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What is the most important ingredient to a successful career?

According to Malcolm Gladwell, it is becoming exceptionally good at doing something by leveraging your advantages and putting 10.000 hours into it. This is similar to what Cal Newport describes when he states that you shouldn’t always follow your passion. On the other hand, Angela Ducksworth, a psychology professor, sees grit as the most important trait.

So yes, there are a lot of different opinions on that topic.

In March 2025, Jenny Wood (a former manager at Google) published Wild Courage, a book about another important ingredient: courage.

I honestly loved the book.

It feels real and honest—like you’re hearing someone’s true story over coffee. But it’s not just that. It’s full of practical advice to help you build your courage and go after the career you’ve always wanted.

Sound interesting?

Grab a cup of coffee and let’s get into it!

Quick Summary for those in a hurry

A good career requires not only talent and willpower but also courage.

Jenny Wood uses 9 stereotypes, which she redefines in her book as traits you should go for:

  • Weird: The courage to stand out.
  • Selfish: The courage to stand up for what you really want.
  • Shameless: The courage to stand behind your attitudes and abilities.
  • Obsessed: The courage to set your standard.
  • Nosy: The courage to dig deeper.
  • Manipulative: The courage to influence others.
  • Brutal: The courage to protect your time and energy.
  • Reckless: The courage to take calculated risks.
  • Bossy: The courage to listen and lead.

That’s it for the quick summary.

Before we start with the deep dive, I want to highlight that I’ve structured the summary just as the book itself (headings being the chapter titles) and with quick summaries per trait at the end.

Gather your courage

Jenny Wood emphasizes the importance of courage - courage in the sense of doing your own thing and not caring what others think.

Have the courage to be special.

That’s why she has titled the chapters with actually negative characteristics. She believes that we still need more of them: weird, selfish, shameless, obsessed, nosy, manipulative, brutal, reckless, bossy.

You define success yourself.

No one else.

This is what distinguishes the high-achievers.

Weird

Weird redefined: The courage to stand out.

Jenny Wood starts off by mentioning the Red sneaker effect: If you wear red sneakers to a formal event,  it stands out and people think that the person must have a higher status (if they wear such shoes). But it has to be intentional (e.g. a worn-out suit doesn’t do that).

You should not act cool, but “hot”. This means that you should draw attention to yourself and dare to do things: say what you think instead of nodding along quietly in a meeting.

How can you draw attention to yourself?

  • If you like speaking and are good at it, you should interview a manager you find interesting (see also: be nosy).
  • If you like writing and are good at it, you should start posting articles.

It takes sharp elbows to rub shoulders. - Jenny Wood

Large organizations have a constant need for enthusiastic leadership (but it has to be real). What’s the most dangerous thing about being weird?

Just the brief feeling of embarrassment. Nothing more.

Lead with enthusiasm. - Jenny Wood

Quick Summary:

  • Be hot, not cool
  • Be visible
  • Sharpen those elbows
  • Say yes to 3 out of 4 opportunities
  • Have a short (4–5 sentence) bio ready and use it everywhere

Selfish

Selfish redefined: The courage to stand up for what you really want.

A career is not about doing things well, it’s about what the manager sees/believes you are doing.

But selfishness is not only important in a career, but in all areas.

So be (more) selfish. It’s uncomfortable at first, but selfishness is a muscle: the more you use it, the easier it gets.

Career-wise, you should be selfish by saying no to the small things and yes only to the big things - the things that help advance your career.

Success requires a continuous flow of energy and enthusiasm. If you rarely feel this flow, you should change.

What truly helps is having a good manager who makes (implicit) use of the START Framework:

  • Style
  • Thoughtfulness
  • Attitude
  • Responsiveness
  • Transparency

Quick Summary:

  • Saying yes to the big things and no to the small ones. 10% less nap work (work that cannot be marketed).
  • Renegotiate targets if the framework conditions change.
  • Smart START (the right manager counts!)
  • If possible, enlarge the cake instead of “only” taking the biggest slice.

Shameless

Shameless redefined: The courage to stand behind your attitudes and abilities.

No is just an opening offer. - Jenny Wood’s grandmother

Shame can be a compass.

The feeling often pops up when you feel slightly overwhelmed or that you don’t belong in a situation (see Impostor Syndrome). In reality, however, the feeling tells you that you are in the growth zone (which is actually a good thing).

Putting together a good power portfolio (exciting projects that emphasize your strengths) can be very helpful. You can take it out of the drawer at the right time when an opportunity arises.

A good practice is to try to always ask questions first in every Q&A section of a presentation.

Being shameless also means, if you bring up something unpleasant, you should get to the point more quickly and not beat around the bush. The most unpleasant point should be addressed within the first 90 seconds.

And if there is something pleasant: We should celebrate our wins (preferably in a town hall meeting). Celebrating successes is easier for managers because you celebrate the successes of your team or employees. After all, the goal of a manager is to create something great in others.

