This article was originally written in June 2020 and has since been updated in November 2023 to reflect new findings, assessments, and analyses of how Threes can navigate the entrepreneurial world.

Entrepreneurs are often Enneagram 3, and this guide teaches a Three how to bolster your strengths, be aware of your weaknesses, and learn how to excel in whatever space you’re in – whether that’s work or leisure. Plus, we’ll even dive into how you can best achieve your goals and overcome Enneagram 3-related hurdles in 2024 and beyond. 

The Enneagram is a personality system designed to help people better understand the ways they view the world, react to certain situations, handle trauma, and interpret their emotions. There are nine different Enneagram types, and they include:

  • One – The Reformer (Conscientious and Ethical)
  • Two – The Helper (Supportive and Sincere)
  • Three – The Achiever (Self-Assured and Charismatic)
  • Four – The Individualist (Self-Aware and Reserved)
  • Five – The Investigator (Alert and Curious)
  • Six – The Loyalist (Committed and Reliable)
  • Seven – The Enthusiast (Enthusiastic and Spontaneous)
  • Eight – The Challenger (Confident and Controlling)
  • Nine – The Peacemaker (Calm and Trusting)

Success-oriented, pragmatic, and adaptable, it comes as no surprise that Threes often find themselves starting businesses and leading teams. There is, of course, a dark side to such outwardly influential attributes. Threes can find themselves entirely overworked, overly critical, and acting extremely vain. Sound like a business person you know?

It’s not to say that the Enneagram system dictates exactly how someone will always react to certain stimuli, but it does give a good view into the rationale and behaviors that people have. In the business world, it’s a great tool to help people learn how to better communicate, especially when navigating stress (e.g. Fours love to frantically clean when they’re in distress, so perhaps helping a friend-Four maintain an organized workspace is a way you can help them.)

For teams and leaders, the Enneagram is a great option to understand your peers’ driving motivations behind certain actions. We can use this knowledge, as leaders, to have the most beneficial meetings and conversations with different members of our organization, and to successfully arrive at desired outcomes together.

BTW – wondering why one of the best SEO agencies in the game is so obsessed with the Enneagram? Read on.

Playing to Enneagram Type 3 Strengths

Intense Work Ethic

Enneagram 3 are magical leaders. They’re excited, adaptable, and love involving the whole team. They are visionaries who see the strengths in others, and love involving the whole team. Seriously, they’re everything you want out of a leader. Oprah’s a Three, what else do you want?

As an entrepreneur, it’s your job to invigorate your team. Use your contagious charm to your advantage, because after all, it’s genuine. A positive, infectious attitude trickles down in a company, and if you show your team that you’re excited about the work you do, they will be too.

Don’t let your infectious Three energy stop at your team, though. Let it seep into the interactions you have with prospects and other entrepreneurs. If founders and CEOs are in your ICP, remember that you’re probably dealing with other Enneagram Type 3 folks. As our Type 3 CEO Alex Boyd puts it:

“We [founders] are empaths, and yet we have to control the instinct to become deeply invested in everything and everyone, because we’ll be non-functional if we’re constantly vulnerable all the time.”

Be a beacon of strength and calmness for the founders you’re interacting with. They’re looking for someone’s whose strength, knowledge, and experience they can rely on. While it comes naturally, putting yourself out there isn’t always easy, so use your vulnerability wisely.

Threes Are Chameleons

As a Three, you have it within yourself to mirror others and adapt to social settings in the moment. This is extremely valuable as an entrepreneur, because you’ll often find yourself amongst people that you feel “out of your league.” Well guess what? You deserve a seat at the table just as much as they do. Remind yourself of that! And if need be, remind those you’re talking to that as well. Give the assurance and affirmation to the founders you’re working with, because they likely want it.

When it comes to finalizing a deal, remember the value in mirroring the tone and language of your prospects. As humans, when we hear something we’re familiar with, we automatically have an emotional connection to it. Whether it’s a song we know we heard once before, or a phrase you might have read, don’t underestimate the importance of showing prospects you’re listening and adjusting to what they say and do. That isn’t to say you should take on their accent or completely mirror their motions. That’d be pretty strange! But, definitely use the nuances someone is giving you as part of your deal-making arsenal.

