Jennifer Madden Jennifer Madden

What If Life Is a Marathon, Not a Sprint?

I realized recently that I have spent most of my life behaving as though I am running late.

There is always somewhere I should be getting.

A problem I should have solved.

A goal I should have reached.

A version of my life I should already be living.

Even when nothing is particularly wrong, I can find something that needs to be fixed.

My finances.

My weight.

My work.

My business.

My mother's health.

My future.

There is always a finish line somewhere in the distance.

And apparently, I have decided I should be sprinting toward it.

I'm 52 years old.

This seems like an exhausting way to spend the second half of my life.

I'll Be Able to Relax When...

I've noticed how often my thoughts begin with some version of when.

When I lose the weight.

When I make more money.

When my business is working.

When I know what's going to happen with my mother.

When I'm through my knee surgeries.

When I'm living completely on my own again.

When I know what the next chapter looks like.

Then I'll relax.

Then I'll enjoy myself.

Then I'll feel secure.

Then my actual life can begin.

Except I've been alive long enough to know what happens when you finally reach one of those imaginary finish lines.

Another one appears.

There is always another problem to solve.

That's life.

What If There Is No Finish Line?

I wrote something in my journal recently that stopped me:

What if life is a marathon?

Not in the usual inspirational sense of pushing through and proving how tough you are.

I mean something much simpler.

What if I'm supposed to pace myself?

What if I don't need to solve everything right now?

That idea changes almost everything.

I don't need to know exactly what my career will look like five years from now.

I need to do something useful today.

I don't need to know whether one of my businesses will become successful.

I need to give them a legitimate chance to become something.

I don't need to solve my entire financial future this month.

I need to make responsible decisions with the money I have now.

I don't need to know exactly what my life will look like after my mother dies.

I need to live the life that exists while she's still here.

That feels very different from waiting.

The Problem With Living in the Future

This season of my life has contained an enormous amount of uncertainty.

And uncertainty makes my brain want to plan.

I actually like planning.

Give me a problem, a spreadsheet and a few hours and I'm quite happy.

Planning makes me feel as though I have some control.

Sometimes I do.

But there are things I cannot spreadsheet my way out of.

I don't know how long my mother will be here.

I don't know exactly what will happen with my businesses.

I don't know what my finances will look like several years from now.

I don't know where I'll ultimately live.

I don't know who will be part of my life.

And when I try hard enough to answer questions that don't have answers yet, planning stops being useful.

It becomes anxiety wearing sensible shoes.

Today Is Not the Waiting Room

For a long time, I've thought of this period as an in-between season.

There's the life before caregiving.

And someday there will be the life after it.

This is the middle.

The waiting room.

Except something has been changing.

I'm realizing I actually like quite a lot about my life.

I love my home.

I love my neighborhood.

I love being close to my family.

I love working in my garden and making the house beautiful.

I like seeing my nieces.

I like having ideas and building things.

I like the simplicity of my days.

I even like being home more than I used to.

There are things I desperately miss.

Freedom is probably the biggest one.

There are things about caregiving that are difficult and frustrating and sometimes deeply sad.

But both things can be true.

This season can be hard without being a throwaway season.

My life hasn't stopped.

This is my life.

Maybe the Goal Is a Good Pace

There are things I want.

I want more financial security.

I want my businesses to work.

I want to continue getting stronger.

I want more independence.

I want love and companionship.

I want adventures I haven't had yet.

I'm not giving any of that up.

But maybe wanting something doesn't require being dissatisfied until I have it.

Maybe I can build toward a different future without treating my current life like an obstacle standing in its way.

That might be the lesson I'm learning at 52.

I don't need to sprint toward the woman I'm becoming.

I don't need to catch up.

I don't need to have the next ten years figured out.

I can take care of what is mine to take care of today.

I can build things slowly.

I can change my mind.

I can rest.

I can enjoy what is already good.

And tomorrow, I can get up and take another step.

There is no prize for getting to the end faster.

