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A Field Guide to Professional Mountaineering

At your first job, you filled your shelves with obscure books to impress your colleagues. As a first-time manager, you probably tried to be a super hero to save a project but were confused when your team seemed unhappy afterwards. In senior leadership, you probably realized you needed to hire a team but regretted not spending more time expanding upon your nine LinkedIn connections. As a VP, you were probably surprised when you had to repeat a goal not once, not twice, but fifty times before anyone took notice.

For six years, I chronicled my hundreds of mistakes co-founding Meebo. I initially assumed that my faults were my own but after hiring folks to fill my shoes, I realized that everyone weathers similar rites of passage as we move from individual contributor, to manager, to senior leadership.

I've spent countless hours hand-illustrating the scenes for this professional tell-all with the hope of helping others avoid "I wish someone had told me that!" moments.


  1. How can I make professional pivots easier? What's the checklist of future obstacles to avoid?
  2. How does the measure of success differ between being an individual contributor, manager, director, vice president, and a C-level leader?
  3. Shoot - I just hired a <insert role here> and they are already flubbing it up! How can I help my direct report in the first 90 days?
  4. How do you deal with any role identity crisis - the guilt, fear of becoming obsolete, and the nagging feeling that you're not actually *doing* anything!
  5. Not everyone's a VP or C-level. When do you stop mountaineering and say, "Hey, I think this is where I think I'm happiest and most effective?"


  • Elaine Wherry, Co-founder & CXO of Meebo, Meebo


Elaine Wherry, Co-founder & CXO of Meebo, Meebo

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