As someone with significant personal goals and a track record of incompletion to match, the productivity advice I’ve consumed over the years melts together into a mess of contradictions in my mind:
Do it every day, without fail, but remember to embrace failure.
Do what you’re passionate about, but do what you’re good at.
Be strict with yourself about meeting deadlines, but get enough sleep.
The devil is in the details, but remember: perfect is the enemy of good.
I think most of us know that, deep down, our productivity issues stem from, well, our Issues: things that might be better addressed with a therapist than through a trendy life hack. We turn to quick fixes because we want the path to productivity to be easy and we need it to happen now, with deadlines looming and goals slipping through our fingertips.
The problem is, we read advice that may be geared towards someone with completely different hang-ups. Where one of us needs a motivational kick in the butt, the other desperately needs to be told to take something off their plate. Where you might need to be reminded to let go of perfection, I might need a better system of keeping track of details.
A few years ago, I found something that broke through all the noise, a tool that allowed me to confront my work in ways that were consistent, meaningful, and practical: The Enneagram.
The Enneagram is a personality typing system that offered me guiding principles for my growth, grounded in a new understanding of my strengths, patterns, and challenges. It led to practical changes in my routines and productivity strategies, but also changes in my career and the type of work I feel capable of taking on. As someone who used to swear that I “could not do work by myself,” freelance writing would have been a non-starter for my former self.
Where other productivity techniques and personality systems can linger on the surface or are confined to one corner of life, the Enneagram is holistic and deep. Best of all, working with the Enneagram is fun. Rather than just a quick run-down of your traits, it’s an exploration into human behavior and motivation – why you do the things you do – that’s inherently fascinating.
You might be dubious. There are, after all, two types of people in the world: people who love personality typing and people who can’t stand it. I have met many people who fall into the latter category who end up loving the Enneagram because it’s truly unique as a personality system.
Chelsea Forbrook, a certified Enneagram coach from Minneapolis, puts it like this:
“It doesn’t just put you in a box and leave you there. It shows you the box you’re already in so that you can get out of it. It introduces choice and freedom to let go of the things that are no longer serving us.”
When we see the behavior patterns we fall into, and understand the motivations and fears that lie beneath, we begin to have a choice in how we respond where we previously didn’t see one. It works in the short term and the long term, providing insight that can help you choose the tools to get work done now, but also opening a path of self-discovery that can lead you to a healthier relationship with work (and yourself) overall.
What is the Enneagram?
Though purported to have roots in several ancient traditions, from Kabala to Sufism to Christian Mystics, the Enneagram was modernized by Bolivian philosopher Oscar Ichazo in the 1960s and became popular in the U.S. pop psychology scene beginning in the 1970s. Its following has been growing ever since. The Enneagram is used by therapists and social workers to help people better understand themselves, as well as by organizations — whether profit-driven (Best Buy, Mitsubishi), or mission-driven (Jesuit Volunteer Corps, Catholic Worker Houses) — to maximize strengths, address weaknesses, and increase empathy and cooperation among people who approach work and life in different ways.
The Enneagram is based on the idea that there are nine types of people, each centered around a different core belief we have about what makes us a safe, worthwhile, and lovable person. This becomes our core identity, and a series of logical patterns of behavior arise around the need to uphold it. Each type has strengths and weaknesses built upon a worldview that fuels and inspires them but can limit them when it becomes too rigid. I’ll provide a brief summary of each type, its basic fears and desires, as well as its most common productivity challenges. I also delve into the productivity strategies and orientations towards work that each type should consider.
How do you know which type you are?
You may be tempted to take a quiz, and there are various versions online, some for free and some more reputable options that charge a fee. While quizzes can be a helpful jumping off point for figuring out your type, they aren’t always accurate. In fact, I almost always get answers that aren’t my actual type.
The best way to determine your type is to learn about the patterns of thought and action each type struggles with and to notice which ones give you a twinge of recognition. Be ready to be simultaneously flattered and offended. As Forbrook says of the Enneagram, “It shows us things that we previously had not seen about ourselves. It shows us our gifts and our beautiful essence and our virtues. But to get to those things we have to slog through the shadow. People wanting to get into the Enneagram have to be willing to get uncomfortable.”
Pro tip: If you read about a type and feel personally attacked, it’s probably yours. If you read one and think, “that’s obviously the worst type, I’m glad that’s not me,” it’s probably yours. Even if you start out thinking you’re one type and change your mind, no worries: the process of examining your motives and increasing awareness of your behavior is valuable in itself.
