Here’s a lesser-known secret to success in the business world: Learn how to pick up the tab. 

Notice the wording there.

Not, “be willing to pick up the tab”, but “learn HOW to pick up the tab”.

Maybe you are a natural at this. If so, congratulations. Just like people with shampoo commercial hair or fast metabolisms, you were born with an unfair advantage over the rest of us. 

Two things kept me from understanding HOW to pay for a meal or cocktails or when I was first starting out in business…

  1. Being broke AF for most of my life
  2. Having a dad with “crocodile arms”

I’m not one to blame my upbringing for any shortcomings in my adult life – especially not at fifty.  I’ve had PLENTY of time to recognize and reconstruct any glaring deficiencies. 

We’re never finished with this project, of course.

If we’re fortunate, we get the opportunity to address the big stuff that can make life extra challenging. Like, trust issues, jealousy, victim mentality, and other weird hangups we acquire on our way to adulthood. 

And then we get to focus on the “soft skills”.

Buying someone a meal, or even a coffee, is a soft skill.

One that, done well, signals all kinds of positive character traits, and done poorly, leaves everyone feeling awkward at best, and at worst, ANGRY with you!

I’ve achieved both.


The cringiest tab grabbing crime I ever committed was loudly declaring, “I’ll get it!” at a family dinner during… Mother’s Day! 

I was just beginning to make a bit of money as a copywriter and I was so excited that I could actually afford to treat my extended family to a meal. So when the bill arrived, I had the notion and just blurted it out. 

The instant backlash made it painfully obvious that what I intended as a nice gesture had come across showy… like a two-bit crime boss waving his cologne drenched cash wad in front of his underlings to remind everyone who’s in charge. 

The passionate protest from the four other men at the table, also there to celebrate the women who perform daily feats of awe-inspiring motherhood, put my unintentional act of hubris into mortifying context.  

No one needed any help with the tab, and my ill-timed show of “generosity” was the social equivalent of slam dunking on a 9-year-old; just because you can do it, doesn’t mean you should. Especially when doing the exact opposite would be the better way to show some character.

Tough lesson. Very embarrassing. The kind of mistake you ponder restlessly for months. 

An unrequested gift of awareness about how a seemingly innocent act of kindness – particularly when involving money – can easily explode in your face like a gas station firework.

That’s the bitch about soft skills; you gotta screw ‘em up before you can find a better way. 

At least I did. A lot. 

The storage cloud of my mind is beyond capacity with clucky verbal exchanges, off-target attempts at humor, and hastily dashed off emails that I’d kill to have back.

But hey, the embarrassment of practicing in public is better than never evolving, right? 

Truth is, like most social slip ups, they live far longer, and repeat much louder, in our own heads than anyone else’s. 

A truly evolved person will recognize your good intentions (or that you don’t normally drink whiskey) and appreciate the clunkier moments for what they are: progress in action.   

Those who can’t are not evolving themselves, so, fuck ‘em. 🙂

Here then, are 3 practical tips on how to perform the simple act of “picking up the tab” from a guy who’s screwed it up more than most…

1) Practice on yourself.

Like any pleasure-giving scenario, the fastest way to get educated is to privately serve yourself first. (Fill in your own joke here. I’ve evolved! haha)

Seriously, start by taking YOURSELF out for a nice meal. 

Pick a joint you “can’t afford” and go have breakfast or lunch there once a month. It’ll get you comfortable with the scenario and the environment. 

Folding good linen onto your lap and learning to chat comfortably with well manicured servers who often say words you’ve never heard before is the best way to get cozy in the chair. 

Plus it’s a tax write off and the food is friggin delicious. 

Save up and take one day a month to visit your future reality. You deserve it, and it’s a key part of the evolution. 

2) Know your reason for buying and express it.

My Mother’s Day blunder was a knee-jerk reaction that could have been avoided if I’d thought it through. 

Leave room for spontaneity, sure, but ideally you want to decide if you’re picking up the check before it arrives. That way when you say, “This one’s on me”, you can also add the reason you’re compelled to buy, so it doesn’t feel like an awkward one-upping.

(Grateful) “Please, allow me. I really appreciate your great advice.”

(Sentimental) “This one’s on me. I enjoyed spending this time with you.”

(Playful) “My treat. I would’ve looked weird sitting here talking to myself.” 

No big production, just close the loop. 

Whatever it is, be sincere and avoid infusing guilt by saying things like, “You always buy” or something dismissive like, “Who cares? It’s a write off.”

3) In larger parties, pay before the bill arrives.

If you’re treating an entire group of people you invited to dinner, of course you’re paying and you should let them know in advance so no one is wondering while they order.

Make it clear they should go ape shit on the menu and you’ll be happy to see them happy. 

If it hasn’t been established who is buying and you’ve decided to pick up the check, then be sure to establish this with your server long before the bill arrives. 

Either call ahead and set up payment with the restaurant, or head off your server early in the meal and slip them your card. 

This means you will not be able to review the bill before it arrives. They will deliver it to you, already charged, so you can discreetly sign and move along. 

If you have “dinner check OCD” and insist on adding up the bill before you pay, then make that clear to the server so they can signal you to meet them for the hand off. Don’t scrutinize the bill you are paying in front of your guests. It’s dinner, not a tax audit. Who cares if one extra margarita gets tacked on? Budget for the bill and sign the thing. 

Finally… learn to gracefully accept a tab grab from others. 

Don’t fight them, or announce that they “didn’t have to do that” (No shit! That’s what makes it nice to do)… just say, “Hey, thanks a lot!” and enjoy the extra shekels.

Again, I’m no Emily Post, but I’ve fumbled more of these moments than I care to admit. So if I can save any of my well-meaning friends some face, then salvation is at hand.

It’s on me.


P.S. The soft skills of client-handling and network-building is one of the things we help each other with in my Freelancer’s Journey Accelerator coaching group. If you want to learn more about how it works, go here and tell me more about your business here.  


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