility onto my team member, I’m like; you know what? We need to change the system that we have, because I don’t want you working on Saturday night. I know you don’t want you working on Saturday night. I’m just obviously not delivering fast enough. Because I don’t really want to work on Friday. I don’t generally schedule much to do work on Friday. Work, but I don’t want to be like;

Cassy Joy: Scheduled.

Diane Sanfilippo: I have to work. I never want to be scheduled. We know that.

Cassy Joy: {laughs}

Diane Sanfilippo: You somehow like scheduling more than I do. But maybe…

Cassy Joy: I just chose it. {laughs}

Diane Sanfilippo: Because it’s the only way to get it done, right?

Cassy Joy: It is. And if we go back to the Enneagram a little bit. So, like Diane said, I’m a type 3 Enneagram who also has Rebel tendencies. And I actually, in hearing you talk, I wonder what percentage; I would love to see a giant set of data that cross-references these two frameworks. Because I bet there actually are a lot of Rebel type 3s. Because part of type 3 is we are constantly aware of who we are in any given situation. Which is kind of the lens through which we move through the world. Which is; who am I, and how am I showing up, and how am I being interpreted in this room of these people under these circumstances? And as a Rebel, I chose that identity. So it puts me in the driver’s seat of it. So I think that’s really interesting.

And in working with others, I would add really quickly to self; you said this about Upholders. It’s true for all of the types, and Obligers, but especially for a Rebel. When you do overcommit, I think that that could be a pitfall. Because let’s say you choose; I choose, for example. I’m a Rebel who kind of masquerades; if you know me really well, you know that I’m a Rebel. You know that my knee jerk reaction is to say no to everything asked of me {laughs}. But, I do kind of masquerade a little bit as an upholder in some ways, because that’s what I’ve chosen to be. I’ve chosen to be somebody. I choose to be somebody who meets deadlines. Who meets my own expectations of myself, because I’ve chosen that role. I will see it through. But I do resist it on a granular, immediate level.

So I would say; if you overcommit, it doesn’t give you a whole lot of white space to make those decisions. To really put yourself first. Because if you are overcommitted, as a Rebel. Even though you’re like; I choose to be somebody who does all the things. Right? Then like what Diane just described; I’ve definitely been there, where I’m like; ok. And also as a 3, we tend to take advantage of the people around us more. It’s kind of a pitfall of a type 3 Enneagram. I think the language, which I think is really harsh, but I’m going to use it; we use people to get our agenda accomplished.

Diane Sanfilippo: 8s are the same way.

Cassy Joy: Yeah. So, I think that if you’re an overcommitted Rebel, that is a real possibility. Because of the scenario you just described.

Diane Sanfilippo: 100%.

Cassy Joy: And then when working with others; I mean, gosh, my team. I just, gold stars all around. Amber messaged me last week, and we were chatting about this beforehand. But it was the gentle reminder. She’s like; gentle reminder. Because we had workday scheduled Monday and Tuesday. Because she’s just so respectful, just a wonderful professional. But she’s like; you know, I know we’re working heavy on the book stuff and the email stuff, because I have all these wild butterflies I’m chasing and all these ideas that I want to knock out before the baby is born. And she says; if we don’t take photos and these recipes we’ve developed for the website Monday and Tuesday, we’re going to have no content to go live on the website for three months. She’s like; and that’s fine!

Diane Sanfilippo: Gold star, consequence description.

Cassy Joy: Exactly! And that’s all; I don’t interpret that as a dig. I don’t see anything emotionally wrong with that. She knows me well enough now to know to be up front with me about that stuff. And she was ready to walk away. She was ready to say; if you don’t want to publish anything new on the website, that’s fine. We can do whatever you want to do. But it gave me the ability to choose; what do I want to spend this time and these days on.

Diane Sanfilippo: Mastering working for a Rebel.

Cassy Joy: She could write a book at this point, right?! {laughs}

Diane Sanfilippo: Amber Golden. Yeah.

Cassy Joy: I mean, she nailed it. And then she also showed up with half of the dishes already made, because she knew that I would find things to do during the day that would siderail us. So I think that; I hate to say this, but you have to put on sometimes in working with a less self-aware or an overcommitted Rebel, you almost have to feel like you’re putting on the kid gloves a little bit until you get to a really good balanced spot where maybe they are less overcommitted. Is that fair?

