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Organize a Career-planning Weekend Retreat

There are many parts of life that require regular maintenance and check-ups to run smoothly—cars need regular maintenance, your body needs a yearly physical—and the plan for your career is no different. If you conduct a yearly career-planning retreat, you will feel more confident in your career choice, better prepared for a change of direction, and motivated to pursue what matters most to you.

Depending on how much planning you need to do, your retreat could be one, two, or three days long. You can hold your retreat at home, in a local hotel, or in a beach-side cottage or secluded cabin. Wherever you go, it should be a place where you can think clearly and deeply, where you aren’t distracted by the normal hubbub of everyday-life.

Your retreat will break down into three stages of reflection, brainstorming, and planning.

Where You Are Currently in Your Career

To give yourself a complete picture of where you are in your career (and how it affects the other parts of your life), ask yourself:

  • Does your current career path facilitate the lifestyle you want? Think about salary, benefits, time off, personal fulfillment, impact on the world, overall satisfaction, work-life balance, etc.
  • Are you able to pursue your passions with your current path?
  • Are you using enough of your talents and strengths on your current career path, or does this path exploit your weak areas?
  • How will you know when you’ve succeeded in your career?
  • What do you value in your work and life, and do your values coincide with your current path?

Where You Want to Go Next

How you answer the questions in the first part will determine how much time you spend here and on the third section. If you are very satisfied in your current position, you will spend less time here; more time if you are less satisfied or dissatisfied.

What you want to achieve in your career in the near and distant future may include: to earn/receive a promotion, to increase your professional development efforts, to find a better balance between work and your personal life, to make a larger or different impact in the world. Once you decide these things, you’ll need to determine what needs to change and what the desired change looks like.


  • Your dream job/career: What would you want to do if no obstacles stood in your way?
  • What’s missing: What qualifications do you lack for getting to where you want to go?
  • Your interim move: If your dream job or career is not readily in your grasp, what could you do to get you one step closer?
  • What are the trends: What employment trends affect your desired career path?

How to Get There

Here’s where the rubber hits the road and you develop an action plan, or several plans: a brand-new five-year plan, a refined existing plan, or a detailed one-year plan.

Answer the questions:

  • Do you need to learn and investigate more about the career path that interests you? How will you do this (be specific)?
  • Do you need more training to get where you want to be? Again, how?
  • Do you need to relocate? Where?
  • Do you need to make a case with your employer for a promotion?
  • Do you need to brush up on your job-search skills?
  • Do you need better balance between your work life and professional life?

You should end your retreat with a detailed roadmap for what you need to achieve, learn, and change by next year’s retreat to obtain—or move closer to—your career goals.