The Resilient Retiree: Planning Your Perfect Retirement

By the time I was old enough to move out, I was off to university. While the first three years were jam-packed with classes, homework, and boyfriends, the final year was a taste of freedom. I had a class schedule that resembled a part-time job, if a full-time course load: I could do it my way.

After graduation, I had a full-time salaried job to keep. There was a day when I had career ambitions, then there was the day I voiced them. I was told, “You’ll never be CEO; you don’t wear a 42 tall.”

It’s always impossible until someone does it, but I thought, why fight here for something that’s easily done elsewhere?

With my ambitions already in question, a senior employee told me that if I wasn’t prepared to let my managers decide which job I would do for the rest of my career, I should leave now. As my employer was global, this would likely mean living not in Canada and not in glamorous places either. In fact, I’d met people who lived in these locations, and I’d heard enough about them. I’d visited a few and felt the poverty and sticky weather firsthand. Without much prodding, I pulled together my resume and headed to the classifieds.

If I thought I’d escaped a future where a manager was deciding how I’d spend the bulk of my time, and with whom, and where, I was sorely mistaken. I ran from potential promotions I didn’t want to ones I couldn’t avoid. I ran from companies sure to go bankrupt to abusers and bullies to ones that were committing acts I didn’t want to be a part of.

If you are anything like me, before you are settled into a career, you are planning your perfect retirement.

In Exchange for Employment

As a retiree, my resume is one of a job hopper. Funny, when all I wanted to do was set roots, create a nest, and call it home. Instead, I have thirty addresses to my name, and only two of them were homes I actually owned.

As an employee, there were certain things I was willing to part with for cash. But I was unwilling ever to sign my life away. Not being able to pick what city I lived in horrified me. When I got to the root of that fear, I couldn’t imagine being able to only afford an apartment. I’d endured enough living situations that, above all else, I wanted the freedom to choose how I live, and I wanted that to be a home with a backyard. In Canada, and to be more specific, in Ontario.

To me, life came first, then career. The latter supports the former. I know many people for whom the latter defines the former, and that just wasn’t me. I am not a hustle-bustler, I am not one for crowds, cameras, or community.

If I spend my years in the pursuit of freedom, and the ever-expanding idea of what that would entail, it was not lost on me that an earlier generation wouldn’t have had the opportunity to pursue the education I did, let alone the career expected to follow, and the experiences I was honored to have.

Maybe planning your perfect retirement only comes about when you experience the difference between the idea of achievement and actually getting it. There is always a difference between expectations and reality, between the postcard and the vacation that it is marketing.

A Real Whack Job

I was a whack job for walking away from something many other women wouldn’t have a crack at.

Beyonce would never have to say she’s a feminist – you can tell she is one by the way she lives her life, even if you never listen to a word of what she sings. She breaks ground, doing so with style and grace.

In the year I was born, women weren’t allowed to have credit cards, and certainly not mortgages. Ina Garten tells the story of being the sole breadwinner in the house who couldn’t get a mortgage, while her husband could. She immediately got cards in her own name, and now we all know her name as The Barefoot Contessa.

I hope today’s children know equality as a right, not as a fight. Yet it’s important to recognize that rights aren’t handed out freely or justly. They must be wrestled out of the grip of the group that’s been benefitting, protecting, and propagating what they only know of as no other way.

When everyone pretends it’s natural and normal, get ready – you might be next to be infected. Managers are promoted on the belief that the company is the dominant force in their lives. They’ve made the moves and taken the jobs. When people like me came along refuse to go with the flow, they couldn’t imagine what might be wrong. It must have been all on me; a real whack job.

Planning your perfect retirement requires knowing what you do want and how much it will cost.

You will also realize what it takes to afford those dreams. I was willing to give up a lot to avoid certain people, meaningless tasks, and unwanted travel. It means not having to keep to an orderly, boring, and tiresome schedule.

Available Capacity

When it comes to my time, I can do whatever I want. Is my smile ever radiant now? I didn’t pursue happiness; I pursued freedom, and to me, they must be inseparable.

I was in my late forties when I first felt the freedom to do whatever I wanted. Finally, I dove into answering questions that dogged me, wherever I went. It was a three-year dedication to unravelling why people do what they do and how to have the freedom of will, when science estimates that only 2 percent of decisions are actually thought through and made, and that, in those decisions, emotion usually reigns.

Having watched managers, CEO’s, engineers, statisticians, actuaries, and some very smart people make some shockingly bad moves, some in very slow-motion dumpster fires, I couldn’t help but want to know more, to know why, and more importantly, to take back the right to decide for myself, if only for myself.

Along my journey through cognitive biases, behavioral economics, and evolutionary psychology, I discovered that everyone else thought they made wonderful decisions, all the time. No one needed my help learning how to avoid these traps. No, not them. Their teams, yes, all of them make stupid decisions and need training to do it better, but not them.

Guess what? Everyone is capable of passing it to the team below them, until I’m faced with a class so micro-managed that they don’t have the authority to make any decisions.

Entrepreneurialism is a risk. It turned out no one needed what I was selling. No human being whatsoever. Science knows this fact, and they don’t even need to know what I look like, act like, or sound like.

Planning your perfect retirement might include recognizing that it could come earlier than you think.

Every single human is trapped inside a body they didn’t choose.

Look at me and see a little girl, and not the wrath-filled dragon I’ve been proven to be. Human beings look, see, judge, and move on. It’s what we do, while we strive to do better, at least on the outside. I dye my hair, for vanity, for youth, so go ahead and call me a girl, while it’s plain to see that I’m a grown woman.

