How to Look More Thoughtful Than You Really Are

Alright, kiddos, today I’m offering a lesson that will serve you well in the new year. Listen up, because I’m about to share 5 straight-up steps to looking more thoughtful than you do today.

Thoughtfulness, you ask?  Where’s the relevance? What’s the pay off? Whether it’s at work, in your love life or — for God’s sake — with your own sweet mother, thoughtfulness will smooth out many a bump in the road of life.

Square one: understand why this matters.

Think back to a pleasant surprise you’ve experienced (I said pleasant, so please play along). Got one? Now, think of another. And, since I’m seeking to demonstrate a point, please think of one more.

What do those surprises have in common? Ah, yes. Thoughtfulness. It is, don’t you see, the root of all surprises and delights.

If you’re not a “surprises and delights” kind of person, that’s cool. Let’s me give it to you another way… demonstrating thoughtfulness is the ticket to being memorable.  And in the words of novelist Isabel Allende, “You only have what you give.”

You only have what you give. True thoughtfulness, therefore, will get you everything.

Shall I repeat that?  True thoughtfulness will get you everything. It will keep you top of mind. It will reciprocate in surprising ways, at times when you least expect it. Thoughtfulness — as I like to say — is good karma.

On the flip side, its absence will cost you dearly. Thought-less-ness is an acid to any relationship, be it business or personal.  It will erode the foundation, that ethereal place where trust and respect find safe harbor.

“You only have what you give…” If you don’t get this point now, you may learn the lesson when it’s too late to make any difference. The thoughtful person prevails, every single time.

It’s a funny little thing, and by that I do mean little.

What the heck is thoughtfulness, anyway? In fancy words, it’s having or showing heed for the well being or happiness of others and a propensity for anticipating their needs or wishes.

More simply:  thoughtfulness is doing something that makes another person feel very, very special.

The charm of thoughtfulness lies in its simplicity.

Size doesn’t matter here, folks. It never has; it never will.  The charm of thoughtfulness lies in its simplicity. By tuning in and tending to subtle clues, you demonstrate a profound attention to detail.

Side note:  if, by chance, you are saddled with people who accept nothing but the grand and the glittery, then do accept my sincere empathy. They are an altogether different beast. You’ll never lack in a to-do or to-give list from these self-absorbed darlings.

Your 5 steps to looking thoughtful.

I’ll ‘fess up. To look thoughtful is to act thoughtful, so these steps aren’t shortcuts.  I believe in you, though, so let’s give this a whirl.

Start here:

  1. Get out of your own damn head. This one isn’t rocket science. Learn to mute your own self-centered thoughts. I’m not calling you an ogre, but the distracted, self-absorbed mind can’t be others-focused. Your ego will be eagerly waiting for you to return, so never fear this act of will.
  2. Listen, and look. Take that precious attention and shift it — away from you and toward others. First, listen. When you least expect it, others will reveal the things they hold dear. Their voice may change. They may sound wistful; I myself shift into a really humble place when I’m talking about things I love and enjoy. Watch for body language. It, too, will change when someone is on a topic of emotional significance.
  3. Jot it down. Insights into others don’t come served on a silver platter, nor is this like net fishing. Instead, the things you’ll notice come in bits and pieces. So write them down. One word, two words… it doesn’t matter. All you’re doing is just noticing and making note. Open a notes page on your smart phone and start keeping track.  Do whatever works best; but just jot it down.
  4. Look for the opportunity. Alright, now we’re moving into advanced level territory. Paying attention, listening, jotting things down — Let’s call these the “science” of thoughtfulness. The art of it, therefore, lies in the action. The art — its magic — is all about your timing and delivery. It’s as much about when you do something kind as it is what you do out of kindness. Choose a time that would otherwise be least expected.  If someone pops in your head, they need you. They need something that only you can give — whether it’s a call, a note, a cup of coffee or a dog-eared book from your collection.
  5. Go do or go get help.  So do it. Whatever it is, go do it. Use as little fanfare as possible. Go subtle. Go rogue. If need be, take yourself out of the picture and enlist someone’s help in delivering or doing the good deed.  Don’t overhype yourself and — of all things — expect nothing in return.

Heed this: what thoughtful isn’t.

Thoughtful isn’t an object. It’s not about the thing. Thoughtful, I hope you see, is the act of doing. Thoughtful is the state of being then acting unselfishly on it.

If you’re struggling with the how of being thoughtful, just start. Get over the fear of doing it wrong or how to do it right. I’ll let you in on a secret … any attempt at thoughtfulness is charming in itself.

No matter what you do, when you do it, and for whom you do it, remember this:  thoughtfulness is an act of kindness for THEM, not you.

Good luck! And — let me know me know how it goes.


4 thoughts on “How to Look More Thoughtful Than You Really Are

  1. I love this. Now you just need to post more often. The whole idea of being thoughtful is so important to who we are as individuals, and who are are professionally. Somehow we seem to have separated the two and we don’t believe that we need to apply things like this to how we act and behave on the professional side of things. We need more of this.

    • Ken ~

      A few months ago, an unexpected email landed in my inbox. It arrived as if the day was made for it. The email was personal, it was written directly to me — about me — and from someone who had something very personal to say to me. It was (and remains) a perfect example of genuine thoughtfulness.

      That email was from you. In it, you asked me to write more. You described what it’s like to read what I write. You nudged me to share the gift that I’ve been given. You asked me to share.

      As you share the link to this latest post, please take pride in knowing that you are are woven into the meaning. You exemplify the point that I strive to make.

      Deepest respect.

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