Type One: * The Perfectionist * The Reformer * The Idealist *
Ones see the world in terms of good and bad, and they want their behavior, the people, and the systems around them to be consistent with their moral values. They are inspiring people who work tirelessly to improve themselves and the world and are capable of making great sacrifices for a higher cause.
They also get frustrated when they or others don’t live up to their high standards: a harsh inner critic constantly points out the way they and others could do better. Forbrook, an Enneagram One who works in schools, explains it this way:
“Being an Enneagram One, I notice how continuously high my standards are and how frustrated I get, either with myself or with the system or with my coworkers, for not doing enough. The Enneagram helps me remember: ‘that’s just your inner critic, it’s not the truth.’”
Core belief: “I am good because I do things right.”
Strengths in work: Diligent, meticulous, honest, champions of their values.
Challenges at work: Black-and-white thinking that alienates them from people and potential compromises, overwork leading to burnout, procrastination due to the pressure of perfectionism.
Getting things done: Decide what needs to be done perfectly and what can be just “good enough” and act accordingly. Schedule relaxation. Ask for help.
Big picture question: Is this about what is really good for myself or others? Or is this about my own personal purity?
Type Two: * The Helper * The Giver * The Mentor *
Twos measure their worth in terms of the strength of their relationships. They strive constantly for connection and are great at creating it; they are empathetic, supportive, and caring. Twos are the co-workers who bring cookies for your birthday and remember that you’re a bigger fan of chocolate chunk cookies than chocolate chip.
It’s hard work to be so considerate, and all Twos want is to feel loved and appreciated in return. When they don’t feel valued for their efforts, it can call a Two’s self worth into question. If a connection is uncertain or threatened, they can be desperate to manufacture it, serving others in the hopes of getting care in return and overexerting themselves (and annoying others) in the process. Twos grow when they learn that asserting and/or serving their own needs doesn’t make them unworthy of love. On the contrary, it makes it easier for others to give them the love they desire.
Core belief: “I am good because I am needed.”
Strengths in work: Warm, perceiving the needs of others, creating a culture of caring and connection, attracting powerful supporters.
Challenges in work: Overcommitting to please others, not stating their own needs, resenting a lack of appreciation.
Getting things done: Twos can do more by doing less. Start saying “No,” or “Let me get back to you tomorrow” when you are asked to do a task for someone. Evaluate why you truly want to do a task: is it because you are expecting something in return? Can you ask for what you need instead?
Big picture question: What if I took my own needs as seriously as the needs of others?
Type Three: * The Achiever * The Performer * The Motivator *
Threes are productivity royalty: they get things done and make it look easy. They adapt intuitively to different environments, figuring out what the expectations are so that they can exceed them. They want to be useful and admirable, and they have the stamina, finesse, and work ethic to do it.
The downside: they can get so focused on performing success, however their community defines it, that they lose sight of what they really want themselves. Emotions, insecurities, or doubts can feel like an irritating drag on the Three’s success train, so they try to leave their feelings behind and are irritated when others don’t do the same. As the achievements stack up, so can exhaustion and alienation. Threes grow when they learn to appreciate the wisdom and value in feelings, their own and others’.
Core belief: I am good because I am successful.
Strengths in work: Hardworking, practical, cheers on and mentors others, charming.
Challenges: Burnout from overwork, impatient with the needs of others, putting image above reality.
Getting things done: Threes need to slow down and check in with what they want to do, rather than what others want them to do. A meditation or journaling practice can be a great way to do this.
Big picture question: What would I want to do if no one was going to find out about my accomplishments?
Type Four: * The Individualist * The Romantic * The Original *
Type Fours see their life as a work of art: it should be beautiful, original, and true. The truth Fours seek is not what’s on the surface but instead in the depths of the human experience. Fours are creative, artistic, and romantic. They don’t shy away from the darker or absurd parts of life, and their love of honesty makes them excellent friends for those seeking a co-conspirator and a non-judgemental audience.
Fours are constantly aware of the romantic, idealized version of their life that reality doesn’t live up to, which can result in depressive, self-loathing spirals where Fours retreat into fantasy and resentment; if they can’t be special, at least they have the intellect to notice how unspecial they are. Fours grow when they move toward action and give themselves permission to find brilliance in everyday acts of expression and care.
