Some people slide into retirement like a boat launched into water. There’s a bit of splash at the beginning and then they happily float along.

Other people hit the rocks lying just under the surface and need help lifting off intact and ready for the journey ahead.

You probably have some sense of which of those people you’re likely to be, but retirement can surprise us. It’s one the biggest transitions we make in life, and, without some forethought, it can be a bit rocky. The question is: what exactly should you be thinking about to be reasonably well prepared?

Lost in transition

A recent survey I conducted on thoughts and attitudes about retirement, indicated that the top 4 things people believe they will miss most about the working world after they leave it are:

1. A sense of purpose or a compelling reason to get out of bed in the morning;
2. The steady income;
3. Ongoing challenge and achievement; and
4. The companionship of work colleagues and built-in social ties.

A good place to start your retirement preparedness is to ask, if and how you’ll replace those aspects of work that enliven you enough that you’ll miss them when they’re gone. They might be some or all of the top 4 or other things like the work itself, a sense of belonging and contributing, or having the influence or power to make things happen. Identifying your top 3-5 while you’re still working will allow you to fully appreciate them and get your mind thinking about whether, post-career, you’ll still crave the positive energy they create.

Let’s look each of the top 4 with an eye to strategies you might apply as you prepare to enter a new, very different time of life.

Steady income

Most people – no matter their income – are concerned about this, and for many different reasons. Commonly, there’s uncertainty about outliving their savings or not having enough to cover the costs of extra health care if needed.

Getting very clear about what your resources will provide reduces uncertainty and future bad surprises. Do it sooner rather than later so that you have time to change your investment strategy or retirement date if absolutely necessary.

If you have a financial advisor you trust, ask them to help you forecast your retirement income from all sources against your expected expenses, assuming you live to 100. If you don’t have a relationship with an advisor, consider establishing one with someone who has experience as a financial planner. You can also do the forecasting yourself. There are lots of free apps available that will guide you through the process. But what you won’t get with the DIY route is the insight and occasional reassurance provided by a good financial planner. Independent financial planners are fee based but it can be money well spent to get some peace of mind and a foundation on which to build a sustainable retirement plan.

Companionship and social ties

Many people find their social universe (and consequently their world) shrinks when they retire. Give some thought to whether your non-work social universe is enough to sustain you if your work relationships wither without daily contact.

Everyone’s relationship needs are different. Some of us are good with a few close relationships and the odd casual acquaintance. For others, more is truly merrier. Regardless of your needs, maintaining existing, and developing new relationships as we get older is how we avoid isolation and loneliness which, over time, can creep in like a bad fog. And, with solid relationships, we get the added benefit of greater happiness and potentially a longer life.

Like anything else, expanding or consolidating our social universe does take some effort and may push you out of your comfort zone.

• Be the initiator with work friends you want to stay in touch with when you retire.
• Commit to spend more quality time with the people who are most important to you and the ones you want to be closer to.
• Find your “people” by engaging with groups doing activities that energize you physically, mentally and/or emotionally. Volunteering falls into this bucket.
• Be curious about people you meet. Talk to strangers. Listen to them too. You may never see them again, but you’ll walk away feeling lifted and practice your connecting skills.

Challenge + Achievement = Growth

We don’t stop growing as we age. If we choose to stop, we invite boredom, a feeling of irrelevance, deterioration of relationships, possibly poorer health, and a greater chance of dementia.

Thankfully, in today’s connected, information loaded world, it’s not hard to find ways to challenge ourselves mentally and/or physically to whatever degree we choose, no matter our age. The virtually unlimited, always expanding options may themselves be the biggest challenge to deal with. Where do you begin? Here are 4 ideas:

• Think about the tasks and activities that have repeatedly jazzed you over your lifetime. They probably challenged you enough to be interesting but not so much they were defeating. Do you want to do more of those kinds of things? Continuing to work full or part-time in a new role might fit here.
• What pursuits did you abandon because you couldn’t find the time to do them? Perhaps now you have the time to resurrect them and dig in again. Going back to school to study anything falls into this bucket.
• Check your bucket list. If the items on it don’t seem very challenging, how can you add new elements that, for instance, make a long-desired trip more of an adventure.
• Roll the dice. Try a whole bunch of things you’ve never done before and see what sticks. You may find this process a challenge in and of itself with lots of opportunity for big and small victories along the way.

A sense of purpose

“Purpose” means different things to different people. Figuring out what it means to you is the first step to establishing the sense of purpose you’ll need post-career. Which of these resonate for you?

• In order to feel a sense of purpose, I need to know that I’m having an impact, making a difference.
• I feel purposeful as long as I’m growing as a person.
• My sense of purpose comes from having goals I’m actively working towards.
• I believe that all living things serve a purpose in the grand ecology of our planet, therefore, my life has purpose.

If your work gives you a vital sense of purpose, try to define exactly why that’s true. Have you felt purposeful in other situations? Get specific about what made you feel that way. Keep peeling back the layers until you literally get to heart of it. In other words, landing on what gives you purpose may actually cause you to well up a bit.

And why does purpose matter? To paraphrase Barbara Bradley Hagerty in her book Life Reimagined: The Science, Art, and Opportunity of Midlife, (a great read, by the way) if you pursue happiness, it will always be one step ahead of you. If you pursue purpose, you’ll find happiness.

Sliding or stuck

The great thing about retirement is that you have the freedom to choose how it will play out for you. That is also the hardest thing about retiring. Just when you think you can finally relax, you’ll discover you’re in charge of piloting your boat. Avoiding the rocks isn’t hard if you figure out where they are in advance and get comfortable navigating around them.

If you’d like to examine your own retirement readiness in more detail while making new connections, Marilyn Hintsa will be facilitating a comprehensive Zoom-based group program, The Retirement Sandbox, starting October 18, 2023. This is a 6-session, interactive course for up to 15 people who will convene weekly for 90 minutes until November 29. Go to www.uleadu.ca/retirement-sandbox for more information and book an exploratory call with Marilyn.

Marilyn Hintsa is an accredited Retirement Readiness Coach who works with leaders of all kinds that want to continue making a difference in their post-career lives. On her own retirement journey since 2019, Marilyn lives the perspective that retirement is no reason to stop and go out to pasture, and every reason to now “do life” your way.  She is dedicated to helping her clients navigate one of life’s biggest transitions with confidence and excitement for what comes next. Connect with Marilyn at linkedin.com/in/hintsa/ or book a Retirement Readiness Chat at www.ulead.ca.