How Older Professionals Can Re-Imagine Their Career Past 50

How Older Professionals Can Re-Imagine Their Career Past 50
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By 2024, almost a quarter of the US workforce will be made up of individuals 55 or older with more and more baby boomers rejecting retirement. Yet as the median age of the average professional gets higher, workplace ageism remains; managers being more interested in hiring on younger (and often cheaper) employees to replace older, more experienced workers.

Around 60% of workers aged 45+ have seen or experienced blatant age discrimination in the workplace. Described in situations from being passed up for a position or promotion to even being fired for unclear reasons and quickly replaced with a younger professional. From 2013 and onward, even IBM has been setting up ageist policies and has since forced over 20,000 employees, many aged 40 and over, into early retirement in a move to “correct seniority mix.”

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Almost 50% of self-employed workers are baby boomers and are excelling far beyond millennials in the gig economy. Calling on decades of experience in business and their own network of connections, older professionals do not necessarily have to rely on social media to tech clients, partners, and new business. “Many baby boomers are not interested in retirement,” says Sylvia DeWitt, administrator of the Iowa Entrepreneurs Coalition, “They’re always interested in building something.” Older workers enjoy and utilize the gig economy more than any other generation, using their extensive network of friends, colleagues, and other professionals to propel them forwards.

So what does it take to start working for yourself? “Greyprenuers” are the growing number of older workers that are choosing to start their own business, and what they find may even surprise them in the long run. At its core, the first thing to consider is simply “what do I want to do for a living?” For those who have been in corporate positions their whole life, this may be an unfamiliar question. But it’s never too late to build the career of your dreams. From following your passions or compounding on a former career, being your own boss comes with heavy responsibilities and endless freedoms. From construction and repair work to business and financial consulting services, older Americans are excelling in industries that want to see them fail.

In the face of youthful favoritism and unchecked age-discrimination, staying ahead of the curve can be tough for older professionals. A fresh start, new career, and success can be built at any age - here’s how to get started.

Older Professionals Can Re-Imagine Career

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Jacob Wolinsky is the founder of, a popular value investing and hedge fund focused investment website. Jacob worked as an equity analyst first at a micro-cap focused private equity firm, followed by a stint at a smid cap focused research shop. Jacob lives with his wife and four kids in Passaic NJ. - Email: jacob(at) - Twitter username: JacobWolinsky - Full Disclosure: I do not purchase any equities anymore to avoid even the appearance of a conflict of interest and because at times I may receive grey areas of insider information. I have a few existing holdings from years ago, but I have sold off most of the equities and now only purchase mutual funds and some ETFs. I also own a few grams of Gold and Silver

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