Threes Create Security

Self-preservation and sufficiency are vital to Threes. As an entrepreneur, part of your company ethos is running a business that gives others the same sense of security that you so badly desire. You want your team to thrive, have freedom to create, and be paid well. You also want that for yourself. Don’t ever let that go! You’re not a selfish person for wanting those things. Quite the opposite.

One thing you can do to ensure that your team always stays ahead of the curve is by diversifying what your company offers. I once had a CEO say to me, “If you’re not coming up with something to put yourself out of business then someone else will. So come up with whatever that is.”

As a Three, you already go to great lengths to advance your work, so this should come easily to you. Perhaps you started as a service company, started using an internal software, and now you’re thinking of packaging that software for others. Start by looking at what your organization does well internally and think about how you can make that work for others.

Weaknesses for Enneagram 3 & What to Avoid

Core Fears

Entrepreneurial Threes hold their appearance to the highest standards. More than just physical appearance, the way others view their education, income, influence, social standing, and career is extremely important to them. While that fuels them, it also is their Achilles heel. The hyper-emphasis on external validation for any entrepreneur is futile, though painfully present. (Why can’t we just believe in ourselves!?)

Though external validation isn’t inherently bad, for an Enneagram 3 it can be a problem when your only source of pride comes from other people telling you you’re doing a good job. As a CEO, you’re often going to be someone that people run to when something breaks. That’s never going to feel good, and it can be extremely easy to fixate on the one bad thing going on instead of the multitude of positive things your team is doing.

Don’t strive for approval; strive for authenticity. Inc. looks at external validation as “an empty victory at best and elusive and confidence and soul crushing at worst.” Train your brain to find approval from within yourself, because quite frankly, people are too busy to constantly tell you “good job!” By affirming yourself, you set the precedent that you have control over which metrics you get to use to determine success. There’s power in that.

Chart showing the best and worst career choices for Enneagram 3s.

Threes deeply fear not reaching their full potential, but they also fear losing themselves in producing for recognition. This ties into their grander fears of being viewed as ingenuine and fraudulent. As an entrepreneur, Threes are extremely likely to fall into deep Imposter Syndrome, thinking they don’t deserve anything they’ve achieved and that somehow someone will come away and reveal them to be a fake. (Heck, even Adele told Rolling Stone she feels “[my career] is going to turn out to be a hidden-camera show, and someone is going to send me back to Tottenham.”)

If you find yourself rolling in the deep pit of self-doubt, at least make sure you’re aware of it and don’t linger there too long.

Excel as an Enneagram 3 in 2024 and Beyond 

Enneagram 3’s are known for their achievement-oriented mentality, which means that 2024 is an excellent time to realign on goals and objectives. But some of the pitfalls of Threes (such as fear of failure and those workaholic tendencies) might lead to challenges when it comes to actually following through on your dream initiatives.

Here’s how you can play to your strengths and mitigate your roadblocks as you look to 2024 to knock your goals out of the park.

  1. Set (crystal) clear goals

Your ability to hone in on goals and achievements is a massive strength during this time, when you’re recalibrating your goals and aligning on your desired outcomes for the upcoming year. Take advantage of your inherent nature to achieve by setting clear and realistic objectives for yourself, whether they involve your work or personal life. Don’t be vague (i.e., make more money) but really dial in precise results. Pro tip: break down large goals into smaller, bite-sized tasks and milestones. 

  1. Remain authentic and true to yourself

Adaptability can be a blessing, but also a challenge. It can be easy to lose yourself in the shuffle, and to strictly stick to mirroring, instead of leading. Strive for authenticity with your goals and actions, and look to forge genuine connections, instead of focusing on what others are doing and how they’re perceiving you.

  1. Maintain a healthy work life balance

By now, we know that a healthy work-life balance is central to success across the board. For example, research shows us that prioritizing work-life balance can lead to higher productivity, higher rates of happiness, and even fewer healthcare costs. 

While it can be all-too-easy for Threes to go-go-go, instead, you can avoid burnout by establishing and maintaining a healthy work-life balance. Understand that success is not only about professional achievements but also includes personal well-being and relationships.

