Bullish: Use The Holidays To Get Ahead (While Sitting On Your Mom’s Couch)


‘Tis the season, and I am headed to the familial homestead in Virginia to engage in a small, somewhat sarcastic Christmas gift-exchange and going-out-to-dinner in which the youngest participant is my twenty-nine-year-old brother — hence, little magic-making is needed or expected. No one will be dressing up as Santa and making out with Mom (unless there’s something I don’t know about).

Business has slowed down for me this month, as it always does, which has given me some time to clear out my inbox, pitch things, and schedule my new year to my satisfaction.

So, today, in the spirit of Bullish Life: 5 Ways to Improve Your Life in 5 Minutes, here are a few ways to use the holidays to get ahead.

I tried to suggest things you can do while sitting on Mom’s couch, half-paying-attention to a laptop, or in little snippets in between chopping onions and adding more booze to the eggnog.

Oh, and if you’re not celebrating Christmas, you have a productivity bonus already! Get some Chinese food and take over the world.

Use the season as an excuse for thank-yous and compliments

You know what I don’t believe in? Emailed holiday cards. The whole point of paper holiday cards (which I personally don’t bother to send, as I think that a lot of scrapbooking and holiday-newsletter-making and making things by gluing shit to other shit are just ways to keep women occupied and not accruing actual power) is that someone thought of you in advance, and knows where you live, and also it’s nice to see people’s handwriting from time to time. It’s sort of intimate.


But email holiday cards take little effort or forethought, and can be sent to entire mailing lists without even a thoughtfully-chosen Love stamp. Furthermore, say those who work in IT, they clog mail servers with their HTML-heavy bells and whistles and activate everybody’s spam filters.

However, the holiday season is a lovely opportunity to email anyone you want to pitch something to, or to just make nice and build up goodwill. Try, “I was just cleaning out my inbox for the end of the year and noticed that I never followed up about your amazing idea!” or “I was just making plans for the new year and wanted to thank you for helping my out with my files all throughout 2013!” or “Happy New Year! Did you know that you’re my favorite web designer ever? Thanks for the amazing work.”

Holiday greetings mean more when they’re jammed full of professional respect. Also, you can easily send two dozen of these while half-listening to tales about your relatives’ children and arthritis.

Ask, “How do you think I’m doing?”

Harvard Business Review’s You Are Not the Best Judge of You makes the point that you need outside feedback; our own self-perceptions are often quite off. (For instance, I was once told that I was terrifying.)

Just as the new year is a fine excuse to get back in touch with people whose email threads you’ve dropped, or to offer thanks or compliments or pitch crazy ideas, the new year is also a fine excuse to ask a boss or client, “I’m just closing up some business for the end of 2013 and wanted to ask if there’s anything you’d like me to do differently in 2014.” Doesn’t that seem reasonable and not-too-abrupt?

Also, if you’re the sort of person who avoids asking for feedback because you can’t take criticism (hey, you’re a real human who bleeds real blood!), the holiday season will probably result in much softer replies to this question. Everyone’s nice (er, nicer) this time of year! It’s the perfect time to ask for feedback and change course if needed.

Decide there’s something so disgusting to you that you’ll never do it again

I have mixed opinions about New Year’s resolutions (see Bullish: Screw New Year’s Resolutions – Try Designing Your Career), especially since science has determined that willpower exists in limited quantities — you don’t want to spend it on something like “giving up gum.”

However, I do believe in the motivating power of disgust, which I wrote about in Bullish: How to Motivate Yourself to be Motivated. If you decide something is so disgusting that you’ll never do it again, you no longer have to expend willpower, the same way you don’t really consider peeing your pants, even when a bathroom is not in convenient proximity to you.

What’s gross? How about “going to sleep on a weeknight without planning my goals for the next day” or “showing up at a meeting unprepared to impress the boss.” Gross. Try to feel the disgust.


Once I realized how sugar sticks to your teeth, now I can’t un-think it — I haven’t eaten dessert in about five years because I’m literally grossed out by it. Don’t get me wrong — my four food groups are espresso, booze, fat, and salt, so I have my vices. But, if I wanted to give up any of those four food groups, I’d use the same technique — do a little research on just what alcohol does to your liver or salt to your arteries, and then cultivate a healthy sense of disgust.

