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Are You Satisfied With Your Current Career and Life?
Are you satisfied with your current career and life? You may want to act more boldly, gain more influence, and grow as a leader — yet find yourself unable to take that first step. Fear of failure, anxiety about an uncertain future, concern about how others see you... These are the "invisible cages" that bind our unlimited potential. But what if you had the "courage" to break those cages and get what you want? Jenny Wood spent 18 years at Google rising from entry level to executive, achieving success at every stage. Drawing on her own experience and research, she proposes nine bold traits — "Wild Courage" — that turn conventional thinking upside down.
In this article, drawing on the content of a talk Jenny gave at Google, we dig deep into the specific ways of thinking and practical techniques for breaking through stagnation and accelerating goal achievement and leadership. By the time you finish reading, the "wild courage" sleeping inside you should awaken and you will have found clear hints for taking action.
Unconventional Leadership: How to Redefine "Bossy" and Generate Influence Through Listening The "Brutal" Power of Decision-Making: The Secret of Prioritization That Guards Your Time and Energy The "Obsessed" Mindset That Produces Exceptional Results: Four Communication Techniques From a Google High Performer Monday Manifesto Pulit and Bullet Tame the Octopus Woo with You Summary Unconventional Leadership: How to Redefine "Bossy" and Generate Influence Through Listening
At the root of the stagnation many people feel in their careers and lives is "fear." When Jenny Wood had a fateful encounter on the New York subway, what made her hesitate were three fears: "What if he has a criminal record?" "What if he's married?" "What if I get laughed at on a crowded train?" These are classic psychological patterns that cause us to hold back from acting — the fear of failure, the fear of uncertainty, and the fear of other people's judgment. Within organizations in particular, the "fear of other people's judgment" is especially troublesome. It generates an inner voice that says "What will people think if I do this?" or "Will I get labelled as...?" — and limits our actions.
Jenny Argues That the Negative Labels Born From This "Fear"
Jenny argues that the negative labels born from this "fear" are precisely what we need to redefine and reclaim to become bold leaders. The nine traits she cites — Weird, Selfish, Shameless, Obsessed, Nosy, Manipulative, Brutal, Reckless, and Bossy — may at first glance seem to be the opposite of qualities a leader should have. But the fear of these words is exactly the lattice of the "invisible cage" that keeps us small, quiet, and followings. Jenny teaches that if these traits are channeled "in a sane and intelligent way," they can dramatically accelerate success. For example, "Bossy" can be elevated into "the courage to listen and lead"; "Brutal" into "the courage to protect your time, energy, and priorities"; and "Obsessed" into "the courage to set your own standards."
In this section, we focus specifically on the trait of "Bossy" — digging into its redefinition and how to practice it. When most people hear "Bossy," they picture someone who issues one-sided commands and tries to control others. But Jenny points out that this is the behavior of a "frightened leader." A failure story from her own past speaks volumes.
When she first became a leader managing managers as a senior leader, she was plagued by serious imposter syndrome (the psychological state of feeling like a fraud). Faced with a major project — the closure and reconstruction of an entire business division — she worked alone overnight to create a 30-page presentation for the next day's offsite meeting in an attempt to silence her anxiety. Mission statement, pillars of the transition plan, the leader for each pillar... she thought she had prepared everything perfectly. But the moment she began her presentation, the room went cold. Her plan was received as an insult to the experienced managers. "Why didn't you ask for our expertise first?" "We know this business far better than you do" — their feedback was withering.
