“Knowing our Tendency can help us set up situations in the ways that make it more likely that we’ll achieve our aims. We can motivate ourselves to make better decisions, meet deadlines, meet our promises to ourselves, suffer less stress, and engage more deeply with others.”

– Gretchen Rubin

How to Motivate Yourself as an Entrepreneur – Stephanie Pellett CreativeRecently, I was lucky enough to give a talk on productivity and prioritization at a coworking space here in Toronto. I tried to fill the presentation with strategies for making the most of our time and working more efficiently, with an emphasis on evaluating all your activities and projects and ensuring that you’re working on the right things. At the end, one of the attendees asked a great question about how to motivate himself:

“Do you have any suggestions for how to implement these ideas on a daily basis? If I know what I need to do, why can’t I find the motivation to actually apply what I know?” 

In my answer, I referenced the The Four Tendencies framework by Gretchen Rubin, a system that has helped me tremendously both personally and in the work I do with clients. No matter what kind of work we do, it’s crucial that we learn how to motivate ourselves and feel confident that we can effectively work towards our goals. So many of my clients struggle to take action or follow through on their plans, and wind up feeling ashamed or guilty. No, thank you!

Instead, let’s learn about ourselves, figure out exactly what we need, and then give that to ourselves without wishing we were different. We may still occasionally procrastinate or spin our wheels, but hopefully we’ll trust ourselves more. We’ll know how to make things happen in our lives and businesses, consistently.

What are The Four Tendencies?

How to Motivate Yourself as an Entrepreneur – Stephanie Pellett Creative

According to Gretchen Rubin, all of humanity fits into one of four tendencies, specifically when it comes to answering the question, “How do I respond to expectations?”.

From her site: “We all face two kinds of expectations – outer expectations (meet work deadlines, answer a request from a friend) and inner expectations (keep a New Year’s resolution, start meditating).”

Depending on how we respond to both kinds of expectations, we’ll fit into one of the tendencies:

  • Upholders: easily meet both outer and inner expectations, without much fuss
  • Questioners: question all expectations, and respond to an expectation only if they conclude that it makes sense—in essence, they meet only inner expectations
  • Obligers: easily meet outer expectations of others, but have a hard time keeping their own promises to themselves
  • Rebels: resist ALL expectations, outer and inner alike

You’ll probably find the rest of this article a lot more interesting if you know your own tendency, so start by taking the Four Tendencies Quiz here. 

How to Use Your Tendency

Once you’ve learned which type you are, you might totally hate the results, or maybe they’ll make complete sense to you. I’m a die-hard Questioner, and as soon as I read the definition for the first time I breathed a huge sigh of relief. So many parts of my character and my past made a lot more sense. I suddenly understood myself much more deeply.

If you kind of hate your type, I hear you, but I promise it’s okay. None of the types is inherently “better” than the other, they all come with their own unique pros and cons. Importantly, through her research Rubin has come to believe that everyone fits pretty firmly into just one of the four categories and that your tendency can’t be changed over time.

But no matter which tendency you are, understanding what motivates you can only lead to deeper insight and self-knowledge. Learning the tendencies of my loved ones and clients has been tremendously helpful in understanding how to engage with them!

Now that you know your type, let’s talk about how to motivate yourself as an entrepreneur or small business owner. This is the cheat sheet I wish I could give to all my clients to help keep them on track.


Upholders: Be careful what you commit to

How to Motivate Yourself as an Entrepreneur – Stephanie Pellett Creative

Upholders have no problem following through on their goals and responsibilities. They’re not afraid of expectations from themselves or others, and tend to get things done quickly and efficiently. But Upholders also tend to be perfectionists, and can experience a phenomenon called “tightening” which makes them unable to loosen an expectation, make an exception, or ramp down their responsibilities. Once they’re committed, they’re committed, and it can be hard to take a step back or re-assess their activities. Upholders have such little trouble responding to expectations that they have a tendency to overcommit and agree to do things without enough reflection or intention.

If you’re an upholder entrepreneur, find ways to ramp up your responsibilities slowly. For example, if you decide you want to post on Instagram daily, you’ll be able to follow through on that. But it’s important to make sure that’s the best use of your time before you commit to doing so! Otherwise, you’ll find yourself “locked in” to a habit that may not actually serve you. Instead, start by committing to fewer posts and evaluate how you feel as you go.

On a macro scale, be careful about which projects you decide to take on and when. Your tendency allows you to accomplish a lot, but you can still get burned out or overwhelmed.

Learn more about Upholders here


Questioners: Keep coming back to your big “why”

How to Motivate Yourself as an Entrepreneur – Stephanie Pellett Creative

As a Questioner, you have very little trouble completing tasksand activities that you have a good reason for accomplishing. If you understand why you’re doing something and find the reason compelling enough, execution of the task itself won’t be hard for you. As a solopreneur, this is both a blessing and a curse. It’s a blessing, because you don’t have a boss looking over your shoulder instructing you to do tasks you think are stupid or pointless. But it’s a curse because if you don’t have clarity on the value of your various tasks, you might end up focusing on the wrong “why” to motivate you.

