The Questions Every Empty Nester Should Ask Herself This Year
Because while they are planning their next chapter — it is time to plan yours
My kids are in full planning mode. Meetings with academic advisors. Conversations about majors and minors. Decisions about which classes to take and which opportunities to pursue and what they want the coming year to look like. Long thoughtful discussions about the direction of their lives — what they are building toward, what they want to become, what they are choosing on purpose.
I watch them with a mix of pride and something else I have been sitting with this week.
Something that feels a lot like recognition.
Because the questions they are asking themselves — the big orienting ones, the ones that require stillness and honesty and a willingness to look clearly at where you are and where you want to go — those are not just questions for twenty-year-olds standing at the beginning of their lives.
They are questions for us too.
Maybe especially for us.
We have spent so many years being the ones who helped them answer their questions — the homework, the college essays, the what do I want to be when I grow up conversations at the dinner table — that we forgot to keep asking our own.
But this is our year.
Our planning season.
Our chance to sit down with ourselves the way they are sitting down with their advisors and say — okay. Where am I? Where do I want to go? What do I want the coming year to look like? What am I choosing on purpose?
This post is that conversation.
Pull out a journal if you have one.
Make something warm to drink.
Take your time.
These questions deserve it.
Before the Questions — A Note on How to Use This Post
I want to say something before we begin.
These questions are not a test.
There are no right answers. No wrong ones. No answers that are too small or too ambitious or too late or too early.
The only wrong answer is the one you give because you think it is what you are supposed to say rather than what is actually true for you.
So as you read through these — and I hope you do this slowly, one question at a time, with a pen in your hand or a blank document open — I want to ask one thing of you.
Tell the truth.
Not the truth that sounds good. Not the truth that is easy. Not the truth you would tell someone at a dinner party.
The real one.
The one that lives underneath all the noise and the obligation and the years of putting everyone else first.
That truth.
She is the one worth listening to.
She has been waiting for you to ask.
Part One — Who Am I Now?
The identity questions
Who was I before I became somebody’s mother — and is she still in there?
Start here.
Not because this is the most important question — though it might be — but because it is the one that most of us have been avoiding the longest.
Before the pregnancy test. Before the nursery painted and the name chosen and the life reorganized around a small person’s needs.
There was a woman.
With her own preferences and passions and ideas about what she wanted her life to look like.
What did she love? What did she dream about? What were the things she was going to do — someday, later, when there was more time?
Is she still in there?
She is.
I promise she is.
Write about her. Remember her. And then ask yourself — what does she want?
Journal prompt: Who was I at twenty-five before the roles took over — and what did that woman know about herself that I have forgotten?
Who am I right now — honestly?
Not who you were. Not who you are becoming. Who you actually are today.
The things that energize you and the things that drain you. The relationships that fill you and the ones that quietly deplete you. The version of yourself you are most proud of and the version you are still working on.
Be honest.
Not harshly. Not critically. Just honestly.
Because you cannot build a year that fits if you do not know who you are building it for.
Journal prompt: If I described myself completely honestly to a stranger — not my resume, not my roles, but who I actually am — what would I say?
What parts of my identity am I ready to release?
We carry identities that no longer fit.
The one who does everything herself. The one who says yes when she means no. The one who makes herself small to keep the peace. The one who waits for permission. The one who is still trying to prove something to someone who stopped paying attention years ago.
Which of those are you ready to set down?
Not with drama. Not with a big announcement.
Just quietly. Gently. The way you set down something heavy after carrying it for too long.
Journal prompt: What story about myself am I still telling that I no longer believe — and what would I tell instead?
Part Two — What Lights Me Up?
The passion questions
What did I used to love that I stopped making time for?
Writing. Reading. Creating. Moving. Making things with your hands. Being in nature. Making music. Making art. Making people laugh. Making things grow.
What was yours?
What got quietly set aside in the busy years — not because you stopped loving it but because there was always something more urgent, someone who needed something, a reason to defer it to later?
Later is here.
Journal prompt: If I had one completely free Saturday with no obligations and no one needing anything — what would I do with it? What does that tell me?
What have I always wanted to try but talked myself out of?
I have been trying things this year.
Yoga. Pickleball. Golf. Water aerobics. Art classes. Painting. Piano.
Not all of them have stuck. Not all of them were meant to. But the trying itself — the act of showing up somewhere new as a beginner without knowing the outcome — has been one of the most nourishing things I have done in this season.
What have you been almost doing?
