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Ben Tossell's Squiggly Path To Impact

Ben Tossell's career defies traditional narratives while demonstrating how curiosity-led paths can create remarkable impact. His journey began with failed attempts selling a mobile app to London pubs, followed by creating social media ads and working at his father's law firm.

Everything changed when he discovered Product Hunt, the launch platform for tech products. Fascinated by the community, he began volunteering to transcribe maker interviews and publicize member projects: "I just wanted to talk about ideas and chat with people, to be helpful and connect with others who were building stuff." This unpaid contribution led to employment at Product Hunt, where he engaged their European audience while experimenting with side projects.

Learning about no-code tools, Tossell created Makerpad to teach others how to build digital products without coding knowledge. The platform grew rapidly, eventually being acquired by Zapier (valued at $5 billion). When ChatGPT sparked massive interest in AI, Tossell saw another opportunity to contribute meaningfully. He launched Ben's Bites, a newsletter about AI that reached over 100,000 subscribers in its first year.

What connects these ventures isn't a predefined career plan but a consistent approach: following curiosity, surrounding himself with interesting people, and creating value by making complex topics accessible. "How can I learn from everybody? How do I get in the room with these people? How can I play a small part here in doing something that could be helpful to people?"

Section: 4, Chapter: 12

Book: Tiny Experiments

Author: Anne-Laure Le Cunff

People Change, So Should Your Management Of Them

An important nuance is that individuals will likely move between gradual and steep growth trajectories over the course of their career as their life circumstances and priorities change.

For example, the author describes having an aspiring Olympic athlete on her team at Google. Right out of college, this woman was training intensely and so wanted a more gradual growth trajectory at work. But a few years later, when her athletic goals changed, her career ambition kicked into high gear and she started seeking much more challenge and growth from her job.

As a manager, you can't put a person into a category of "rock star" or "superstar" and expect them to stay there permanently. Check in frequently, look for signs that priorities are shifting, and adjust your management style accordingly. Be responsive to the individual in front of you, not who they used to be or who you assume they should be.

Section: 1, Chapter: 3

Book: Radical Candor

Author: Kim Malone Scott

The Courage To Leave Your Dream Job

At 27, Anne-Laure Le Cunff resigned from her dream job at Google, a position that offered excellent pay, international travel, challenging work, and limitless career potential. Her resignation puzzled her manager, who asked, "Are you sure?" This seemingly irrational career move came after a health scare—a blood clot that required surgery—and a Christmas visit home where she realized she had become disconnected from herself.

Despite being trained to climb the corporate ladder with clearly mapped metrics for success, she found herself burned out, bored, and blindly pursuing predefined goals. The once-enthusiastic employee had lost touch with her natural curiosity and creative spirit that had driven her earlier adventures, including leaving her native France to study in Japan and later Canada.

Section: 1, Chapter: 0

Book: Tiny Experiments

Author: Anne-Laure Le Cunff

There Is No Perfect Job Or Perfect Time

Many people, especially women, strive to find the perfect job or await the perfect time to make a career move, have children, or make another big life decision. But there is no perfect job or time. Trade-offs are inevitable. Every choice involves sacrificing other options and possibilities.

Sandberg herself turned down a dream job at LinkedIn because she was pregnant, only to get an even better opportunity at Facebook a few years later. Don't agonize over finding the perfect situation. Make the best choice you can in the moment and trust that the pieces will fall into place.

Section: 1, Chapter: 4

Book: Lean In

Author: Sheryl Sandberg

Career Conversations - Helping People Achieve Their Dreams

Beyond regular 1:1s, it's important to have periodic "career conversations" to understand what really motivates and inspires your direct reports. Recommend doing these annually and focusing on three key areas:

  1. Life story - What have been the high and low points in their life and career? What are they proud of and what was challenging? Look for patterns in what drives them.
  2. Dreams - If nothing was holding them back, what would they want to achieve in the next 5-10 years? Have them describe 3-5 different dream scenarios.
  3. 18 month plan - Based on their dreams, what skills and experiences do they need to gain in the next 18 months? Make a concrete action plan. The goal is to really listen and draw out what matters to the person, not impose your own view of what their career path should be. Then look for ways to align their work with their long-term aspirations as much as you can.

Section: 1, Chapter: 7

Book: Radical Candor

Author: Kim Malone Scott

Take Recruiters' Calls

Most companies discourage employees from talking to competitors. Netflix does the opposite. Employees are actively encouraged to take calls from recruiters and even interview elsewhere.

