How The Enneagram Helped Me Become A Better Entrepreneur

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I love a good personality quiz or really anything that gives me a new perspective or a fresh look into the human mind and our behavior. And I’m not talking about those silly “what kind of avocado toast are you?” kind of quizzes, though those are a funny way to pass the time. I’m taking anything that’s gonna dig a little deeper and make you really introspective . 

I’ve always been interested in the zodiac, though not technically a personality “quiz” it still kind of falls under the category of life analyzing human categorization, and I’m fascinated by those that truly believe it and that plan their lives around it. I only vaguely identify with my Gemini sign but I still find it interesting when my zodiac lines up with something in my life. I like to know my Myers-Briggs and I’ve taken it a few times, once in high school when it was supposed to somehow determine what we would do with our lives and what career path we should go down, once in college for a psychology class, and once now as an adult just to see if my results had changed. It hadn’t, I’m still an INFJ. 

I’ve learned a ton about myself as an INFJ, but to be totally honest I’ve never put a ton of stock into these forms of categorization. Yes, they are extremely interesting and certainly make you analyze a lot about yourself but for any quiz of this sort, your answers are subject to change on any given day of any given year, based on your mood, what is going on in your life, and how you interpret the questions. But last year I was introduced to the enneagram, several friends swearing that I needed to take it, and I just thought “sure, fine, I like a good personality quiz as much as the next person. Tell me something new about myself!” 

If you’ve never heard of the enneagram, it’s similar to other personality quizzes in that you have to answer questions in situational examples to help determine your answer. The enneagram then separates people into nine different categories, simply numbered one through nine. Once you have your base number there are also wings that can attach to your number that explain your personality a bit further. 

What I loved about the enneagram is that one of the letdowns of other personality quizzes is actually an asset here. Like I was saying other personality quizzes can give you different answers based on how you’re feeling that day or even how you perceive the question being asked. One of the biggest faults people find with quizzes like this in general is that the person taking the test knows they’re being tested and that may change how they answer, thus changing the end result. 

But because the enneagram focuses so heavily on what motivates you, how you want to be perceived is just as important as how you naturally act. In other words, it’s OK if you answer more inline with what you aim to be like rather than how you naturally are because our desires to change and adapt our personality are just as important in defining who we are as individuals. The test will always give you your top highest numbers, you can read about each one, and then YOU can decide which one really aligns with how you see yourself. I find that super fascinating that you have a say so even in the end result, and honestly I saw aspects of myself in all three of my highest numbers. There just happened to be one in particular that I read and wholeheartedly, enthusiastically found myself saying “oh my gosh that is ME.” I bet you can guess which one it was! 😉 

Yep! I’m a four, the individualist or the romantic as it so often titled. Fours are highly creative and emotionally driven and strive to be completely unique and set themselves apart from everyone else. Sometimes they will even purposely find ways to be an individual, but then get all emotional about it and think that no one understands them. But being thought of as normal or boring is somehow way worse. In the end it all comes down to trying to fully understand themselves and their emotions and turn it into creating something of significance. The good, the bad, the embarrassing, yep, I’m all number four, through and through.

Around the same time that I was being encouraged by friends to try the enneagram I started seeing a lot of posts from a fellow designer, Kadie from Drop Cap Design posting more and more about how the enneagram could affect business owners and entrepreneurs. If I was intrigued before, now I was hooked. Show me anything that will give me better insight on how to more effectively run my business and I’m first in line for it. If you haven’t come across her work on the Enneagram for Entrepreneurs yet, I highly encourage you to take a second and go browse her blog. Her wealth of knowledge will astound you.

All that to say, the enneagram has surprised me by being one of the best personality tests I’ve taken, possibly ever. I’ve learned so much about not only myself, but how this affects my work, and how this affects how I serve others based on my skill sets. It’s wild that something as simple as answering a few questions about yourself can provide such insight, and trust me, it was shocking to me as well. 

So instead of keeping things surface level here, let’s dig a little deeper into some of the things I’ve learned about being a business owner from the enneagram. This isn’t necessarily about me being a four, though I will use some examples of four behaviors in my points, but rather I hope that this will show all the ways the enneagram can boost your own business practices, no matter what number you are and encourage you to find out your number if you haven’t already done so.