Core belief: I am good because I am unique.
Strengths in work: Visionary, unafraid of difficult topics, attentive to aesthetics and beauty, original.
Challenges: Feeling demeaned by ordinary (and often necessary) tasks that do not utilize their talents, envious of the success of others, delaying action by entering their internal world.
Getting things done: Create a beautiful workspace — light incense, use a nice pen, and play inspiring music, etc. Remember that any task can be dignified and beautiful when performed with your own original spin or with a larger cause in mind. Remind yourself that technical and practical work and knowledge are often the foundation of creative inspiration.
Big picture question: Does it have to be exceptional to be meaningful?
Type Five: * The Investigator * The Observer * The Thinker *
Fives are the most cerebral type of the enneagram. They want to know the truth, and the path to truth is through dispassionate, objective study. They are thoughtful, diligent, and often ridiculously good at trivia. Too much time with people can exhaust Fives, who feel most comfortable in the neat and solitary world of ideas and facts, uncluttered by messy emotions and urgent demands.
In an effort to remain objective, Fives can ignore their own feelings and look down on those of others, but in doing so they deny an essential truth of life: everyone has a perspective, and no one owns the truth. Fives grow when they stop feeling threatened by emotion and realize it’s easy for them to stay dispassionate when they stay out of the fray. They learn that a part of their comfort living in their heads comes from a fear of making mistakes or revealing incompetence. When they move out of research and into action they feel more connected and less alone.
Core belief: I am good because I know the truth.
Strengths in work: Excellent researchers, curious, eager to learn, excel at objective analysis.
Challenges: Over-researching when a decision needs to be made, appearing insensitive and aloof to the emotions of others, undervaluing the opinions of others (especially if they aren’t presented in a dispassionate way).
Getting things done: Make a list of what you need to know and why before jumping into research, take a walk or do something active to get in touch with your gut feelings, and offer to help others on your team to get out of your own head.
Big picture questions: “What if understanding people, their feelings, and relationships was just as important as understanding facts?”
Type Six: * The Loyalist * The Skeptic * The Trooper *
In a few, shining moments in their life, Sixes have felt safe and secure. When the illusion is shattered, Sixes spend their mental energy trying to earn back the safety they crave and to game out all of the disruptions that could take it away again. Safety presents itself as a combination of community, relationships, ideology, and the ability to predictably meet core needs. On the lookout for danger, Sixes are excellent at troubleshooting and addressing problems before they happen. Interested in building alliances and creating networks of support that can weather tough times, Sixes are loyal, supportive, and hardworking members of a team and ride-or-die friends (often with a witty and self-deprecating sense of humor).
When they let their anxiety and doubt control them, they can become defensive, pessimistic, and reactionary. They have fraught relationships with authority figures who they idealize as their protectors and guides, only to become highly critical and disillusioned when these figures are unable to live up to those high expectations. When they accept the fact that they cannot control everything and choose to trust in themselves, Sixes can grow as leaders and exemplify courage in the face of adversity.
Core belief: I am good because I am safe.
Strengths in work: Community-builder, excellent troubleshooter, synthesizes information, loyal to a team or cause through difficulty.
Challenges: Anxiety leads to procrastination, endless gathering of others’ opinions, researching to try to avoid mistakes, and outsourcing decision-making due to self-doubt.
Getting things done: Create comforting routines and boundaries around work (such as the Pomodoro method), end each day with a list of what you did get done in addition to what you will do tomorrow, and quiet the mind with a body-focused meditation practice.
Big picture questions: What would I do if I trusted that things are not as fragile as I think they are?
Type Seven: * The Enthusiast * The Epicure * The Visionary *
A Seven builds their sense of self out of experiencing all of the joy and excitement that life has to offer. It’s always fun and exciting when a seven is around, and when things get boring they may suddenly have other plans. They want to focus on the positive and love to learn new things and meet new people. They have a boundless, generative energy and bring with them a feeling of abundance.
However, their endless activity and excess of plans can be a way to avoid the anxiety of what it would mean to slow down and confront the darker sides of life. They can miss out on experiences of depth by jumping to a new thing as soon as the going gets boring. Being truly present to the joy they create, instead of constantly thinking about the next great thing, will mean slowing down enough to confront the challenging and mundane aspects of life.
Core belief: I am good because I am joyful.
