Every year, my inbox starts blowing up in predictable fashion 1 week before Thanksgiving, with all caps subject lines to the tune of, “HELP!”, followed by emails filled with lots of expletives and/or sad face emojis, as well as some very elegant prose about why everything and everyone sucks, and all the things that the author “has to” do, and is rendered helpless in the face of these obligations. Typically, this ends with a claim of, “All I really want to do is [insert custom escape plan here].” 

No doubt the end of the year holiday season can be a hugely challenging time of year for many reasons, but for the Underfulfilled Overachiever among us, this is basically ground zero for “good solider-ing”, and doing a lot of things we think we are “supposed to” do and “should” do in the name of not being selfish! 

“Tradition” can be beautiful and meaningful, but it has a “shadow” side and it can also be manipulative and weaponized against us, and a tool for just keeping us stuck. “Family”, whatever that looks like and means to you, can, of course, be incredibly supportive, joyful, aligned and meaningful, and it, too, can be used as a tool for manipulation and obligation and demands for self-abandonment. 

This doesn’t just happen around the holidays, of course. I talk about this with clients 365 days a year, but this is just the time of year when many people are all addressing these same concerns all at once, which makes it the most extraordinary sandbox to practice aligned answers, versus blind “yeses”. 

If you build a holiday season that is uniquely well-suited to you, then I promise you that you can build a career, and a life!, that is uniquely well-suited to you the other 365. 


What is a “sandpaper situation” you ask? 

Well, it’s exactly what it sounds like! A “sandpaper situation” is one that makes you feel like “sandpaper” to be in, or even to imagine being present for: it chafes, it’s uncomfortable, there’s a quality of friction and roughness, and it’s just plain unpleasant. My guess is you can already feel what it is for you, and that’s precisely why this label is so effective. You’re welcome.

Here are my 3-steps to go from “sandpaper situations” to “smooth(er) celebrations”:

1) SCAN for the “sandpaper situations”! 

  • Scan your calendar for the next month, or in your mind’s eye, and imagine yourself at each event, trip, interaction, notable day, gathering, location, car ride etc. 
  • Make a 2-column list: sandpaper vs. smooth. 
  • Ask yourself simply: is this a “sandpaper situation” or is this a “smooth situation”?

Note: no one is asking you to say “no” to anything or to change anything yet–just scan for the sandpaper! So give yourself permission to call “sandpaper” on every single thing happening this month if you must! We can decide what to do about them later. 

If you’ve never given yourself the permission or the opportunity to ask yourself how you actually feel doing each of the “obligations” in your life, particularly holiday ones, this can be incredibly challenging, and your mind may even decide to “go offline” in protest. That’s ok. Take a break, and come back to it. 

Bonus step: Get beyond the ” because I have to’s”.

Let’s revisit to the “I just want to…escape to a desert island!” claim from earlier I wouldn’t be doing my job correctly if I didn’t say, “Well, why don’t you escape to that desert island?” (And not in that annoying mom tone of, “if so and so jumped off a bridge, would you do it, too?” ) It’s not rhetorical. Of course there are many excellent reasons why you are not on a desert island, but they are worth articulating to yourself so that you can decide if you want to accept these reasons as valid. Push past the “I just cants”.

2) IMAGINE the “smooth”. 

If every human on earth bent to your will and got on board with your plans peacefully and happily, what would this holiday season (or other non-holiday occurrence) look like? 

These are some reflection prompts to help this process:

  • What is the best, most joyful, meaningful, dreamy, uniquely well-suited to you holiday season that you can imagine?
  • What would happen? What would not happen?
  • Who would be present/not present? Where would you be?
  • What can you do now to get closer to that vision?
  • What would you need to say “yes” to, and “no” to in order create this?
  • What are you willing to do in order to take responsibility for creating this for yourself?

3) BRIDGE the gap with the “3 Bs”.

One of the most life-changing tools I’ve ever known, via Martha Beck, is the 3 Bs: bag, barter, better. 

Now, we want to bridge the gap between the sandpaper situations and the smoothest celebrations we can imagine for ourselves, using the 3 Bs. The goal here is to get less “sandpaper-y” and more “smooth”.

For each “sandpaper situation” you’ve identified, we evaluate and make adjustments, according ” The 3 Bs”:

  • Bag: Just don’t do it. Full-fledged cancel culture. 
  • Barter: Offer an alternative. This sounds like, “I can’t do this, but I can do this.”
  • Better: Make an adjustment to improve the situation. This may or may not involve communication. Bring a friend, set a time limit, “bookend” with your most favorite activities in the world. 

Let’s take a most ridiculous example from one of my favorite columns, The Cut’s “Ask Polly”. Just for fun, in this scenario, you are the person described who has a deadly allergy to mushrooms and yet your family-in-law refuses to not cook with mushrooms for their holiday family gatherings. (Real life scenario: worth a read!) 

So, yea, major seasonal sandpaper situation…what to do?!

  • Bag: might you consider just saying that you won’t be attending this year?!  Usually this is the last resort, if you’re doing this exercise in the first place, so you can come back to this after the other two, if you must. 
  • Barter: Figure out what part of this is actually important to you and why you find it difficult to say “no” to sandpaper. Perhaps you discover that you don’t want to disappoint your in-laws, and you want your kids to have a relationship with their grandparents and to have fond memories of family holidays. A “barter” would be to suggest that you spend part of the holiday doing some sort of activity that isn’t around food or kitchens, like ice skating on Christmas Eve, or a movie date on the 1st day of Hanukkah, or maybe you offer to host the meal so you can control all the things. It sounds like, “I can’t attend the family meal, but I’d love to do a gift exchange and dessert on Christmas (or other holiday) morning before you start preparing the holiday meal!”  (Because these people are huge assholes, I would not actually recommend “bartering” with them, but for the sake of the exercise…)
  • Better: Perhaps you decide that it really is important to you to attend this mushroom-laden feast, but it HAS to get less sandpaper-y! Brainstorm on how you can make it better! It would look something like, preparing your most favorite of all time mushroom-free comfort food that just delights you to no end to think about eating, and bring that to enjoy. Or, decide to arrive after dinner (and dishes) are done and just for a mushroom-free dessert and egg nog couple of hours. 

Some additional tips:

  • Don’t do anything that you will be resentful about, or for which you can’t find an excellent reason to make that choice. It might be as simple as a gift to your parents to attend something, but it must be from a place of generosity and being at choice, rather than a place of old habits of people-pleasing for fear of losing their love etc. 
  • Remember that nothing is permanent. You are allowed to experiment with the holidays (and your life). Launch and iterate! Directionally right holidays! 
  • Finally, to repeat, this does not apply just to the holidays. I’m a big fan of “sandpaper situation”-free living in all seasons, and I highly recommend that you consider this approach as well! 


Want to go deeper?

I talk about more about this approach more in my article on what I call HAYWALTs

Is your “Fear of Being Mean” holding you back? Check out my article on that here. 

Or learn how to “Kondo Your Career”!