I’ve also got a free worksheet that you can fill out while you do some research on your own enneagram type and this is perfect for anyone interested in pinpointing areas of focus in your business, no matter if you are new to the enneagram or a total pro. Just sign up for my resource library to snag your free worksheet!

1. How to Stay Inspired and Motivated

With any of the enneagram types it’s so important to know what things keep you motivated and inspired in your work, especially when you’re a business owner and everything is funneled directly from you to your ideal client. There are always days you feel more inspired, more energetic, and seemingly bursting with ideas. Then there are also times you may feel like the complete opposite. You may feel like you have no ideas at all, the ideas you do have are trash, and trying to be productive literally feels like walking against a current. Now let me be clear, I don’t just mean inspired in a creative sense. There are a million ways to feel inspired, whether it’s inspiration to get fit, inspiration to clean your house, inspiration to travel, even inspiration to have a girls night and of course, inspiration to do your work. Whatever inspires you, there’s always an ebb and flow to how motivated you are to do something. Some days you are all in. Some days you’d really rather not. This happens to all of us from time to time and while there are outside factors that can affect this, whether that’s hormones, stress, or health, there are also things each of us can do to jumpstart our motivation and reinspire ourselves. And different things work for different people. That’s where the enneagram comes in.

Inspiration itself is a weird thing simply because of how unpredictable it can be. Tell me if this has ever happened to you: you think you have a fantastic idea and then you sit down to actually bring that idea to life and it just doesn’t seem to be translating from your mind to the page like you thought it would. This can be extremely frustrating and a total inspiration and creativity killer. In this situation you have to know what will help you further your progress on your work and what you absolutely need to avoid in order to stay in the working mindset. Some numbers may just need a change of scenery while others may find the new work area to distract them even more. Some numbers may need to pause on their work for a time being, do another activity for a bit, and then revisit the work after some time away. For other numbers this stop and start tactic may cause them to feel like they are procrastinating and make the dread of work even worse. 

I know that as a four the worst possible thing I can do when I’m feeling uninspired is look at other peoples work for inspiration. Fours have a tendency to compare themselves to everyone else and because of this I know I will no doubt compare my lack of creativity to what seems like everyone else’s constant stream of beautiful ideas. Of course the reality here is that everyone is posting their best work on all of their social media platforms to market themselves so what’s actually happening here is I am comparing a low point in my inspiration to literally everyone else’s best work. In no way shape or form is it a fair comparison and all I’m doing is damaging my own self worth. 

I know for me the best way to stay inspired is to just put my blinders on and keep on working. That may seem silly because it’s such a simple thing but somehow it’s something that took me a long time to figure out. If I can keep working at an idea and playing with different versions of it, at some point I will inevitably find something I’m reinspired by, without the influence of other people’s work.

By knowing your enneagram number you can start to pinpoint things that boost your work ethic and avoid those that don’t. Staying motivated in your work is the only way you are going to be successful and happy with what you’ve done at the end of every day.

2. How to handle stress and time management 

Along with our differences in what keeps us feeling motivated comes the differences in what causes us stress and how we manage our time while we work. Stress actually plays a huge role in your overall motivation so it’s important to know what causes you stress, how to avoid it, but also how to handle it when it inevitably happens. 

Each enneagram type has something that causes them stress when it comes to their work, whether that’s a dirty work environment, dealing with clients one on one, marketing themselves, being productive on a set timeline, money management, or simply struggling to find work. I kind of just think owning your own business is accepting the fact that you’re going to deal with stress from time to time. It’s one of the main things that I talk about with new freelancers. I think it’s so important to know how to handle stress without letting it damage you or your business, because trust me, stress will happen.

One of the biggest components I think to handling stress as a solo entrepreneur is learning about your own time management preferences. Again, everyone is different, so everyone will have their own preferences when it comes to how they want to set up their client work and timelines. Some business owners preferred to stay really busy and take on large numbers of clients at one time. Some prefer to space out their availability to one client at a time in order to avoid the overwhelm of overworking themselves. Some business owners prefer strict deadlines when it comes to sending work to their clients and receiving feedback, while others prefer to play it by ear and work through each section of the project whenever they come to it without worrying about keeping pace with deadlines. Some business owners may feel like they do their best work when they put it off until they feel really inspired while others may avoid any form of procrastination by wanting to get work done ahead of schedule. 