In more ways, I can do whatever I want because I’ve studied the invisible automatic mistakes that we make all the time and mastered ways around, under, and over them. I have a freedom of mind, of will, that was hard-earned, and I get, completely unmarketable.

It might only be me who’s interested. It was only me in the room a lot of times in my life, and only me raising my hand, and only me walking out, and only me causing a disturbance, and many, many only-me’s in my life. Even if it’s only me who’s interested in maximizing personal freedom, in planning your perfect retirement, after a decade of Liberals, there might be a whole generation who doesn’t even know what it is, how much they have, where it went, and what to do when they get it back.

When the whole country is held hostage by one man, it’s clear that we need democratic reform. Eighty percent of Canadians polled did not support the federal government, yet all efforts to get an election called went unanswered. A democratic system means that the federal government is there at the will and service of the people, and data said otherwise for an entire year.

Contradicting Democracy

That contradicts democracy.

While it is clear I am Conservative, I’ve voted Liberal in the past. I don’t need you to agree with my politics; I need you to have a clear understanding of the decision at stake and to make the one you feel is right for you. Above partisanship, there is democracy, and in my pursuit of freedom, I wish the same for you. In the end, tick a ballot, and do so with good information. Planning your perfect retirement relies on a stable and sure government.

For many voters, casting a ballot may be their first major decision to make alone. They are in that booth, without their parents, without their peers, and, hopefully, without their phones, and their lives are at stake. Is their life going to get easier or more difficult, because one thing is for sure: an election marks a new direction and a new momentum. Every vote matters, and there are no take-backs.

I didn’t want to vote for Trudeau, but I thought O’Toole was too much of a tool, and in my specific riding, the conservative candidate was similarly weak. As I became more interested in politics during the pandemic, when I finally had the personal attachment to it and the time to investigate, I wished I could take it back, for a weak leader is better than a productive tyrant.

It would have been better to have had no progress than to have the wrecking crew of the minority coalition, but we can debate that all day long with people who have donated to the Liberal Party. I know too well how we pick and choose our own facts and dismiss contrary evidence.

At the very least, pretend to be unbiased and gather information on the track record.

Voting at Will

Assess your life, your community, your country, and decide what matters to you the most and who will make the biggest difference to your issue, and then decide. Or, you could follow the masses and vote with the polls, assuming that everyone else did your work for you.

You could vote locally and not nationally. You could vote nationally and not locally. Or, out of fear, or out of hope. You could decide to abstain, because that is a decision; a lack of voter turnout is always part of the end result. You might decide not to participate until you, too, lose something important to you and want it back.

One day, you won’t be able to do whatever you want, no matter what you have. You will head to the hospital because you want to be healed, but they turn you away. You sign up with a family doctor to be tested, but there isn’t one available. Assaulted, robbed, and threatened, you will head to the legal system because you want justice, but there isn’t any to be found.

That day will be the one when you launch your own pursuit of freedom. Planning your perfect retirement means considering what you will do with this freedom, beyond the postcard you show all those ex-colleagues who are still hard at it.

We give up freedoms to the government in exchange for certain protections, and we need to ensure the deal is fair and equal for all. No matter what box you check on that ballot, know that this is the constant negotiation we have with government, and that much work needs to be done to accomplish this vision.

Your assistance is greatly appreciated.

Sacrificial Attention

I learned that all you can measure in decisions is faster, better, or cheaper. Usually, you can get it fast and cheap, but the quality will suffer. Or you can get the best, but you will have to wait for it. Businesses pick where they want to be in the little triangle, and we, with our cash, decide what matters in what.

In theory, anyway. In reality, we let our emotions decide; I used to try to escape boredom, bullies, and treachery through online shopping. Or we let social pressure decide. I attended a home party and bought some expensive stuff I didn’t need and couldn’t afford. It’s not often that we let our hearts, our guts, and both the left and right brains of our minds all come to a unanimous decision before we set fate into motion.

Planning your perfect retirement is setting fate in motion. If you don’t, the wheel of fortune might roll you over.

Be aware of your reality, in your big decisions and genuine trajectory, and in how you pay attention in every moment, every day. Where you have gaps in memory, it’s because you weren’t paying attention. Instead, you were tuning in to your thoughts while your body told you, “Don’t worry, we’ve got it.” You are behind the wheel on the way to work, and not there at all. On the phone nodding and murmuring, but your eyes are on the television? You lost your keys because what else were you thinking about?

In big ways and in small, our attention is quite literally robbed from the present moment. Give yourself the time and space, and be respectful of those thoughts; they will emerge and disappear. It’s like trying to live life with children screaming, dogs barking, alarms blaring, phones ringing, and the constant din of life.

When I was younger, I couldn’t do long math problems without Van Halen in my stereo. Loud. Loud enough to capture my attention and keep it focused. Otherwise, any small thing would cause my thoughts to whirl and wind away the time, and get nowhere. My sister was the opposite. Feuds ensued. No one thought of headphones as the simple solution.

Technology can alleviate problems, but not always solve them, especially when you see your credit card statement. Planning your perfect retirement isn’t about the end of problems. It is the beginning of freedom, of using freedom to solve problems with different means than money, because now you have so many more resources at your disposal.

When you can stand the silence on its own, or the Van Halen blaring from the neighbor when you wish it was a silent night, what you can hear is priceless. Truth, reality, and your inner authentic voice.