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Deep Dive with Ali Abdaal

5 Skills To Succeed in ANY Career - Helen Tupper (Squiggly Careers)

Fri Jul 21 2023
ProductivitySquiggly CareersValuesStrengthsConfidenceNetworkingCareer Development


The episode discusses the release of the book 'Feel Good Productivity' and explores the concept of squiggly careers. It challenges the traditional ladder model of career progression and emphasizes the importance of values, strengths, confidence, networking, and exploring future possibilities. The episode also delves into finding fulfillment in work, identifying core values and strengths, building confidence, networking effectively, and proactively exploring different career avenues. It provides practical advice and tools for navigating a squiggly career and making intentional choices for personal growth and development.


Productivity can be enhanced by making work feel good

The book 'Feel Good Productivity' focuses on strategies to make work enjoyable and sustainable, challenging the notion that productivity is solely driven by external factors.

Squiggly careers offer freedom and flexibility

Squiggly careers allow individuals to develop in different directions, breaking free from the traditional ladder-like progression and focusing on personal growth and fulfillment.

Values and strengths are key in career decision-making

Identifying core values and leveraging strengths can help individuals make better career choices and find fulfillment in their work.

Confidence is crucial for navigating a squiggly career

Building confidence and overcoming common gremlins are essential for taking action, making difficult decisions, and embracing the challenges of a non-linear career path.

Networking plays a vital role in career success

Building a diverse network of mentors, peers, sponsors, and coaches can open doors, provide learning opportunities, and support personal and professional growth.

Exploring future possibilities leads to personal growth

Being curious about different career avenues, engaging in conversations, and considering both realistic and ambitious possibilities can lead to new opportunities and personal development.


  1. Introduction
  2. Squiggly Careers
  3. The End of Ladder Careers
  4. Balancing Work and Life
  5. Finding Fulfillment in Work
  6. Identifying Strengths and Values
  7. Building Confidence and Networking
  8. Exploring Future Possibilities


00:00 - 05:39

  • The host announces the release of their book, 'Feel Good Productivity', which focuses on making work enjoyable and sustainable.
  • The book is based on the idea that productivity can be enhanced by finding ways to make work feel good.
  • The author conducted extensive research and interviews with experts in psychology and motivation to create the book.
  • The book contains nine chapters with a total of 54 experiments and strategies for readers to try out.
  • Pre-ordering the book will provide access to exclusive bonuses.
  • The host expresses gratitude towards listeners for their support in making the book possible.

Squiggly Careers

05:23 - 17:57

  • The podcast episode features a guest who discusses squiggly careers and how to navigate them.
  • Squiggly careers are non-linear paths that require flexibility and exploration.
  • Five key skills for navigating squiggly careers are discussed: values, strengths, confidence, networking, and exploring future possibilities.
  • The founders of the podcast started by helping people develop in different directions and succeed in more individual careers.
  • They realized that a squiggly career allows for development in different directions, not being limited by a ladder-like progression.
  • A squiggly career is about freedom and flexibility to develop in a way that's right for you.
  • It's not necessary to make dramatic changes to have a squiggly career; it can be achieved within the same company or industry.
  • Squiggly careers allow people to look inward and focus on what they want from work rather than outward appearances of success.
  • A career is simply a collection of jobs throughout one's working life.
  • Having a squiggly career gives individuals more choice and freedom compared to a ladder-like career where promotions are the only means of progress.
  • Squiggly careers can be created even within traditionally hierarchical fields like medicine or law.
  • The concept of squiggly goes beyond job titles and focuses on talents and strengths.
  • Stretching strengths within the current job, volunteering, or side hustles can help build a squiggly career.
  • Frequency builds competency, so using strengths more frequently leads to improvement and opportunities.
  • Being open about talents and allowing others to see them increases the chances of spotting opportunities for growth and success.

