Why You Should Plan While Working

As many Boomers approach their retirement years, there’s a good reason to start planning for a second career. Whether because of pursuit of interest or economic necessity, chances are many of them will spend part of their golden years working. In an often quoted recent survey by the Transamerica Center for Retirement Studies, two-thirds of workers age 50 and older said they plan to work past age 65 — or don’t plan to retire at all.

Hopefully work in retirement means part-time work as an independent freelancer, allowing for some well-deserved rest after 40+ years in labor force. There are great benefits to having this as your encore career choice. So when should you start planning for their next step?

As with any regular job hunt, it is best to start planning your next career phase while working your regular job. For many this is not an easy task as they are busy at their jobs and with family lives. However, starting to plan early will help to avoid any surprises if they suddenly get laid off or have to quit their job for personal reasons. It might be tempting to postpone planning and instead focus on working your regular job or planning vacation, but everyone should go into their 60s with a plan for transitioning to semi-retirement on their own terms. Planning and examining your options while gainfully employed is a great way to do some pressure free exploration. It’s much less stressful and much more satisfying to plan for the next chapter out of curiosity rather than strict necessity.

Here are a few key steps to take in your planning process:

Make a Financial Plan

As you transition into the next phase of your career, you need to consider your overall financial health. Freelance part-time work is unlikely to pay the same as full-time work, so you need to consider how much you need to earn to supplement your retirement income. Many Boomers also consider some downsizing to adjust their lifestyle which reduces pressure to work full-time for a paycheck. Financial plan is key to help you determine how much you need to charge and how much you will need to work to maintain desired level of living.

Determine What Field You Want to Focus on

Working in retirement may be a perfect time to pursue your interests or take full advantage of your skills and experience. Freelance work is not only for creative writing or technology services. Truth of the matter is that pretty much anything can be done by a freelancer these days, offering plenty of exciting opportunities. Small businesses have needs in many areas that go unmet every day.

In selecting your focus area, it is natural to fall back on what your core area of expertise is. But you may have to dig deep and think outside of the box to identify your "secondary" skills can also offer up freelancing opportunities. You should also look at your talents outside the context of your current industry, says Marc Miller, co-author of Repurpose Your Career: A Practical Guide for Baby Boomers. The manager of operations for a manufacturer, for example, possesses skills that can translate to firms outside their existing sector.

Explore Your Current Employer's Policies

For some Boomers best transition to part time work might be with their existing employer. Many companies, faced with potential loss of talent as their most senior workers retire, are putting programs in place to provide for part time work. If such a program is available, it will be the best place to start. If not, you may have to consider how and when to transition away from your current employer to an independent career. Even after you retire from your current employer, you may want to let management know that you are available for some part time work. It is also worth reaching out to past employers and letting them know that you are starting an independent career.

Line Up Work Ahead of Time

Although you may be planning to work only part time as a freelancer, you do not want to have long gaps in your career. Re-entry is always more difficult than transition. Even 6 months gap may have a negative impact. While you may not plan on working full-time, doing some part time gig relatively soon after retirement from your full-time job will help to ensure that your skills stay current, your network active and your profile remains attractive.

You may want to start applying for some freelance jobs while you’re still working. There are plenty of opportunities for work that does not require to be physically present in the office. Search for such opportunities is a low risk proposition with plenty of upside. You will learn about the market, rates and types of clients. If you decide to apply for some projects, you will get better at pitching your services, giving you more confidence when you transition permanently. If you see many great responses, you may want to jump sooner rather than later. If not, it may be a sign that you need to refresh your skills or explore new ways of searching for freelance jobs. Key is you won’t be forced to make any tough choices because you are under pressure to find something!

Refresh Your Network

There is a massive value in your network that you have built up over the years. Your network is not only your past colleagues, but also other people whom you’ve met in professional settings. Pre-transition period might be a good time to re-connect and refresh your contacts. You can simply let them know that you are considering some independent work and ask for their advice. Your contacts will be happy to share suggestions, as long as you do not ask them directly for work. Since age discrimination is a fact of life, your network may uncover some opportunities that you cannot get simply by looking on-line.

Take a Test-Drive

Whether you intend to continue working in your own field or try something new, testing the waters for freelancing can provide some valuable insights. Try to find a way to explore the field before quitting your current job. To test-drive your new career, try picking up small projects or even volunteer work to get a feel for the work, client interaction, etc. You can leverage social media and join groups, attend industry conferences where you can learn about the latest trends. “Start hanging out in the world you want to move into,” says Marci Alboher, author of The Encore Career Handbook: How to Make a Living and a Difference in the Second Half of Life.

“As people live longer and fewer people have access to pensions, we’re seeing more and more Americans working in retirement,” says career coach Nancy Collamer, author of Second-Act Careers: 50+ Ways to Profit from Your Passions During Semi-Retirement. Planning for that encore career while you are still gainfully employed will help to ensure a smooth transition.


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