The class you researched but did not register for. The instrument you thought about picking up. The language you started an app for and then stopped. The trip you planned in your head but never booked.
What is your almost?
Journal prompt: If I knew I could not fail and nobody was watching — what would I try?
What makes me lose track of time?
This is one of the most reliable indicators of what you are meant to be doing more of.
Not what you think should light you up. Not what looks good from the outside. What actually makes the hours disappear without you noticing.
For me it is writing. I sit down with a blank page and look up and three hours have passed and it did not feel like three minutes.
What is yours?
That thing is telling you something important.
Journal prompt: When was the last time I completely lost track of time — what was I doing and what does that tell me about what I should be doing more of?
What would I create if I believed it was possible?
The snail mail club. The Substack. The affirmation ebook. The coaching practice taking shape.
None of these were on my radar three years ago.
They emerged from the question — what would I create if I believed it was possible?
I started with a journal. Then a vision board. Then words that became phrases that became something real.
You have something in you that wants to be made.
A project. A community. A practice. A business. A creative pursuit that would not exist without you.
What is it?
Journal prompt: If I could build anything — anything at all — with the experience and the time and the freedom I now have, what would I build?
Part Three — How Do I Want to Feel?
The wellbeing questions
What does my body need that I have been ignoring?
Rest. Movement. Nourishment. Medical attention you have been putting off. The hot springs afternoon. The spa day you keep saying you will book when things calm down.
Things do not calm down.
What has your body been asking for that you have been too busy to hear?
Journal prompt: If my body could speak to me directly right now — what would it say it needs most?
What does my morning feel like right now — and what do I want it to feel like?
The morning sets the tone for everything.
And the morning — for the first time in twenty years — is yours to design.
Does your current morning reflect who you are and what you need? Or is it still organized around the rhythms of a life that no longer exists — rushing toward obligations, checking the phone before you check in with yourself, starting the day in someone else’s energy before you have found your own?
What would your ideal morning look like?
Not perfect. Not elaborate.
Just yours.
Journal prompt: I will design my ideal morning in detail — from the moment I wake up to the moment the workday begins — and identify one thing I can change this week to move toward it.
Where am I holding stress in my body — and what do I do about it?
Twenty years of managing everything leaves a physical residue.
The shoulders that live near your ears. The jaw that clenches at night. The breath that is consistently shallower than it should be. The tension that has been there so long you stopped noticing it.
Where is yours?
And what would it feel like to release it?
Journal prompt: I will do a slow body scan right now — starting at the top of my head and moving down — and notice where I am holding tension. What does that tension need?
What fills my cup — and am I doing enough of it?
The walk in the morning before the world gets loud. The bath on a Wednesday night for no reason. The candle lit in the middle of the afternoon. The playlist that shifts everything. The book finished in one sitting. The phone call with the woman who makes me feel completely seen.
What fills yours?
And are you doing it consistently enough to sustain yourself through the demands of this season?
Journal prompt: I will list five things that genuinely fill my cup and honestly assess how often I am doing each one. What needs to change?
Part Four — Who Do I Want Around Me?
The relationship questions
What relationships do I want to invest in this year?
Not all relationships are equal.
Some fill you. Some drain you. Some have grown and deepened alongside you and some have quietly revealed themselves as seasonal — right for a chapter that has now closed.
This year — with intention and with the limited energy that all of us have — where do you want to put your relational investment?
The friendships worth deepening. The family connections worth tending. The new relationships worth pursuing. The romantic possibilities worth being open to.
Choose deliberately.
Journal prompt: I will list the five relationships I want to invest in most this year and one specific way I will show up differently in each one.
Who have I been meaning to reach back toward?
There is always someone.
The friend from before who understood you in a way nobody since quite has. The relationship that faded not because it ran its course but because life got busy and neither of you kept reaching. The woman you met briefly and felt an immediate recognition with and never followed up.
Who is yours?
Reach back.
This week.
Not next month.
This week.
Journal prompt: Who have I been meaning to contact for longer than I want to admit — and what is actually stopping me?
What kind of friend do I want to be in this chapter?
Not the friend you were in the busy years — showing up when you could, loving from a distance, meaning to call and not quite getting there.
The friend you want to be now.
With the time and the intention and the genuine desire for deep reciprocal connection that this season has created space for.
What does that friendship look like? How does she show up? What does she offer and what does she ask for in return?
Journal prompt: I will describe the friend I want to be in this next chapter — specific, honest, aspirational — and identify one thing I can do this week to start being her.