What Jenny learned from this experience was that the essence of "Bossy" is not giving commands — it's "guiding others toward success" and "having the courage to lead through listening." True leadership comes not from one-way directives but from building collaborative relationships through working together. One of the crucial lessons she should have known is the principle that "people only buy in when they participate." This is backed up by a psychological phenomenon known as the "IKEA Effect." In an experiment conducted by Duke University researchers, participants were divided into two groups — one given a pre-assembled IKEA box, and the other given a kit to assemble themselves (with a hex key, instructions, and all the parts). When both groups were subsequently given the opportunity to sell their box to the researchers at whatever price they named, the self-assembly group set prices an average of 63% higher than the group that had been given the pre-assembled box. This demonstrates that people place a higher value on and feel more attached to things they have personally put effort into creating. Jenny's offsite failure was precisely the result of ignoring this IKEA Effect. She should have involved the leadership team in the planning process from the very beginning. True "Bossy" is not pushing your own ideas — it is collaborative leadership that draws out the team's knowledge and charts a course toward shared goals together. This experience teaches us how leaders should draw out the full power of their teams and guide them toward common goals — and that "listening" is the key.
The "Brutal" Power of Decision-Making: Protecting Your Time and Energy
The "Brutal" Power of Decision-Making: The Secret of Prioritization That Guards Your Time and Energy
The next trait to explore is "Brutal." This means "the courage" to protect your time, energy, and most important priorities. While this word sounds negative at first, Jenny redefines it as "the power to draw a line between what you will and will not do, what you will and will not take on" — in other words, ruthless prioritization. But drawing this line is sometimes harder than you might expect. A painful experience Jenny shared from her own life throws the difficulty and importance of this into sharp relief.
A few years ago, Jenny was flying from Boulder, Colorado to New York for a Google business trip. Because her in-laws lived in New York, she left her five-year-old daughter Noah with her grandparents for the first time, handing her off to them at the airport before heading into Manhattan for several days of in-person meetings. Mid-morning meeting with direct reports, team members, her manager in New York — an important lineup of appointments. During a breakfast meeting with a direct report, just as she took her first bite of an egg and cheese sandwich, a text from her mother-in-law appeared: "Please call me." When she picked up, her mother-in-law said "Noah is fine" by way of preface — before telling her there had been an accident. During morning cookie making, Noah's hair had gotten caught in the mixer and a piece had been pulled from her scalp. Checking via FaceTime, she could indeed see that some hair was gone. Fortunately there was no bleeding, and a video consult with a relative who was a pediatrician concluded it was a minor injury. Her hair would grow back.
But Noah's emotional distress was immense. "Mommy, please come. I can't go back to school. Everyone will laugh at me for having no hair. Please, Mommy, come." Naturally, part of Jenny wanted to drop everything and rush to her daughter. But when her mother-in-law asked "How soon could you get here by car from Manhattan?" Jenny hesitated. She checked her calendar — only a 30-minute lunch slot and a short afternoon break were open. And then the rationalizations began. "Noah will calm down quickly." "She'll just be bored in the car for two hours." "My poor in-laws are already near hysteria. No need to bring a bored five-year-old all the way into Manhattan." "If Noah doesn't want to go back to her grandparents' place, I'll have to rescheduling everything." She ran through it all and made her decision: "Noah will be fine. No need to bring her to the city. I'll see her in a few days." Ending the FaceTime, turning back to the now-lukewarm egg and cheese sandwich, her direct report said "Go to your daughter — we can reschedule everything." Jenny replied "No, these meetings are too important." She couldn't cancel with the teammate who had flown in for 16 hours from India. She couldn't miss this rare in-person one-on-one with her New York manager. She kept telling herself this. Later, when she called her in-laws, Noah had found a new pink sequined hat she loved and was doing fine — playing with cousins, doing a dance routine, playing house with the babysitter, exactly as expected.
But Two Days Later, When Jenny Met Noah in Person, the Reality
But two days later, when Jenny met Noah in person, the reality was far more serious than she had been telling herself. When Noah nervously removed her hat, the extent of the hair loss was much worse than Jenny had imagined. "What was I thinking?" The regret hit her hard. All she needed to do was say "no" to the work schedule and "yes" to her daughter. Instead she went to her meetings. All she had needed to do was be "Brutal" — to coldly prioritize, to say no to her calendar.