Why? It's the best way for both the employee and Netflix to understand their current market value. Knowing this allows Netflix to adjust salaries proactively to stay top-of-market and retain top talent. Sneaking around erodes trust; open dialogue about market value benefits everyone. The rule is: 'Before you say, ‘No thanks!’ ask, ‘How much?’”

Section: 2, Chapter: 4

Book: No Rules Rules

Author: Reed Hastings, Erin Meyer

The Five Keys For Generative Adventures

To unlock a generative life where your path can zigzag while creating meaningful impact, use these five keys:
1. Do the Work First : Instead of waiting for permission or credentials, create tangible proof of your abilities. This increases your "surface area of luck" by demonstrating problem-solving skills and showcasing knowledge. Examples include organizing events if interested in event planning, building apps if exploring software engineering, or creating recipes if aspiring to be a chef.
2. Grow Lateral Roots : Expand skills horizontally rather than just vertically in one domain. Like a plant's lateral roots accessing wider resources, interdisciplinary knowledge helps you thrive in evolving environments. Take on side projects outside your core expertise, attend conferences on unfamiliar topics, and seek unlikely mentors.
3. Prioritize Impact Over Image : Resist pressure to maintain a consistent personal brand. As editor Farrah Storr puts it, "You're not a commodity. You're a constantly shifting human being with complex emotions, needs, and interests." Let your career evolve with your curiosity to discover new ways of creating value.
4. Close the Loop to Open Doors : Build trust by consistently completing what you start and reflecting on lessons learned, even when outcomes differ from expectations. Share these insights to help others navigate similar challenges, turning even failures into generative contributions.
5. Play Along the Way : Cultivate playfulness alongside professionalism. Framing experiments as "just for fun" reduces pressure and often leads to unexpected value. As entrepreneur Josh Pigford, who has launched dozens of ventures, says: "I'll choose to shut something down if I'm not having fun anymore."

Section: 4, Chapter: 12

Book: Tiny Experiments

Author: Anne-Laure Le Cunff

The Myth Of Perfect Balance

"I don't know what I want to do when they graduated. What people are doing now is usually not something that they'd even heard of in undergrad. One of my friends is a marine biologist and works at an aquarium. Another is in grad school for epidemiology. I'm in cinematography. None of us knew any of these jobs even existed when we graduated."

  • Shonda Rhimes

Section: 2, Chapter: 6

Book: Tiny Experiments

Author: Anne-Laure Le Cunff

Avoid Making Decisions Based On A Potential Future

Too many women start quietly making career decisions based on a future family they don't yet have. They turn down opportunities, travel, and promotions - or choose more flexible paths - with an eye to kids they might want five or ten years down the line. Pursue your career as ambitiously as possible until those life-changing moments actually arrive. You'll have more options and resources at your disposal.

Keep your foot on the professional gas pedal until the moment a big life decision is imminent. If you're offered a promotion while trying to conceive, take it. If you're considering a career change but also might want to get pregnant soon, make the change. Keep pursuing challenging, exciting opportunities until you have to make a concrete choice between paths. Don't opt out prematurely for a family you don't yet have.

Section: 1, Chapter: 7

Book: Lean In

Author: Sheryl Sandberg

Setting Boundaries With Bosses And Colleagues

  • Be very clear on your role and responsibilities. Gracefully turn down requests outside that scope.
  • Create a system for saying no. Have go-to phrases or strategies to decline nonessential requests.
  • Suggest an alternative. "I can't take on that project, but here is something I could do..."Offer a referral. "I'm not able to do it, but I know Sarah is great at that sort of analysis."
  • Appeal to your essential intent. "My top priority is delivering Project X, so I need to focus there." Setting boundaries is an ongoing practice, but it gets easier with time as others learn to honor them.

Section: 3, Chapter: 14

Book: Essentialism

Author: Greg McKeown

Finding Your Purpose

Your purpose is not one job, relationship, or career field. Your purpose is, first and foremost, just to be here. Without you, nothing would exist just as it is right now. This perspective prevents you from identifying your entire purpose with a specific role that might end.

Your life purpose exists at the intersection of three elements:

  1. Your skills - what you're naturally good at
  2. Your interests - what calls to you and flows effortlessly
  3. Market needs - where your abilities can serve the world

Often, purpose is discovered through pain. Most people don't find their purpose through easy clarity, but because they find themselves lost, depleted, or against a wall. In these challenging moments, we realize what truly matters and are forced to become the heroes of our own lives.

