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Deep Dive with Ali Abdaal

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

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Helen TupperguestAli Abdaalhost

Jul 21, 20231h 39mWatch on YouTube

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CHAPTERS

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Chapter summaries

Why work shouldn’t be your only source of fulfillment
Helen Tupper opens with the risk of expecting work to provide all meaning and happiness. She argues for finding balanced sources of fulfillment across work and life outside work, so career bumps don’t destabilize everything.
- •Work can become an unhealthy “sole source” of fulfillment if everything meaningful is tied to it
- •Balanced fulfillment means intentionally building meaning both inside and outside work
- •Separating identity and happiness from day-to-day work volatility helps resilience
Ali’s setup: squiggly careers and the five skills roadmap
Ali introduces Helen, her book, and the core promise of the episode. He frames the conversation around understanding squiggly careers and then building five skills to navigate them.
- •Helen is introduced as co-author of a book focused on “ditching the ladder”
- •Ali previews the episode structure: squiggly careers first, then five skills
- •The five skills are framed as values, strengths, confidence, networking, and exploring future possibilities
Special announcement: Ali’s book and “feel-good productivity” premise
Ali pauses the episode to announce his upcoming book and explains its central idea. He describes the writing journey, what the book contains, and how it aims to make productivity feel energizing and sustainable.
- •Ali announces he has written a book and shares where to find it for pre-order
- •He emphasizes joy as a more sustainable driver than discipline alone
- •He describes the book’s structure (chapters and experiments) and his research/interview process
- •He thanks the audience for supporting the work that made the book possible
Helen’s “squiggly path”: from corporate marketing to building Amazing If
Helen explains her own career trajectory and how Squiggly Careers began. She describes noticing others stuck in ladder thinking and turning what started as evening sessions into a business, book, podcast, and training company.
- •Helen worked in large organizations primarily in marketing
- •She and a university friend reflected on careers shifting away from ladder-like progression
- •They started helping others via evening sessions alongside full-time jobs
- •The work expanded into a business with a team helping people build “squiggly” skills globally
What a squiggly career is (and why it’s liberating)
Helen defines a squiggly career as development in multiple directions rather than only upward. She emphasizes focusing inward on what you want from work instead of chasing surface-level markers of success.
- •A squiggly career allows sideways moves, returns, and experimentation without stigma
- •Squiggly doesn’t require changing industries; you can “squiggle” within one company
- •It challenges the belief that success equals becoming more senior
- •The approach shifts attention from external comparison to personal definitions of success
Talents over titles: stretching strengths inside and outside work
Helen explains how squiggly thinking goes beyond job titles to focus on talents and energy. Using Ali’s example of wanting to become better at songwriting, she describes how repeating a strength across contexts builds competence and opportunities.
- •The goal is to be known for talents, not defined by your last job title
- •Using a strength more frequently builds competency; being seen using it increases opportunity
- •Stretch strengths first within your organization so others can spot opportunities for you
- •Side projects and volunteering can extend strengths into new settings and communities
Where “career ladders” came from—and how they shape unhealthy comparison
Helen traces ladder thinking to early 1900s management practices and explains why it fits poorly today. She describes how ladder definitions of success create conformity, competition, and binary thinking about “right” vs “wrong” moves.
- •The ladder model was designed for conformity and control in a different era
- •Modern careers are less predictable and often span multiple roles and companies
- •Ladder success encourages comparison and competition for roles people may not want
- •Binary thinking can fuel “progression perfectionism” that discourages experimentation
Why people end up in jobs they don’t enjoy: low self-awareness and “shiny objects”
Helen explains common reasons people choose roles that later feel wrong. She highlights insufficient reflection, being seduced by status symbols, and defaulting to others’ opinions when uncertain.
- •People often move quickly between roles hoping clarity will appear after the move
- •“Shiny objects” include grades/levels, company cars, and sometimes salary as status
- •Others’ expectations (managers, family, partners) can override personal fit
- •Pressing pause to reflect inward can prevent drifting into mismatched roles
Skill 1 — Values: career graph, balanced fulfillment, and the meaning behind money