If we stick with the Instagram example, we can see this in action. Posting on Instagram generally creates a good amount of instant feedback, which a Questioner could easily misinterpret as a ‘good reason’ to keep posting daily. That is, until you realize that only a tiny percentage of your sales come from Instagram! Suddenly, that doesn’t seem like such a great use of time, no matter how many ‘likes’ you’re getting. Or perhaps you’re trying to keep up with The Business Joneses? Seeing our business role models doing something can feel like a good reason to do it ourselves, even if it doesn’t make sense for us. Not all “whys” are created equal. Make sure you’re choosing yours based on the metrics that actually matter to your business specifically.

And if you’re a Questioner struggling to complete an activity? Chances are, you’re not convinced that you should do it at all. Re-assess it and figure out whether it’s necessary for your business. If not, drop it without guilt! If it is necessary, take a few minutes to bolster your reasoning. Do some research, read some articles, convince yourself that it’s a worthwhile use of time.

Learn more about Questioners here


Obligers: Get yourself accountability, without guilt

How to Motivate Yourself as an Entrepreneur – Stephanie Pellett Creative

As an Obliger, you need external accountability to accomplish your personal goals, and that is not a bad thing. You’ll have no trouble completing work for your clients, meeting deadlines, or responding to customer inquiries – those all have a measure of accountability baked into them. But you will likely struggle to work on projects that nobody is waiting for or expecting, like developing new income streams, optimizing your systems and website, or committing to habits like content creation.

Obligers tend to wish they had a different tendency, because they’re annoyed that they need external accountability. They often feel in some way “ashamed” of this need, even though Obligers are the biggest group of the population! In many ways, it’s more normal to need accountability than it is not to need it.

Accountability can take a lot of different forms, so experimentation is encouraged! For some Obligers, thinking about their future selves is enough to motivate them to get things done. But for most, real people are required to keep them engaged. Try forming or joining a free peer mastermind group that meets regularly to stay on track with business goals. Pick an accountability buddy in a similar field and schedule daily check-ins with them. Do some virtual coworking with a total stranger using an app. Or start working with a coach or join a group program (wink wink, check out mine here!). Just make sure you’re accountable to someone you don’t want to let down, and you will find that you won’t.

Learn more about Obligers here


Rebels: You can do whatever you want to do

How to Motivate Yourself as an Entrepreneur – Stephanie Pellett Creative

Rebels hate all kinds of expectations, and that includes their own expectations of themselves! I have talked to Rebels who feel so frustrated by their tendency that leads them to avoid or procrastinate on certain projects for months or years, just because they don’t want to feel like they “have to” do anything. That said, Rebels can occasionally have random strokes of genius and get things done in no time.

The keys to learning to motivate yourself as a Rebel are to think about identity, consequences, and choice. Identity asks: “Am I the kind of person who would do this? Am I the kind of person who would prioritize this?” Let’s say you want to post on Instagram more often but feel a huge amount of resistance to doing so. As a Rebel, you might ask, “Do we have the kind of business that has no social media presence? Or are we the kind of business with beautiful and consistent branding?”

Then, you get clear on the consequences of your actions. If you only sporadically post to Instagram, you won’t have beautiful and consistent branding. If you don’t answer this client inquiry, you may not make any money this summer. And if you don’t take this speaking gig, it may take you a whole lot longer to establish yourself as a thoughtleader.

Finally, you give yourself a choice. Knowing the kind of identity you want for yourself and your business, and understanding the consequences of any given choice or activity, you may find it easier to motivate yourself to complete certain kinds of tasks. Or, you might find ways to get those tasks done by someone else so that you can get back to the parts of your business that you do feel excited to work on.

Learn more about Rebels here


Know Thyself

Of course, there are so many different facets to understanding yourself – knowing your Tendency is only one aspect to consider. That said, I’ve seen people make enormous gains just by learning this one simple truth about themselves and setting up their businesses and systems accordingly. Instead of resisting the facts of who we are and what we need, we can embrace ourselves and our unique styles of working. Not only will we get more done, we’ll also trust ourselves more and it will be more exciting to have big ideas…because we’ll know we can accomplish them.

I’d love to know: What is your Tendency? How do you feel about your type? What habits in your business could you tweak or improve to leverage the way you work best? Let me know in the comments below or on Instagram @stephpellett.

PS. Need more accountability and strategy in your business life? Learn more about my group strategy program, The Foundery, designed for solopreneurs with big ideas to share with the world.

The Foundery | Stephanie Pellett Creative

All Four Tendencies graphics on this page are from GretchenRubin.com.