The Financial Hurdles Women Face (And How to Overcome Them)

My daughter is hitting fifty this year. So are my daughter-in-law and many of their friends. They have partners, good jobs, and a sense of financial independence. But I still worry about them, because women face distinct financial hurdles that men simply do not.

The numbers are stark. Women earn less than men over a career, which means lower saving and investment potential. They take time off work for maternity or family care, which reduces cumulative income and retirement fund contributions. They live longer than men, which means their retirement nest egg must stretch across more years. And in general, women tend to take a more conservative investment approach, preferring the safety of money-market or fixed deposit accounts. That means more safety, but often less growth.

On top of that, women are the main caregivers of dependent children and aging parents. There is a cost to this caregiving—not just emotional, but financial. Time out of the workforce means lower earnings, lower pension contributions, and less compound growth over decades.

So, what can you do?

Do not delay investing. Start now, even if you are starting small. Time in the market is your greatest asset.

Most of us underestimate what we will need. If you can contribute consistently to retirement accounts and increase your contributions whenever your income grows, you will be in a much stronger position.

 Carrying debt into retirement is a heavy weight. Prioritize paying off credit cards and personal loans while continuing minimum payments on others.

Whether you manage the day-to-day finances or not, stay involved in budgeting, investments, taxes, insurance, and long-term planning. Knowledge is power, and it also gives you peace of mind. 

The Moment the Panic Sets In (And What to Do About It)

I remember the exact moment. I was in my early fifties, sitting at the kitchen table, staring at a spreadsheet that was supposed to tell me if we would be okay in retirement. We had some savings. We had a good defined benefit plan. And yet, something felt off. The numbers looked fine, but the knot in my stomach said otherwise.

That was the moment I realized: I needed to start building our own savings. Not because we had to, but because I wanted to. I wanted to know that we would be okay, no matter what happened.

If you are in your forties or fifties and reading this, you might be feeling that same knot. You might be wondering if you have saved enough, if you have started too late, or if you will ever be able to retire comfortably. And you are not alone.

A recent survey from Money Stress Tracker reveals that women are 10–15% more financially stressed than men. Financial anxiety is rising, especially as women shoulder heavier burdens across home life, personal health, and workplace demands. The weight of caregiving, the reality of living longer, and the persistent wage gap all contribute to that stress.

But here is the good news: building savings isn't about perfection. It is about making consistent, informed decisions over time. I did not start early, but I started. And that is the most important step you can take, starting.

The best time to start saving for retirement was twenty years ago. The second-best time is today. If you have not started, do not wait. Start now, even with a small amount. Time in the market is often more important than trying to find the perfect moment to invest. And for women, who on average live longer than men, time is both a challenge and an opportunity. Your money needs to stretch further, but it also has more time to grow.

Life Is a Game, But Don't Forget to Play

I have always liked games.

Maybe that is because games make life seem a little easier to understand.

There are rules.

There is usually a goal.

There are ways of getting there.

And, if you are lucky, there are other people sitting around the table or standing on the field with you.

Life, unfortunately, doesn't come with quite such a useful instruction manual.

Bernard Suits, the philosopher who wrote The Grasshopper: Games, Life and Utopia, spent a great deal of time thinking about games. His definition is complicated enough to make you wish you were playing Scrabble instead, but his central idea is wonderfully simple.

A game has a goal. It has rules. It has ways of achieving the goal. And, most importantly, we agree to accept the rules even when they make achieving the goal harder.

Think about golf.

The object is to get the ball into the hole.

If that were the only thing that mattered, I could walk up to the green, pick up the ball and put it in the cup.At times I may have done that just to end the hole, bujt don't tell anyone.

Goal accomplished.

Except it wouldn't be golf.

Golf is golf because we agree to make it difficult.

We stand on a tee hundreds of yards from the hole and attempt to hit a tiny ball with a club. We then chase it around the course, occasionally finding water, sand, trees and other places where golf balls go to disappear.

We voluntarily accept all those unnecessary obstacles.

That is what makes it a game.

Suits calls this attitude toward the rules the "lusory attitude."

In plain English, we agree to play by the rules because we want to play the game.

And that got me thinking.

Maybe life works the same way.

We spend an enormous amount of time trying to make life easier.

We want fewer obstacles.

Fewer disappointments.

Fewer complications.

Fewer things going wrong.

But without obstacles, there is no game.

The difficulty is part of what gives the game meaning.

A chess player doesn't complain that the opponent is making things difficult. That's the point.

A golfer doesn't object to the fact that the hole is too far away. That's the point.

A Scrabble player doesn't complain that the letters are inconvenient. That's the point.

Perhaps life is much the same.

The obstacles are not always interruptions to the story.

Sometimes they are the story.

There is another important distinction in Suits' thinking. There are people who participate in a game without really playing it properly.

The trifler recognizes the rules but ignores the goal.

The cheat recognizes the goal but ignores the rules.

And the spoilsport recognizes neither.

We have all met them.

The person who changes the rules when they start losing.

The person who will do anything to win.

The person who doesn't care whether anyone else is having a good time.

And then there is the true player.

The true player understands both the goal and the rules.

But here is the part I find most interesting: the reward is not simply winning.

The reward is playing.

That may be one of the most useful ideas we can carry into retirement.

We have spent much of our lives being measured by outcomes.

Grades.

Promotions.

Paycheques.

Titles.

Houses.

Savings.

Awards.

Achievements.

