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There are memes that go around this time of year, encouraging you to ask if you really need to send that email now, or if it’s more a next-year email instead. I get that. People don’t always want tons of work or work stress dumped on them before their holiday breaks. That makes sense.

But sometimes we cause work stress by inaction. Sometimes, you put people’s minds at ease by sharing, by sending the email, by giving the information. If you’re the boss — or frankly, if you’re simply the sender — it’s your job to craft a workplace (or an email) that makes clear no immediate response is needed; you’re just sharing the info you can, while it’s top of mind for you, so that the other person has it.

I don't know exactly where this post is going, by the way. I have three or four disparate thoughts in my head to share. But as you know, my feeling is just start writing, and let the thing sort itself out.

It’s been more than a month since I published here last, because it’s my site and I can choose to wait for inspiration to strike. But I knew I didn’t want to end the year with a post from early November as the last thing here. Hence, this post.

There are some things in life — and work — that we don’t decide for ourselves. The parts we do control, however, we should relish that special power: You get to make the choices that work for you. In this case, I get to decide when I write here, and what I write here, and even how much I proofread. You, too, have agency in your work, even if there are other bosses/managers to report to. Make the decisions that work for you.

This site has moved. Read this article, subscribe, and find lots more Lex content at the new home for Your Intermittent Lex.

It’s also really important to make decisions that don’t keep you up at night. I’m writing this post on Substack. Substack monetizes Nazis. It’s more nuanced than that, but it is also that, and that’s a problem. I feel bad publishing here. I’m working on migrating to another platform. It takes time, but should be done soon — but that could mean early January. I’m writing it here because I know some folks object to the fact that I (or anyone!) use Substack, and I hear and even share that concern, but moving isn’t as easy as flipping a switch. But again, I make the rules, so I get to announce that I’m moving, even though I haven’t moved yet.

If it’s at all possible, I of course encourage you to take time off during your break. Unplug, if you can, by all means — if that works for you. Some of us (I could be looking in the mirror as I write this) get too stressed out if we let our inboxes and other feeds go unmanaged. I’d rather take fifteen minutes to triage each day and come back to less chaos; your mileage (or kilometerage) may vary. That’s okay. Be kind to yourself, and find the approach that works for you.

Really, though. Don’t be shy about emailing over the holidays, so long as you’re not using that email as a tool to say look how hardworking I am! If your frame is “I wanted to share this while I was thinking about it, but please note you can read and reply come January 2,” you’re in good shape.

Happy everything.

This site has moved. Read this article, subscribe, and find lots more Lex content at the new home for Your Intermittent Lex.

“Eschew Obfuscation” means “avoid making things unclear.” The phrase is a little funny. But it’s also good advice.

I was on a call with a client recently where a key employee from the team was new to the conversation with a potential partner. And the employee said so right at the top: “Forgive me, I’m new to this conversation, and I don’t actually know the context.”

His boss was concerned. I wasn’t.

Listen, ideally, the key employee would have been prepped before the call, and have the necessary context going into the conversation. But we’re all busy, and that step got missed here. I’d much rather the employee speak up and thus bring more value to the call by participating in it well-informed, even if there’s an awkward moment at the start of “whoops, let’s catch you up.”

In this particular case, a very close friend runs things at the potential partner. So I reached out to her afterwards and asked if she and her team had been offended by the employee’s directness about not knowing the topic at the start. “Not at all,” was the response — something very similar had happened with her team on a recent call.

Directness matters. Sometimes — oftentimes! — the best move is to just say the thing. When it comes to pricing, for example, we often think we should start high so that the buyer can come in low. Or we worry that if we come in too high, the potential partner will ghost, so we negotiate against ourselves and come in low to begin with.

My strategy is to say the price, and say that it’s the price. “I’ve worked to get the price as aggressive as possible, and that’s X.” If I’m asked whether there’s room for negotiation, I give the honest answer: No, if there’s not. “Possibly,” if there is — but perhaps acknowledging that we might have to change exactly what we’re offering if we need to land at a lower rate.