Maybe the point is to actually be here for the miles along the way.

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Jennifer Madden Jennifer Madden

Who Is Driving the Bus Today?

There are days when I am absolutely convinced I need to get a job.

Not eventually.

Immediately.

I need a steady paycheck. Benefits. Security. A plan.

There are other days when I think getting a traditional job is the last thing I want to do. I have businesses I want to build. Ideas I want to explore. I finally have some control over my time, and I don't particularly want to hand it back.

Then another voice joins the conversation.

You should be spending more time with your mother.

Followed closely by:

You need to start building your own life.

And somewhere in the back:

What are you doing about money?

It's quite a crowd in there.

For a long time, I treated whichever voice was loudest as though it represented what I actually believed.

I'm beginning to realize that's not necessarily true.

Sometimes a passenger has just gotten hold of the steering wheel.

The Passengers on the Bus

Years ago, I learned a metaphor that has stayed with me: imagine that your life is a bus.

You're the driver.

But you're not alone.

There are passengers riding along with you, and every one of them has an opinion about where you're going.

I've also found a similar idea in Internal Family Systems, a therapeutic model that describes us as having different "parts." These parts can carry different beliefs, fears, desires and ways of protecting us.

I don't need to understand every piece of the psychology to recognize myself in it.

I have parts.

Oh, do I have parts.

There's the responsible one.

She would like everyone to calm down, make a spreadsheet and follow the plan.

There's the anxious one.

She would like to know exactly what will happen for approximately the next 30 years.

There's the entrepreneur.

She thinks we should stop messing around and see what we're capable of building.

There's the employee.

She would like someone to deposit a predictable amount of money into our checking account every two weeks.

There's the caregiver.

She reminds me that this time with my mother is finite.

There's the daughter who still feels guilty when she sets a boundary.

There's the independent woman who would very much like everyone to stop telling her what to do.

And apparently they all bought tickets for the same bus.

They're Usually Trying to Help

Here's the part I've started to understand differently.

I used to think I needed to get rid of certain thoughts.

I shouldn't be anxious.

I shouldn't care what someone thinks.

I shouldn't be afraid.

I shouldn't want security if I also want freedom.

I shouldn't feel resentful when I chose to be a caregiver.

I shouldn't be irritated with someone I love.

But what if none of these parts needs to disappear?

What if they're simply trying to protect me?

The part demanding that I find a job isn't trying to ruin my entrepreneurial dreams. She's scared about money.

The part that wants to control everything isn't trying to make me miserable. She learned somewhere along the way that being prepared feels safer than being surprised.

The part that feels guilty about my mother isn't weak. She loves her.

Even the parts of me that create the most anxiety are usually trying, in their own slightly dysfunctional ways, to help.

Maybe I don't have to fight them.

I just don't have to give them the keys.

The Loudest Voice Isn't Necessarily the Truth

This has been particularly useful for me lately.

I can wake up feeling anxious about money and suddenly my entire future looks different.

You need a job.

These businesses aren't going to work.

You've wasted too much time.

You need to fix this.

A few hours later, I can feel completely differently.

The circumstances haven't changed.

My bank account hasn't magically increased.

Nobody has offered me a job.

My businesses haven't suddenly become wildly successful.

What changed was the passenger speaking the loudest.

That's an important distinction.

Because when I don't recognize what's happening, I start reorganizing my life around a temporary emotional state.

Anxiety becomes a five-year plan.

Fear becomes a decision.

Guilt becomes an obligation.

Someone else's opinion becomes my truth.

I've done all of those.

I'm trying to do less of them.

Sometimes the Passengers Aren't Even Ours

This is where it gets especially interesting.

Some of the voices riding around in my head sound suspiciously like other people.

A parent.

A former partner.

A boss.

A friend.

Someone who once made a comment about my body, my money, my choices, my career or the way I live.

Eventually they don't even have to say it anymore.

I say it for them.

You shouldn't spend money on that.

You should have a real job.

You should weigh less.

