PDF Summary:Wild Courage, by Jenny Wood

In Wild Courage, Jenny Wood explains that many people struggle in their lives and careers because they’re afraid of taking the bold actions necessary to succeed. They fear being judged as strange, pushy, or self-centered rather than authentic, driven, or confident. However, Wood counters that the negative stigma around bold actions is unfounded—people judge others who break conventions because they feel threatened by their courage. Therefore, to become a success, Wood says to be courageous and act boldly—be authentic, driven, curious, and persuasive. Advocate for yourself, enforce your boundaries, and don’t be afraid to lead others.

In this guide, we’ll first explain why courage is crucial for taking bold action. Then, we'll discuss the actions Wood says are necessary for both professional and personal success. We’ll also supplement Wood’s advice with insights on authentic living and professional success from authors like Brené Brown, Stephen R. Covey (The 7 Habits of Highly Effective People), and Patrick Lencioni (The Advantage).

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Finally, Wood warns not to let your driven nature slip into negative territory: Don’t get sucked into perfectionism, set realistic standards, and be sure to set personal time aside to care for your well-being.

(Shortform note: Emily and Amelia Nagoski explain in Burnout that engaging in perfectionism, setting unrealistic standards, and failing to care for your well-being can lead to burnout. This state of stress overload leaves you feeling exhausted, apathetic, and antisocial, and it can be detrimental to both your professional performance and your physical and mental health.)

Action 4: Be Curious

People often equate curiosity with nosiness; however, Wood recommends braving your fear of being judged as nosy. She explains that practicing curiosity is crucial to success for two reasons: It introduces us to new knowledge, opportunities, and people, and it helps us stand out—asking questions shows engagement, and this is what bosses look for.

(Shortform note: While Wood focuses on the benefits of curiosity to professional success, Scott Barry Kaufman explains in Transcend that curiosity is also a fundamental human need. This is because curiosity triggers growth, and constant growth is how humans reach their full potential and ultimately attain fulfillment in life.)

How to Encourage Curiosity

First, use your curiosity to help you make connections with new people. Making connections is important because our network is often where we turn to get help or learn about new opportunities. However, many professionals struggle to make connections due to anxiety about how others perceive them. Wood says you can overcome this by focusing on the other person rather than yourself. Make it your objective to learn about them—you can even do some research about them before your introduction and ask them about things you know they’re interested in or that you have in common.

(Shortform note: Keith Ferrazzi reiterates the importance of networking in Never Eat Alone and offers alternative advice for overcoming networking anxiety: Solve the issue at the root by improving your communication skills. One way to do this is by choosing a confident role model and observing their behaviors during communication—over time, you’ll naturally start to adopt their mannerisms and confidence. Further, practice your public speaking skills—if you’re confident in your abilities to communicate well, you’ll feel less anxious when reaching out to new people.)

Wood also notes that asking simple questions during meetings is a great way to build connections. Asking seemingly obvious questions may seem silly, but there are probably others who were too nervous to ask the same question. Being the one to speak up will make people appreciate you and see you as an approachable person.

(Shortform note: If you find yourself at a loss for words during a meeting, consider compiling a cheat sheet of expert-recommended questions you can ask. For example, in team meetings, ask about the team’s next priorities, tasks or behaviors the team should stop doing, whether there’s anything extra you can do if you have the time, and what the team’s biggest challenge is at the moment.)

Further, if you find yourself envious of others, Wood says to turn your envy into curiosity about how they succeeded so you can achieve the same success. You can observe their techniques, habits, and methods of communication and test them out to see which ones work the best for you. Or, you can even ask the people you envy to mentor you.

(Shortform note: To turn envy into curiosity, experts recommend first pausing to consider what about the situation made you envious. This will help you pinpoint what exactly you desire so you can go after it. For example, imagine you felt envious when you saw your coworker wearing a unique new outfit to the office. Were you envious because she had a new outfit and you didn’t, or was it because she had the confidence to wear something out-of-the-box to work? Pinpointing what exactly caused your envy will direct your next actions.)

Finally, Wood warns of two specific situations where you should consider checking your curiosity to ensure it continues serving you:

• Be aware of social contexts and others’ boundaries when getting curious about others, so you don’t ask something inappropriate or insensitive. (Shortform note: While it’s useful to try and read social cues to ensure you act appropriately, remember that some people struggle with social cues—especially neurodivergent people. Rather than judging people if they misstep, try understanding their experience.)
• Don’t pursue higher education just because it sounds good or you think it will be expected of you to advance your career. Instead, spend time seriously investigating your career goals, the industry norms, and the financial implications and benefits of pursuing a degree, and pursue areas of study that you’re genuinely interested in. (Shortform note: Online tools like Career Explorer can help you determine not only the best career path or job for you, but the specific experience and degrees it requires so you can spend your time and effort in the right areas.)