I’m quite an introvert, but I may have to cultivate a sense of disgust for not networking. Oh my god, I haven’t been to a networking event in four months — nasty!

Ask for something far, far in advance

Are you going to need recommendations for grad school? Do you want to take a two-month honeymoon? Do you want your coworkers to invest in your company?

I just discovered that, in June, I’m going to need a supervisor and a peer to each write a review of all the work I’ve done in my entire master’s degree program. That sounds like a lot of work. So, now — six months in advance — is a great time to ask.

Asking a big favor from someone two weeks in advance sounds like maybe you’re not clear on how big a favor it is — and therefore, maybe you won’t give appropriate gratitude, or pay the favor back appropriately later. If you ask very far in advance, you’re acknowledging the magnitude of what you’re asking.

Also, if your stab at lifestyle and career design involves a sabbatical in a foreign country, or some kind of crazy plan wherein you work from a treehouse you built with your own hands, you are more likely to get what you want the further in advance you ask. Read more about this in Bullish: Extreme Advance Planning for Very Smart Women.

Get your finances in order

I finally joined Mint.com. It’s easy, but you’ll probably spend two hours linking up all your accounts and categorizing your expenses.

Most immediate cool feature: all your purchases from all your different cards are aggregated, and you can assign them to various categories, and then you’ll get a pie chart of your spending. As I start various companies in the new year, I’ll be writing more about personal finance — for instance, when I think it’s smart to be frugal, and when it makes sense to hire a maid and use the time to optimize one’s Google ads.

The holidays are also a fine time to get your damn receipts in order (at least for those of us with freelance income). Organizing receipts is remarkably like gift-wrapping, actually. Kind of old-school. Easy to do while your mom is attaching ribbons to things.

Win at knowing more than your older and more experienced colleagues


Read a book that recently came out about whatever it is that you do. If you’re self-employed, blog about it. If you work for a boss, write up a short summary of the book, and end it with “actionable items” — a bulleted list of tips from the book that would actually help your company’s business.

Send this to the boss, who ideally will forward it to others, with your name on it. Don’t call it a summary — call it a “briefing.” Important people love to be “briefed” because then they feel like Kiefer Sutherland in 24.

You now look like someone who has an active intellectual and professional life outside of office hours. Your boss may start to see you are more of a peer, or at least as someone who has options outside of the company. The more of an outside professional life you have, the less you can be made to be someone’s lackey.

If this works out, you might end up in charge of some kind of company e-newsletter or something, or contributing to the company blog, or maintaining the Twitter account. Maybe busy executives become addicted to your concise and actionable briefings. Fabulous.

Brainstorm business ideas

You never know when you’ll be unemployed, or just so overflowing with mojo that you simply must expand your empire, now.

In Bullish: Responding to Disappointment with Awesomeness, I talked about keeping some truly awesome (in both senses of the word) plans in your back pocket so that you are no longer afraid of losing your job, relationship, and whatever else you now have.

Great ideas often come from getting outside of your usual social circle, habitat, and habits. For instance, while sitting and talking with Grandma, who would really appreciate a simpler keyboard or a padded bathroom rug or a yoga class for elderly women.

Here’s a business idea I had in Virginia: adhesive goldtone Christian hood ornaments. You know, like crosses, and Jesus on a cross. Like those Jesus-fish you put on the back of the car, this would be a something you can stick to the front of your car! With Jesus on it! Come on, you know people would buy that. And I sure as hell didn’t think of that in Manhattan.

In Bullish: How to Be a Productivity Unicorn, I wrote:

I will help you pick a new business right now. Take something exciting that you do actually like, and that many other people also like. Now think of something very scary, difficult, or boring. Merge those things; make your enthusiasm for the fun thing bleed into the scary, difficult, or boring thing; help scared, frustrated, and bored people; become a millionaire.


Now’s the time to imbibe a little eggnog, loosen up your thoughts, and plan. I’ll see you back here next year for more plotting and world domination.

Originally published on The Grindstone.

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