You should be further along.

You should do more for your mother.

You shouldn't feel that way.

The person may be nowhere near my actual life.

But somehow I've given them a permanent seat on the bus.

Worse, occasionally I've handed them the wheel.

I'm starting to question why.

I Can Hear You Without Obeying You

The goal isn't to become a person without fear, insecurity, guilt or contradictory desires.

I'm not sure that person exists.

And frankly, trying to become her sounds exhausting.

What I'm practicing instead is noticing.

Oh. The scared-about-money part is here today.

There's the daughter who doesn't want to disappoint anyone.

There's the part of me who desperately wants someone to tell me what happens next.

I don't have to argue with her.

I don't have to prove her wrong.

I don't even have to make her leave.

I can listen.

Sometimes she has useful information.

Maybe I do need to pay closer attention to money.

Maybe I do need a boundary.

Maybe my business needs more effort.

Maybe something genuinely needs to change.

But listening to a passenger isn't the same thing as letting her drive.

Someone Still Has to Drive

This is the part I'm still learning.

There isn't going to be a day when all of my different parts finally agree.

The entrepreneur and the security seeker may always have slightly different agendas.

The caregiver and the independent woman may continue negotiating.

The planner is probably never going to be thrilled about uncertainty.

That's okay.

They can come along.

But ultimately somebody has to decide where we're going.

And increasingly, I want that to be the version of me who can hear all of them without becoming any one of them.

The one who can say:

I know you're scared.

I know you want certainty.

I know you don't want to disappoint anyone.

I know you're trying to protect me.

But I'm driving.

Maybe that's what becoming more fully ourselves actually looks like.

Not finally silencing all the voices in our heads.

Just remembering whose hands belong on the wheel.

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Jennifer Madden Jennifer Madden

Behind on What?

I woke up the other morning with the unmistakable feeling that I was behind.

You know the feeling.

There are things I should be doing. Things I haven't gotten to. Things everyone else has apparently figured out while I've been over here wasting time.

Except when I stopped and asked myself a fairly obvious question — Behind on what? — I couldn't come up with an answer.

There wasn't a deadline I'd missed. No forgotten appointment. No urgent email sitting unanswered.

Just the feeling.

My brain, however, seemed determined to find an explanation for it.

It started pulling things off the shelves.

Money. Work. My businesses. My mother's health. My body. My future.

And because apparently none of that was enough, it started digging through the archives.

Old conversations. Things that happened years ago. People I haven't seen in forever. Situations that have absolutely nothing to do with the Tuesday morning I am currently living.

My brain can be remarkably resourceful when it is looking for a problem.

Maybe Nothing Is Wrong

I've been thinking about this a lot lately because I'm starting to recognize how much of my life I've spent assuming that discomfort means something needs my attention.

If I feel anxious, there must be a problem.

If I feel restless, I must need to make a decision.

If I feel uncertain, I should probably figure something out.

If I don't know what's coming next, perhaps I should make a plan.

And if there isn't actually a problem?

Give me a few minutes. I'll find one.

I'm joking, but only a little.

I think I've spent a lot of my life trying to stay one step ahead of whatever might go wrong. There is a certain comfort in believing that if I think about something long enough, prepare enough, anticipate enough and make the right decisions, I can protect myself from uncertainty.

The problem is that life contains an awful lot of uncertainty.

Especially mine right now.

A Life That Doesn't Fit Neatly on a Timeline

I'm in one of those strange seasons where some parts of my life are moving forward and others feel suspended.

I'm caring for my mother.

I'm trying to figure out what work looks like next.

I'm building businesses that may become something substantial or may teach me what I'm supposed to do after them.

I'm working on my health.

I'm thinking about money.

And there are parts of my future I simply cannot plan because they depend on things I cannot control.

For someone who likes a plan, this is not my preferred arrangement.

So my brain keeps trying to turn uncertainty into urgency.

You should be further along.

You should be earning more by now.

You need to figure this out.

You are running out of time.