Action 5: Be Persuasive

We’re often taught that trying to persuade other people to give us what we want is manipulative; however, Wood says that persuasion is natural and necessary to achieve your goals. You often need to get others on board to help you succeed, whether that’s convincing your manager to promote you or recruiting a colleague to teach you a new skill. The key to being persuasive and not manipulative is using empathy to tune into what others want and make sure they also benefit from helping you.

(Shortform note: Robert Greene reiterates in The Laws of Human Nature that learning persuasion is necessary because you’ll eventually need to influence others to get what you want. Additionally, Greene cites a few other reasons why learning persuasion is important, one being that persuasion is unavoidable—people respond and react to each other daily, so whether you intend to or not, you will inevitably influence others. Further, being influential rather than bluntly honest can benefit others by giving you the ability to change people’s minds. For example, rather than simply explaining the facts of a given war, you can influence people to be on the correct side.)

How to Be Persuasive

Wood suggests that influencing others starts with understanding the politics of your organization. The person who’s technically your superior isn’t necessarily the person with the most power or influence over your future at the company; a co-worker from another department who’s friends with the boss might have more leverage in getting you a promotion. You might have to play politics with that person rather than your direct manager. Understanding politics is also useful so you know how to get on people’s good sides, what bothers them, and what you can do to help them—doing nice things for other people is one of the best ways to get help from them in the future.

(Shortform note: Other experts offer some concrete tips on how to use politics to help you succeed. First, before getting involved in office politics, clarify your goal—for example, are you trying to quickly advance your career, or just trying to network? Then, observe what is praised and punished within the culture to understand how you should act. Once you’re ready to jump in, experts recommend, like Wood, that you start by doing things for others before asking favors. Further, when you get power or an advantage, leverage it quickly; these opportunities don’t stick around unless they’re used.)

Wood also advises managing your relationships from all sides to maintain strong connections with potential allies. Rather than solely focusing on making nice with your direct superiors, try to improve relationships with those who work next to you, below you, far above you, and diagonally to you. Strive to have face-to-face conversations with your superior’s superior and your superior’s colleagues. To get your foot in the door, try getting a meeting by offering praise and requesting advice from them. Further, don’t neglect the relationships with your colleagues and those working below you—you never know who could one day end up in charge or who may have valuable skills you’ll need down the road.

(Shortform note: While Wood says building a broad network is important, Helen Tupper and Sarah Ellis argue in The Squiggly Career that you must be intentional about who you include—don’t build relationships with people just because you can. This is because humans can maintain only around 220 relationships at a time—with roughly 150 of those being the casual kind you have with most professional contacts—so who you let in matters. In particular, the authors recommend networking with people who can help you achieve your current job goals, future career aspirations, and personal objectives.)

While persuasion is crucial, Wood offers some advice to ensure your persuasion doesn’t backfire. First, acknowledge that managing relationships with others sometimes means putting on a happy face even if you’re not totally feeling it. Second, don’t try to win people over by fawning—this doesn’t demand respect. Instead, interact with everyone as their equal, no matter their standing.

(Shortform note: In The Laws of Human Nature, Greene reiterates that to successfully persuade people, we need to give them what they want—even if it means being a little inauthentic. Greene elaborates that in the majority of situations, what people want most is to be validated. Validating someone's self-opinion lowers their defenses, allowing more space for your persuasion to enter their mind. Greene emphasizes that if you try to persuade people with any method other than validation—like fawning or guilting them—you might get them to do what you want, but only once. Afterward, they’ll end up resenting you and be unhelpful.)

Action 6: Be Firm

Wood explains that setting boundaries is crucial for meeting your personal and professional goals, even if people judge you as being harsh. This is because your boundaries protect your peace and priorities, helping you live a life you’re proud of without regrets. But your boundaries are only beneficial if you enforce them. Enforcing your boundaries means drawing a line between what you are and aren’t willing to accept, and taking action when this line is crossed. For example, if you prioritize family over work, tell your boss that asking you to cancel a family plan for a last-minute meeting is crossing a boundary.

(Shortform note: Greg McKeown reiterates the importance of enforcing boundaries in Essentialism, and warns of what could happen if you don’t. According to McKeown, failing to enforce your boundaries will allow people to encroach to the point where your boundaries no longer exist. Other people will then be in control of your agenda. Eventually, you’ll be spread so thin that you’ll no longer be productive.)

How to Set and Enforce Boundaries

First, Wood recommends getting comfortable enforcing your boundaries. Initially, enforcing boundaries—like saying no to a task someone asks you to do so you can focus on something more important—might make you feel anxious or guilty. While this is normal, Wood suggests remembering the favor you’re doing yourself—you’re putting your time and effort toward the things that are going to make the biggest positive difference for you.

