Week 6: Why You Can't Answer "What Do You Want for the Holidays?"

Permission to Desire Impractical Things

I found a vivid turquoise sequined dress at Goodwill last week.

My practical brain had a thousand reasons not to buy it: You have nowhere to wear it. Save your money for practical gifts for other people. Your closet is way too small for things you won’t wear every day.

I bought it anyway. Because when I tried it on, I felt fancy.

Now? I’m on the lookout. When an invite comes that even remotely fits, I’ll be ready to say yes. I’ll create opportunities to wear the dress instead of waiting for an invitation.

‘Tis the season when people ask: “What do you want for the holidays?” It’s the one time of year we’re explicitly invited to desire things. And still, most of us freeze. We say “I don’t know.” We list socks and practical items we need anyway.

If we can’t acknowledge what we want when someone’s literally asking us what we want, how can we possibly build a life around our genuine desires?

Last week in our 2026 strategic planning process, we re-aligned our measures of success with our values. Now comes the harder question: What do you actually want?

Not what you should want. Not what would be practical. Not what would serve others or look impressive. What lights you up? What brings you pleasure?

We talk ourselves out of wanting things before we even fully acknowledge we want them:

We want to write a book but tell ourselves nobody would read it.
We want to travel for six months but tell ourselves we can’t leave our job.
We want to pivot careers but tell ourselves we’re too old.
We want to make art but tell ourselves it’s not a real contribution.
We want to buy the sequined dress but tell ourselves we have nowhere to wear it.

What Research Tells Us

Here’s what we know about desire and regret:

People who pursue authentic desires, even “impractical” ones, report higher well-being than those who only pursue practical goals. Suppressing what we genuinely want creates a chronic sense of something missing.

The biggest regrets people report aren’t about things they tried that didn’t work out. They’re about desires they never pursued because they seemed impractical, unrealistic, or selfish.

These regrets intensify in midlife. We start realizing we’re running out of time to pursue what we actually want.

“Approach goals”, ones that move us toward what we want, are more sustainably motivating than “avoidance goals”, that move us away from what we don’t want. But we can’t pursue what we want if we won’t let ourselves even acknowledge what that is.

Three permissions I am giving myself in midlife

Permission to want impractical things.
Not everything needs to be practical. Joy is worth money and space. It’s ok if you can’t explain it. Feeling it is enough.

Permission to want things that don’t serve others.
We’ve spent decades wanting things that would help someone else, make someone proud, prove something to someone. What do you want? Not for your family, your company, your community. For you.

Permission to want something different than what you’ve been working toward.
Just because you’ve invested years working toward something doesn’t mean you have to keep wanting it. You’re allowed to change your mind about what matters. That’s growth.

The Questions That Reveal Desire

Here are the questions I’ll spend 30 minutes a day exploring this week in my morning pages to help inform my strategic vision for 2026:

• What do you want that you’ve been telling yourself is impractical?

• What do you want that feels selfish?

• What do you want that’s different from what you’ve been working toward?

• What would you do if you couldn’t fail?
  What are you jealous of? (Jealousy is excellent data for revealing deep desire.)

Buy the Dress First

We think we need the occasion before we can buy the dress. We need the job offer before we can want the career change. We need the guarantee before we can pursue the dream.

But it works backwards. We buy the dress, then we create opportunities to wear it. We identify what we want, then we figure out how to make it possible.

When you’re clear on your values (Week 5) and honest about your desires (this week), next week’s vision work becomes obvious. You’ll know what you’re building toward because you’ll finally let yourself want it.

Most strategic plans fail because they’re built on what we think we should want. The ones that work are built on authentic desire guided by clear values.

This Cyber Monday

While everyone’s shopping for others today, I’m inviting you to shop for yourself. Not necessarily with money - but with permission.

Give yourself permission to want the impractical thing. The thing that lights you up. The thing you can’t justify but that makes something in you say yes.

And if you ARE shopping for gifts this season, check out our Uplifters gift guide featuring incredible women entrepreneurs and creatives over 40. Every purchase supports a woman building something brave in her second half. It’s full of impractical, delightful things that make life better.

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