A good template to showcase your successes is ROI (Role, Objective, Impact).

But there is even more to being shameless.

Quick Summary:

  • Find your swagger
  • Know your 3 Power Assets
  • Speak up: shame means you’re growing
  • Celebrate wins
  • Admit and fix mistakes

Obsessed

Obsessed redefined: The courage to set your standard.

Obsession gives you the discipline to avoid the part of yourself that is holding you back.

A great method from the chapter is having a pencil sharpener: The aim of meetings, phone calls, etc. should be a tangible output. Even if it is “only” a document. If it is a (joint) idea, project, or an intimidating task, you should create a first draft (document, slides) within the first 24 hours. This distinguishes high performers from low performers.

Obsession also means persevering - not just for 1-2 times, but consistently.

After having read the chapter, I think that Jenny Wood talks about something Angela Ducksworth would name “grit” - so the two books are similar here.

Quick Summary:

  • Push, Perform & Persist
  • Benefits of the Pencil Sharpener
  • Growth Mindset
  • Take care of your own physical & mental health: plan a 10-25% buffer for projects.

Nosy

Nosy redefined: The courage to dig deeper.

The author is convinced that her curiosity is the skill that has brought her to where she is today.

Knowledge is something you can’t lose (even if you lose everything/your possessions). And, how do you get knowledge?

With curiosity.

With questions.

Curiosity can also be a door opener. People like to be asked about themselves - so you can point out common interests and increase mutual sympathy.

This can also be a good way to prepare yourself to meet someone new (important). You can ask mutual acquaintances about the person.

You can also make use of this in Emails: use “you” instead of “I”: Emails can have a completely different effect if you avoid the “I” and focus more on the other person. This works particularly well by asking questions.

Questions are great. They increase the energy in a room. How do you ask a good question?

  • Questions must be honest.
  • The simplest questions are often the most brilliant: If you ask yourself something simple, at least half the room will probably ask the same thing.
  • You should avoid questions that show off your knowledge. If you are already well versed in the topic, you can ask how you can best provide support.
  • And another important thing: Ask open questions.

Envy has a negative interpretation, but in the context of being nosy, it can be a great indicator. If you envy someone, it shows that the person is good at something that you would also like to be able to do. Why can’t you just ask the person and learn from them?

And one more thing: Take notes. If you learn something new, you should record it or possibly even convert it into a usable format (template, slide, …).

Quick Summary:

  • Questions are great icebreakers
  • How & What » Yes/No questions
  • Avoid sentences that start with “I”
  • Ask simple questions
  • Take notes

Manipulative

Manipulative redefined: The courage to influence others.

Relationships are high-effort & high-reward kind of things. When we make an effort to meet someone or need something from someone, it is easy to get lost in niceties. If you want something from someone, you should make it as easy as possible for the other person to help you. This chapter reads a little differently. In the beginning, Jenny Wood argues for a long time that “manipulating” is not a negative thing at all. After all, conversations aim to get the other person(s) to do or think something that you want.

Jenny Wood sees manipulation as a method of building and maintaining good relationships.

The most important tools of manipulation are

  • Honesty
  • Generosity of time & praise
  • Thoughtfulness

In the corporate world, there is politics. Whether you like it or not is there and it will stay, so you should be playing politics: this is something that many see as a negative in the job. But politics becomes easier once we accept that politics exists. Honestly, it’s mainly about relationships.

A simple method that can support in the context of politics is drawing a power chart. In order to be able to manipulate effectively, you first need to know the political situation.

A good way to build or improve relationships is generosity (time, praise & gifts). Nevertheless, you should avoid the following 3 pitfalls:

  • Not giving too much (e.g. not solving the whole problem).
  • Not being too nice.
  • Wrong audience

Giving feedback to higher-ups is also an underestimated form of improving your relationships (and it is also a bit shameless).

Quick Summary:

  • Play politics.
  • Build/maintain relationships in every direction (upwards)

Brutal

Brutal redefined: The courage to protect your time and energy.

Brutal means drawing boundaries between our time/energy and others to prioritize what is important.

In the corporate world, we often shy away from saying “No”.

However, “No.” is a complete sentence.

There are people who find saying no particularly difficult. But this is not meant to be demotivating. On the contrary: it means that you have a lot of potential to improve. You have to learn to be…

  • more direct
  • clearer and
  • consistent with what you say and do.

Setting boundaries is difficult. But it is necessary to achieve your goals.

You should also be brutal when giving feedback - in the sense that you should say directly and clearly what is going on (don’t beat around the bush).

If you keep the ones who aren’t fit, you’ll lose the ones who are. - Jenny Wood

As we all know, emails can be a huge time waster and unfortunately, they are like rabbits - they multiply quickly. But the thing is: many of the emails we receive are not necessary.