  1. Embrace vulnerability

You might be a powerhouse leader who is confident and creative – most of the time. But everyone has their off-days. As we mentioned, imposter syndrome is rampant in Threes. Instead of acting high-and-mighty all of the time, allow yourself to be vulnerable and acknowledge your emotions. Remember: it’s okay (and normal) not to be perfect all of the time, and there are going to be natural ebbs and flows in how you feel. 

Instead of bulldozing on and disregarding these natural fluctuations, you can leverage them as strengths. This vulnerability and authenticity is not only good for you – it can help enhance your connections with others. 

  1. Delegate and collaborate

Oh, Threes. We know how much you love to do things on your own. But don’t forget there’s strength in numbers, and an excellent strategy in the business landscape is to “divide and conquer.” Instead of taking on everything on your own, or always just assuming that you can do it best, look for ways to delegate to your team, and collaborate with other strong leaders. 

Why bother when you do things so well on your own? Firstly, working with others to achieve shared goals can help lead to more effective and sustainable success. Secondly, this tactic can help you avoid major (and debilitating) burnout. Lastly, you’ll arrive at richer outcomes when you have input from other strong, innovative collaborators. 

  1. Cultivate self-awareness

For us Threes, it’s extremely easy to get caught up in our goals and image, and to even over-adapt to the situations around us. Sharpening your self-awareness can help you understand exactly how you’re acting in certain situations and why, and to “reel it in.” Instead of getting lost in your pitfalls, you’ll be able to recognize when they’re influencing you. 

Reflecting on your motivations and behaviors can help cultivate this self-awareness, which will help you understand the deeper reasons behind your drive for success, and ensure your goals and efforts align with your authentic self. 

Enneagram 3 Under Stress: How to Deal With It

As a Three myself, I can say I’ve personally felt myself succumbing to the common Three downfalls, often entering manic fits of creation to plow through work. As an entrepreneur, try the following tactics to address your Type 3 weaknesses:

  • Have an Unscheduled Day: give yourself space to not look at your Google Calendar (even if it means you’ve blocked the whole day on your calendar, so technically you have used the calendar but we need to be realistic.) It might not be easy to have an unpredictable day, but let it happen.
  • Affirm Yourself With These Ideas:
    • The expert in anything was once a beginner.
    • Someone way less informed than me was able to create something huge. I can do it too!
    • I deserve a break.
    • People depend on me and respect me.
  • Let Your Mind Wander: don’t control your thoughts! Let your mind drift and don’t stimulate it with work or tasks. When we hold space to breathe, we often find that in the long term we can innovate more and come up with fresh ideas.
  • Take On a New Craft: having a side project unrelated to work can be a source of fulfillment. As an Enneagram Type 3, you’re likely pleased by checking off your to-do list. Having a project separate from your business endeavors gives you something to accomplish which is yours and yours alone, with an entirely different set of “success metrics.”
  • Don’t “Impress”: really focus on not over-sharing every small accomplishment you have. It might be tough, but slowing down the amount you “brag” about what you’re doing will help you start to curb the amount you seek external validation.
  • Practice Gratitude and Humility: don’t inflate your importance, especially to your close circle. Your inner circle gets to see the real you, entrepreneur hat off. Let that be the case.
  • Spend Energy on the Right People: if someone isn’t thinking about you, don’t spend your energy thinking about them! It’s easy to fixate on others, but let that energy be spent on people that deserve it.
  • Listen to Music: like this song, specifically designed for an Enneagram 3.

Enneagram 3 and Overpromising

Eager as Threes are, and with the zeal they have for new projects, it’s easy for a Three to get swept up into saying yes to everything thrown their way. Often, that means they take on projects that are beyond their skill level that they might not be a great fit for. While taking on projects beyond our skill levels can lead to immense growth, if done to a) please others or b) project confidence, the stress associated with the project may not be worth it.

Entrepreneurial Threes may feel obligated to take on everything thrown their way, but knowing when to say no and when to take on a big project is crucial. Remind yourself you’re allowed to set boundaries, and likely those boundaries start from within.

This is where rational Type 1s and decisive Type 8s thrive. They know how to say no, and take on projects that match up with their skills. Their internal goals, to be safe and protected often leads them to take on work they know they’ll thrive at, which in ways is admirable. They go into new projects with a sense of security that Threes typically are willing to forego.

