Retirement? 8 things to consider when Retirement is your next career move

Retirement is a career all on its own, and if you’re taking the time to read this then quite likely retirement is going to be your next career, or you know someone who is headed down that path.

I’ve written other blog posts about being ready for retirement, and being prepared.  When pressed about my own plan for retirement I tend to deliver a spirited lecture about the difference between ready and prepared, and it’s delivered with the assertion that ‘on balance’ I am prepared.

Prepared for what?

I know what I am going to do once I am fully retired, how I am going to manage our money, and how the home we live in will be maintained. .  The fun part is about what I intend to do with my time.

While I was packing up the accumulated stuff in my work cubicle, a sort of prelude to leaving the job-site I’d been at for ten years, I got cornered by a co-worker who asked me what I was going to do in retirement.  What a loaded question!  I dithered and fumbled with the answer, not wanting to reveal too much about the ‘me’ I’d managed to keep hidden from my co-workers for years.  Searching desperately for a cutesy, clever response I finally said that I was going to treat whatever it was that came next as my new career. That answer was a bit of sophistry that I’m discovering is much closer to the reality of the situation than I originally thought.

It’s interesting to discover what your co-workers know or believe they know about your world outside the brick and mortar confines of your job.  Now to be fair to my coworkers I was more than just a bit duplicitous in what I had allowed them to believe that they knew about me.    There won’t be much opportunity for many of them to get to really know me, and for me to know them.  There will be the occasional ‘coffee date’ with a small group, but not much more.

At the lacklustre retirement celebration hosted by the organization I was leaving my darling wife engaged in her usual style of mingling, socializing and networking.  While building and strengthening connections with my co-workers she shared anecdotes about some of the things that made my non-working time so precious.  I joked with those folks who were finally beginning to clue into the wide range of things that interest me beyond our shared working lives that I was not going to be looking for gainful employment, but that I would be pursuing my other interests.  During my impromptu speech I said that because of my multiple interests which include life-long learning, I was actually contemplating getting my Masters degree in Diversified Studies (which is a real thing available at York University and holds a great deal of attraction for me).  My darling wife and partner punctuated my declaration with the statement that my first credit course would be in ‘DeCluttering’.

I’ve heard it said that retirement is like every day is a Saturday.  That’s too bad; I’m not overly fond of the traditional Saturday because it’s a day of errands and chores, with the occasional trip to Canadian Tire or Lee Valley Tools, and seems to always involve the spending of money.  Sunday is the magical day of a weekend for me, full of family time, time to read, time for introspection, the occasional trip to a festival or other event, a random round of golf and of course sketching, writing and spending time with like-minded friends.

Retirement for me will be a surfeit of Sundays.

It has also been suggested that I think of retirement as perpetually being on vacation.  Given the way I think about proper vacations that is an analogy I could get behind.

Vacations, unless they are freeform staycations, tend to have a lot of structure to them.  Even Day One of a vacation is loaded with activity and structure.  Day one is usually simply about hitting the road, not that there is anything simple about the act of heading out.  You’ve planned, packed and prepared.  Now you’re moving.  Each subsequent day, each actual day on vacation begins with a definite structure, one that drags you out of bed, gets you dressing and preparing for the day’s activities, breakfasting appropriately, then moving forward through the events of the day, even if it’s just to go sit on a beach.

Structured. Yes, that’s the term and concept I’m using.

Most vacations in my experience are organized and structured.  The early years of retirement need to be similarly managed.  Sure, there will be a few days of sleeping in, followed by more mornings trying to break the habit of waking at a specific time to get to a job that no longer dictates the format of your days, but you still need to get up, , find that morning coffee or tea,  get dressed and then feed yourself.

You’re going to find that your ‘normal’ is missing.  Something that you can’t quite explain isn’t going to feel quite right after the first couple of days.  The celebratory atmosphere that came after the announcement of your retirement is going to dissipate.

What comes next?  Find your place in your new normal.  Having trouble finding your new normal?  Create your new normal. You are in control.  Act like it.  Create your new normal.

Here are 8 different things to consider as you move towards finding your new normal.  They’re not necessarily in the order in which you should consider doing them.