(Shortform note: Enforcing your boundaries with people who are demanding or lack respect can be difficult—in Essentialism, McKeown offers tips to help you handle these situations. First, if someone asks you to handle their responsibility or help with issues they haven't attempted to solve, decline or offer to help at a later stage. Second, if someone repeatedly disrespects your boundaries by demanding your time, identify common requests from them that you’ll refuse unless circumstances require otherwise. Finally, when working with repeat boundary-crossers, create a clear agreement outlining what you will and won’t do.)

Further, Wood advises setting boundaries around email to conserve your time—spend less time reading emails and send fewer responses. To do this, Wood offers a four-step formula: First, filter emails to separate unimportant ones like promotions from important correspondence, and unsubscribe from useless email lists. Second, set aside a time-block for email and only respond during that period. Third, when taking time off, create an automatic response requesting that people indicate the importance of their email so you can read what’s necessary when you return. Finally, consider whether a response is necessary—if you’re only responding because you feel like you should, you probably don’t need to.

Minimize Email Time-Wasters

In Indistractable, Nir Eyal provides additional information about spending less time on email. First, he explains that filtering email also saves time by reducing email addiction. We compulsively check email because we never know what we’ll find, and this search for random rewards is addictive—filtering out non-essential messages and unsubscribing from promotions removes this uncertainty and the urge to constantly check.

Second, during your email time-block, Neyal recommends sorting emails into folders for immediate responses and those needing later attention. This prevents you from rereading emails later to reassess response timing. Asking people to indicate the urgency of their email as Wood recommends can further simplify this process.

Finally, rather than simply not responding to non-crucial emails, consider Eyal’s recommendation to intentionally slow down the rate of correspondence. You might still want to respond to an email even if it’s not technically important. Waiting a few days before responding can allow you to do this while still minimizing email influx. Giving a slow response will make the matter seem less urgent and encourage the other person to respond slower as well, reducing the number of emails exchanged and the overall time spent on the chain.

Finally, Wood recommends reminding yourself to be respectful when enforcing boundaries. There’s no need to be aggressive or dramatic. Simply inform people of your boundaries, and kindly detach from those who don’t respect these limits.

(Shortform note: How do you respectfully enforce boundaries and detach when necessary? Experts provide a few tips. To enforce your boundaries when they’re crossed, restate your needs to the other person, have appropriate consequences for when boundaries are crossed, and be willing to assert those consequences. To detach from someone, determine what type of detachment is necessary—in some cases, you might want to cut all contact. In others, you may want to limit the access this person has to you—for example, you might be OK in a group situation with them but not spending time with them one on one.)

Action 7: Be a Go-Getter

Many people fail to achieve their goals because they’re afraid of taking risks and being called impulsive or reckless—instead, they let overthinking delay action. But Wood says that being successful requires you to have the courage to act fast and be willing to take risks. If you wait for the perfect moment or to have 100% certainty in your plan before starting something, you’ll never start. Further, risks are necessary for you to progress, and people are generally more regretful over the risks they didn’t take than the unsuccessful ones that they did.

(Shortform note: Wood’s sentiment to take risks and embrace failure is a popular one—so much so that “fail fast, fail often” has become the unofficial motto of the technology industry in its ongoing quest to experiment and innovate. However, some experts believe this motto can be dangerous as it causes people to rush into half-baked plans. The key to succeeding from failures is taking time to learn from your mistakes—not just rushing in to correct with another half-baked idea. Make sure each action is targeted toward a specific goal, and minimize risks whenever possible.)

How to Prioritize Action

Wood says that to prioritize action, you should release your desire for perfection and embrace your mistakes. She explains that many people wait to take action until they feel their plan or skills are perfect. In reality, perfection doesn’t exist—so instead of waiting, identify first steps, get started, and iron out the rest as you go. It’s also crucial to acknowledge that, as perfection doesn’t exist, you’ll naturally make mistakes—instead of letting them scare you off, embrace and learn from them. When you make a mistake, recognize that it’s normal, fix it, apologize where apologies are necessary, look for any positives the situation may offer, and lean on trusted colleagues to help you out.

(Shortform note: Julia Cameron reiterates the importance of overcoming perfectionism in The Artist’s Way, explaining that it’s one of the biggest barriers to creative success. Like Wood, Cameron says that getting started and working through mistakes as they come is the only way to accomplish something. To help you in this process, Cameron recommends aiming for “good enough” rather than perfect, and being OK with producing “bad” work—before you produce something great, you’ll have to produce a lot of mediocre work.)

To ensure you avoid taking unnecessary risks, Wood recommends spending the appropriate time making decisions. Pause to ensure you’ve given yourself time to properly consider your options, and don’t let pride drive you to quick and unnecessarily reckless action.

