12 Days of Giving Day 3: When Generosity Wrecks Your Retirement

There’s a certain type of person I see over and over again.

They’re not reckless. They’re not out here blowing money on cars and flexing on Instagram.
They’re the glue.

They host the holiday dinners.
They show up with the “I saw this and thought of you” gift.
They quietly pick up the tab because “it’s just easier that way.”

And a lot of them are terrified about the future.

In our 12 Days of Giving series, I sat down with therapist and NoBS Collective member Rachel Duncan to talk about this exact person: late 50s, single, no kids, strong friend group, nonprofit paycheck… and a deep fear that retirement might not be possible because so much of her money goes to everyone else.

If that hits a little too close to home, stay with me.


The Holiday Script That’s Draining You

From the time we’re kids, we’re fed one script about the holidays:

If you love people, you spend money on them.

More gifts. Bigger gestures. More “stuff” to prove you care.
If you show up empty-handed, you feel like you’ve failed the assignment.

By the time you’re a teenager and you get your first job, you start using money as social superglue:

  • You pay for the pizza

  • You cover gas

  • You buy the “fun” snacks

  • You jump on every group gift

And here’s the key: nobody questions it, because you’re “just generous.”
It becomes part of your identity.

Fast forward 20–30 years. The numbers are bigger, but the script hasn’t changed:

You’re still the one who hosts.
You’re still the one buying the “perfect” gifts.
You’re still the one saying yes to every fundraiser, every GoFundMe, every “can you help?”

Except now, there’s a 401(k) statement, a retirement calculator, and a very real sense that time is not on your side.

The BS We’re Fed About “Fixing” It

Here’s where we usually go wrong.

When someone like this finally raises their hand and says, “I’m worried,” the advice they get is trash:

“Just stop spending so much.”
“You need more discipline.”
“Make a budget and stick to it.”

Cool. Thanks. Very helpful. 🙄

If generosity is tied to your identity, your relationships, and your sense of safety…
Then telling you to “just stop spending” is like telling you to “just stop breathing.”

It doesn’t work because it doesn’t respect what’s actually happening underneath:

  • You’re using giving as a way to belong

  • You’re afraid that if you stop, you’ll be seen as selfish or distant

  • You might not even know who you are without being the generous one

This is why so many “money plans” fail for people like you.
The spreadsheet never stood a chance against decades of emotional wiring.


What’s Really Going On (It’s Not Just About Money)

Rachel and I dug into the psychology, and here’s the uncomfortable truth:

A lot of “over-giving” started as survival.

When you were younger, spending money was a shortcut to connection:

  • “If I pay for this, they’ll include me.”

  • “If I bring the gift, I’ll be appreciated.”

  • “If I always show up, I’ll never be left out.”

It worked. You became the reliable one. The thoughtful one. The rock.

But your nervous system doesn’t know the difference between:

  • “I want to be generous” and

  • “I have to do this or I’ll lose my place in this group.”

So now, every holiday, your brain runs the same program:

“If I don’t go big, I’ll disappoint people. I’ll feel like I’m not enough.”

At the same time, there’s another voice starting to get louder:

“If I keep doing this, I’m never going to be able to retire.”

That tension is brutal. And most people just push it down and swipe the card anyway.


Presence vs Presents: What Your People Actually Want

Here’s the part nobody says out loud:

Most of your people already have too much stuff.

Ask them what they actually want, and the answers sound like:

  • “Time together.”

  • “Less stress.”

  • “A meal where nobody’s on their phone.”

  • “Help with the kids.”

  • “Someone who really listens.”

In other words: presence, not presents.

The story in your head might be,
“If I don’t bring the gift, I’m letting them down.”

The story in their head might be,
“I just want you there. I miss you.”

We talked in the episode about how many clients feel awkward receiving big gifts.
They don’t know how to respond. They feel pressured to reciprocate.
Sometimes your generosity is accidentally creating stress for them, too.

Let that sink in for a second.

You’re torching your future to give people things they may not even want,
in a way that doesn’t always feel good to them anyway.

So no, the answer isn’t “stop being generous.”
The answer is change what generosity looks like.


Redefining Your 12 Days of Giving

If this is you, I’m not asking you to become a different person.

I’m asking you to run a different play this year.

Here’s how you can start to shift your own 12 Days of Giving without blowing up your relationships or ghosting your friends:

1. Set a “Future-Protecting” Limit

Before you buy a single thing, decide:

  • “This is how much I can spend on gifts this year without harming Future Me.”

Not “how much can I stretch if I move things around.”
Not “I’ll figure it out on the card and deal with it in January.”

A real number that respects your retirement, your savings, and your sanity.

That number is the container.
If it’s smaller than what you’re used to, good. You finally have to get creative.

2. Have One Honest Conversation

Pick one person in your circle — the one you trust most — and say something like:

“Hey, I’ve been doing a lot of thinking about money and the future.
I still want to show up for the holidays, but I’m changing how I do gifts this year.
I’m focusing more on time together and small, meaningful stuff instead of big spending.
I just wanted you to know it’s not about caring less. It’s actually about making sure I can be around a lot longer.”

Watch how many people say, “Honestly, I’m relieved.”

That one conversation often unlocks a whole new way for the group to do things.

3. Switch from Stuff to Story

If you still love the act of giving, cool. Don’t kill it. Rebuild it.

Ideas:

  • Write handwritten letters to the people who matter most

  • Put together a small photo book or digital album

  • Gift an experience you can share together (a walk, a coffee, a game night, a day trip)

  • Cook a meal and make that the gift

Generosity isn’t about the price tag. It’s about the story it creates for both of you.

4. Practice Receiving Without Deflecting

This one is going to sting a little.

A lot of over-givers are terrible at receiving.

You downplay it. You joke it off. You instantly try to “even the score.”

If that’s you, try this instead:

When someone gives you something (time, help, a gift), say:

“Thank you. This really means a lot to me.”

And then shut up. Don’t rush to balance it out. Let yourself be cared for.

You’re not just changing how you give — you’re changing your identity from “only the giver” to “someone who can also receive.”


If You’re the Generous One, This Is Your Wake-Up Call

If you see yourself in this — the host, the planner, the gift-giver, the bill-grabber — I’m not here to shame you.

I’m here to tell you the truth:

You can’t keep giving like this and magically end up with a secure retirement.
You’re not the exception. The math doesn’t care how big your heart is.

But you also don’t have to pick between:

  • “Cold, selfish budget person” and

  • “Beloved, broke giver.”

There’s a middle ground where your generosity is still loud, but your future isn’t the sacrifice.

That’s what this 12 Days of Giving series is about — stripping away the holiday BS and rebuilding giving in a way that works emotionally and financially.

If this hit you, go watch the full conversation with Rachel.
Let it challenge the stories you’ve been carrying.

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