There are so many scenarios where just saying the thing helps a ton:

• If a meeting can’t continue because a key stakeholder is missing, just end the meeting. “I know we all need this answer, but it doesn’t make sense without Marie here, so let’s not waste cycles that we’ll have to repeat when we reschedule — and just reschedule.” Everyone likes getting time back!

• I wish more people were comfortable saying, “I know you just asked me a question, but I was distracted. Can you repeat it?” We can tell when you’re guessing at the question, or hemming and hawing. Save us time, own you missed it, and let’s keep things moving.

• And perhaps the hardest way to be direct of all for some of us: “I actually don’t see a path forward here.” Often we want to avoid bearing bad news, so we let meetings drag on. We schedule follow-ups. We keep the conversation going. Sometimes there’s no fit, and it’s better to say it and end things vs. humoring a partner you just can’t work with.

It’s easy to conflate obfuscating reality with politeness, but the real kindness is just saying the thing.

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This is a crucial step in a sale — and it’s one so many people get wrong. We get in our heads about whether the price we intend to quote is too high, so we start low. You’re negotiating against yourself. You’re making less money. It’s a problem.

Our fear is that if our prospect doesn’t like the price, they’ll ghost us and no longer engage.

That’s a misplaced fear. Real prospects don’t ghost.

If you email over a proposal and the price is too high, prospects who are genuinely interested will write back and say, “Boy, we’d love to do this, but the price is too high.” They won’t just go dead silent.

And by the way, if they do go dead silent, you can always nudge them again, too. But the ones who vanish because they don’t like the price are almost never serious customers. Real prospects respond.

Recently I joined a client on a sales call. We met prior to the call to talk about which discounts to include and how to frame pricing. I asked the same question you should remember to ask yourself: What do you actually want to get paid for this deal?

Obviously many, many of us have the instinct that we need to start higher than that number, since many, many of us also have the instinct that everything’s negotiable — so we often assume most prospects will ask for some sort of discount.

(My approach isn’t for everyone, but I hate that dance. I tend to start by saying this is the price I need, I didn’t start high, so this is what I need you to pay. It works for me.)

With the above client, we had the call, and we gave the price without a bunch of discounts built in; we simply said, here’s what we charge. And the client’s response? “That’s a great price.”

Don’t be afraid that your price will scare off your buyer. If they’re serious, they’ll tell you what their concerns are, and you can figure out if there’s a solution that works for everyone.

Do it.

Here’s the thing: Once you’ve considered firing the person, they’re doomed. Once you’re contemplating quitting, you’ll never love the job the same way again.

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A month ago, I started sharing my own take on Connections puzzles, which my name requires I call Conlextions. I love making these puzzles, because they make my brain work in a fun way. And because I’m making them, I’m also of course sharing them, with a new puzzle appearing each day on my site.

I share each puzzle I make on Mastodon, Threads, Bluesky, and Facebook. Sometimes I post them on LinkedIn.

It’s not for profit; it’s for fun. (Donations have raked in a whopping $26 for Conlextions to date 😂.) But I share each new puzzle in all those places because not everyone has seen them yet. People who already like my puzzles may use my posts to remember to play (and then share their scores, which I love!). Other folks — folks who haven’t yet seen any of my posts, or saw them and ignored them — might eventually discover my puzzles. And it’s fun for me that a few hundred people play my puzzles each day. I’d like that number to keep growing.

Of course, there are some people who never want to play one of my puzzles. To them, my daily posts might be a little annoying. That’s a tradeoff I’m willing to accept, because social posts that don’t interest you are easy to scroll right past.

I’m bringing all this up for a reason, and it’s not to stealth market my Conlextions puzzles to another audience via my Substack. (Though, please, feel free to check them out.)

Just yesterday, a client mentioned he’d discovered my music album after a mutual contact pointed him to it. And that same client mentioned that he only discovered that same day that I publish this very Substack.

I’ve written before about shameless self-promotion. If you don’t tell the world what you’re doing, the world won’t know. My puzzles are meant to be shared and played; if I don’t tell folks about them, they can’t possibly know they exist.

