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My first 2 attempts at writing new headlines for my old content were miserable. I hated them both, and they felt like cheap click bait. They were templated schlock and required zero thought. Just 100 lines of fill-in-the-blanks.

But I have a theory…

My dismay may have been due to the type of content I was covering. Informational rather than entertaining.

So today I’m going to mix it up.

About a year ago, I wrote this piece about making work presentations funny. I’ve been meaning to revisit it for a while because I think it could become a cornerstone piece if it’s fleshed out. Right now, it’s more of a quick hit. But it’s got a terrible headline. It fits the piece but ain’t nobody is gonna click it.

(Truth be told; my old blog was more therapeutic than anything. It’s got nothing to do with my writing today—and it’s been dormant for ages.)

Anyway, I wanted to see if I’d have better luck with a fun content post.

Turns out, I did.

Here are 102 way better headlines than Tryin’a Be Funny At Work:

1 5 tips for being funny at work
2 Want to be funny at work? Follow these 5 steps
3 This is how you balance our being mean & funny in presentations
4 hello snarkness my old my friend
5 5 Things you should do to become a funnier presenter
6 5 Silly reasons to be funny at work
7 Punch up your presentation and knock ’em down
8 5 Comedy commandments for crafting a funnier presentation
9 How snarky should you be to become funny
10 How to pepper some laughs into your work day
11 How to make your co-workers like you
12 How to be funny at work
13 Please tell me you didn’t try doing THIS at work
14 Need to make a funny sketch at work?
15 How to make comedy at work, work
16 Can insulting your boss actually be good for your career?
17 Funny presentations are better. Here’s why.
18 Present like a stand-up comic
19 Boss ask you to do something funny again?
20 Ever been to great presentation before?
21 Give your workplace presentations a much-need kick in the keester
22 Your guide to creating funny work presentations
23 There’s more to being funny at work than a comic sans font
24 How to be make jokes about your boss while she’s watching
25 Bringing the silly to work
26 Tips for making your office more fun
27 Things you should never do during presentations
28 The someday-comic’s guide to making your presentation funnier
29 5 Funny ways to punch up your presentation (and be funny at work)
30 How to own the room while you present (and fill it with laughter)
31 What do when your boss thinks he’s a clown
32 How being a little mean can help your career
33 How to be funny at work (without getting in trouble with HR)
34 I work funny and you are too
35 The worst thing you can do is try to help someone be funny
36 How to help your co-workers be funny
37 Just because you want to funny doesn’t mean you should be
38 How to write a group sketch at work
39 Does your boss think he’s funny? Here’s how to help him make it real
40 Where to draw the line while being funny at work
41 Want to make life at the office more interesting? Here’s how
42 Nobody likes to give boring presentations
43 5 ways to funny up your workplace
44 What to consider before trying to make your presentation funny
45 Everything you need to know about being funny at work
46 Why you owe it to your audience to be funny
47 Making corporate life a bit more funny
48 There’s funny, then there’s work funny
49 How to knock ’em out with your presentation by punching up the comedy
50 How to spice up the workplace with some humor
51 Ever want to be the funny one at work?
52 How to give a funny presentation
53 Comedy hacking with your co-workers
54 Why it’s bad to force funny
55 Get the laughs at work
56 The dangers of being funny at work (and how you can avoid them)
57 How to add punch(lines) to your presentation
58 Here’s why you should never make fun of your boss in public
59 Laugh your way to the top
60 Reach your maximum hilarity presentation potential
61 How to make HR nervous
62 Yes, even you can be funny at work. Here’s how.
63 What to do when you’re asked to write a sketch
64 Do you want to be the class clown of your office?
65 Here’s what to do if someone asks for help them make their presentation funny
66 What you should know about being funny at work
67 How to make your co-workers laugh (with ought upsetting your boss)
68 How to be the funniest (looking!) guy at the office
69 What’s the proper balance for insulting your audience
70 Is it better to make fun of your boss or your assistant (getting this wrong could get you fired!)
71 Better presentations take practice
72 How to turn your presentation into an open-mic at a comedy club
73 How to be funny at the office
74 Hearing an uncomfortable silence after you make a joke in your presentation?
75 Put some personality into your presentation
76 How to make your work presentation funny
77 Here are 6 methods that are transforming offices into comedy clubs
78 Always leave your audience with a smile. Here’s how:
79 Practice your stand-up on unsuspecting co-workers
80 Take your silly to work day
81 How a hat for pot-bellied pigs can make you a better presenter
82 Stand-up comedy from a cubicle
83 Punch up your punchlines
84 Can being a little mean make you more likeable?
85 Are you missing these presentation opportunities for comedy gold?
86 5 ways to create a presentation good enough to take on the road
87 How to be the office clown
88 The hidden meaning behind mean at work
89 Should you be a little mean when you present?
90 The art of being funny
91 5 surefire tips to make your presentations punchier
92 Comedy hacks to make your presentation funny
93 How to get more laughs per minute when you present
94 Why it’s safer to write ridiculous insults than real ones
95 How to make being a smart mouth pay off
96 The fine line between funny and mean at work
97 Punch up your presentations with these 5 tips
98 Leave your co-workers with a smile
99 5 easy ways to be funny at work
100 What happens if you make fun of the wrong person at work?
101 Funny presentations take practice
102 Here’s who you should be making fun of at work


Overall: Considerably better! I always knew that original headline sucked, so the bar was set pretty low. And while I did use the templates a good bit, and it’s not the most interesting post to read, the results are a vast improvement over the original.

Lessons: I think the difference between this and my previous content headline posts was that I wasn’t swapping a formula for a formula. I was making an upgrade.

  • I have more of a personal connection to this piece. Yes, I wrote the other 2, but they aren’t in my voice. This one is.
  • I was able to be more specific and allude to jokes within the content.
  • Some of these still feel generic or like click bait, but they’re all better than the original line.
  • Writing this gave me a few ideas about how to improve this post.
  • Watch for me to re-purpose and expand this piece once the headline project is over.
  • Wow, the “bigly” line is definitely dated. The meme was right.
  • Content templates do have a place. It’s not necessarily a place I’ll visit often because I’ve pivoted from that medium, but I won’t dismiss them as quickly as I did before.

Using templates isn’t a challenge. But it can produce decent results.

Time: This was quick. Just over 50 minutes in 1 session. Mostly fiil-in-the-blanks.