The Day I Threw Away My Five-Year Career Plan

How following curiosity instead of planning led to four careers and a more creative life

Sep 22, 2025

man holding yellow surfboard while walking on seashore during daytime

I had it all mapped out.

Five-year plan. Clear progression steps. Industry certifications. The “smart” career path that everyone said would lead to stability and success.

For three years, I followed the plan perfectly. Got the promotions. Checked the boxes. Built the resume that looked impressive on LinkedIn.

And felt completely dead inside.

I was optimizing for a career that might not exist in five years while ignoring every spark of curiosity that could have led somewhere unexpected.

Rigid career planning was killing my creativity, not protecting it.

Reading books for knowledge was helpful, but it wasn’t how creativity grows. Creativity grows through exploration, experimentation, and cross-pollination between seemingly unrelated fields.

I was just following curiosity and adapting as life unfolded.

Over twenty years, I’ve had four completely different careers:

Career 1: Software Engineer - Started because I was curious about how websites worked Career 2: Writer - Began when I started documenting what I learned as an engineer Career 3: Founder - Emerged from a side project that grew beyond expectations Career 4: Advisor - Developed from teaching others what I’d learned across all previous careers

None of it was planned. Each transition happened because I followed genuine interest instead of forcing predetermined outcomes.

When something sparked my curiosity, I explored it. Often, I discovered opportunities I never could have predicted. I pursued skills long before knowing they would benefit my career, but each one shaped a more creative life.

The insight that changed everything: careers can be navigated like a Skill Surfer.

The conventional wisdom says:

Plan your career five to ten years ahead
Get expensive degrees before pursuing new skills
Stick to your chosen path for “stability”
Read extensively before practicing anything

To develop a skill, you need to practice it.

You can’t surf by studying wave theory.
You can’t write by reading about writing.
You can’t build software by memorizing programming concepts.

The practice creates the desire to improve. Once you begin, expert guidance becomes valuable—not before you’ve even started.

The problem with long-term career planning: Industries change faster than five-year plans. The job you’re planning for might not exist. The skills you’re avoiding might become essential.

A Skill Surfer grows through flexibility and willingness to learn. This mindset has guided me through four completely different careers without expensive retraining or starting over from scratch.

Step 1: Follow Curiosity Over Planning

When something sparks your interest, explore it immediately. Don’t ask whether it fits your current career plan.

The practice: Keep a “curiosity list” of things you want to learn. When you have 30 minutes, pick something and start practicing.

Why this works: The connection between curiosity and career might not be obvious until later. But following genuine interest keeps momentum alive better than forced learning.

Step 2: Practice First, Plan Second

Start doing the skill, not just reading about it. Books are supplements to practice, not substitutes for it.

The approach:

Spend 80% of learning time practicing
Spend 20% of learning time reading/studying
Use books to improve what you’re already doing

The result: You develop intuition through experience, then use knowledge to refine your intuition.

Step 3: Teach Others to Reinforce Learning

I started writing to share what I learned through reading and research. Teaching others reinforced my own understanding and opened unexpected doors.

Why teaching accelerates learning:

Explaining forces clarity in your own thinking
Questions from others reveal gaps in your understanding
Building in public creates opportunities and connections
Helping others feels meaningful, which sustains motivation

Step 4: Embrace Change as Opportunity

Each field I studied offered unique lessons. What looked like career pivots were actually skill accumulation that made me more valuable, not less focused.

The reframe:

Career changes aren’t instability—they’re skill portfolio diversification
“Unrelated” skills often combine in unexpected ways
Broad experience makes you antifragile in changing markets
Cross-pollination between fields creates unique value

Step 5: Enjoy the Process

The real key is enjoying the learning itself. Explore freely, learn deeply, and let curiosity guide your choices.

The mindset: Mastery takes more time than quick-fix advice suggests. But the journey should be enjoyable, not just the destination.

