How to Prepare For An Encore Career

Ready for a career change?

More and more people are rethinking success at midlife or retirement, and considering a shift to more meaningful, purpose-driven work. More and more people are rethinking success at midlife or retirement, and considering a shift to more meaningful, purpose-driven work. Combining a desire for social contribution, entrepreneurial passion, a job that’s not-just-a-job, and – often – continued income, encore careers are an appealing fresh start. Whatever your encore career goals, these strategies can increase the odds you’ll reach them.


Another name for an ‘encore career’, many Americans are looking for work that is more than a ‘job’; a meaningful expression of what you have to offer the world.

There are several encore variations I see with my clients: those mid-career corporate professionals in search of a more fulfilling focus, and folks at retirement age who want to stay engaged and do meaningful work. Continued income, social impact, flexibility, pursuing a passion – second-act careers have many different motivations.

Here is a great place to start: what would you answer to the ‘Tell me about yourself’ interview question? Your response will help uncover the values and priorities that we often don’t pay enough attention in our day to day life. And then ask a friend: ‘What am I best at?’, for more insight (and possibly a few surprises).


This is the time for self-assessment. What skills, talents, and strengths have made you successful in your professional career? Can you repurpose your corporate skills? What ignites your fire? Do you want to continue working for a paycheck, a passion, or both?

Explore new opportunities while still employed, if possible: research, research, research; do informational interviews; volunteer; take a class or consider an internship. Knowledge is power.


Find a like-minded group – whether a casual meeting of people volunteering in the arena you find interesting, or an established organization or professional group.

The feedback you’ll get from your network will provide motivation, expertise, and experience, as well as the invaluable contacts you will want as you consider a career move. (And if you aren’t already harnessing the positive aspects of social media, now is the time to dive in! It’s an effective tool, and one you might find valuable in your ‘second act’.)


If you are leaving a corporate career to pursue more meaningful work, or if you are nearing retirement and want to embark on a fulfilling new chapter — be prepared!

Before you embark on a major life change, outline the specific outcomes that could result, and develop the plans to get there. Inspiration and passion are a starting point, but sustaining a change will require planning and adaptability… two things most of us have learned a lot about by the time we are considering an encore path. Take advantage of your life experience for real motivational mojo.


A survey recently found we are less comfortable talking about money than death. I want to change that! Given that the average encore career transition takes about 18 months, and 67% of those ‘transitioners’ had reduced (or zero!) income during that time, we need to redesign our approach to thinking about – and talking about – money.

Planning with your financial advisor ahead of your career transition will prepare you for the practicalities of pursuing your passion, and can help strategize ways to make the math work during your encore career. And, while some encore careers are the intended result of long-held dreams, others come on the heels of an unexpected job loss.

Planning ahead makes even an unplanned career change an opportunity, rather than a misfortune, allowing you to move forward with the confidence that a solid financial plan provides.

You Need Not Reinvent Yourself

The encore career movement has become a mainstream conversation, including books, conferences, consultants, and coaches. You needn’t reinvent yourself for your second act; instead focus on the expertise, skills, experience, and passion you have – and how your talents can lay the foundation for your encore career.

Do you want to manage your money (and life!) better?

The Happiness SpreadsheetIf you want to think differently about the relationship between your spending, your values and your happiness, then sign up to get your FREE copy of The Happiness Spreadsheet.

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