This is important in closing deals, too. I had multiple conversations with clients this week about when and how to check-in with leads who’ve gone quiet. When a prospect you’ve had real live meetings with, and that prospect showed interest, and now they’re ghosting you… It means one of two things:

1. They’re no longer interested and are too embarrassed or busy to tell you so, or

2. They’re still interested, but they’re too busy to tell you so

You can’t do anything to screw things up with the folks who fall into bucket one: They’re already not interested. The folks in bucket two remain interested, maybe are even ready to ink the deal — but you’re not the top priority.

Ideally, though, you’re your own top priority.

So you have to nudge these folks. A month and a half ago, I had someone email me “Agreed! Let’s do it.” in response to a proposal I’d sent. I sent paperwork their way that same day for signature.

Two weeks later, I nudged them. Dead silence.

A week later, I nudged again. Except I did it eight days later so they wouldn’t think I’d set a weeklong reminder. (Which is precisely what I’d done.)

Six days after that, I sent a still friendly but slightly sterner email. It was short. This was it, verbatim:

Wanted to check in once more on if you’re still looking to lock in the quarterly consulting work. Thanks for any update!

Not brusque, but not warm. I first wrote — and then edited out — an additional sentiment, that I needed an answer by end of week, so that I could know if I still had Q4 hours I could allocate. It’s true, but felt too salesy to me, so I didn’t include it. I ended up with a version of my email with a near-100% success rate.

I received the signed contract six hours later.

This now-signed client definitely wanted to work with me, and had been clear about it — but is also busy running the day-to-day at his company, swamped with work. Getting that contract inked was hugely important to me, but only moderately important to him. I know sending a third email on top of two prior unanswered ones is pushy or annoying, but I also know that if I don’t get a signed contract, I haven’t closed the deal.

So I annoyed this contact a few times, past the point of my own comfort, to make sure I stayed top of mind and got the signature. He knew I was annoying him, and he knew why — but he respected the fact that I did it as politely as possible.

Anyway… go try out my Connections puzzles? 😂

We had a nice dinner catching up on the intervening decade. But my iPhone 3G started buzzing. “I’m sorry,” I told Matt. “I have a work emergency I’m dealing with.”

Throughout high school, and as a full-fledged adult, Matt was unfailingly polite. So though my memory is that he laughed his head off, I’m guessing that in fact Matt chuckled politely instead as he said, “I’m guessing your work emergencies aren’t like my work emergencies.”

See, Matt was in charge of some aspect of the United States’s nuclear arsenal. He was high ranking in the US Air Force then, and is even more senior now, and not all of his job was super public, but it definitely involved nuclear missiles and their security. Either way, his point was simple: When he had a work emergency, it was a different thing entirely.

To his credit, Matt actually went further. I got embarrassed at calling my thing an emergency, and he defended me. I don’t remember what he said verbatim, but the message was yeah, your work emergencies are important, they’re just not my level of emergency.

This conversation stuck in my head forever.

That said, I have absolutely no idea what my work emergency was that day.

Matt’s right: Sometimes there is urgent stuff, sometimes there are work emergencies, and your emergencies might not be the same as my emergencies, and vice-versa.

This isn’t a screed advising you to improve your work/life balance and leave work at work (though, seriously, try to do those things). Rather, it’s a reminder that not every emergency is an emergency. Angry customers can absolutely be a work emergency. Angry bosses, too.

But if everything’s an emergency, nothing is. If work is constantly putting out fires, you either work at a literal or metaphorical fire department, and if you don’t like living that way, it’s time for a change. It’s easy — and in many cases, wonderful — to think of work as the most important thing.

Even if that sounds like you, it’s important to remember — and perhaps to remind yourself frequently — that daily emergencies are for ER staff and other first responders. Your job shouldn’t be an endless cavalcade of emergencies that need solving.

I recently started meditating. Not for the first time. But I’m once again trying to make it a habit, because I keep reading about the positive effects of meditation. I’m no hippie, and I don’t think most of my close friends would assume I’m a meditator, and maybe I won’t stick with it. (I will this time, though. It’s in the Peloton app. I got this.) I am right now, though, and I appreciate the reserved periods of reflection.

