627: Jenny Wood - How To Go After What You Want and Get It (Wild Courage)

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Mar 23, 2025

Join Jenny Wood, a former Google executive and author of "Wild Courage," as she shares her insights on leadership and career development. She emphasizes that making your own luck is key to success and recounts a bold moment at a subway that changed her life. Jenny discusses overcoming fear, the importance of proactive communication, and building impactful relationships. With strategies like the 'dynamic dozen' and 'Monday mini-festo,' she inspires listeners to chase their ambitions and embrace a shameless approach to self-promotion.

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ANECDOTE

Subway Courage

Jenny Wood spotted an attractive man on the subway and, despite her fears, chased him after he got off.
This act of courage led to their marriage and demonstrates the importance of taking action despite fear.

INSIGHT

Creating Serendipity

Serendipity isn't something you stumble upon; it's something you create through action.
Jenny Wood emphasizes that taking initiative and making your own luck is essential for success.

ADVICE

Networking and Planning

Identify your "dynamic dozen," twelve people you should connect with professionally.
Use a "Monday mini-festo" to reflect on past successes and plan for the upcoming week; share it with your team and superiors.

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Notes:

Serendipity isn’t found. It’s made. Make your own luck. The best leaders create serendipity for their teams. A success mindset precedes success.
- From Jenny - In 2011, I was single and living in New York City. I spotted an attractive guy across the train from me. I wanted to talk to him, but I was too nervous. Then he got off the train. She met her future husband by chasing after him off a train in NYC. "I was letting life pass me by." She used some wild courage to approach him.
What sits between you and the thing you want is fear. Who are your dynamic dozen? The 12 people you need to meet.
Monday mini-festo. In 15 minutes, write the 2 things you did last week that you're proud of. Write 2 things you're excited about for this upcoming week.
Focus on doing the work that helps the company be better. Solve problems. Read the VP email. Know your stuff.
Get to know your boss's boss. Do it the right way by talking with your boss.
Jenny's career at Google - First 11 years in sales, Go To Market, Operations. Own your Career project. She got 2,000 people to come to her first training. Used all resources within the company to do it.
Use "for example." Don't speak in generalities.
Role, Objective, Impact - ROI
At work, say no to the small. Don’t reply all to the Happy Birthday emails. Don’t do the NAP work. NAP stands for “Not Actually Promotable” Work. Sign up for the projects that help make your company better.
Carlye Kosiak is one of their best hires at Google. She had the courage to stand out. She was specific. Her resume indicated interest in “recipe tasting in pursuit of the perfect oatmeal raisin cookie." Personality popped off the page. She was weird, reckless, nosy, obsessed, brutal. Must be yourself. Don’t just be weird to play a role.
Goal Setting framework - Rock, Chalk, Talk, Walk.
Jenny's goal is to sell 15,000 books by the end of week 1 and hit the NY Times best seller list.
If you sell 12,000 copies in week 1, how will you feel? "You ask such great questions."
Don't play it cool. Play it hot. Don't decide to fit in. Stand out.
Watermark your work. Put your name and picture on the deck. Let people know you made it.
Lady Gaga – A group of students at NYU created a Facebook group called “Stefani Germanotta, you will never be famous." Have the courage to stand behind your work. Lady Gaga wanted to be a big star.
Life and Career Advice - Performance reviews - Focus 75% of your time on your strengths. Say yes to 75% of the things asked of you. Start sentences with "YOU" instead of "I" - Focus on them. Build influence thru empathy.