This story is not a simple tale of choosing between work and family. Both matter. But Jenny honestly acknowledges that she "chose the easy path" in that moment. It was a moment of truth, and she misjudged it. She failed to summon the "Wild Courage" to honor her boundary. Noah's hair took two years to fully grow back, but it did. Yet for those two years, every time she watched it slowly grow back in, Jenny says the feeling was heartbreaking.
This may be an extreme example, but in our everyday lives too, our calendars are always asking "what are you voting for?" In a given hour, week, or month — what will you prioritize? Sometimes, saying the simple word "no" requires "Wild Courage." That is the essence of "Brutal." The courage to protect your time and energy. The power to say "small no" for the "big yes" that truly matters to you right now. It is the courage to discern what is truly valuable to you and draw a firm line against everything else.
The "Obsessed" Mindset That Produces Exceptional Results
The "Obsessed" Mindset That Produces Exceptional Results: Four Communication Techniques From a Google High Performer
The final trait to explore is "Obsessed." This means "the courage" to refuse to settle for average — to set your own high standards and drive toward them. The example of Annabelle, a top performer on Jenny's team, illustrates the power of this trait. The reason Annabelle made remarkable progress at Google was that she was "Obsessed" in the healthy sense. The word "average" did not exist in her vocabulary. This version of "Obsessed" refers to an attitude of engaging with passion, sparing no effort, and persistently pursuing goals. Her enthusiasm powerfully propelled both her performance and her career.
Here are four specific communication techniques Annabelle practiced that will accelerate both results and career — concrete tools you can put to work in your daily practice of healthy "Obsessed." As you read through, select the one you most want to try.
Monday Manifesto
This Is Not a Simple Progress Report
This is not a simple progress report. It is an opportunity to demonstrate your value and effectively highlight what you are proud of. Every Monday, in under 15 minutes, create a brief email summarizing two things you were proud of last week and two things you are looking forward to this week, and send it to your manager. Even if you hold regular one-on-ones, creating this email creates a record of your achievements that your manager can easily forward and share with their own manager. In Jenny's experience, team members who did this consistently stood out as top performers. They clearly demonstrated that they were truly creating value and approaching their work with pride. As a leader, Annabelle would write her manifesto to her team members and CC Jenny, using it to help share priorities across the whole team.
A further tip to amplify the effect: "double the numbers." Annabelle's manifesto was full of specific figures. "Improved the sign-up process from 3 steps to 2," "70% completion rate," "meetings with 6 stakeholders" — concrete numbers are far more persuasive than vague reports. Saying "met with 6 stakeholders" conveys far more specificity and impact than simply "met with stakeholders."
And the most important point: Annabelle used the words "I'm proud." Expressing positive emotions about what you have accomplished not only raises your own sense of self-worth but has a positive influence on those around you. Whether big or small — "made Ube cookies," "booked a trip to the Galápagos for myself and my parents," "asked for help preparing for an interview," "set expectations in under an hour" — recognizing what you are proud of and sharing it is enormously powerful.
Pulit and Bullet
Pulit and Bullet
This is a technique for making communication — especially written communication like email — more concise and effective. If an email to an important stakeholder or someone senior is filled with long paragraphs of text, cut 50% of that text and replace it with bullet points. "Pulit and Bullet" makes it easier for the recipient to quickly and accurately understand your intent, and raises your influence. The very first email Annabelle sent when she wanted to join Jenny's team was a perfect execution of this technique. Three bullet points describing her strengths, the first few words of each bulleted in bold to draw attention, and each bullet deliberately kept to a single line. This was a powerful signal of how clearly and effectively she communicated with clients and partners. By contrast, an email Jenny herself had sent in the past to request a meeting was "a garbage fire" — stuffed with so much information the intent was unclear. The more important the email, the more worth it to take the time to "Pulit and Bullet."
Tame the Octopus
If "Pulit and Bullet" is for written communication, "Tame the Octopus" is a technique for making verbal communication concise. This was not something Annabelle was naturally good at from the start — it was a skill she developed through effort. That fact carries an important message: these skills and traits are not innate; anyone can learn and develop them.