And lately I've started answering it with:

According to whom?

Because I'm 52 years old. There is no syllabus anymore.

Nobody handed me the curriculum for this year of my life.

There isn't a page that says:

By September, Jennifer should have completed the following…

And yet sometimes I live as though there is.

The Imaginary Finish Line

I think many of us carry around an invisible timeline for our lives.

By this age, I should have enough money.

By this age, my career should be settled.

By this age, I should know where I'm going to live.

My body should look a certain way.

My relationships should look a certain way.

I should be more successful, more secure, more evolved, more certain.

More something.

We rarely stop to ask who created the timeline.

Or whether we even want the life waiting at the end of it.

I've spent much of the past few years feeling as though my life was on hold. And there are legitimate reasons for that. Caregiving changes what is possible. Financial limitations are real. Responsibilities are real.

But something else is also true.

My life is happening.

Right now.

Not the life I'll have when this caregiving season ends.

Not the life I'll have when I know what happens with my businesses.

Not the life I'll have when my finances feel more secure.

This one.

And when I actually look around at it, rather than looking ahead of it, there is quite a lot here that I love.

What If I'm Not Behind?

This may be the harder idea for me to accept.

What if I'm not behind at all?

What if there isn't some version of my life happening three miles up the road that I'm desperately supposed to catch?

Maybe I'm simply here.

In September 2026.

Living in a house I love.

Caring for someone I love.

Building some things.

Letting go of others.

Getting stronger.

Learning things about myself I probably couldn't have learned during easier seasons.

Still uncertain about plenty.

Still wanting things.

Still changing.

But not behind.

I've spent years treating life a little like a sprint — hurry up, solve this problem, get through this season, reach the next milestone.

Then I'll relax.

Then I'll feel secure.

Then I'll start living.

But the finish line keeps moving.

Maybe that's because there isn't one.

Just Today

I'm trying something different.

Instead of asking myself how I'm going to fix my entire financial future, I can ask what needs my attention today.

Instead of demanding that I know exactly where my businesses are going, I can do the next useful thing for them.

Instead of trying to predict how this season with my mother will end, I can live the day we're actually having.

Instead of turning every uncomfortable feeling into a problem to solve, maybe sometimes I can notice it and let it be there.

That anxious morning eventually passed.

Nothing dramatic happened.

I didn't solve my life.

I just stopped treating the feeling that I was behind as evidence that I actually was.

And then I went on with my day.

I'm beginning to think there may be more wisdom in that than I've given it credit for.

Maybe the goal isn't to finally get ahead of my life.

Maybe it's to stop running long enough to realize I'm already in it.

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Caregiving & Family Jennifer Madden Caregiving & Family Jennifer Madden

You Can Love Someone and Still Want Your Life Back

You can love someone deeply and still miss your freedom. Caregiving has taught me that two seemingly contradictory things can be true at exactly the same time.

There are thoughts you're apparently not supposed to have when you're taking care of someone you love.

I miss having the house to myself.

I wish I could leave without thinking about anyone else's schedule.

I want to make a decision without considering how it affects someone else.

I want my time back.

That last one is particularly difficult to admit.

Because when the person you're caring for is someone you love, wanting your own life can feel uncomfortably close to wishing they weren't in it.

Those are not the same thing.

But some days they can feel dangerously close.

Caregiving is made up of very ordinary sacrifices

When people hear the word caregiver, I think they imagine the obvious things.

Doctor's appointments.

Medications.

Emergencies.

Physical care.

Those things are real.

But there's another part that's much harder to explain.

It's the constant consideration of another person.

Can I go?

How long can I be gone?

Does she need anything?

What's happening tomorrow?

When is that appointment?

Did I take care of that?

Should I be home?

It's not always difficult.

Sometimes it's barely noticeable.

But it's always there.

A small calculation running quietly in the background.

And sometimes I resent it

There.

I said it.

Not her.

It.

The responsibility.

The limitation.

The fact that there are times when I'd like to think only about what I want to do and then simply do it.