Diane Sanfilippo: That’s great advice. And I think the flipside of that is; if you are a really aware person who does work with/for a Rebel as your boss, I think when you identify that they have overcommitted, perhaps asking what you can take off their plate is helpful. Perhaps recognizing that to say; should we sit down and reprioritize so that you’re getting the white space you need. I don’t expect people to say that to me. But hearing you say that, I was like; yeah.

Literally, my favorite days are the ones where there’s nothing on my calendar. My favorite week; I don’t want to be scheduled for anything, because I know that in order to actually be productive in the ways that I identify with; as the dreamer, as the manifestor, as the leader of my team and company, I need that open space. I need to not have expectations of me in those moments because that is what it takes, and having a little more time to decide when I will get a task done when it fits into the flow of whatever it is I have decided to handle that day.

I mean, I also don’t know if this is a little bit of 8-ness running in there. Because I’ve seen other 8s talk about this. But I pretty much don’t do something until it absolutely has to be done. I’m never going to deliver early. Because there are 10 other things on my mind that are important and need to get done that are not on a list that everyone is looking at, or I’ve just decided what my own needs and agenda are or I’ve overcommitted, like you said. I’ve extended myself to a friend and said; I can totally help you with that. Let me help you. And that’s something that; I don’t know if that’s unique to Rebels or what the case is. But, I think the white space is so important for a Rebel, and I’m just super glad that you identified that.

And I think, just to reiterate, identifying that a Rebel is comfortable saying, “this is the thing I want to do.” But also saying, in a moment, it’s ok if I decide we don’t do it today. So to your point about the content; we have the situation often with things like an email newsletter. And sometimes, it’s just not ready to go the day that I’ve said let’s send them on this day always. Monday. Whatever it is. And if I’m like; you know what? I can’t get to the edits today. Let’s send it on Tuesday; I have to have people who are working with me who either are ok with that consequence that I’ve decided, or together we look to make a better system so that we are delivering at the right time.

But I will say, the growth that I’ve had as a Rebel is to not let the pressure fall on the other person when I don’t uphold whatever deadline or whatever it is that I’ve set as the expectation, if that makes sense. I just think emails are the best example for me, because it’s every single week. {laughs} I’m like; ugh. It’s heavy sometimes. But sometimes I just don’t get the feedback in as quickly as I wish I could. I think we’re going to start working on a further ahead timeline for emails, with just a little; there are a couple of blocks that might get edited. Or something more timely.

That’s the hard part with emails, right? You want them to be timely and have something relevant that’s in them that matters right now. But I think we can get ahead on those a little bit more. Anyway. That’s just pressing on my mind.

Cassy Joy: I get it.

Diane Sanfilippo: Ok, so to wrap things up, Upholders readily meet outer and inner expectations, Obligers readily meet outer expectations, resist internal expectations. Questioners resist external expectations; they need something to meet their internal expectation or filter. And Rebels resist both inner and outer expectations. And hopefully we have given you guys a great way to look at all of these different tendencies, whether it is you. Whether it is someone you’re working with. A loved one, a friend, etc. So that we can all kind of get along, figure things out together, partially based on our tendencies.

7. Tip of The Week: Take the test [1:15:13]

Cassy Joy: Tip of The Week! In this segment, we give you one tip that you can take action on this week to move your business or life forward. Diane, I know you’ve got a good one.

Diane Sanfilippo: Alright, well this is the easiest one, right? Do a Four Tendencies audit. Go take the test if you haven’t already. GretchenRubin.com/FourTendencies. I also love her podcast, it’s called Happier with Gretchen Rubin. She and her sister do this podcast.

And I would recommend that you have four to five folks who are closest to you, whether in work. If you don’t have a close work situation where you can do this, maybe have your family members take the test; it is a free test. Definitely recommend doing that, because it will help you to know yourself and know each other better so that we can all get along just a little bit better.

That’s it for Driven this week. If you liked this episode, be sure to subscribe in Apple podcast, on Stitcher, Spotify, or wherever you listen to podcasts. Follow us on Instagram @TheDrivenPodcast. Cassy is @FedandFit and I am @DianeSanfilippo.

Tune in next week for more on personality tests in the workplace.