Helen outlines how to uncover values by mapping career highs and lows and looking for patterns. She warns against enmeshment (needing work to satisfy everything) and reframes money by asking what meaning sits behind it.
- •A “career graph” helps identify what was present in highs and missing in lows
- •Values show up as recurring themes: people, environment, and day-to-day work details
- •Balanced fulfillment reduces the emotional impact of inevitable work setbacks
- •Money is reframed by asking what it represents (status, security, freedom, significance)
Skill 1 deep dive: how Helen extracts values from Ali (and how to narrow them)
Helen demonstrates a live values discovery conversation with Ali, listening for repeated words, “sticky” language, and body cues. She then shows how to reduce many possible values to a manageable core set and explains why repetition matters to avoid external influence.
- •Values can be inferred from preferred teammates, ideal work, and cultural environment
- •Repeated words and physical energy shifts are treated as clues to what feels “most you”
- •Three to four core values are emphasized over long lists for memorability and usability
- •Comparing values pairwise helps rank and cluster similar ideas (e.g., community/friendly)
- •Revisiting the exercise over time helps check for environmental or social influence
Skill 2 — Strengths: energizers vs drainers, and choosing what you want to be known for
Helen reframes strengths as activities that give you energy, even if you’re not great at them yet. She also defines weaknesses as energy-drainers even when you’re good at them, and emphasizes intentionally selecting a small set of strengths to become known for.
- •Strengths are defined as energy-giving activities, not simply what you’re good at
- •Weaknesses are energy-drainers even when competence is high, creating a career trap
- •She suggests limiting draining work rather than trying to eliminate it instantly
- •A key step is choosing (not guessing) what you want your reputation to be built on
- •Building a consistent “brand” comes from repeatedly using strengths across contexts
Skill 3 — Confidence: naming and ‘caging’ confidence gremlins
Helen argues confidence is what turns awareness into action in a squiggly career. She introduces “confidence gremlins,” shows how common they are, and explains that surfacing them makes it possible to regain control rather than letting them steer decisions.
- •Confidence enables action: conversations, decisions, experimentation, and progress
- •Common gremlins include fear of not knowing enough, needing to be liked, fear of failure, and age-related beliefs
- •A room exercise (hands up to gremlins) reveals how universal these doubts are
- •The process is to identify the gremlin, externalize it, and repeatedly put it ‘back in its cage’
- •Seeking others’ perspectives can reveal how distorted a gremlin-driven view can be
Skill 4 — Networks: building ‘people helping people’ communities (mentors, peers, sponsors, coaches)
Helen explains why relationships accelerate learning and open doors you can’t see alone. She reframes networking away from collecting contacts and toward active, effective help, then outlines four key relationship roles and how to approach mentoring without making it a burdensome commitment.
- •Networks help uncover opportunities, accelerate learning, and provide feedback
- •A strong network is “active and effective,” not measured by follower counts or connections
- •Helping first reduces awkwardness and builds “career karma” over time
- •Four roles to build: mentor (done what you want), peer (going through what you are), sponsor (advocates with influence), coach (asks great questions)
- •Finding a mentor starts with clarity on what you want to learn and a small, specific ask; following up with actions increases future support
Skill 5 — Future possibilities: curious career conversations over rigid plans
Helen contrasts ladder-like planning with proactively exploring possibilities through conversation and observation. She proposes four categories—obvious, ambitious, pivot, and dream—and explains how talking about them turns possibilities into probabilities.
- •Rigid plans can create blinkers; curiosity keeps options flexible
- •Exploring is done through conversations and context exposure, not immediate job applications
- •Four possibility types: obvious, ambitious, pivots (talents-based matching), and dream (unconstrained)
- •Ambitious options feel closer when you engage early instead of postponing
- •Speaking your interests out loud increases the chance others can enable or connect you
Closing: three favorite pieces of career advice and wrap-up
To end, Helen shares three standout pieces of advice drawn from different sources, and Ali closes the conversation. The episode ends with thanks, a recap-style outro, and pointers to links and resources.
- •Helen’s favorite: run your own race to reduce comparison and build confidence
- •Her business partner’s favorite: never live the same year twice, emphasizing variety and growth
- •A favorite from a podcast guest: you don’t have to have all the answers or pretend you do
- •Ali wraps up with where to find resources and how to support the show

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