That isn't how this stage of my life works.

And I've spent enough time feeling guilty about that resentment to understand something:

Guilt doesn't actually make me a better caregiver.

It just makes an already complicated situation heavier.

Two things can be true

I can love my mother and wish I had more freedom.

I can be grateful she's here and imagine the life I'll have someday when caregiving is over.

I can know that this time matters and still have days when I desperately want a break from it.

I can understand intellectually that this chapter won't last forever and still feel impatient while I'm living it.

Those things don't cancel each other out.

That's something I'm learning about midlife in general.

We spend so much time trying to decide which feeling is the correct one.

Grateful or frustrated.

Hopeful or scared.

Content or restless.

Loving or resentful.

Maybe adulthood is realizing the answer is very often:

Both.

The future gets complicated

There's another uncomfortable part of caregiving that I don't hear people talk about very much.

You still have a future.

And eventually, that future may exist without the person you're caring for.

So you think about it.

Of course you do.

Where will I live?

What will I do?

What will my days look like?

What might become possible?

And then sometimes you catch yourself looking forward to something that can only happen after something you absolutely do not want to happen.

That's a strange emotional place to live.

Wanting a future while not wanting the thing that has to happen before it arrives.

There isn't a neat way to resolve that.

I've stopped trying.

I don't want to disappear inside this role

Maybe that's the part I feel most strongly about.

Caregiving is something I'm doing.

It's not all that I am.

I still have work I want to do.

Things I want to build.

Places I want to go.

A body I want to make stronger.

A home I want to create.

People I want to spend time with.

Ideas I want to follow.

A future I'm curious about.

Those things aren't selfish distractions from caregiving.

They're my life.

And my life didn't stop being important because someone I love needs me.

I think we need to say this more often

You can be a good daughter and need space.

You can be loving and frustrated.

You can show up for someone and occasionally wish nobody needed anything from you.

You can appreciate the time you have and still wonder what comes next.

You can love someone deeply and want your life back.

Maybe the guilt doesn't disappear when we admit that.

But at least we stop pretending we're the only ones who feel it.

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Work & Money Jennifer Madden Work & Money Jennifer Madden

What I Want From Work at 52 Is Different Than What I Wanted at 32

I'm not less ambitious at 52. I'm just becoming much more particular about what I'm willing to trade for that ambition.

For most of my adult life, I thought the goal was to keep moving up.

More responsibility.

More money.

A better title.

A bigger opportunity.

The next thing.

I don't think I ever questioned that very much. That's just what you did. You built a career by accumulating things—experience, responsibility, accomplishments, income.

At 52, I'm looking at work very differently.

I'm not less ambitious.

I'm just becoming much more particular about what I'm willing to trade for that ambition.

I used to think more responsibility was always better

There was a time when being needed at work felt good.

Being the person who could figure things out.

The person people came to.

The person who could take something messy and make it work.

I still like that.

I'm good at it.

But I've also learned there's a very short distance between being valuable and becoming responsible for everything.

And these days, I'm much more interested in the difference.

I don't need to be indispensable.

Actually, I'd rather not be.

I want to do good work, solve interesting problems, be paid fairly, and then have enough of myself left for the rest of my life.

That last part didn't used to be nearly as important to me.

Now it might be the most important part.

Money matters more to me now—and less

This sounds contradictory, but it isn't.

Financial security matters enormously to me.

Maybe more than it ever has.

At 52, retirement isn't some abstract event happening to an old woman decades from now.

The old woman is getting suspiciously close to being me.

I think about savings.

I think about retirement.

I think about what it costs to live.

I think about having enough money that an unexpected expense doesn't rearrange my entire month.

So yes, money matters.

But the things I want money for have changed.

I'm less interested in what it can buy and more interested in what it can give me.

Options.

Breathing room.

The ability to say no.

The ability to leave something that isn't working.

The ability to help someone I love.

The ability to make decisions without fear making all of them for me.