What This Approach Built Over 20 Years

Career Flexibility:

Four successful career transitions without expensive retraining
Skills from each field that enhanced the others in unexpected ways
Ability to adapt when entire industries shifted or disappeared
Multiple income streams instead of dependence on single employer

Creative Growth:

A creative life shaped by genuine interest rather than forced planning
Ideas that emerged from combining knowledge across different fields
Solutions that others missed because they stayed within single disciplines
Work that felt meaningful because it aligned with natural curiosity

Professional Opportunities:

Opportunities I never could have predicted through traditional career mapping
Network that spans multiple industries and disciplines
Reputation for bringing fresh perspectives to old problems
Consulting requests that value cross-domain experience

Personal Satisfaction:

Days that feel energizing rather than draining
Confidence that comes from adapting successfully to change
Relationships with people across diverse fields and interests
Sense of agency over career direction rather than dependence on external validation

The Skills That Seemed “Useless” But Weren’t

Looking back, every skill I developed “for fun” eventually became professionally valuable:

Writing (started as personal journaling): Led to content opportunities, clearer communication, better documentation, thought leadership

System thinking (started as curiosity about software design): Improved product development, client communication, problem-solving approach

Teaching (started as informal mentoring): Created consulting opportunities, publishished a couple of books

Skills developed through genuine curiosity compound in ways you can’t predict through planning alone.

Why This Approach Works Better in The Knowledge Economy

The traditional career model assumed:

Industries remained stable for decades
Companies provided lifetime employment
Specialization was more valuable than adaptation
Experience in one field didn’t transfer to others

The new reality:

Industries transform every 5-7 years
Average job tenure is 2-4 years
Adaptation is more valuable than specialization
Cross-domain experience creates unique value

Career development is like surfing—you can’t plan which waves will come, but you can learn to ride them skillfully when they do.

Along the way, others supported my growth and helped me move faster through challenges I couldn’t navigate alone.

What worked:

Finding mentors in each new field who could accelerate learning
Joining communities of people exploring similar interests
Sharing progress publicly to create accountability and feedback
Offering help to others learning skills I’d already developed

As you help others in fields you’ve learned, they help you in fields where you’re learning. Your network becomes a skill-sharing ecosystem.

The Resistance You’ll Face (and How to Handle It)

Internal resistance: “What if I waste time on the wrong skills?” Reality: The “wrong” skills don’t exist. Every skill you develop authentically adds to your unique combination of capabilities.

Family/social pressure: “You need stability and focus” Response: “I’m building anti-fragility and adaptability, which are more stable than any single career path”

Professional skepticism: “This looks unfocused on your resume” Reframe: “I bring cross-domain perspective that most specialists lack”

Financial concerns: “Career changes mean starting over financially” Truth: Skills transfer, and diverse experience often commands premium compensation

This isn’t about constant career changes. It’s about maintaining curiosity and adaptability within whatever you’re currently doing:

Daily (15 minutes):

Notice what sparks curiosity during regular work
Spend brief time practicing something new
Connect new learning to existing skills

Weekly (1 hour):

Explore one skill that seems “irrelevant” to current role
Teach someone else something you’ve learned
Document connections between different areas of learning

Monthly (2-3 hours):

Evaluate which curiosities are worth deeper exploration
Connect with others in fields you’re exploring
Share progress or insights publicly

Annually:

Review how “unrelated” skills have become professionally valuable
Plan deeper exploration of 2-3 areas that maintain strong interest
Consider whether current career still aligns with evolving interests

Don’t quit your job tomorrow. Start building skill diversity within your current situation:

Week 1: Make a list of 10 things you’re curious about but have dismissed as “irrelevant” to your career.

Week 2: Pick one item from that list. Spend 30 minutes practicing it (not reading about it). Notice what happens to your energy and interest.

Week 3: Find one way to connect this new skill to your current work. Share the connection with a colleague or on social media.

Week 4: Teach someone else what you learned. Document what teaching revealed about your own understanding.

Skill Surfing isn’t about changing careers constantly. It’s about building a career that can surf the waves of change instead of being destroyed by them.

The goal: Become someone who adapts skillfully to change rather than someone who hopes change won’t happen.

The outcome: A creative life shaped by genuine curiosity, a diverse skill portfolio that creates unique value, and the confidence that comes from successful adaptation.

The practice: Follow curiosity, practice immediately, teach others, embrace change, enjoy the process.

Instead of “What should my career be in five years?” ask:

What am I curious about right now?
What would I practice if it didn’t have to fit my career plan?
How could this seemingly unrelated skill enhance what I already do?
What would I explore if I trusted that connections would emerge over time?

Your career is a collection of skills, not a single path. Each skill you develop authentically adds to your unique value in ways you can’t predict through planning alone.

The next wave might be the one that changes everything. But you can only catch it if you’re paying attention and ready to adapt.

What are you avoiding exploring because it doesn’t fit your current career plan?

Your next career might be hidden in your current curiosity.

Stop making five-year plans. Start following what sparks your interest. Practice immediately. Trust that the connections will emerge.

The waves are coming whether you’re ready or not. The question is: are you prepared to surf them?

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