Imagine Speaking With Your Thoughts Sprawling in All Directions
Imagine speaking with your thoughts sprawling in all directions like octopus tentacles — making it hard to land the key point. That does not convey your intent efficiently. "Taming the octopus" means developing a way of speaking that delivers points more efficiently. As Jenny demonstrated, the key is to take a "pause" when asked a question. Taking a pause does not make you appear less confident — it actually conveys composure, confidence, and thoughtfulness. During a meeting, take the time to gather your thoughts before unmuting yourself; in an interview or important one-on-one, say "Let me think about that for a moment" and collect yourself. Then organize your thoughts in your head (or take a note), narrow down to about three key points to convey. When you speak, start by stating just the keywords (e.g., "Priorities, tools, global coordination"), then add a brief explanation for each keyword, and close by repeating the keywords again (e.g., "In summary, our biggest challenges are priorities, tools, and global coordination"). "Tame the Octopus" is one of the most important skills for building credibility as a leader and earning the trust of others.
This is also a communication technique focused on showing respect to the other person and understanding their needs. It connects to the positive side of "Manipulative" — "the courage to build influence through empathy and create lasting relationships." When selling a product, an idea, or yourself, the key to success is always "mutual benefit." Find what the other person wants and give it to them — in other words, shift the focus from yourself to the other person.
Annabelle was deliberate about reducing the number of sentences she began with "I" and increasing the number she began with "You." In a first draft of a follow-up email to send to a team after a product training, many sentences began with "I." But in the final version revised based on Annabelle's advice, every sentence started with "You." This transformed the email into something far more centered on the recipient, conveying consideration and respect. "Woo with You" is a powerful tool for building stronger trust and influence by standing in the other person's shoes and thinking about their interests.
These Four Tools — Monday Manifesto, Pulit and Bullet, Tame the Octopus, and Woo with You
These four tools — Monday Manifesto, Pulit and Bullet, Tame the Octopus, and Woo with You — are concrete weapons for bringing out healthy "Obsessed" in your daily work and accelerating both your business and your own career. Why not try at least one of them starting tomorrow?
Jenny Wood's grandmother, Grandma Raya, was a remarkable person. She served as a bridesmaid at Jenny's wedding at 88, and served as CEO of her own financial services company until she was 92. Her signature phrase was "No is just an opening offer." On the night early in Jenny's marriage when she learned her husband John had been laid off in a large-scale restructuring, when the two were devastated, Grandma Raya said what she always said: "No is just an opening offer." John argued "The layoff is final," but Grandma Raya counseled him: "Of course, it's easier to accept no. But that discomfort will fade. Set your ego aside and find a middle ground. You each want something. The company needs the work done but can't afford to pay you. You need the job, because being employed makes it easier to find the next one." Ultimately John relented — and the next day proposed to his manager: "Let me keep working 10% of the time for 10% of my salary while I look for my next job." Remarkably, the company accepted.
This story is not simply about negotiation tactics. The essence of Grandma Raya's teaching is "don't let fear drive your decisions." How often do we hesitate to act because of fear? Unable to ask our partner for what we need, unable to ask a client for help, unable to approach someone we're interested in on the subway... When we don't act, there is almost always "fear" at the root. Fear of failure, fear of uncertainty, fear of judgment from others — or fear of being labeled "selfish," "shameless," "bossy," "obsessed," or "brutal."
But Jenny Emphasizes This
But Jenny emphasizes: "If fear is at the root, that's wonderful news." Because fear is something we can address. We can act on fear with agency. When we summon "Wild Courage" — the courage to pursue what we want in life — we discover an essential truth: whether we succeed or fail in any individual attempt, there is no moment when we feel more purposeful, powerful, and alive than when we are overcoming fear and pushing forward toward the joy and success on the other side.
Reference: https://www.youtube.com/watch?v=MTzhQ-E5wcQ
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