The End of Ladder Careers

11:24 - 23:57

  • The concept of ladder career progression originated in the financial services sector over a hundred years ago.
  • It was created to manage and motivate a rapidly growing workforce.
  • The idea of a linear career path no longer fits the modern working world.
  • Work has become a bigger part of people's identity, leading to questions about purpose and meaning.
  • Forcing everyone into one definition of success leads to competition and comparison.
  • Many people lose confidence when their careers don't align with the traditional ladder model.
  • The ladder concept has been reinforced by organizational structures and societal pressures.
  • Promotions may not always be possible, but that doesn't mean lack of success or development.
  • Becoming too focused on promotions can limit personal growth and lead to disillusionment.
  • Success should not be solely defined by seniority or upward progression in one's career.
  • The traditional model of work-life balance from the past no longer applies in today's society.
  • Equal opportunities in the workplace have changed family dynamics and require new approaches to balancing life and work.
  • Men's success in the 1950s was enabled by women staying at home, but now with more equal opportunities in the workplace, it's different and not necessarily easy to balance work and life.
  • Majority of people are reflecting on their development and whether they're doing the right thing in their career.
  • Creating clarity and giving people confidence about their career choices is important to help them navigate uncertainty.
  • Career support should be available to everyone, not just senior people later in their careers.
  • Squiggly aims to help people navigate their careers by providing tools and frameworks for self-awareness and reflection.
  • Lack of self-awareness and shiny objects (grades, salaries, status symbols) can lead people into jobs they don't enjoy.
  • Reflection before making career decisions is crucial for better choices.
  • The five skills discussed in the podcast are important for figuring out one's desired career path and growth.

Balancing Work and Life

17:29 - 29:22

  • The five skills discussed in the podcast are equally important in determining one's career path and growth.
  • For individuals who are unhappy in their current role, it is recommended to work on identifying their values before considering a new position.
  • For those who are excited about exploring new career possibilities, it is suggested to proactively engage in curious conversations and collect data for decision-making.
  • There is no one-size-fits-all approach to managing career development; it depends on an individual's current situation and the most relevant skill for them.
  • To discover personal values, reflect on past experiences and identify moments of high satisfaction and low fulfillment. Look for consistencies in themes or words that stand out.
  • It is important to find sources of fulfillment both within and outside of work to avoid relying solely on work for happiness.
  • Finding balance in multiple sources of fulfillment is important to avoid being solely dependent on work for happiness.
  • Understanding the meaning behind money can help reduce dependency on pay and find alternative ways to fulfill one's needs.
  • Money may represent status, significance, security, or freedom, so it's essential to identify the underlying motivation for wanting more money.
  • Unhooking from the dependency on pay can lead to greater happiness and fulfillment.
  • Investing in broad stock market index funds is a recommended approach for most people.
  • Trading212 is an app that allows free trading of stocks, funds, ETFs, and foreign exchange with a practice mode available for beginners.
  • The Pies feature on Trading212 enables users to follow and copy investment portfolios created by others.
  • The book 'Your Money or Your Life' by Vicki Robin offers valuable insights into changing one's approach to money and work.

Finding Fulfillment in Work

23:32 - 34:39

  • The book 'Your Money or Your Life' by Vicki Robin fundamentally argues that a job is about money, and fulfillment and meaning can be found outside of it.
  • Making the decision to focus on meaningful work instead of climbing the corporate ladder had a positive impact on personal development, happiness, and family life.
  • Separating work and money can help make different choices.
  • A step-by-step process for figuring out values involves considering traits and behaviors desired in team members, the type of work that energizes and fulfills, and the culture of the workplace.
  • Physical responses can indicate alignment with values.
  • When people talk about their values, you can see it in their physical response and body language.
  • Repeated words and themes can provide clues to someone's values.
  • Listening for sticky words that are meaningful and memorable to the person.
  • Reflecting on what a brilliant day looks like and talking to someone before looking at a list of values.
  • Core values should be narrowed down to three to four from a longer list of satellite values.
  • Asking comparative questions to determine the importance of different values.