That kind of money interests me very much.

I don't want my job to be my whole identity

Maybe this is another thing age changes.

For years, one of the first questions people asked when they met you was:

What do you do?

And somehow the answer was supposed to explain quite a lot about who you were.

I'm less convinced of that now.

Work matters to me.

I want to be useful.

I want to use my brain.

I want to solve problems.

I want to build things.

I want to earn good money.

But I also want to be a person who gardens.

Who gets stronger.

Who has time for people she loves.

Who reads.

Who travels.

Who has projects that may never make a dime.

Who can spend an afternoon doing absolutely nothing productive without feeling like she's committed some sort of moral failure.

My job can be an important part of my life without becoming the organizing principle of it.

Flexibility has become incredibly valuable

There are things I didn't fully appreciate when I was younger because I assumed I would always have control over my time.

Then life teaches you otherwise.

Parents age.

People need you.

Bodies need maintenance.

Appointments multiply.

Unexpected things happen on Wednesday mornings.

Suddenly flexibility isn't a perk.

It's part of compensation.

So when I think about a job now, salary isn't the only number I'm calculating.

I'm calculating commute.

Hours.

Stress.

Energy.

Autonomy.

How much of my brain will still belong to me at 6 p.m.

What will this job make possible?

And what will it make harder?

Those things have value too.

I still want to build something

This is the part that surprised me.

For all my talk about wanting peace and flexibility and a simpler life, I haven't lost the desire to create.

If anything, it's stronger.

I still get excited about ideas.

I still love figuring out how something could work.

I still want to make things that are useful.

I still wonder what's possible.

Maybe ambition doesn't disappear as we get older.

Maybe it just gets more selective.

I'm no longer interested in succeeding at something simply because success is available.

I want the success to be worth having.

So what do I want from work now?

Enough money to build security.

Interesting problems.

People I respect.

A reasonable amount of autonomy.

Work I'm good at.

Room to keep learning.

Enough flexibility for real life.

And enough energy left at the end of the day to still be myself.

That doesn't sound like a lack of ambition to me.

It sounds like I've finally started calculating the entire cost of a job instead of just looking at the salary.

At 32, I wanted work that could take me somewhere.

At 52, I still do.

I'm just much more interested in where it's taking me.

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Home & Everyday Life Jennifer Madden Home & Everyday Life Jennifer Madden

I Don't Want a Bigger Life. I Want to Like the One I Have.

I'm still interested in what comes next. But I'm learning that a good life isn't only built through big changes. Sometimes it starts with making an ordinary Tuesday feel good.

For a long time, I thought wanting more from life meant wanting a bigger life.

More success.

More money.

More experiences.

More interesting plans.

Something different enough that I could point to it and say, There. That's what I've been waiting for.

I'm not sure I believe that anymore.

Lately, I've been thinking about something much less exciting:

I want to like my regular life.

Not vacation life.

Not someday life.

Not the life I'll have when I make more money or have fewer responsibilities or finally figure out what I'm doing.

The one I'm living on a Tuesday afternoon.

I've spent a lot of time thinking about what's next

I'm naturally future-oriented.

I like plans. Projects. Possibilities.

There's always something that could be improved, organized, changed or figured out.

And there's nothing wrong with wanting things.

I still want things.

I want financial security. I want meaningful work. I want to travel. I want to keep making my home better. I want new experiences. I want to see what else I can build.

But I'm starting to notice how easy it is to spend your whole life leaning toward the next version of it.

When I get the job.

When I lose the weight.

When the house is finished.

When I have more money.

When caregiving ends.

When things settle down.

Then I'll...

What?

Start enjoying myself?

Most of life isn't the big stuff

This is embarrassingly obvious, but it took me a long time to really understand it.

Most of my life is ordinary.

I make coffee.

I work.

I run errands.

I figure out dinner.

I take care of things around the house.

I exercise.

I answer emails.

I water plants.

I watch television.

I go to bed.

Then I get up and do another version of it.

