Side Hustles & Semi-retirement
"Don't let retirement 'creep up' on you—get ahead of it." The shift from full-time career to semi-retirement is one of the most significant transitions you’ll ever make. Whether you’re staying put out of passion or a paycheck, success in your 60s requires more than just showing up; it requires a strategy. And the kind of things that work well for semi-retirement can work at any age as a side-hustle; sometimes turning in to the full-time thing.
Freedom 55 was only ever an ad campaign. And today we’re staying in the workforce even longer than we used to. In fact, the share of workers aged 65 is roughly one-in-five, nearly doubled since the late 1980s. Nearly 2/3 are working full-time and another ¼ are self-employed. Older people are good at filling gaps because they’re typically willing to be flexible: full-time, part-time, contract, temporary. It’s what the academics call non-standard employment. Does it sound good to you?
Whether it sounds good or not, even more people are working longer if you count the under the table side-hustle, which is, or course, uncounted. More than half of those still in the workforce past the age of 60 are there by necessity, not choice.
It’s all a bit risky because retirement is one of those things that can creep up on you. You think you’ll keep going a few more years and then all of a sudden you can’t. A significant number of people, often over half, retire earlier than planned, primarily due to unexpected health issues, job loss, or workplace changes, rather than financial stability.
The easiest way in to semi-retirement is to do contract work in the field you’ve officially retired from. Often that’s not available. Sometimes you really badly want something different.
Most people who successfully make the shift in to semi-retirement with something new, choose something they’re already good at, or can become good at fairly quickly. Think about how hard you want to work, if you’re willing to upskill, and how much stress you’re willing to tolerate. Many small businesses are willing to hire older people. Your maturity and reliability are a benefit to them, one they are willing to pay a premium for, but you’ll likely have to ask for that raise.
You might build on something you already really enjoy doing and turn it into something people will pay for, maybe starting your own small business. The key here is to make sure there’s good demand, like trades work, or something you’re very skilled at, like furniture building. Consider how much retraining you’ll need as well as how long it will take you to get good at something new and build a customer base. If you want to be a full-blown entrepreneur there are other factors to consider, I’ll get in to that in another post soon, but if you’re doing it as a side-hustle, you can keep it pretty simple.
But as always, some gigs are better than others. And everything goes better with a plan. The quiz below can help you get real about what you can do, as well as what you want to do:
Take the quiz below to focus your semi-retirement/side-hustle options:
Do you want to work for yourself
Do you want to work for someone else?
Are you willing to invest money in a new venture
Are you willing to invest time in a new venture?
How much stress are you willing to tolerate?
How willing are you to upskill or retrain?
How many hours a week do you want to work?
How long do you want to keep working?
How much time off do you want?
How much flexibility do you need?
How physically able are you?
The Career Lab’s next post will include a list of jobs suitable for semi-retirement, and then one on entrepreneurship. These are discussions we can keep having. Find out more on our website or take our 5-part web series on career imagination and career development.
Also look for our free video on upskilling, it’s on our YouTube channel, or email us at hello@careerimaginationlab.com