The opportunity to calm down and focus and breathe — even for just five minutes at a time — is a welcome one. And one we almost never get at work.

The next time what feels like a work emergency lands in your inbox or Slack DM, I encourage you to try to reframe it. Is this truly a fire that needs extinguishing? If you were to do nothing on this for five minutes or five hours, what would suffer? And if that choice meant you could finish what you’re already working on, or stay focused on a different challenge, or not cancel three meetings, would the net positive effects be worth it?

There are emergencies. But I believe there are many more fauxmergencies that demand more immediate attention than they deserve.

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That’s how a prospect started a call with a client of mine. (I know, because I saw the video.) My client rightly said “no problem, I can turn off the recording” — and did so. And I absolutely respect the right of a prospect not to want to be recorded; that’s fair and reasonable. But this was a case of a prospect coming in hot.

I saw another call where a potential customer was throwing my client a lot of questions — which, again, is reasonable! — but was doing so aggressively: cutting her off mid-sentence, barking out cutting feedback, and so on. This prospect had done the math and was pointing out the per-month price based on the annual price… which of course wasn’t a secret, but the prospect was treating as a gotcha! moment.

Whether consciously or not, this prospect’s goal was to put the seller on the defensive. Couldn’t this be cheaper? Doesn’t X just mean Y? How much harder could it be to add this in?

There’s definitely a careful-what-you-wish-for lesson in closing deals with potential customers like these. In my own business, I’d likely pass; I don’t need to sign a difficult customer. But sometimes we don’t have the luxury of turning away business, and it’s even true that sometimes prospects who are difficult in this phase can (surprisingly) turn into great, lovable customers. (You’ve handled them at their worst, so…)

My approach if I do hope to close business with the know-it-all is simply this: Let them do the talking. They want to talk, they feel at their smartest when they’re talking, and it’s typically important to them that everyone know they’re the smartest person on the call. So I sit back and let them take the wheel.

They don’t get carte blanche, though: My time is valuable. That’s why I try to tee up the know-it-all with specific questions to which they can then monologue responses. The crux of my question is simply this:

What do you want?

What’s your desired outcome? Tell me what you think the price should be and what you should get for that price. Explain to me where you think we should land. What does this look like?

Once I’ve heard that, if it makes sense for my business, I’ll tell you so, and we’re potentially good to go. But if it doesn’t make sense, I’ll tell you that, too:

• I can offer everything you’re looking for, but it costs 50 percent more than the price you floated.

• We don’t actually offer service X, so if that’s important to you, we might not be the right fit. But we can do Y and Z that you’re after, and we do it better than anyone else.

• It sounds like you want premium services for budget prices. I’m never going to win on price alone, because I don’t compete on price. My advantage is how I outperform my competition.

The know-it-all wants to be heard. The know-it-all doesn’t want to be sold to. And the know-it-all wants you to know that they’re smart, they can’t be fooled, and that they know what they want. So let them tell you what they want, and then tell them whether you can do it, and how much it costs. But make sure you let them be heard first; that’s the best way to get them in good spirits.

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There’s a tendency to overthink these situations. My technique is always to aim for directness, to call the thing what it is. In this case, my buddy goofed by not having sent a follow-up sooner. Okay. Now what?

Here’s the email I recommended my friend send:

I wanted to check in. I really enjoyed our conversation last month and would love to check in on the status of those two deals you were working on. Looking forward to hearing any updates, because I remain excited about the possibility of working together!

That’s it. Nothing fancy. I don’t go deep on the fact that I waited too long to email you. I’m certainly not looking to make you feel guilty for not writing me sooner, but I’m also not beating myself up. Maybe there’s even a tiny win I can subtly take here, from the fact that I was chill and patient and not crazily in your face after our initial meeting.

We all get too busy and we’ve all missed followups. When it happens, fix it without drama by sending the right message — even if it’s later than it should have been.