  1. Daily activity planning
  2. Goal setting
  3. Calendaring
  4. Drawing the line
  5. Managing finances and your environment
  6. Decluttering
  7. Partnering
  8. Finding a new sense of Community

1.      Daily Activity Plan

How do you go about structuring a day that needs no structure?  Make a Daily Activity Plan.

What are you going to do with your time?  We’ve talked before about ‘ready’ vs. ‘prepared’ in previous posts..  Let’s talk about prepared again, at least obliquely.

You’re going to need to decide how your days are going to look.  Why do I use the word ‘decide’?  Because at first, it isn’t always going to be comfortable to let your days structure themselves organically.  For instance, what time do you get up?  It depends on how your day is structured.  You could always start at the other end and decide when your day will come to a close and then work backwards.

How you spend your days will evolve and morph into a routine that works for you, and your spouse/partner over time, but it is my opinion that you need to start with a roughed out activity schedule and let it evolve over time.

Consider what activities will make up your days.

Now that you’re outside of the structure imposed by the working world you can determine what activities make up a day.  You decide whether or not you want take a daily walk, or a bike ride or a quick trip to the pool.  You might want to try venturing into the senior’s centre, the curling rink on Thursdays, and the grocery store on Tuesdays.  What about the farmers’ market every other Saturday, or the Friday Night-Market?  What’s happening in your community that should become a regular part of how you spend your time?

Make up a daily activity plan so you don’t miss out on anything, yet still manage cover off all the necessities, like the trip to the butcher’s, the baker’s or the fish monger.  You are going to need meals; when and where become new options.  Leave some room for the unexpected opportunities that will come your way.

You’re going to want to find your rhythm.  Regularity is about more than bowel movements.   😉

It basically boils down to the question; what are you going to do with your time?

2. Goal Setting

There will come a point where you will want to, and need to articulate what it is you expect to get out of your retirement, and what you hope to accomplish in the next couple of years before you finally settle into a lawn chair at the end of your driveway watching the world pass you by.

I’m sure you’ve thought about it over the years, but now it’s here and demanding your attention.

Are you going to pursue that college or university degree you’ve been putting off for however long it’s been because you never had the time?  Is there a challenge about rekindling the flames of the passion you once had for the subject matter, or is the stumbling block simply about reviving the interest?  I’m learning how to play the piano, something that I never did as a kid which I’ve regretted since I hit my 20’s.  I’m thinking seriously about going after my master’s degree, for real.

You’ve got the flexibility and maybe even the elbow room to follow up on things like  that landscaping project you’ve been threatening to do, setting up that wood working shop, the potting studio, making those quilts for your grandkids, rebuilding that old car, or even getting into that volunteering initiative that piqued your interest..

And then there’s the traveling to those places you want to see that are still gnawing at the back of your mind.  I have every intention of doing the ‘whiskey tour’ in Scotland, and I’d like to follow the path of the Cathars just to see their castles. So yes, travel might be a goal to be explored.  Travel in retirement for me will be something more than just hanging out on a tropical beach.

There are those books you wanted to have a go at because everybody says they’re important, the movies and Netflix shows that held some interest for you but that you never were able to take the time to enjoy. Digital technologies delivers some wonderful stuff in readable, visual and audio formats.

Go ahead.  Be bold!  Set some goals.  Ignore those who suggest that you’re supposed to do ‘nothing’ in retirement.

Try this; build a new resume.  Think about what it is you want to do, approach the planning of it like a job interview and build a new resume with those goals in mind.  Consider making up a small stack of business cards to help introduce yourself when you meet new people and renew acquaintances and friendships.  Job; freelance daydreamer…uh, no.  That doesn’t work.  Job; Freelance hobbyist and lobbyist for seniors’ rights, advocate of life-long learning.  That would work although it’s a bit cumbersome.  Keep it light with just the right bit of whimsy.

Being able to articulate those goals will help you to explain to your life partner where you want to be and how you want your joint retirement to look if you haven’t already let them know.  Eventually you will be telling your extended family.  Setting those goals will help you formulate the daily activity schedule, and, even better, they will help to build out your calendar for the next few years.

Your goals, once defined, will help you set and manage expectations, and help you to explain to others so they can adjust their expectations accordingly.  Sounds a bit like annual review time at your job, doesn’t it?