When you are first starting out you may not know what time management specifications will work best for you, and while you could spend time testing several options, the enneagram can give you a pretty good place to start. Your number can show you what time management will line up with your core motivations best and cause you the least amount of stress. Even if you’ve been working for awhile now, the enneagram may introduce you to a new way of organizing your time management that you haven’t thought of before.

But of course, not all stressors come from how we spend our time. There are a lot of stressful situations you can find yourself in as a business owner and it can sometimes be difficult to know how to handle them. Undoubtedly every business owner encounters a difficult client at least once, and some types may prefer to handle these situations in a personal, one on one scenario while others may choose to outsource their customer care to a third party that will handle difficult situations for them. Some business owners may find comfort in organizing all their client files in one place that they share with the client, like a portal of some sort, while others prefer to keep the files private until they send it to the client or have a more haphazard way of keeping track of their work. Some may want a pristine work environment in order to be able to focus on their work while others may be invigorated by a more chaotic and loose environment. 

Even stresses outside of your control will come up occasionally and when you don’t necessarily have the option to change things it’s important to know what you need to do in order to destress. I think one of the most encouraging things I read about while digging into type fours is that I was already doing so much in my daily life that helps fours destress. Fours need things to encourage their creativity as well as things to get them out of their own head. Another creative hobby outside of work is huge for helping fours feel confident in their creativity. For me that comes in the form of writing, painting, and photography. Since fours tend to obsess over their work, making sure that I get out of the house and focus on something else for a change is massively important, and it’s even better if that involves nurturing something else and helping fours take care of another thing’s emotional state instead of their own. Some of the recommendations were tending a garden, having a dog to go on walks, and scheduling social interactions with friends, all of which I do consistently to make sure I stay feeling good and in a healthy headspace. It’s incredibly encouraging to know you are doing things to better your own well being and I was thrilled to find out that I was already doing things that benefit my enneagram type. When you realize exactly what your enneagram type needs, then you know you can make the best choices for yourself and your business!

3. Why my work environment is so important

I mentioned briefly how our working environment plays into our overall stress and motivation and I’m realizing from the enneagram just how important it is to set up a work environment that we feel most at home in and productive while working. 

If you’re someone that needs quiet to think your own thoughts while you work, a coffee shop or even being home with the TV on in the background may be a complete productivity killer for you. But if you’re someone that gets energy from the hustle and bustle around you, or even if you get lonely working from home, a coffee shop or the noise from the TV maybe just the thing you need. Like I mentioned before, there are types that need an immaculately organized office, where all their tools are beautifully organized in order to be productive. But there are also types that thrive in an environment that allows them to create freely without worrying about putting tools back in their proper place. 

There’s even some psychology at work if you prefer an environment that’s mostly white, clean, andvoid of any bright colors or bold patterns as this may help your mind to rest and think about your work. But you may have friends that prefer a darker or bolder color palette and lots of contrast between patterns and shapes within their environment. Further still, you may prefer to work inside, in an office or in a space specifically set up for your work or you may prefer to work outside, in a more organic environment, in order to produce your best work. It’s fascinating that what we surround ourselves with can play such an important role in what we create and how we create as business owners and how wonderful that the enneagram can give us insight in how we can set up our work environments so that we are most productive every single day.

When I was first diving into the enneagram I had a mentorship call with Kadie from dropcap design that I mentioned earlier. Our conversation was not related to the enneagram in any way, but at the end of the call I just had to tell her how much I appreciated her enneagram for entrepreneurs insights. I told her I was a type four and that her blog posts had given me such a new understanding of what that means as a business owner. The first thing she said to me was “I knew you were a type four because of how much you show off your environment in your pictures“. Since I was new to the enneagram I didn’t even know that that was a thing that type fours did, but I did know exactly what she was talking about. I do love showing off my environment constantly in all of my imagery. It’s a huge part of what helps me create and most of my inspiration for my design work actually comes from looking through interior design, spaces, and decor. Somehow this is just not something I realized I had in common with other people, or that this could help me understand my own work process, until I took the enneagram. 

