Which of the 4 types of entrepreneurs are you?

Starting a business takes more than just understanding numbers like open rates, pricing, profits, and losses. Walking the path as an entrepreneur also requires an intimate understanding and mastery of your own psychology — so you stay focused and motivated in the face of so much uncertainty.

Sound daunting? Gretchen Rubin would like to help.

The best-selling author of Better Than Before and The Happiness Project has dedicated her working life to figuring out what makes us all tick — and she thinks she has cracked a big part of what motivates us. Which, if you’re struggling to make headway on your business, just may be the thing you need to jumpstart your progress.

Her system works like this: After interviewing hundreds of people about expectations and habits, she’s found that when it comes to behavior change and motivation, all of us can be sorted into four categories. Rubin calls them “The Four Tendencies.” They are:

  • Upholders, who respond readily to outer and inner expectations.
  • Questioners, who question all expectations; they’ll meet an expectation if they think it makes sense — essentially, they make all expectations into inner expectations.
  • Obligers, who meet outer expectations, but struggle to meet expectations they impose on themselves.
  • Rebels, who resist all expectations, outer and inner alike.

You may already see yourself in one of the above tendencies. Neither is “better” or “worse,” but each kind of person has their own unique way of getting stuff done. And when you’re starting a business, knowing yourself is an unfair advantage.

(Learn which one you are by taking this quiz. I’m a Questioner. Rubin is an Upholder.)

And, lucky for you, Rubin will be one of the keynote speakers at Forefront in September, where she’ll be sharing more about The Four Tendencies and how they can help us live the lives we’d like.

Answers edited for length and clarity.

What can we expect to hear from you at Forefront?

How to hack your life to use the four personality types (Obliger, Upholder, Questioner, Rebel) to your advantage — especially if you’re trying to start a side hustle, be more effective, or manage yourself.

But the four types aren’t just about you, they’re also about how do you get people, including yourself, to do what you want them to do. Because oftentimes we project what works for us onto those around us, and that won’t always work.

It’s the great challenge of adult life.


What are some frameworks solo entrepreneurs and creative acts can use to help prevent self-sabotage?

I’m going to start with the Obligers because they have the most trouble with going alone. Obligers often make a serious mistake: They think only if they had lighter outer expectations, THEN they would make time for themselves.

I’ve talked to people who took early retirement, dropped out of school, or went on sabbatical thinking, “If only I could get rid of this onerous responsibility that is imposed on me, then I would have the wherewithal to meet the inner expectations!” That doesn’t happen. It just doesn’t.

And then people around them make Obligers feel bad by saying, “If it’s important to you, you should be able to do it!” Obligers need that outer accountability.

Obligers will also usually say things like, “I need to put myself first” or “I’m having problems getting motivated” or “I’m sacrificing my own dreams to my bosses.” No! That’s not what’s going on.

What they need is outer accountability. They could join a group. Work with a coach. They could get a client customer or student, even if they aren’t paying.

Want to write an e-book? Get 30 people signed up for a free copy. Now you have to write it. It’s an easy thing to fix once you realize what’s missing. But if all you do is sit around thinking of your motivation, that could work for other tendencies but it won’t work for an Obliger. So figure out what works for you and build it into your life.

Then take Questioners. They often have analysis paralysis. They always want more information and could spend months on something as silly as finding the perfect billing system. Remember: It’s not efficient at a certain point. Use deadlines, limits, or trusted authorities. Remind yourself of the core value of efficiency.

Upholders are pretty self-directed. But they can struggle if the rules aren’t clear. They might find it easy to be an associate in a law firm. But they find it hard to start freelancing because everyone’s freelance career is different. They don’t know what’s expected of them.

Rebels will do anything they want to do. But they have to want to. Which is why they are good at sales because they can do anything they need to in order to make the sale. And a thing I noticed, almost all Rebels in business are partnered with an Obliger. There was one woman who was like, “I’m the voice and face of the brand! I give the keynote! Then I have this partner who does things like billing, invoicing, dealing with vendors, and HR.” It sounded to me like the Rebel did the fun part but it worked for them!


We’ve found an important part of living a Rich Life is being unapologetic when setting up your life and daily routine to support your psychology. Have you seen the same? And what is your advice for pulling that off?

Yes! People always ask me, “What’s the best tendency? What’s the happiest tendency? What’s the most successful tendency?” They want to know what should they be. To that I always say two things:

  • First, it doesn’t matter because you are who you are so deal with it.
  • Second, there is no best tendency because they all include big successes and big losers.

Successful people set up their lives to take advantage of their tendency, exploit the benefits, mitigate their weaknesses, and get to where they want to go in the easiest way.

