3 Tips for Slowly Easing Into Retirement

By on April 22, 2021

Retirement always seemed an ethereal milestone in the distant future. Even if you have been meticulously planning for retirement your entire working life, it can come as a shock to the system. This can be especially surprising for people that bemoan their current employer or have felt undervalued or overworked for some time now.

 While it is the case that some people are forced into retirement before their time, many others also find it challenging to let go of their career identity in one fell swoop. The question of what to do can be difficult to answer. More research is undoubtedly needed into the mental health effects of retirement, however, baby steps might be one of the best ways to test the retirement waters. Keep reading while we show you three tips for slowly easing into retirement.


In your 30s and 40s, you were likely working all the time, pushing your career forward, and trying to juggle family life and paying the mortgage. Planning for retirement back then simply meant dutifully putting money aside every month towards retirement savings plans. Then came the financial stress of putting kids through college and staying relevant in your chosen field while the younger generation appeared.

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 It can be challenging to picture what retirement genuinely means while being in the daily grind. You may have set yourself up financially, but have you considered what you will do to fill your days once the initial holiday feeling wears off? Think about what gives your life purpose and meaning. Is it spending more time with family, or traveling, or diving into a hobby? In the years before you retire, try to routinely re-evaluate what will make you happiest in the short and long term, and then you can create aims and goals.

Create a side hustle

A growing number of people rely on a side hustle to supplement their income and get a leg up on the financial ladder. If there has been any benefit to the pandemic, it’s that the world has opened up for online working in almost every sector. You don’t need to be incredibly tech-savvy to take advantage of these opportunities either.

There are two aspects to the side hustle that make them ideal for retirees: they bring in additional income, and you can do them as little, or as often, as you like. If you enjoy walking, then consider freelancing for a dog walking service. If you have expertise in a particular field, you could link up with others for tutoring, coaching, or mentoring. Project management services are often short-term, contract-based positions that can make use of your years of knowledge. For example, medical professionals know about the rigors of managing the clinical trial process.

A side hustle can start before you officially retire and merge the gap until (or if!) you decide to stop working altogether. The key is isolating a side hustle that fits your current interests rather than focusing on any long-term career objectives. The additional income can mean that you don’t need to dip as far into your nest egg every month, or you can treat yourself to an extra annual holiday.

Stay connected          

Retirement is so much more than just not showing up for work from one day to the next. For many people, the social aspect of engaging with coworkers is part of the appeal of working. Whether you find yourself nearing retirement as a single person, divorcee, or widower, loneliness can be a significant issue. This may be particularly true for those acting as a caregiver or those that are naturally more introverted.

Social connections are instrumental to the humankind at every age. It can be of some comfort knowing that you are not alone in your feelings of isolation and your disenchantment of retirement. While not everyone is a natural ‘joiner,’ you may need to extend a welcome to friends and neighbors. Consider signing up for some classes or making a standing date with a group of friends for lunch.

The abrupt change from having a daily routine of alarm clocks, showers, suits, and commutes to having an expansive day ahead to fill with whatever takes your fancy may seem blissful. Often it isn’t until you or your spouse experience the sudden lack of routine that you realize it might not be all it’s cracked up to be. Retirement can be a surprisingly emotional transition, especially when the process is done cold turkey, so think about the benefits of easing yourself slowly into it.

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3 Tips for Slowly Easing Into Retirement