Jenny Wood even recommends that you set an automatic reply during your vacation, which answers that all emails you receive while on vacation are moved to an archive without being read. If a message must be read, the author should write “Please read” in the subject line.

Other than emails, “nap work” can also be a waste of time.

Tasks that are not part of the job description and do not help to advance your career must be limited to 15% of your time. Examples:

  • Taking notes during a meeting
  • Planning a team dinner

You should focus on a few (2-3) important things and do them very well and with full energy while dropping small things. Less quantity often means more quality and no one can argue with good results.

Being brutal and still showing empathy should not be mutually exclusive. So say “no”, but show empathy!

Why are we brutal? We need to look for ourselves and our energy. Think of Maslow’s pyramid of needs upside down: taking care of your physical needs is important (food, drink, sleep, exercise). This level is more fragile (narrower) than we think. If it fails, so the rest of the pyramid will fail.

Quick Summary:

  • Set boundaries and stick to them
  • Escape the trap of “performative” work and focus on “rewardative” work instead
  • Minimize email work
  • Drop unimportant thing

Reckless

Reckless redefined: The courage to take calculated risks.

Successful people fail much more often than other people. Why?

They risk failing more often.

You should have a “reckless mindset” (in the sense of taking calculated risks).

And if you make a mistake: they can turn out to have a positive effect too, or even open up a new opportunity.

Jenny Wood explains this using her example: once she sent a testimonial to all Google employees instead of just her team. Even though she wanted to sink into the ground at first, it turned out that it wasn’t so bad. Her next newsletter (about making mistakes) became her most successful ever.

Default to action. - Jenny Wood

We shouldn’t think too much and plan ahead. Action is often better than (too much) thinking.

But being reckless should never mean acting out of pride. You should take risks, but SMART risks.

Quick Summary:

  • Take risks
  • Own your mistakes
  • Despite everything, you should take your time before making important decisions - at least for a moment.

Bossy

Bossy redefined: The courage to listen and lead.

The task of a leader is not to do everything themselves or to have all the answers. The task is to ask questions and create a framework so that the team can do a good job.

The main goal of a leader is to awaken the best in others.

Important tools for leaders are the “Humble Two” answers:

  • I don’t know.
  • I was wrong.

Jenny Wood recommends that you sometimes shadow your employees, colleagues, and managers. As a manager, you have the opportunity to do this shadowing and learn a lot from your peers.

Leading is listening. - Jenny Wood

Another great recommendation from Jenny Wood is: If you are faced with a supposed quick fix for a problem, you should QUASH it first:

  • Quantity: Use metrics.
  • Understand: Discuss with the team.
  • Assess: Involve those affected.
  • Support: Coordinate with the person who raised the issue.
  • Hypothesize: Don’t be too reactive. Do a small experiment before implementing a big quick fix.

QUASH doesn’t (just) solve problems, it solves patterns.

Solving a problem for the team instead of helping the team solve the problem pattern is performative work for leaders (and should be avoided).

Jenny Wood also mentions feedback as an important leadership tool. Good leaders give positive feedback all the time (and not just negative feedback sometimes). The ratio should be at least 5:1.

Good talent is rented, not owned. - Jenny Wood

And most importantly: A good manager creates a (psychologically) safe environment.

Quick Summary:

  • As a manager, you get more credit when the team solves problems instead of you.
  • Patterns instead of problems
  • Use QUASH for quick fixes
  • Feedback is a good leadership tool (5:1 / positive to negative).

My takeaways

I enjoyed the book a lot. It is written in a fun and engaging way (not that common in leadership literature) and there are many insights in it you can easily apply.

The insights that stood out to me most are the following.

Rock-Chalk-Talk-Walk

  • Rock: a big milestone that you currently want to achieve.
  • Chalk: Write down the goal and pursue it like any other goal.
  • Talk: Talk openly about the goal.
  • Walk: consistent “action” in the direction of the goal.

START Framework

  • Style
  • Thoughtfulness
  • Attitude
  • Responsiveness
  • Transparency

Self-advertise with watermarks

Even if you are not creative: give everything you do a watermark (slides, templates, .. ).

Proposing solutions

When proposing a solution to your manager, it is best to propose several (3) options and recommend the favorite.

Make helping you easy.

You should make it as easy as possible for someone to help you.

QUASH

Before you apply a supposed quick fix to an upcoming problem, you should QUASH it first.


Additionally, I noted some To Dos after reading the book, which I’ll personally incorporate. You might find them helpful too

  • Prepare a short bio (4-5 sentences) and place it everywhere (especially in meetings).
  • Create a power portfolio (≥ 2 business skills).
  • Send your manager the week’s successes and current priorities once a week (preferably on Monday morning).
  • Document/save methods and learnings in a format that can be reused (template, …).
  • Write down the Dynamic Dozen

Thank you so much for reading! I hope that you’ve enjoyed my summary. If you are interested in more details I can highly recommend reading the whole book or listening to it as an audiobook.