Slides from my presentation at BSides Detroit 2017. How I think about career plans in InfoSec, based on a strategic outlook using Wardley maps.

1. Navigating Career Choices
Fernando Montenegro
@fsmontenegro
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2. About me
@fsmontenegro
• Independent Consultant
– Sales Engineer (NetSec,AntiFraud)
– Previous PS, Ops, Arch roles…
• CompSci ’94
• Greying hair
• Curious
– Finance (DIY)
– Economics (EMH, Behaviour)
– Data Science (Coursera)
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Source:memegenerator.net
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3. About this presentation…
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5. STRATEGY
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6. Strategy Cycle (S.Wardley)
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7. PURPOSE
Strategic Objectives
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8. LANDSCAPE
Understanding the Terrain
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9. You are a business [PersonalMBA]
“Every successful business:
(1) creates or provides something of value that
(2) other people want or need
(3) at a price they’re willing to pay, in a way that
(4) satisfies the purchaser’s needs and expectations and
(5) provides the business sufficient revenue to make it
worthwhile for the owners to continue operation”
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Value Creation
Customer Demand
Transactions
Value Delivery
Profit Sufficiency
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10. Who Are You?
Robert Cringely, 1993
• Pioneers
• Settlers
• Town Planners
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12. Now discover your strengths
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13. CLIMATE
Trends affecting scenario
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src:Howard Rees

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Plan Create Verify Package Release Configure Monitor
Shift Left

16. Tidal Forces [Rich Mogull]
• Endpoints are More Secure but Less Open
• SaaS is the new Back Office
• IaaS is the new Data Centre
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17. DOCTRINE
General, recommended practices
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19. Opportunity Evaluation
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Career Fit
• Aligned with Plan
• Opportunistic
Technology
• Impact/Future
• Belief/Behind
Projects/Customers
• Vertical, Size
• Aptitude
People
• Teamwork
• Culture
• Mentorship
Everything Else
• Work-Life
Balance
• Compensation
• Learning

20. Lessons Learned
• Know Thyself
• Deep Focus is Valuable
• Commute is hardest
• Travel is fun (to a point)
– Delivery/Sales
• Organizations are Courts
– “Laws of Power”
• Career has 10,000 days
• “This tall to ride” exists
– Startups
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21. LEADERSHIP
Context-specific gameplay
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22. Choices have to be made
• Understand strategy
• Iterative Process / Every single day
– 1-2 off for a while, might be ok
– Chronic/hopeless? -> consider moving
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23. Additional Topics
• Develop and maintain a craftsman mindset
• Develop and grow career capital
• Deep work!
• Reduce Information Asymmetry:
– community participation, networking
– Certification, degree
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24. WRAP UP
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25. 25
Value Creation
Customer Demand
Transactions
Value Delivery
Profit Sufficiency
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26. Further Resources
• Personal MBA
• So Good They Can't Ignore
You
• How To Fail At Almost
Everything and Still Win Big
• The Obstacle Is The Way
• Simon Wardley /
WardleyMaps
• Securosis Tidal Forces
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27. @fsmontenegro
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28. Other Resources
• https://danielmiessler.com/blog/build-successful-infosec-career/
• https://www.slideshare.net/kshortridge/diy-education-in-cyber-security
• https://tisiphone.net/2015/10/12/starting-an-infosec-career-the-megamix-
chapters-1-3/
• http://www.tandfonline.com/doi/full/10.1080/13598139.2017.1302874
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