Even looking around me while I write this blog post here in my house I can definitely see my brand influencing my own house decor. Or maybe it’s the other way around and my house decor taste influenced my branding? Who’s to say really at this point since we are 4 years in. But there’s no doubting that my environment has played a huge role in how I create on a daily basis and how I choose to show up on all of my social media platforms for my business.

Aside from the physical environment that I create around myself, an important aspect of the enneagram is the environment we put our clients into when we work together. By this I mean how I communicate with my clientele, how I’m bringing them into my creative process, and how we approach the actual designing and work. A work environment in this context mainly comes in the form of the on-boarding process for new clients, the work process itself, and finally the off-boarding or final takeaways of the project. If my physical work environment is so important to me, there’s absolutely no way I can ignore the digital work environment that I’m setting up for myself and my clients. After all, I’m working with some of my clients for several months at a time, and making sure that they feel comfortable in the collaborative environment I’ve set up for them is crucial to the overall success of the project. I also have to be aware that I need to set up a work environment that will work for my type four self and for the client, as they may not be a type four (and honestly, they probably aren’t if they are hiring me.) While I don’t have my clients take the enneagram, it’s just important for me to be aware that each of my clients may need a slightly customized type of environment to fit their needs and help the project flourish.

I also have to be cognizant of the work environment that I’m setting up for myself during each project, as in how many hours I’m working each day, how quick of a turnaround I’m promising on a project, the amount of projects I’ve taken on at once and if it’s too many to give each the attention it deserves. In other words, am I approaching this project from a place of inspiration or a place of stress? Yep, it comes back to inspiration and stress! See how all of this is connected? As a four I know that when I get overworked or overly stressed I don’t produce my best work. It’s important for me to set boundaries not only with the client but with myself so that I make sure I’m not only meeting the project guidelines but also taking care of myself in the process. Only then will I create the best work for my clients.

4. Productive ways to use emotion

This one is pretty specific to type fours in general because as creatives we tend to be deeply rooted in our own emotions. This can be a beautiful thing because we’re in touch with our own emotions in a way that most of the other types are not, meaning that everything we do we put our heart into and our creativity stems from this innate desire to express emotion. But this can also be a not so great thing because not all emotion is productive. While we are trying to serve others from a place of true passion, we are also opening ourselves up to any negative emotions that may arise. Fours have a way of sitting in their emotion, almost stewing in it, and when that emotion is negative, such as a feeling of inferiority, a feeling of jealousy or envy, or simply a feeling of doubt or sadness, not only does that cause us to question our ability to create in the first place but usually we struggle to create things that we truly are happy with when it’s all said and done. 

So full disclosure here, I’m actually a four wing three, the three being the achiever, so there’s always a part of me that wants to plan and set goals for my creative work. Some days I feel so productive you wouldn’t believe all that I can accomplish, then other days I feel completely suffocated in self-doubt and feeling like a total imposter. I know that this stems from comparing myself to others and I’m also aware that this is part of what makes fours the individualist: this predisposition or desire that we have to compare and size up our own work as it relates to others. 

I’ve begun to recognize in myself when I’m starting to feel that imposter syndrome or when I feel like my work is somehow inferior to those that are also in my industry and the best way for me to combat that is to make a plan, with actionable steps or goals, that will help me step up my game and set myself apart. Not only does brainstorming new, invigorating ideas allow me to harness those negative emotions and use them to propel my own creative journey forward but it also comforts the individualist in me if I can plan something that feels original or inspiring in some way. 

I can easily harness any productive emotions on the days that they show up and crank out work like there’s no tomorrow but learning to tap emotions that could be debilitating to my creative process and turning them into motivation to experiment and try new things is honestly my only way to keep from spiraling into self pity. Emotions are a tricky thing, especially for fours, and while we may be individualists, it’s always nice to know we aren’t alone and that there are in fact ways to use emotion as a powerful tool in our work.

5. How to show up with authenticity

I suppose my intrigue into personality quizzes in general comes from a place of wanting to know myself. Yes, that’s a very four thing to say, but I think on some level most people want to know more about themselves and understand what their core motivations are. That’s why personality quizzes exist in the first place, right?