Section: 1, Chapter: 6

Book: The Mountain Is You

Author: Brianna Wiest

The Dangers of "Leaving Before You Leave"

A talented Facebook employee was offered a big job managing a new business line. The role would involve a major leap in responsibility and travel. She confessed to Sandberg that she was unsure about taking it because she hoped to have a child in a few years. Sandberg convinced her to accept, explaining that being in an engaging, high-profile role would make her more, not less, likely to return to work after a maternity leave. If she had declined the promotion to a less demanding role, she would be more likely to quit entirely after starting a family. Turning down opportunities, even years in advance of starting a family, can become a self-fulfilling prophecy for eventually leaving the workforce.

Section: 1, Chapter: 2

Book: Lean In

Author: Sheryl Sandberg

Becoming A Parent Can Provide Valuable Career Skills

Many new parents, especially mothers, worry that having a baby will derail their professional skills and advancement. But parenthood actually builds many abilities that serve people well at work:

  • Efficiency and prioritization
  • Emotional intelligence and empathy
  • Patience and resilience
  • Complex problem-solving
  • Stakeholder management

If you approach both roles with curiosity, you'll find many areas of growth to apply across domains. Becoming a working parent doesn't have to hinder your professional development. It can deepen and round it in unexpected ways.

Section: 1, Chapter: 8

Book: Lean In

Author: Sheryl Sandberg

Bias, Gender, And The "Abrasive" Trap

Studies have shown that the more competent a woman is perceived to be, the less likeable she is found to be. This plays out in performance reviews, where women tend to get much more critical feedback about their personality and communication style than men do. Women are much more likely to be labeled as "abrasive", "judgmental" or "strident" when they assert themselves or challenge others directly. As a manager, it's important to be aware of this bias. A few tips:

  • Evaluate your feedback for gendered language - are you using words like "abrasive", "bossy", or "aggressive" with women more than men?
  • Consider the individual's context - is this a woman in a role/field where she is a minority? Is she being held to an unfair double standard?
  • Focus on actions and impacts, not personality - give feedback on specific behaviors and results rather than vague judgments of character. Base assessments on facts.

Section: 1, Chapter: 6

Book: Radical Candor

Author: Kim Malone Scott

Rethinking Career Growth For Companies Of One

In a traditional corporate career path, "success" means managing more and more people over time. Your scope of responsibility grows, but you often get further away from the craft you love. Companies of one need an alternate model for advancement that doesn't require endless team expansion.

Buffer has pioneered a clever framework for progression without direct reports:

  1. Scope of Influence - Master your core skill at increasing levels of impact, from individual work to team-wide to company-wide to industry-wide contribution.
  2. Ownership - Take on more responsibility and strategic importance over your domain. Progress from executing tasks to owning projects to shaping entire functions.

The takeaway is to redefine advancement in terms of mastery, impact and ownership - not raw headcount. You can evolve in your role and compensation without the added overhead.

Section: 1, Chapter: 4

Book: Company Of One

Author: Paul Jarvis

Pick The Right Life Partner

The most important career decision a woman makes is who she chooses as a life partner. An equal, supportive partner at home makes all the difference in a woman's ability to follow her ambitions at work. Before committing to someone, look for indicators that they will actively support your career and share the load at home. Do they encourage you to take risks and reach for opportunities? Do they believe in equally dividing housework and childcare? The right life partner is a true equal and a critical ingredient to "leaning in."

Section: 1, Chapter: 1

Book: Lean In

Author: Sheryl Sandberg

Mentorship Won't Come From Simply Asking

Many young women are advised to seek out mentors to advance their careers. But simply asking a virtual stranger "Will you be my mentor?" rarely works. The strongest mentoring relationships develop organically from real working relationships. Focus on doing excellent work and make yourself indispensable to senior leaders.

While most people seek mentors at a much higher level, colleagues at your same level are often the best source of day-to-day support and advice. Especially early in your career, your peers may have more релевантная guidance than a senior leader far removed from your situation. A group of women at McKinsey formed a "Boom Boom" peer group to share struggles, give honest feedback, and champion each other's successes.

Section: 1, Chapter: 5

Book: Lean In

Author: Sheryl Sandberg

Only One Criterion For Picking Jobs

When evaluating jobs, Sandberg recommends ignoring prestige and focusing on one factor above all: fast growth. Whether you're at a company or deciding between offers, look for the teams, projects, and businesses that are growing quickly. In a rapid growth environment, there are endless opportunities to take on responsibility and get promoted, often into newly created roles. Seek out the "rocket ships," even if the specific position is a step down. You'll rise faster than you ever thought possible.

Section: 1, Chapter: 4

Book: Lean In

Author: Sheryl Sandberg

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