There are trips and holidays and celebrations and big moments mixed in.

But they're not most of it.

Most of it is Tuesday.

And if I'm always waiting for something bigger to make life feel good, I'm essentially deciding that most of my life doesn't count.

I've become strangely interested in small improvements

Maybe this is why I've become so invested in my house.

And my garden.

And making spaces work better.

And getting stronger.

And figuring out routines.

None of these things are particularly glamorous.

But they affect my actual life.

A garden I enjoy looking at changes an ordinary morning.

A room that works well changes how it feels to live in the house.

Being stronger changes what my body can do.

Having food I like in the refrigerator makes Wednesday night easier.

Getting rid of something that's been annoying me for six months is surprisingly satisfying.

These are tiny things.

But I'm starting to think tiny things have been seriously underestimated.

Maybe this is what getting older changes

At 30, I think I wanted my life to be exciting.

At 40, I wanted it to be successful.

At 52, I'm increasingly interested in whether it feels good.

Do I like being in my home?

Do I have people I can be myself around?

Does my work leave room for the rest of me?

Can I pay my bills without panic?

Is my body strong enough to let me do the things I want to do?

Do I have something to look forward to?

Do I laugh?

Do I have enough time when nobody needs anything from me?

Those questions feel much more important to me now.

Maybe because I've finally realized there isn't going to be some future point when ordinary life ends and the real one begins.

This is the real one.

That doesn't mean settling

I think that's an important distinction.

Liking the life you have doesn't mean deciding you shouldn't want anything else.

There are parts of my life I absolutely want to change.

There are circumstances I wouldn't have chosen.

There are things I'm actively working toward.

Acceptance and ambition can apparently live in the same house.

I can want more financial security and still enjoy coffee on the patio.

I can want different work and still appreciate having flexibility today.

I can love my mother and still want more of my time to belong to me.

I can want my circumstances to change without treating the present like a waiting room.

That's the part I'm trying to learn.

I want ordinary Tuesdays to be good

Not perfect.

Not productive enough to earn a gold star.

Just good.

A decent cup of coffee.

Work that feels useful.

A walk.

Something growing outside.

Dinner I actually want to eat.

A conversation with someone I love.

A house that feels like home.

Something I'm curious about.

Something I'm looking forward to.

Maybe that's not a small life.

Maybe that's just a life viewed from close enough to notice it.

I'm still interested in what comes next.

I'm still building.

I'm still changing things.

But I don't want to spend the next decade waiting for my life to become something worth enjoying.

I want to make this version good too.

Even the Tuesdays.

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Starting Over Jennifer Madden Starting Over Jennifer Madden

The Life I Planned Isn't the Life I'm Living

There’s a version of my life I assumed I’d be living by now. At 52, I’m learning to stop chasing that version and start asking what I want to do with the life I actually have.

There’s a version of my life I assumed I’d be living by now.

I don’t know that I ever sat down and consciously planned it. But it was there.

By my 50s, I’d be settled.

My career would make sense. My finances would be in good shape. I’d know where I belonged. The big questions would have answers.

I certainly wouldn’t still be wondering what I wanted to do with my life.

And yet, here I am.

I’m 52, living with and caring for my mother, reconsidering what I want from work, rebuilding parts of my financial life, and trying to figure out what I want the next couple of decades to look like.

This is not the life I pictured.

And for a while, I think I treated that like a problem I needed to fix.

The imaginary finish line

We spend so much of our younger lives moving toward things.

Finish school.

Build a career.

Make more money.

Find your people.

Buy the house.

Become established.

There’s always another milestone somewhere ahead of you.

And underneath all of it is this strange assumption that eventually you’ll arrive.

Your life will make sense.

You'll know who you are and what you're doing.

I don't know exactly when I realized there wasn't going to be an arrival.

Maybe that's part of getting older.

You start noticing how many things you were certain about that turned out not to be certain at all.

Careers change.

Relationships change.

Parents age.

People die.

Money comes and goes.

Bodies change.