Strengths in work: Boundless positive energy, endless new ideas, motivating, excited to learn new things.
Challenges: Struggling to complete the many new things they start, overcommitting, dismissing negative emotions or realities (and the people who articulate them).
Getting things done: Before committing to a new project, make a pros and cons list, and write out how you will deal with the cons. Make a habit of promising less than you think you can deliver in the moment (no one will be upset if you over-deliver). Create systems that minimize exciting distractions while you work.
Big picture question: Which of life’s great experiences will I miss out on if I avoid all pain, boredom, and sadness?
Type Eight: * The Challenger * The Boss * The Protector *
Eights are fighters: they have seen (or experienced) the abuse of power and decided they would become strong enough to fight back. They see themselves as the protectors of themselves and their team. There is no time for platitudes, conflict avoidance, or coddling in the battlegrounds where Eights live: they are brutally honest, forceful, action-oriented, and can be downright disdainful of those who baulk at this ethos. Eights often feel they need to be in charge if the mission is to be completed without casualties: they are shouldering authority both to protect others and out of an inflated sense of their own infallibility. Eights challenge and inspire their teammates with their blunt feedback and lofty vision.
They can also be dominating, vengeful, and arrogant when they feel they have been betrayed by disloyalty or weakness. Eights grow when they learn to distinguish a threat to them and their team from a threat to their ego. Then they can start to truly use their heroic efforts in service of others, rather than in service of their own self-image.
Core belief: I am good because I am in control.
Strengths in work: Confident, persuasive, direct, highly productive.
Challenges: Domineering, impatient with perceived weakness, difficulty controlling anger.
Getting things done: Look for the strengths in others that you can build on by delegating responsibility and mentoring, recognize the power of being a good listener and build that skill, pick your battles by asking whether this could be solved diplomatically rather than forcefully.
Big picture question: Am I really acting out of confidence, or to mask an insecurity?
Type Nine: * The Peacemaker * The Harmonizer * The Mediator *
Nines feel safe when their actions, thoughts, and community are in harmony with each other. In a messy world full of opposing viewpoints, they feel the need to minimize their own needs and desires in order to create harmony, not just between themselves and others, but between everyone in their community as well. They are excellent at understanding the validity of multiple points of view and finding points of reconciliation between people and ideas.
The Nine’s desire to avoid conflict can cause them to compartmentalize and ignore or minimize conflict. They can sacrifice their own desires and needs in order to be agreeable, but deep down feel a growing resentment. When the Nine learns to uncover their own deeply held beliefs and take decisive action, they can be inspiring leaders who build consensus, appreciate input, and combine different strengths and methods in pursuit of a common goal.
Core belief: I am good because I am peaceful.
Strengths in work: Creates safe spaces for open dialogue, able to understand many viewpoints, excellent mediator, easygoing and relaxed demeanor.
Challenges: Procrastinates to avoid conflict, merges with others’ viewpoints to avoid disagreement, gets lost in big-picture thinking for small decisions.
Getting things done: Choose what to finish next, not what to do next, ask whether this is your issue to solve or someone else’s, don’t repress your anger; let it lead you to your true opinion/value and motivate you to action.
Big picture question: What could I contribute if I valued my own opinion as much as everyone else’s?
I bet at least one of those jumped out at you as illuminating, familiar, or downright rude. I hope it made you feel seen, not just as a “worker”, “content creator”, or “entrepreneur”, but as a person. That’s what I value the most about the Enneagram and its influence in my work: it wasn’t designed as a way to make productive cyborgs out of employees. It’s rooted in the quest to be true to yourself and to live a good life. Maybe it’s just the Six in me talking, but it’s a relief to have a source of wisdom about myself that I can really trust ––something that is about improving my life, not just a hack to squeeze one more task into the day. It’s that trust, and the awareness of how it fits into my larger life, that keeps me on course when I want to slip back into old habits.
Don’t take my word for it — start exploring! I recommend the following resources to delve further:
Don Richard Riso and Russ Hudson The Wisdom of the Enneagram: The Complete Guide to Psychological and Spiritual Growth for the Nine Personality Types
Beatrice Chestnut The Complete Enneagram: 27 Paths to Greater Self-Knowledge
Helen Palmer The Enneagram in Love and Work: Understanding Your Business and Intimate Relationships
David Daniels, M.D. The Enneagram, Relationships and Intimacy