With all this ‘activity’ and the goals you’re setting for your retirement, you need to keep track of it all.

It may be time to figure out how you will be recording your schedule and ‘calendaring’ it.

This type of calendaring may not be something that you’ve had to do in recent years because of the structure provided by your job.

Here’s a challenge for you; build and maintain a calendar that you and your partner can access, contribute to, and follow.

This may seem very retro, like the period in your life when you had to calendar the kid’s appointments, your appointments, the dance classes, the soccer games, the hockey games, and still keep track of what your partner was up to.

What was recently the calendar format for your job may not have as much effectiveness here.  It’s time to start a new calendar that tracks everything.  You will want an online version tied to your email address as well as a paper-hung –on-the-kitchen-wall version that your partner can see and make contributions to.  There are some fun online calendars available and some equally interesting paper options.  I use both a Tri-View by wells street which is one of the Lang Companies publications, and I will pick a nostalgic pinup calendar from Tushita or Taschen,  or a fine art calendar to hang in my home office space.

Relax.  It is going to take you a bit of time to find your rhythm, and I do mean more than just a minute and a half.  You are coming out of a structured environment that essentially told you what to do, when to do it, when to take your coffee breaks, lunch breaks, and when to start that long annoying walk to your chosen mode of transit to get home at the end of a day.

And just in case I haven’t already said it already, a through line in much of my observations about retirement is the suggestion that t you put aside time to just ‘read’.  Whether it’s reading fiction, non-fiction or doing the research to help frame your retirement, READ.  Which then begs the question; when was the last time you went to your local library?  Get a library card and go occasionally.

4.  Drawing the Line

You are going to have to learn how to say ‘no’.  You don’t have the excuse of ‘my job’ to use as the final arbiter as a response to a request to do something, go somewhere, give something, or buy something that you really don’t want to do.  Learn to say NO.  This is your retirement and not a blank check of your time for others to cash.

Consider picking up or borrowing a book like this from the library.

The Art Of Saying NO: How To Stand Your Ground, Reclaim Your Time And Energy, And Refuse To Be Taken For Granted (Without Feeling Guilty!)  By Damon Zahariades


I have had to reinforce with my own family that I am NOT a car service, not an UBER, not a taxi.  Sure, an occasional evening during the week I am scheduled to take a granddaughter to her dance class which is followed by our shared post-class treats, however that is the point at which I draw a line in the sand.  This is still my active life, my schedule, my interests, my time.  I intend to be the keeper of my own time.  There can be no assumption that I am immediately available on short notice.  It has to be planned.

The other vector that may present challenges is that part of your compass that holds the remnants of the career you are trying to give up.  Depending on the eminence you had in your job you may become the ‘go-to-guy’ for your previous employer when they need advice and short term help, or your professional colleagues may see you as a ‘consultant’ and try to engage you, or even that professional association you belong to for accreditation purposes may try to leverage your almost expired membership by getting you to join a board, or a specific working group.  You may be prodded to take a more active role in the service group you belong to.

Know when to say ‘enough is enough’ and when the full on ‘NO’ is necessary.  It may be a challenge when there is money involved or when your vanity is being stroked, or it’s about family.

The other part of ‘drawing the line’ is being able to recognize when your vices are getting the upper hand in your day-to-day.  You’ll understand this eventually.

Watch your drinking, the gambling, and especially the bitching and whining.  , You’ll get the point about  what my caution really means one day when you step back, take a look and discover that your usual after-work-before-dinner drink turns into a drink about 2 pm, and the tipple that normally happened while you were cooking and prepping dinner turned into an after lunch  glass of something.  How much are you smoking?

Discipline is everything for the next few months.  Find your rhythms.

Be aware.  Don’t be complacent.

5. Managing finances and your environment

Don’t ignore the money or that roof over your head.

Budgets are going to have a lot of meaning to someone on a fixed income, no matter how good your pension is.  Keeping your home in good shape is going to be as important as your health.

When was the last time you really had a solid, in-depth evaluation of your budget and spending plan from a financial planner?  I’m not talking about the meeting you had a couple of years ago that set the timelines for your move into retirement   I’m talking about the meeting that should have validated how your revenue stream and your budget works for the next thirty years.  You did do that, right?  You’re not doing this retirement by the seat of your financial pants, right?