And for me personally I know that I can’t show up for my business in a truly authentic way without first understanding myself. How can you go out into the world and tell your clients “this is exactly what you can expect from me day in and day out”, “this is what my process looks like and this is why that matters”, or “this is who I am”, if you haven’t yet taken the steps to understand those things about yourself. In order to show up authentically on social platforms, on our websites, and in any marketing campaign we may have, it’s important to know why you do what you do, what things are most important to you, the values that propel you forward in your business journey, and how you serve your clients best.

Knowing those things about yourself and your business can immediately give you hundreds of ideas for content creation. Think how easy it is to come up with imagery ideas for your website and social media platforms when you know the things the best exemplify you and your brand. Business coach Jenna Kutcher always encourages her Instagram students to pick the top five things that exemplify what they want to be known for and to show up every single day showing off one of those five parts of their lives. Your enneagram type immediately associates things, either tangible or personality wise, that exemplify your number’s core values. There are an infinite number of memes out there that playfully associate everyday items with each enneagram type so if you are truly lacking ideas, that can be a fun place to start. From there it’s just a matter of photographing those items that best show off those values and sharing them with your audience. 

Writing copy for your website or captions is a piece of cake when you already have so many questions answered for you. When you know why you do what you do and why it’s important to you, you’ll be better at communicating the value of what you bring to the table and why your audience should care about your work as well. When you know how your enneagram type serves their clients best, you’ll have an easier time putting together proposals and projects for your clients that meet all their needs and check all of their boxes. When you know what you value most in your business, you’ll be able to show up in an authentic way everyday and attract clients that perfectly align with your values. 

Being authentic in how you present yourself to your audience and your clientele can be the difference in people liking you and people becoming fans that genuinely connect with you. Connection is the name of the game in this online world and it’s something we all, even the biggest names in business out there, are trying to achieve. In fact, I would say you have better chances of truly connecting with your audience when it’s small than when it’s massive. You have more opportunities to talk one on one and show up as a real person instead of a celebrity of sorts. The more true to yourself you are, the quicker those connections will form and the stronger they will be in the long haul.

6. How to better serve others

Finally, all of this culminates in how we as business owners serve others, whether that’s the impact we have in our own field of work or in how we choose to work with our individual clientele. There’s a level of understanding yourself and understanding others that you need to have in order to run a successful business.

Like I said throughout this article, everyone is different. If we take nothing else away from the enneagram, we should recognize that different things work for different people and that we are each unique in our personalities and experiences. When you work in any customer service business you will undoubtedly come across every personality type and number on the enneagram scale that can exist. And that shouldn’t scare you! How wonderful that we get to own businesses that serve such an array of people and that we can offer them a set of skills that will compliment their own skills and boost their own businesses. Whether you run a service or product based business, you are showing up with your own unique skill set and providing others with something that they need, or that they personally couldn’t do themselves. The better you can become at identifying how you best serve others, the better you will become at actually serving them.

Understanding yourself and what you offer the world plays a huge role in how you work and how others perceive you and your business. If being true to yourself through every part of business is important to you (and it should be!) then I strongly suggest learning about your enneagram and doing some introspective digging so that you understand your own motivations and how you should be showing up for your audience every day. I’ve honestly been astonished at how the enneagram has affected my work life and how I’ve become better at identifying areas in my process that were helping or hindering my workflow. I now can pinpoint stressers easier, find new ways to stay motivated, and plan ways to better serve my clients from a place that feels true to me, just because I can identify how my personality handles different scenarios. If I can learn more about myself and help my business thrive in the process, what could be better? 

Now that you’ve heard a little about my own experience with the enneagram, now’s your chance to dig a little bit deeper into your own business. You can snag your free worksheet that walks you through all the areas that I’ve covered in this article so that you can get the most out of your enneagram results.

I’d love to hear about your own experiences with the enneagram or if it’s something you’ve tried or want to try! Leave a comment, either here or on Instagram and let me know if you’ve learned anything else about your business from the enneagram!

If you haven’t taken the enneagram yet but would like to, here’s a link to a free version of the quiz that I took.

You can also read more about your number and how it relates to your business on Enneagram for Entrepreneurs from Drop Cap Design.

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