A decade ago — and wow does that hit me hard, that this was a full decade ago — Jessica Winter published a story that stuck with me for Slate, which she called “The Kindly Brontosaurus.” (For what it's worth, I always always think of it as “The Friendly Brontosaurus,” and mistakenly used “Friendly” several times in my original draft of this piece.)

The key section is reproduced below, but I strongly encourage you to read the whole thing:

A practitioner, nay, an artist, of the Kindly Brontosaurus method would approach the gate agent as follows. You state your name and request. You make a clear and concise case. And then, after the gate agent informs you that your chances of making it onto this flight are on par with the possibility that a dinosaur will spontaneously reanimate and teach himself to fly an airplane, you nod empathically, say something like “Well, I’m sure we can find a way to work this out,” and step just to the side of the agent’s kiosk.

Here is where the Kindly Brontosaurus rears amiably into the frame. You must stand quietly and lean forward slightly, hands loosely clasped in a faintly prayerful arrangement. You will be in the gate agent’s peripheral vision—close enough that he can’t escape your presence, not so close that you’re crowding him—but you must keep your eyes fixed placidly on the agent’s face at all times. Assemble your features in an understanding, even beatific expression. Do not speak unless asked a question. Whenever the gate agent says anything, whether to you or other would-be passengers, you must nod empathically.

Continue as above until the gate agent gives you your seat number. The Kindly Brontosaurus always gets a seat number.

I have many, many thoughts on this piece.

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It’s okay if you were that “ugh, not another group project” kid. I was that kid. If you were — or are! — that kid (or adult), I have two main thoughts: That’s a totally human and understandable perspective… And it’s one you should try to change.

Sometimes yes, we absolutely can be our most productive or efficient if we get to make our decisions and execute in a silo, on our own. (Heck, I quit my job to be a full-time independent consultant for kind of that reason!) But we don’t each run our own little fiefdom. We are all part of a team. If you’re indie like me, you still have clients you need to work alongside as coworkers. You have customers who expect you to work with them.

We each bring our own perspective and lens, and that’s good and important and frankly is our unique value. But we have to recognize that… so does everyone else. Hearing takes from other folks — even if we disagree with those takes — is of course still incredibly informative.

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I love confidence and I think it serves you well with customers, bosses, colleagues… but I also love humility. You can fake confidence, but you shouldn’t fake confidence when you don’t know the answer.

I’ve written before about the power of saying “I don’t know.” You can confidently not know something. Sometimes you know you don’t know. But when you think you’re right — and face it, most of us think we’re right most of the time — you need to trust that your colleagues may have insights or knowledge that you lack, and that their competing perspectives are worth entertaining.

Trust is all about vulnerability. You are relying on someone else. This is why goofy trust falls are a thing. Some of us are nervous flyers in part because we’re giving up all control — the pilot’s flying the plane, and we have to trust them. 

Trust is hard, because feeling vulnerable — admitting vulnerability — is hard. It’s okay to struggle with trust — as long as you’re willing to work on it.



To trust someone requires three fundamentals:

1. You need to feel they’re being authentic and honest.

2. You need to believe that they have the right information and the right logic.

3. You need to believe that they have the right intentions, that they’re on your side and rooting for your success.

And, of course, to be trusted by others requires that you demonstrate those same qualities.

None of this is easy or automatic. Building trust takes time — but also effort. If, for example, you’re feeling a struggle to trust or be trusted in meetings, I encourage you to make your presence at them more human and involved. That’s not about in-person meetings. I’m saying if you’re on a Zoom, encourage EVERYONE to turn off their computers’ notifications, to put their phones in Do Not Disturb, and to put their cameras on. 

We are all guilty of believing we basically know what everyone else is going to say in some meetings, so we stop paying attention for a moment while we quickly respond to an email, or look at a text, or text someone else in the meeting about the very meeting we are in. 

We are also all guilty of suddenly hearing our name and knowing that we now need to answer a question, but we aren’t sure what the topic was because we were doing something else.

You can cultivate trust for yourself and others, and empathy for yourself and others, by being present and plugged in, which is harder than ever with smartphones and watches, and harder still over video calls. But you can force yourself to do it, and you’ll find you’re perceived as more trustworthy over time — and that you see your colleagues that way, too.