We became very good at keeping score.

Then one day retirement arrives and many of the old scorecards disappear.

There is no boss waiting to tell you that you had a productive Tuesday.

There is no annual performance review.

Nobody gives you a promotion because you finally learned how to make sourdough bread.

You have to create a new definition of success.

Perhaps that definition is less about winning and more about playing well.

Did you help somebody today?

Did you learn something?

Did you laugh?

Did you spend time with someone you care about?

Did you try something you had never tried before?

Did you make somebody else's day a little better?

Did you get out of the house and into the world?

Did you enjoy the game?

I think this is why games have stayed with me.

They remind us that life isn't simply about reaching the final score.

It is about what happens between the opening whistle and the final one.

The conversations.

The surprises.

The mistakes.

The comebacks.

The people we meet.

The stories we collect.

The occasions when we thought we had lost but discovered another opportunity.

When I was young, I thought I played games because they were fun.

Now I suspect I played them because they were teaching me how to live.

Softball taught me to recover from an error.

Football taught me to keep moving.

Scrabble taught me to make the best of what I was given.

Checkers taught me to anticipate.

Chess taught me patience.

And all of them taught me that you cannot play alone.

Life is a game, but it is not a game we play simply to win.

We play because we are alive.

We play because there are people beside us.

We play because the rules give shape to the experience.

We play because obstacles make the journey interesting.

And, eventually, we learn that the greatest prize isn't the trophy sitting at the end of the game.

It is the game itself.

So, if you are retired, don't ask yourself only, "What have I accomplished?"

Ask a different question.

"What game am I playing now?"

And then, whatever your answer, make sure you are actually playing.

The Grasshopper, the Ant and the Trouble with Tomorrow

There is an old story about a grasshopper and an ant.

You probably know it, and told it to your children  and grandchildren, today I want to take a slightly different look at the fable.

All summer long, the grasshopper sings, dances and enjoys himself while the ant works away, storing food for the winter. When winter arrives, the grasshopper discovers that dancing doesn't put food on the table.

So, he goes to the ant for help.

The ant refuses.

The traditional moral is pretty straightforward: work hard, prepare for the future and don't expect somebody else to rescue you when the consequences of your choices arrive.

There is some wisdom in that.

I have spent enough years around seniors to know that preparing for the future matters. Saving money matters. Looking after your health matters. Building friendships matters. Having somewhere to live matters. Thinking about what you will do when you retire matters.

But I have always been troubled by the simple version of this story.

It seems to suggest that we have to choose.

Are you an ant or a grasshopper?

Do you work or do you play?

Do you prepare for tomorrow or enjoy today?

Perhaps the answer is: neither.

Or, more accurately, both.

The philosopher Bernard Suits took the Grasshopper story and turned it upside down. In his book The Grasshopper: Games, Life and Utopia, he uses the grasshopper to challenge the idea that work is automatically more valuable than play.

The argument is surprisingly uncomfortable.

We spend much of our lives working so that we can eventually have the freedom to do something else. We save money so that one day we can retire. We work to create leisure.

In other words, the ant may be working so that he can eventually become a grasshopper.

And there is something worth thinking about here, particularly for those of us who have entered retirement.

For years we were told to prepare for retirement.

Save.

Invest.

Pay off the mortgage.

Build a pension.

Look after your health.

Plan ahead.

All good advice.

But then retirement arrives and we discover that preparing for retirement is different from knowing how to live it.

You can spend forty years preparing for Saturday and then discover you don't know what to do when Saturday finally arrives.

I have met people who were incredibly successful at being ants. They worked hard, saved carefully and did everything they were told they should do.

Then they retired.

And they discovered that nobody had taught them how to be a grasshopper.

That is where games and play become important.

Play is not simply the opposite of work. Play is one of the ways we make sense of ourselves.

Think about a group of seniors sitting around a table playing cards. There may be laughter, teasing, arguments about the rules and somebody insisting that everyone else is cheating.

It looks like a game.

But something much more important is happening.

People are talking.

They are remembering.

They are competing.

They are laughing.

They are belonging.

The game has become a reason to be together.

That is why I worry when we treat play as something frivolous, something we should have grown out of when we became adults.

We haven't.

We still need it.

Perhaps especially as we grow older.

The grasshopper and the ant are not enemies. They are two parts of a balanced life.

The ant reminds us that tomorrow matters.

The grasshopper reminds us that today matters.

The ant says, "Put something aside."

The grasshopper says, "Don't put everything aside."

The ant says, "Think about winter."

The grasshopper says, "It is summer now."

Wisdom may be knowing when to listen to each of them.

There is another lesson hidden in the story.

We should be careful about judging people whose lives look different from ours.

The grasshopper may be irresponsible. Or perhaps he understands something the ant has forgotten.

The ant may be responsible. Or perhaps she is so busy preparing for tomorrow that she has forgotten to live today.

Most of us are somewhere in between.

We work. We save. We plan.

And we also dance, play cards, read books, go fishing, play golf, visit friends, listen to music and tell stories.

That is not a failure of discipline.

That is life.

The older I get, the more convinced I am that the goal isn't to become a perfect ant or a perfect grasshopper.

It is to know when to work, when to prepare and when to put down the tools and enjoy the afternoon.

Winter will come.

It always does.

But that is precisely why we should appreciate summer.

The lesson isn't simply to prepare for winter.

It is to make sure that, while preparing for winter, we don't miss the summer.