Plans that once seemed incredibly important stop mattering.

And sometimes things you never thought much about become the center of your world.

Life keeps moving the furniture around.

I kept thinking I needed a plan

I'm very good at plans.

Give me a problem and I'll make a spreadsheet. I'll organize it. Research it. Create a system. Figure out the next six steps.

That works surprisingly well for a lot of things.

It does not work particularly well for an entire life.

I've spent a lot of time thinking I should know what comes next.

What should I do for work?

How much money do I need?

Where will I live?

What am I building toward?

What do I want my life to look like five years from now?

All reasonable questions.

But lately I've started wondering if I'm asking them too soon.

Because there's another question underneath all of them.

What do I want to do with the life I have now?

Not the life I thought I'd have.

Not the life I might have someday when circumstances change.

This one.

That's harder than it sounds

Because the answer isn't necessarily dramatic.

I don't have a secret dream of selling everything and moving to Italy.

I don't want to reinvent myself.

I'm not interested in becoming unrecognizable in six months.

Actually, I think I'm becoming more interested in the opposite.

I want to recognize myself.

I want work that uses what I'm good at without consuming my life.

I want to feel financially secure again.

I want to take care of my mother without completely disappearing into being a caregiver.

I want a home that feels good to live in.

I want to be strong and healthy enough to keep doing things for a very long time.

I want people I love around me.

I want things on the calendar I'm looking forward to.

I want ordinary Tuesdays that I actually enjoy.

None of that makes for a particularly impressive five-year plan.

But maybe that's the point.

Maybe a good life doesn't need to look impressive

This is one of the things I'm starting to question most.

For a long time, I thought progress needed to be visible.

A better job.

More money.

A bigger accomplishment.

Something you could point to and say, See? I'm moving forward.

Now I think progress might look completely different.

Getting your finances under control.

Making the doctor's appointment.

Planting something and watching it grow.

Getting stronger.

Learning how to enjoy your own company.

Changing your mind about something you thought you wanted.

Creating a home you don't constantly want to escape from.

Finding work that fits your life instead of building your entire life around work.

Saying no without spending three days feeling guilty about it.

Maybe those things count too.

Maybe they count more than I realized.

I'm not starting over from zero

That's another phrase I've been thinking about.

Starting over.

It sounds like everything that came before somehow disappeared.

But at 52, I'm not starting with nothing.

I'm starting with everything I've learned.

I've built things. Lost things. Made money. Made mistakes with money. Had jobs I loved and jobs I couldn't wait to leave. I've taken care of people. I've grieved people. I've moved away and come home. I've been certain about things I've later changed my mind about.

I know myself better than I did at 25.

Maybe not completely.

But better.

And perhaps that's the advantage of building a life at this age.

You're not working with a blank page.

You're working with a lot of information.

So this is where I am

Somewhere in the middle.

Not finished with the life that came before.

Not entirely sure what the next one looks like.

Taking care of what needs taking care of while also trying not to forget that my life is happening too.

And I suspect I'm not the only woman standing in this particular place.

Maybe your circumstances look nothing like mine.

Maybe you're dealing with a divorce.

A career that doesn't fit anymore.

Kids leaving home.

A parent who suddenly needs you.

A financial setback.

A loss.

A move.

Or maybe nothing dramatic happened at all.

Maybe you simply woke up one day and realized the life you've been living doesn't quite fit the person you've become.

So you start asking questions.

What matters to me now?

What am I done with?

What do I want more of?

What could the next chapter look like if I stopped requiring it to resemble the last one?

I don't have those answers yet.

That's why I'm writing.

Letter from Jen isn't about having the next chapter figured out.

It's about paying attention while we figure it out.

To work and money.

To caregiving and family.

To grief and change.

To home and health.

To the ordinary things that make a life feel like your own.

And to that question I keep coming back to:

What do I want to do with the life I have now?

I don't know yet.

But for the first time in a while, I'm less worried about having the answer.

I'm interested in finding out.

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