That’s one small thing: Meeting etiquette. And it’s a tough habit to build and a tough habit to maintain. Trust is also hard to build and maintain. Think of trust as something you’re actively working on and developing.

Give yourself room in each interaction with colleagues to think, how can I build trust in this conversation? How can I demonstrate that they can trust me, and how can I take this opportunity to trust them?

What expertise, patience, empathy, or insight can I share?



There’s no shortcut here, but putting in the work pays off. Trust me.

Let’s say you’ve traded emails with someone you know can go silent for days or weeks at a time. When you finally do get a response — say, one that promises new information or an update “sometime next week,” your instinct, ideally, is to send a thank-you note their way.

I love a thank-you note. Do send one. Just don’t send it right away.

I know you’re excited to get a reply, and I know you want to express gratitude for said reply… But waiting a few days gives you the power of an organic opportunity to tickle the prospect’s inbox again, without seeming (too) annoying.

Monday: You email them

Next Monday: You email them again

Finally, the following Thursday: They reply and say more information will come mid-week the following week

Hold your fire! Don’t reply yet.

Perhaps Tuesday of that following week, you send a note: “Thanks! Looking forward to it.”

You’ve now sent a thank you note (yay!), you’ve nudged them (woohoo!), and you’ve done it without explicitly saying HEY I’M NUDGING YOU.

That’s a win/win/win.

A month ago, I wrote about channeling your inner Mr. Rogers. I stand by that advice — treating people well, offering patience and thoughtfulness — is the right approach. Almost always.

I stressed in that piece that being Mr. Rogers-esque doesn’t mean being a pushover. But sometimes…

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The ceremony included the recitation of all 600 graduates’ names, with each kid collecting a diploma. It was actually pretty efficiently done, with two readers handling names and two columns of students walking at a time. It took maybe 10 minutes total.

Before they started calling the names, the principal gave a request: Please hold all applause until the end. That request makes complete and total sense; applause after each name would make things take for-friggin’-ever. And if some kids get big applause and some don’t, that sucks, too. So hold your applause. No biggie.

They start calling the names, and we’re only a few in when a parent yells “Woooo!” after their kid’s name is called. That, of course, unleashed a dam. About 30% of the time when a kids’s name was called, you’d hear some cheer. Sometimes it was a simple “Woo!”

Sometimes, it was a much longer, louder, “WOOOOOOOOO!!!!!!!”

And occasionally, you’d get things like “Yeahhhhhhhhhhh!!!! WAY TO GO TIMMY!!!! YOU ARE THE GREATEST OF ALL TIME!”

Here’s the problem: These longer, louder cheers would overlap the next name. Or the next two or three names. That sucks.

I didn’t object to a simple, understated, celebratory “Woo.” But I did take offense to the carousers whooping it up like crazy. As did a curmudgeonly grandfather sitting behind me, who kept complaining about it. “They’re covering up other kids’ names. It’s not right!”

Look, I love celebrating folks, praising and cheering good work, and sharing your joy and enthusiasm for successes — especially family successes! But it’s important to lift people up without simultaneously pushing others down. A chiller “Woo” doesn’t mean you love your kid less; it means you also have respect and admiration for everyone else.

Woo!

When I’m selling something, I don’t see myself as a salesperson; I see myself as an entrepreneur flexing a certain muscle to help a potential customer have something that improves their work, or life, or both.

(By the way, I’m sure there are lovely used car salespeople. I just haven’t met them yet.)

So my answer to this question about how not to feel sleazy when you’re selling, and especially when you’re getting into the conversation about pricing, is simply this: Don’t. Don’t feel sleazy, because it’s not sleazy. If you need to, simply pretend you don’t feel sleazy; like confidence, this is definitely a fake-it-til-you-make it situation.

One way these unpleasant feelings often manifest when people are sharing pricing is the instinct to apologize for the pricing — either explicitly, or by negotiating on the other side’s behalf before you’ve even started. Here’s how this often sounds:

• The price is [heavy sigh]… $1,000. Yeah. I know it’s a lot.

