I really like the idea of having your own team to help you as you try new things. Pamela Mitchell’s book “The 10 Laws of Career Reinvention suggests friends like these would be a great team:
“The master connector is a networking expert – someone with great connections who can put you in touch with others who may be able to help you.
The clued-in colleague is someone you’ve worked with, who knows your strengths and weaknesses and can discern whether an opportunity is a good match for you and your skills.
Warm ‘n’ fuzzy is a good friend who will catch you if you fall and can make you feel grounded in moments of despair.
The drill sergeant helps you get over yourself when you’re paralyzed by fear. They have no patience for excuses, but are nevertheless fully supportive.
The native is someone who knows the industry you are planning to enter and has important insider knowledge about the culture – knowledge you wouldn’t otherwise have.”
Of course, I’d add a coach who is willing to do all these roles and walk alongside as you take your first steps to a more satisfying role.