The LavaCon Content Strategy Conference | 5–8 October 2025 | Atlanta, GA
Jayme Perlman

As a career contractor, Jayme specialized in large-scale, high-visibility, V1 projects across the tech industry. She wants to share her unique depth of experience navigating and conquering this parallel universe with other intrepid explorers eager to dodge the pitfalls and reap the rewards of a “patchwork” career.  Jayme is currently a Senior Technical Writer at GitHub defining and implementing information workflows in the never-ending pursuit of better customer support.

Sellsword: Life as a Successful Mercenary Contractor

Is contracting really a viable long-term career option for knowledge management professionals? Absolutely yes! Knowledge management is uniquely suited to contracting — IF you’re prepared financially, mentally, and professionally. It’s a parallel world to the familar FTE experience with its own unique rules, processes, astounding benefits to seize, and unexpected pitfalls to avoid. I spent nearly 30 years as a mercenary highly-successful career contractor. Come explore the Upside Down and discover if this could be the right path for you, too.

 

In this session attendees will learn:

Calling all Adventurers!: Understand the differences between types of contracting

  • Read the Map: Explore the contracting ecosystem
  • Dispel the Mystique: Most “”obvious”” issues really aren’t important
  • Buff up: Evaluate your personal risk/reward/effort tolerance
  • Step 3: Profit: Straight talk about the money
  • Grind Reputation: Build “”triple wins”” to level up fast
  • Join a Guild: Develop your network
  • Cover your… Back: Avoid or escape a bad gig