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Plan to Work After Retirement? 5 Key Questions to Ask

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25 Questions To Help YOU Identify Your Ideal Second Act. You'll also receive my free newsletter filled with second-act ideas, tools and inspiration.

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If you hope to work after retirement, you’ll want to be clear about your lifestyle priorities before moving forward. Here are five key questions to consider when planning your post-retirement work life:

1. How much money do you need to earn? If you need to earn a considerable amount of money to fund your retirement, that will drive your decision-making process. It might be easier to continue working in your current field, either as an employee or consultant, since that is how you’ll earn the most for your experience.

2. How much flexibility do you need? Workplace flexibility comes in many different forms, so it’s helpful to consider these issues:

  • Do you want to be location independent?  Perhaps you could find work that allows you to work from a sailboat. Or, maybe you’d prefer seasonal work that allows you to work in the National Parks during the summer and at a ski resort in the winter.
  • Do you want to work-from-home? You may want to focus on Internet-based opportunities, such as customer service, translation, writing or web design jobs.
  • Do you want part-time hours? If so, you might enjoy working for a local business or organization that typically hires part-time workers, such as a museum, library, sports arena, retail establishment or school.
  • Do you prefer project or gig work? Increasingly, retirees are embracing project, gig and temporary work as a way to work on a more flexible basis. For help with finding those opportunities, click here to access our list of 100+ Great Second-Act Career Resources.

3. How radical of a career change do you want to make? The reinvention stories about the accountant turned winemaker, or the policewoman turned personal chef are inspirational. But making a radical career change is rarely easy.. It takes time, training and a willingness to start over as a beginner. Sometimes a smaller shift – such as moving from a large corporate job to a nonprofit role or downshifting to part-time hours – can provide the boost you need.

4. What are your non-negotiables? Key to second-act satisfaction, is finding (or creating) work that aligns with your non-negotiables. Are you done with sales quotas? Only willing to travel 10% of the time? Do you need work that allows you to take summers off?  Before making a change, list out your non-negotiables so you’ll know a good fit when you find one.

5. What are the 3-5 most important reasons why you want to work after retirement? Finally, as I explain in this post Why Do You Want to Work After Retirement? there are multiple reasons why people choose to work past retirement. Identifying your top 3-5 motivators will help to guide and inform your second-act decision making process.

Get my Free Downloadable Workbook:

25 Questions To Help YOU Identify Your Ideal Second Act. You'll also receive my free newsletter filled with second-act ideas, tools and inspiration.

Get it Now!