What are some phrases that tip you off to a person’s tendency?

Part of it is what we say about ourselves and part is what people say about us, especially the complaints.

Take Questioners. A huge tip off is if they talk about things being “arbitrary.” They won’t keep a New Year’s resolution because January 1st is an arbitrary date.

Upholders are seen as being rigid. Though they don’t consider themselves rigid but they embrace discipline and often have high standards for execution. They’ll say things like, “I know you want me to take 30 minutes to help you, but I have my own deadline.” You may think they are being inflexible. But in their mind, this day is completely planned out and there’s no wiggle room. That can make them seem cold, too.

A sign someone is a Rebel is if you ask them to do something, they resist. They put a lot of value on freedom of expression and choices. They’ll say, “I don’t want a day where everything is the same.” Or they change jobs frequently. So when there is emphasis on routine and schedules and set expectations, they avoid it. If you made a Rebel go to a 10 a.m. staff meeting every Wednesday, it would drive them crazy.

This is the funny thing about these profiles. Almost everyone recognizes themselves and people around them right away. Except Questioners. Mostly because they question the validity of the framework. As they do [laughs].

I heard you say in an interview that you’re a proud Upholder and you find yourself not valuing spontaneity. True?

Yes! I was at a cocktail party and I was describing my ideal situation as an Upholder and the person literally took a step back. They recoiled at my routine and schedule! This makes me feel free because I can do whatever I want, I can count on myself. Discipline is my freedom. But to a Rebel, it’s the opposite. They want choice. All that choosing is exhausting to me.

What are the second-order effects of the tendencies?

Lots of things, but one thing I focus on in the book is communication styles. I like to look at signs and marketing. Like a literal physical sign in a hotel room or in an office and I started to see who they were written for.

There was one I remember in the Willard Hotel [In Washington D.C.] about towels. You know how they are always trying to get you to reuse your towels? So the sign went through this entire thing: There was all this data for the Questioners. There was info about how other guests do this for the Obligers. And then at the bottom it said “But as always, the choice is yours.” They brought it home for the Rebels! Smart!

How has knowing this affected the way you write and market your work?

Hugely! I have a friend who is a Rebel and I asked them for help marketing the book, and the whole way I framed it was, “This is totally up to you. It would really help me. I’m so grateful. And If this is inconvenient for you, I get it.” I framed it as a choice. It was up to them, they could do what they wanted. Rebels will do things out of love or friendship. But I didn’t want to make them feel like they’ve committed.

Or take pre-orders, which are very important for a book these days. My catch phrase used to be “Pre-orders build buzz for booksellers, the media, and other readers. So if you have the time and inclination, please pre-order the book.” But now I’m going to provide more information about why it helps me for the Questioners. I want to say why it works in today’s book publishing environment. I’m not just idly asking this.

Like the towel sign.

Exactly! I’m going to give all the reasons and say that I see the pre-order numbers so I know how many people do it. That’s for the Obligers. And then to hammer it home, “If it works for you, I’d appreciate it!” For my Rebels. I’ll also ask people to guess which framing is for which tendencies. It’s meta but it’s true! https://www.youtube.com/embed/n5LyTqCfj6E

You’re about to speak at our Forefront conference. So what is your recommendation for someone coming to a conference by themselves to be open minded to making new connections?

One good thing about this topic is that it’s a real ice breaker. Even if you had nothing to say to someone you could ask them what their tendency is. It’s something that is specific to you but not so intimate that you wouldn’t want to share it.

Opening up a new conversation with someone is a gift and a skill. At a conference, I suggest you ask about the speakers, because you guys just shared that experience. You can always ask “what brings you here?” But it’s easier to say “I took so many notes when so-and-so spoke!” or “I hate when people read their slides!”

Oftentimes when we change habits, the real hurdle is changing our identity. It’s saying “I am the kind of person that works out now. Or now I’m the kind of person who has a business.” How do The Four Tendencies work with that concept?

That took me like two years to understand. Profound change must occur when you have a new habit. The most important thing is to surface it, so it’s conscious. A lot of times we don’t realize there are conflicts and unresolved issues in our identity.

I had a friend who wanted to drink less. Not give it up. Just drink a little less. And I was talking to her before I understood the tendencies. I tried to schedule out her drinking times, the rules, and exactly how many she’d have every week. She kept resisting me. And then she said, “You don’t understand! I’m Italian! We love wine and food!” That was it! She had to embrace her identity while still also drinking less. The idea that she’s Italian and has to act a certain way was getting in the way.

She didn’t even know the game she was playing.

Right. It was all just floating around in her head. This is why I like frameworks and vocabularies. There are too many thoughts, impulses, memories, and wishes. It’s all tangled in our head.


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