Enneagram 3 Strengths & Social Selling

Threes are really good at talking. Really, really good. They’re often charming and compelling, which makes them excellent when it comes to social selling. As an entrepreneur Type 3, you’re likely hyper passionate about your business. That’s great! Use that to your advantage when you speak to others about what holes your service fills. Use your natural storytelling abilities to talk about what you do without blatantly talking about the features you offer.

Type 3s are notorious for motivating others and helping them find the best in themselves. It comes as no shock that Type 3 CEOs are such good listeners, because they pride themselves on wanting to give genuine and honest advice and guidance. Social selling works when you put the emphasis on the “social part.”

Remove the fluff from your conversations. If you’re speaking with a friend, do you use filler language? Probably not, so don’t do it in your sales conversations. Focus on the person you’re having a conversation with and help them learn how they could do their job better, not on the niche features your product or service has.

As a CEO, it’s easy to want to list off every feature you’ve meticulously worked on creating, but people don’t really care what the feature is, they care what it looks like for them and how it’ll remedy a specific problem they have. As a Type 3, use your sociable and charismatic nature to show your prospects you’re listening. They’ll open up to you and you’ll be able to educate them, which is what social selling is all about.

Resource generously provided by:

Drive Conversations as a Thought Leader

If your target audience is on Linkedin, then a Linkedin selling strategy is right for you. By publishing valuable, insightful, and personal content, with professional relevance, people will turn to you when they’re ready to buy. Easier said than done, right? Sort of.

As a Three, you already have the natural charisma and likability that people work their whole lives to achieve. As an entrepreneur, you possess the knowledge to solve someone’s problems. So write about that! Tell stories, share examples, give insight, and start thought provoking threads.

People no longer blindly make purchases from companies. They do their research and want to know that whoever they’re buying from is an expert in their field. Show people you’re an expert. Use your charming nature to your advantage. Engage with people that engage with your content. Write back to them, and when the time is right, go in for a meeting. By that point, you’re already at an advantage, because they trust you.

There’s no one-size-fits-all strategy to make this work, because there’s only one you.

Enneagram 3s: How They Interact With Customers

As an Enneagram 3, you likely have a very solid vision of what your ideal client looks like and how they interact with you. You’ve likely spent plenty of time synthesizing conversations in your head, only to discover when it doesn’t go exactly as you envision that you get thrown off.

As a natural charmer you might gravitate toward redirecting the conversation in the way you’d like.

Fight this urge.

Enneagram 3s need to focus their energy to truly listen to what they hear. You’re likely interacting with customers to get feedback on your product or business, and you’ll only be able to extract insight from that conversation if you allow yourself to absorb what’s being said. 3s take extreme pride and ownership in their products, so naturally you might avert your ears when something critical is being said. 

It’s also important to focus on only one thing at a time. As an overzealous entrepreneur, you might expect customers to tell you every single thing they think about your product. Likely, a customer will only have a handful of critiques for you at any point. You can always have another conversation!

Enneagram 3 Managers: Their Interactions With Employees

Enneagram 3s can make great managers and leaders. They are forces to be reckoned with and can be endlessly inspiring.

Something to note, however. Many 3 managers make it to managerial roles because they are fantastic individual contributors. Not all individual contributors make incredible leaders though. They might be fantastic at motivating themselves, but require coaching when it comes to leading others.

Enneagram 3s can be over competitive, and while there are elements of competition that are healthy in the workspace, inspiring negative competition can hurt a team. A three’s fear of failure however, likely supersedes any of their other pitfalls, ensuring that they always find a way for their team to succeed.

It’s really fun to find out which Enneagram type you are. Once you do, you’ll have a better understanding of why you act the way you do. It can be empowering to have insight like that. Before you dive into the test (give yourself roughly 15 minutes) which type do you think you are?

At RevenueZen, we work with all types of entrepreneurs to help bolster their growth strategies. Contact us to talk social selling, marketing, content strategy, or anything branding related. All Enneagram types are welcome.

It’s really fun to find out which Enneagram type you are. Once you do, you’ll have a better understanding of why you act the way you do. It can be empowering to have insight like that. Before you dive into the test (give yourself roughly 15 minutes) which type do you think you are?

At RevenueZen, we work with all types of entrepreneurs to help bolster their growth strategies. Contact us to talk social selling, marketing, content strategy, or anything branding related. All Enneagram types are welcome.