How is my relationship with my adult children evolving — and how do I want it to evolve?
This one is worth asking directly.
The relationship you have with your kids now is not the same as the one you had when they were under your roof. It is changing. Growing. Becoming something new and in many ways more extraordinary than what came before.
Peer to peer. Adult to adult. A friendship forming alongside the love that was always there.
What do you want that relationship to look like this year? How do you want to show up for them differently now that they are launching into their adult lives? And how do you want to let them show up for you?
Journal prompt: I will describe the relationship I want with each of my adult children this year — honest, specific, forward looking — and one way I will move toward it.
Part Five — What Does This Year Look Like?
The planning questions
If this year goes exactly right — what does it look like?
Not perfectly. Not without difficulty.
But right in the sense of — true to who you are and where you are going. Right in the sense of — you are proud of how you spent it. Right in the sense of — when you look back at it from next year’s vantage point you will feel that it was a year worth living fully.
What does that year look like?
Where are you? What are you doing? Who are you with? What have you built or created or begun? How do you feel at the end of each day?
Be specific.
Vague vision boards do not become real lives. Specific ones do.
Journal prompt: I will describe my ideal year in as much detail as I can — not what I think is realistic but what I genuinely want — and then identify the first small step toward each element.
What is one brave thing I want to do this year that I have never done before?
Solo travel. A retreat. A creative pursuit started from scratch. A career pivot. A business built from everything I have survived. A relationship pursued. A dream taken seriously for the first time.
One brave thing.
Not ten. Not a list.
One.
The one that sits in the back of your mind quietly and refuses to fully leave.
Journal prompt: I will write about the one brave thing I keep almost doing — and I will make a plan to actually do it this year.
What do I want to learn this year?
Not what you think you should learn. Not what would look impressive. What genuinely excites your curiosity.
A language. An instrument. A creative skill. A subject you have always been interested in and never made time for. A technology that would open new doors. A practice that would deepen your inner life.
The learning is not just about the thing you learn.
It is about the experience of being a student again. Of approaching something with beginner’s mind. Of discovering that your brain is still hungry and curious and capable of being delighted by new information.
What do you want to learn?
Journal prompt: I will identify one thing I genuinely want to learn this year and take the first concrete step toward learning it before the end of this week.
What do I want to let go of this year — for good?
The resentment you have been carrying too long. The habit that no longer serves you. The relationship that has been draining you for years. The story you tell about yourself that was never true. The standard you set for yourself that exhausted you to maintain. The guilt about choices that were right. The grief that has had its season.
What is ready to be released?
Not suppressed. Not ignored.
Released.
With intention. With grace. With the full understanding that letting go is not losing.
It is making room.
Journal prompt: I will identify the one thing I most need to release this year — be honest, be specific — and I will write a letter to it. A real one. Saying goodbye.
The Planning Session — Putting It All Together
My kids will sit down with their advisors and come away with a plan.
A schedule. A direction. A sense of what the coming year is building toward.
I want you to do the same.
Not with an advisor — though therapy is always a gift worth giving yourself if it is available to you.
With yourself.
Set aside an hour this week.
Not a spare moment. An actual hour. On the calendar. Protected.
Make your warm drink. Get your journal. Sit somewhere comfortable.
And go through these questions.
Not all of them at once — that is too much.
Choose five that called to you the most as you read. The ones that made you pause. The ones that made your stomach feel something. The ones you immediately thought I do not want to answer that — because those are always the ones worth answering most.
And then answer them.
Honestly.
Specifically.
Without editing yourself before you have even begun.
And when you are done — look at what you have written.
That is your plan.
That is your curriculum for the coming year.
That is the woman you are choosing to become.
On purpose.
With intention.
In this season that is finally — completely — yours.
One Last Thing
My kids are excited about the coming year.
The new classes. The new possibilities. The sense of something building toward something even if the destination is not fully visible yet.
I am excited too.
Not for their year — though I am proud beyond words of who they are and who they are becoming.
For mine.
For the questions I am still answering. The things I am still trying. The connections I am still building. The woman I am still becoming.
For Letters From The Nest — which exists because I sat down three years ago in a quiet house and started asking myself questions I had been too busy to ask before.
For this community of women — you — who show up here and remind me every single week that these questions matter. That this season matters. That we matter.
Your coming year is full of possibility.
And it starts with a question.
What do you want it to look like?
Answer that.
And then go build it.
With so much love and a journal full of questions,
Bridget
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