• I normally charge $500 an hour, but I usually take $450, and since we’ve known each other a long time, I could do $400, or even $350 if you really need it.

• It costs — and I’m sorry, because it’s a big number — $2,000.

No. No no no no. NO.

No.

Your pricing represents the value of what you’re selling. Apologizing for it is a huge no-no: It devalues both you and whatever it is you’re selling. You know the worth of what you’re offering, so whether it’s a salary request or a sale price, the reality remains: This is what it costs, because this is what it’s worth.

This doesn’t (necessarily) mean you're unwilling to negotiate. Rather, it’s a clear demonstration that you know the value you’re offering, and you’re not ashamed or embarrassed of it.

And here’s the fun followup: I got cast!

I was auditioning for two roles: Trekkie Monster, whose voice and physicality is clearly inspired by Cookie Monster, and Nicky, who is inspired by Ernie.

My role in this upcoming production of Avenue Q? Brian. Brian is one of three non-puppet characters in the show, and the only one traditionally played by a male-identifying actor. So to recap: I auditioned for a puppet-heavy show, brought my own puppet to the audition, used goofy Muppet-inspired voices, got called back… and was cast as a human.

When the director called me to tell me so, I responded enthusiastically that yes, indeed, I’d take the role. And I’m excited! (If you are too, grab your tickets.)

But of course, there was some sadness, too: I love puppets, I love this show, and I was really excited about the possibility of puppeteering onstage. Which, of course, I now won’t do.

On the flip side: I’m in the show with a great, fun role. I’m playing a 32-year-old, which to me means that clearly the production team thinks I look at least that young 🤣 — and who am I to argue?! And I’m playing an aspiring comedian who supports his friends and (spoiler alert) eventually becomes a consultant. In some ways, it’s the part I was born to play.

So of course I allowed myself to feel feelings, to be sad that I wouldn’t get to play with cool, professional-grade puppets on stage. But I also consciously encouraged myself to celebrate all the wins here: I was cast in a role that requires me to use my full, well, humanity, and I get to interact with a bunch of fun puppet characters, I help center the show’s reality, I get to sing some great songs (“It Sucks To Be,” “There Is Life Outside Your Apartment”), and to appear in a show I really love.

Essentially, I coached myself to do a fairly cliché thing: to look on the bright side. To find happiness by being satisfied with what I have.

I think many of us have an understandable instinct to believe that we are who we are, and that we allow ourselves to feel grumpy, sad, or disappointed when we don’t get the role, job, assignment, or other outcome we want. And I’m okay with feeling those negative feelings when something less-than-great happens. Finding the upside can be hard, and I’ve met folks who are willing to say, “nope, that’s not me, that’s not who I am.”

I think it’s all of us, though. By which I mean, I think — without being saccharine or phony or blind to the realities of life — that we’re all capable, with some effort as necessary, of finding those positives.

Let me emphasize, I was cast as a 32-year-old comedian. If I can’t find the joy in that, I’m broken.

The easy path is to feel disappointment and rely on time to heal those emotional wounds, to just wait until you’re less grumpy and move onto the next thing. The harder but more rewarding path is take time to honor that disappointment, but also do the work to find the good stuff, too.

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At work — and in much of life — pretty much everything is negotiation. Whether it’s with outside parties you’re trying to strike a deal with, or you’re debating the best path forward with colleagues, or you’re simply trying to figure out what to have for dinner… We wrangle a lot of negotiations in our day to day lives.

I’ve written about negotiation a couple times already. My opinions on negotiation that I’ve already shared include that transparency is key, and that the best negotiations are conversations.

Quoting myself:

I’ve joked that a successful negotiation is like a successful compromise: everyone feels comparably annoyed about the outcome. The truth, though, is that the best negotiations are the ones where everyone feels like they won — because they feel fair.

I’m no babe in the woods, nor am I a Pollyanna. But another incredibly important key element to successful negotiation is kindness.

