Introduction
"Where do you see yourself in five years?"
It's the classic interview question—and it's built on a flawed assumption: that careers move in predictable, upward trajectories.
In reality, the most interesting, fulfilling careers I've witnessed rarely follow linear paths. They zig-zag. They pivot. They pause. They explore.
Yet we're still conditioned to believe that success looks like:
- Entry-level → 2. Mid-level → 3. Senior → 4. Executive
Anything else feels like failure.
It's time to challenge this narrative.
The Linear Career Myth: Where It Came From
The "career ladder" made sense in the industrial era:
- Jobs were stable
- Industries were predictable
- Loyalty was rewarded
- One company, one climb
But that world no longer exists.
Today:
- The average person changes careers 5-7 times
- Entire industries emerge and disappear within decades
- Skills have shorter shelf lives
- Companies restructure constantly
Yet we're still using a 20th-century career model in a 21st-century reality.
What Modern Careers Actually Look Like
Instead of ladders, think of careers as:
1. Career Lattices
Moving sideways, diagonally, and upwards across different functions, industries, and roles.
Example: Marketing → Product Management → Startup Founder → Corporate Strategy → Consulting
2. Portfolio Careers
Multiple roles simultaneously, each fulfilling different needs.
Example: Part-time lecturer + freelance consultant + board advisor
3. Seasonal Careers
Periods of intense work followed by rest, learning, or exploration.
Example: 3 years in high-growth startup → 6 months travelling/upskilling → Strategic role in established company
4. Squiggly Careers
Non-linear, exploratory paths that follow curiosity and opportunity.
Example: Teacher → EdTech Product Manager → Learning Experience Designer → Educational Consultant
Why "Up" Isn't Always the Answer
Promotion Isn't Always Progress
Not everyone wants to manage people. Not everyone thrives in senior leadership. Not everyone defines success as title and salary.
Questions to ask before pursuing promotion:
- Do I want the actual responsibilities, or just the status?
- Will this role use my strengths or require me to develop new ones I'm less interested in?
- Am I chasing someone else's definition of success?
Lateral Moves Build Broader Skills
Staying in one function limits your perspective. Moving laterally:
- Builds diverse skill sets
- Expands your network
- Increases adaptability
- Opens unexpected opportunities
Example: A finance professional who moves into operations gains cross-functional insight that makes them a stronger future CFO than someone who stayed in finance their whole career.
Strategic "Pauses" Aren't Wasted Time
Career breaks, sabbaticals, and transitions create space for:
- Skill development
- Reflection and recalibration
- Caring for family or health
- Exploring new interests
The myth says: gaps in your CV are red flags. The reality: intentional pauses often lead to better long-term decisions.
Redefining Career Success
Instead of asking "Am I moving up?" ask:
1. Am I Learning?
Growth matters more than titles. Are you developing skills that will serve you long-term?
2. Am I Energised?
Does your work give you energy or drain it? Sustainability matters.
3. Am I Aligned?
Does this role reflect your values, strengths, and interests? Or are you chasing external validation?
4. Am I Building Optionality?
Are you creating opportunities for future moves, or boxing yourself in?
How to Navigate a Non-Linear Career
1. Embrace Exploration
Give yourself permission to try things.
- Volunteer in areas you're curious about
- Take on stretch projects outside your core role
- Experiment through side projects before committing fully
Exploration isn't distraction—it's strategic research.
2. Build Transferable Skills
Invest in skills that travel across industries:
- Communication and storytelling
- Problem-solving and critical thinking
- Relationship-building and influence
- Adaptability and learning agility
These matter more than technical expertise tied to one field.
3. Rewrite Your Narrative
When explaining your non-linear path:
Don't say: "I've jumped around a lot." Do say: "I've intentionally built diverse experience in [X, Y, Z], which gives me a unique perspective on [outcome]."
Example: "I've worked across education, technology, and consulting, which allows me to design learning experiences that are both pedagogically sound and technically feasible."
4. Curate Your Professional Identity
Your CV doesn't have to be chronological. Consider:
- Functional CV: Organised by skill areas, not timeline
- Narrative CV: Tells a story of intentional growth
- Portfolio approach: Show outcomes, not just roles
5. Find Your "Red Thread"
Even in non-linear careers, there's often a consistent theme.
Ask: "What's the through-line in my work?"
Examples:
- Helping organisations scale
- Making complex things accessible
- Building communities
- Solving problems creatively
Your red thread is what connects seemingly disparate experiences into a coherent story.
When to Go Linear vs. Non-Linear
Linear Makes Sense When:
- You're in a field with clear progression (medicine, law, academia)
- You're deeply passionate about a specific craft and want mastery
- You thrive with structure and predictable growth
- You're in an industry that rewards tenure
Non-Linear Makes Sense When:
- You have multiple interests and don't want to pick just one
- You value learning over titles
- You're in fast-changing industries (tech, media, social impact)
- You want flexibility and autonomy
Neither is better. But most people assume linear is the default—and it's not.
Real-World Examples of Non-Linear Success
Example 1: Sara
- Started as a lawyer
- Moved into corporate compliance
- Pivoted to startup operations
- Now runs a consultancy helping startups navigate legal and operational risk
Red thread: Navigating complexity and risk.
Example 2: Raj
- Trained as an engineer
- Became a teacher
- Moved into EdTech product design
- Freelances whilst raising young children
Red thread: Helping people learn technical concepts.
Example 3: Maria
- Worked in banking
- Took a career break for family
- Retrained as a coach
- Now advises financial professionals on career transitions
Red thread: Helping people make informed decisions about their future.
What This Means for You
If your career doesn't look like a neat ladder—good.
You're not behind. You're not confused. You're not failing.
You're navigating the reality of modern work: that fulfilment comes from alignment, not altitude.
The question isn't: "Am I climbing fast enough?"
The question is: "Am I building a career that reflects who I am and what I value?"
Final Thoughts
The career ladder is a myth that no longer serves us.
Modern careers are messy, exploratory, and non-linear—and that's not a bug, it's a feature.
You don't need a five-year plan. You don't need to have it all figured out. You don't need to move "up" to move forward.
You just need to keep asking: "What's the next right move for me?"
And trust that a winding path often leads somewhere more interesting than a straight line ever could.
Reflection Questions
- What does success look like for me (not my parents, not society, not LinkedIn)?
- What's my red thread—the consistent theme across my varied experiences?
- Am I chasing a title, or am I chasing growth, meaning, and alignment?
- Where have I been conditioned to think I should go, vs. where I actually want to go?
About the Author Diana Lee is a Career Development Facilitator and Enterprise Educator at the University of Oxford. She helps individuals design careers that reflect their values, strengths, and evolving identities—linear or otherwise.
Want to explore your unique career path? Get in touch.