(Shortform note: While it’s important to take time to consider your decisions before acting, Ryan Holiday warns in Courage is Calling that taking too much time can be detrimental—you risk the decision being taken out of your hands. For example, if you wait too long to decide to invest in a stock, the prices might increase so much that you’ll have missed your window of opportunity.)

Wood also recommends being conscious about how you bring up risky topics. If you need to have a sensitive conversation, make sure it’s the right time, place, and delivery so your message is relayed appropriately and received well.

(Shortform note: To choose the right time and place for a conversation, make sure it’s a setting that allows you and the other person to fully focus on the conversation. Further, ensure proper delivery by using “I” statements that focus on what you’re feeling rather than blaming the other person—this will help them better receive your message.)

Action 8: Be a Leader

Wood explains that reaching a certain level of career success often puts you in a leadership position where you’re managing others to some extent; therefore, understanding how to lead is crucial. However, many struggle in this position because they fear being called “bossy,” or they end up being overly controlling out of fear of their team underperforming. To be a courageous leader and avoid these pitfalls, Wood says you should enable and empower others to reach their potential. Success as a leader is defined by how successful you help others and your organization become.

(Shortform note: Stephen M.R. Covey makes a similar point in Trust and Inspire, arguing that the key to being an effective leader is maximizing employee creativity, innovation, and collaboration—the key ingredients for quality work, which is necessary for an organization to thrive. The way to maximize these traits, Covey says, is by offering employees trust and inspiration. According to Covey, this leadership style is more effective than older, outdated forms of “command and control” (or bossy) leadership styles.)

How to Be an Empowering Leader

First, rather than micromanaging, Wood suggests spending your time developing employees’ skills so they can complete tasks on their own. Many leaders default to micromanaging because they want things to be done well, and they know how to do them best—that’s what got them where they are. However, this prevents leaders from focusing on higher-level priorities. To be a successful leader, focus on coaching your team to become the best they can be rather than doing everything yourself.

(Shortform note: In Trust and Inspire, Covey emphasizes empowerment over micromanaging and suggests two key strategies for extending trust to employees while ensuring a successful outcome. First, be specific about expectations, deadlines, and resources, and ensure the employee agrees on these parameters and can fulfill expectations. Second, create a collaborative accountability plan that determines check-in schedules and methods to monitor progress without micromanaging.)

Second, Wood advises observing your team to understand everyone’s roles and the different moving parts. This has two benefits. First, you’ll better understand the work that goes into people’s jobs so you can find ways to help make their lives easier—for example, by connecting them to someone who can help or simplifying certain processes. Second, having a detailed understanding of the moving parts will help you solve problems by targeting the root of the issue and recruiting team members with the expertise to help solve it.

(Shortform note: Other experts offer some additional tips that might make your observations more effective. One is to create appointments to shadow your employees for about two hours, and afterward, take them out to eat or for a drink. This will give you time to ask more in-depth questions, like any challenges they have on the job and ideas they might have to improve their work or the organization. You should then use these recommendations to make improvements as soon as possible. This helps you learn about employees’ roles, and asking for their advice gives you ideas about how to solve current problems and potentially avoid future ones.)

Third, Wood says that being a good leader requires you to give effective feedback. To do so, Wood first recommends maintaining morale by offering five pieces of positive feedback for every piece of negative feedback. Further, when giving feedback on problematic behavior, be sure to mention the specific situation, objectively explain what the behavior was, seek to understand the person’s intention and perspective of why it happened, and acknowledge their intention while explaining the consequences of the action. Then, brainstorm ways to improve together. This will make it easier for the person to understand what happened and how to fix it.

(Shortform note: Paul Marciano reiterates Wood’s advice on how to provide effective feedback and offers some additional tips in Carrots and Sticks Don’t Work. He adds that, when giving positive feedback, you should target the areas the employee is most proud of. Further, try to give constructive feedback within 24 hours of becoming aware of a problem to ensure the feedback is timely. Finally, after having the discussion where you explain the problem and brainstorm solutions, be sure to follow up with the employee to hold them accountable.)

Finally, Wood warns to avoid common traps that hinder positive leadership. First, don’t put too much pressure on your employees. Make sure your expectations are realistic and healthy, and judge their effort based on the results they produce rather than how much effort it looks like they're exerting. Further, avoid toxic behaviors like creating unnecessary urgency or being indecisive or inconsistent.

(Shortform note: Following Covey's Trust and Inspire framework helps you avoid these pitfalls common to authority-driven leadership styles. Covey explains that transitioning to “trust and inspire” leadership starts with your mindset—adopt the five doctrines that inspirational leaders embrace: First, everyone has higher potential to achieve. Second, people's needs are dynamic and important. Third, everything—success, money, recognition—exists in abundance. Fourth, your fundamental role as a leader is serving others. Finally, inspirational leaders believe change starts with them.)