I don’t have many parenting regrets, but I do regret that I didn’t have them watch Mr. Rogers’ Neighborhood. I’m not a Fred Rogers historian, but I do know that he was a kind man, and he taught kindness, patience, empathy, and understanding. He told people when he was proud of them, he simplified difficult subjects, and he worked hard to give people his undivided attention.

Mr. Rogers was a good guy.

Without becoming a children’s television host or puppeteer, you can still emulate some of Mr. Rogers’s inspiring qualities in ways that serve you — and the people you work and interact with — well: Regarding that aforelinked piece I shared about transparency in negotiations, I’d actually argue that transparency is a form of kindness.

We’re often worried that someone could be trying to gain an upper hand against us, that the other side — of anything! — might be trying to take some unfair advantage. Showing genuine kindness, patience, and understanding gives people comfort and reassurance. People who sincerely like and trust you are, unsurprisingly enough, more likely to agree to the deal terms you’re after.

I think most humans are pretty good at detecting faked kindness. I’m not asking you to change your personality. I think most people want to be good most of the time. But I also think there’s a too-common inclination that we need to be tough or aggressive or stoic at work.

I think that inclination is wrong. Thanking folks, responding quickly, and showing real humanity, generosity of spirit, and kindness — it works. Even if you don’t put on a cardigan and starting singing to the folks you’re working with, offering patience, niceness, and gratitude works. It helps to get more deals done, and it makes you feel great, too.

Some folks have reputations as being tough as nails. Aim to score the more coveted reputation — that you’re one of the good ones.

But business sense requires that sometimes free subscribers need to see premium posts, or they’ll never upgrade. A couple of you will be annoyed by posts like these and unsubscribe, and I’ll get an email notification that you’ve done so, and I’ll feel bad. Ideally, though, one of you will get motivated to upgrade, and I’ll feel like overall, the system works. You take the good, you take the bad.

Earlier this weekend, I auditioned for a musical. A nearby theater is putting on a production of Avenue Q, one of my absolute favorite musicals — it involves puppets and profanity! — and I’ve been planning my audition for months. A couple trusted friends I spoke to prior to the actual audition mentioned to me that they weren’t used to seeing me nervous. And indeed, I was nervous: I really want to get cast in specific roles in this show, I relish the idea of being on stage puppeteering with Muppet-inspired voices, and auditions are high-stakes, one-and-done deals.

Of course, I aimed to exude confidence when I walked into the audition itself. But I was thinking about my nervousness, and why I’m often less nervous in even a big business meeting, and I have a few thoughts to share. Let’s dive in.

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That era is over.

Every video call obviously requires you (and everyone else) be staring at a computer screen. And if you’re an in-person attendee, you’ll have your laptop in front of you and your iPhone buzzing away. And even if you’re somehow able to avoid the allure of your ever-growing inbox, your Mastodon notifications, your news alerts, your texts, your DMs, the warning that it’s time to BeReal… you still know those alerts are piling up. You know you have another big meeting to prep for. Or maybe there’s just other work weighing on your mind.

My advice? Take notes. Take notes even if you don’t need the notes. Take notes even if you’ll never look at them again. But take great notes.

I could — and maybe one day will! — write a whole essay on how best to take notes. I sometimes get into full transcription mode (because I’m a fast typist), and use bold type for anything I want to follow-up on or ask about, because I can hit Command-B fast without missing a word. You might prefer taking notes by hand, or using a less-verbose outlined approach.

I support whatever note taking method suits you — so long as it’s legit. If you’re playing at taking notes, you’re not going to help yourself focus. I’m a doodler, and every time I try to take handwritten notes I end up with goofy faces in the margins — visual reminders that I stopped paying strict attention.

So if you’re not going full transcription mode (and I don’t blame you!), just make sure you’re taking notes that are good enough that you could talk a non-attendee through everything that was covered in the meeting they missed. Again, if you won’t have to do so — the act of paying good enough attention to take copious notes will help you stay focused on the meeting itself. And as an added bonus, you might sound even more cogent and thoughtful when you chime in on the meeting discussion, since you have all those lovely notes to refer back to!