Identifying Strengths and Values

34:18 - 40:42

  • Identify core values by ranking words that represent them
  • Core values should be memorable, meaningful, and manageable
  • Values can be expressed without using the word 'values'
  • Repetition is important to ensure consistency of core values
  • If core values are not fulfilled in work, explore conversations and possibilities before making a decision
  • Identify what you want to be known for in your company, outside of your company, and in the community
  • Match talents instead of job titles when considering career choices
  • Consider the unconstrained career choice or dream job
  • Speak about your dreams and interests to increase the likelihood of opportunities arising
  • Engage in curious career conversations to explore different possibilities
  • Get closer to potential opportunities and people connected to them through conversations
  • 100 pieces of career advice are shared at the end of the book
  • Three favorite pieces of career advice mentioned by guests on the podcast:
  • Run your own race to avoid comparison and gain confidence
  • Never live the same year twice for personal growth and variety
  • You don't have to have all the answers or pretend that you do

Building Confidence and Networking

46:00 - 1:07:56

  • Confidence is key in navigating a squiggly career.
  • Values are at the core of a squiggly career, as they motivate and drive individuals.
  • Confidence is necessary to take action and make difficult decisions.
  • Common confidence gremlins include not knowing enough, needing to be liked, fear of failure, and belief in lacking certain abilities.
  • Admitting and acknowledging these gremlins is important for growth.
  • Once the gremlin is acknowledged, it can be consciously controlled and actions can be taken despite its presence.
  • The journey involves letting the gremlin out, caging it through activities, and accepting that it may never fully go away.
  • Common confidence gremlins include fear of not knowing enough, fear of not being good enough or liked, fear of failure, age-related confidence issues, fear of presenting or senior people, and fear of uncontrolled bodily reactions.
  • Confidence grabbers create a filter through which we see situations differently than others.
  • Getting feedback from others can help us realize that our gremlins are distorting our perception.
  • Networks play a crucial role in a squiggly career, opening doors and providing learning opportunities.
  • Building a network is about people helping people, not just accumulating connections.
  • Helping others makes us feel good and can lead to more opportunities for ourselves.
  • The three D's of networking are distance, donating, and diversity.
  • Distance refers to having relationships with people outside of your immediate context.
  • Donating means giving back to others in your network.
  • Diversity is important to avoid an echo chamber and gain different perspectives.
  • Recommended roles to have in your network include mentors, peers, and those going through similar experiences.
  • A mentor is someone who has done what you want to do and gives you advice.
  • A peer is someone going through the same experiences as you, and can provide mutual support.
  • A sponsor is someone with access and influence in an area of interest, who can advocate for you.
  • A coach is someone who asks questions and helps you think differently.
  • Focusing on these four roles can be a useful way to build your career community.
  • When seeking a mentor, first determine what specific knowledge or skills you want to learn.
  • Identify people in your network who have the desired knowledge or experience.
  • Be specific when asking for help, explaining why their expertise would be valuable to you.
  • Follow up with the mentor after a meeting, expressing gratitude and sharing progress made.
  • Mentors receive a boost when they help others.
  • Follow up with the mentor after receiving help and share what actions have been taken
  • Mentors feel good when they see the impact of their efforts and are more likely to help again
  • People often underestimate the willingness of important individuals to share knowledge and insights
  • Confidence gremlins can hinder senior people from making time for others, but offering unique insights can change their perspective

Exploring Future Possibilities

1:30:04 - 1:36:16

  • Skill number five is about being proactively curious about future career possibilities
  • Planning every step of a career path can lead to feeling stuck or frustrated when things don't go as expected
  • Instead of fixing the future, it's better to be flexible and explore different career possibilities
  • Start by talking to people in specific roles or positions of interest rather than applying for jobs
  • Consider both obvious career possibilities and ambitious ones that may feel out of reach
  • Pivot possibilities involve looking at future opportunities through the lens of talents rather than job titles
  • Dream possibilities are unconstrained career choices that should be considered if all limitations were removed
  • Identify what you want to be known for in your company, outside of your company, and in the community
  • Match talents instead of job titles when considering career choices
  • Consider the unconstrained career choice or dream job
  • Speak about your dreams and interests to increase the likelihood of opportunities arising
  • Engage in curious career conversations to explore different possibilities
  • Get closer to potential opportunities and people connected to them through conversations