The concept of household budgeting may seem like such a small minded exercise at this time of your life when everything should be automatic and second nature.  AS your world of activities and goals shift every new experience and approach to living is so excitingly expansive in its scope.  “Expansive” can also mean ‘expensive’.

Do you remember what it was like when you first declared yourself an ‘adult’, moved out of your parents’ home and were officially dropped off their payroll?   There were probably times when you weren’t always sure if you were going to come up with the rent or how you were going to pay for groceries.  Do you remember the ‘penny pinching’? How often did you have to dip into the Bank of Mom-&-Dad?

In theory you are now moving to that point in your life when you’re on a ‘fixed income’ and you won’t be wondering where the next cheque is coming from.  Instead, there is the potential that the concern will be as to whether or not the next cheque will be ‘enough’..  There may come moments when every nickel and dime will count.

It’s time to take a run at ‘budgeting’.  There are some great tools out there to do this!

Have you taken into account the state of your accommodations? That roof over your head is more than just shingles or roofing tiles.

One of the questions I ask myself about everything in my home and the physical house I live in is ‘will this last another ten years?’ And then every major purchase I consider is bracketed by the simple “will it last for 20 years?”  There is the other obvious question; did I budget for major repairs or replacement? What are you going to do when the dishwasher, furnace or air conditioner, or the oven and stove top fails?  If you are renting, ask yourself how much support you can expect from your landlord.

Fine tuning how you will be managing your finances and managing the environment you live in is a lot easier to do today, while the ‘retiring’ is still fresh.

6. Decluttering

You may find that your home environment is not really that conducive to spending all your day there, or that it may not reflect your moods, support your motivations and the things that you want to do but haven’t finished preparing for.  You’re probably going to give some serious consideration to ‘decluttering’.  Take a deep breath and think it through before you launch into a haphazard reorganization and clean-up effort.  Try reading “Decluttering at the Speed of Life” by Dana White.

7. Partnering

I’m not saying that it’s time to go out and find a new partner.  You have one.  The message is; Respect your partner.

You might want to solidify relations with a friend or two as a back-up strategy.   Even when you were courting your partner years ago you probably had a wingman who provided you with perspective and advice on what you were doing.  Think back.  Your ‘work day’ friends are going to be busy.  Your partner may be your best friend but it’s a bit unfair to ask them to live in your back pocket.

One of the things you don’t want to do is to start reorganizing your spouse, or their ‘stuff’ without being invited to.  Don’t unilaterally decide the kitchen needs a re-org, nor should you be too vocal about the fact that you just don’t like the way your spouse has things laid out in the garage or the shed.  Are you looking to start a fight?

If your partner has already retired before you or they are a work-from-home partner they probably have things laid out in ways that work for them.

You need to find a way to stay out of your partner’s way, to rediscover all the synergies that brought you together in the first place, and that has kept you together.  It is going to be tough trying to stay out of each other’s way while you work to find that new rhythm that will carry the relationship forward.

8.      Finding a new sense of Community

Sounds all ‘touchy-feely’ doesn’t it?  It is a very real consideration once you begin moving into retirement.  What are you going to replace the community of the job site with once you’re sitting at home all day?  It’s a bit disappointing that so many of the cafes and coffee shops we looked at longingly as we went to work have disappeared now that there is the time to go hang out there.

You’re going hate this, but I’m going to suggest you go visit your local seniors’ centre.

Check out the activities at your church/synagogue/temple.

Go have a look at the programs at the curling club, the rugby club, the artist’s club.

Join a small gym, not one of those monster box store-like franchises.  You want someplace where it’s not going to be full of intimidating young body-beautifuls, but somewhere the other patrons will know your name, join you for a post workout coffee and have a chat.  This isn’t just fitness, which is important, its about being social.

Go to the municipal swimming pool.

Consider getting a ‘social membership’ at a golf club if the finances will allow.

Hang out at the library, join a book club.

Play bridge, dominoes, chess, poker.

Find a community to be part of.

How are you finding retirement?

Eventually, and it will be sooner rather than later, someone is going to ask, in one form or another; how are you finding retirement?

How are you going to answer?

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