Can't Joke My Way Out of This

Startup Hustle Zapped My Sense of Humor

Last night, I went to a Vir Das concert. While I think the guy is super funny, even with his usual "biscuit section" on weekends, he wasn't quite as funny as usual. It made me wonder if we've lost the ability to laugh at ourselves, particularly in the high-pressure world of startups. I thought I was good at laughing at myself, on this blog and in general. Self-deprecating humour always seems to work for me.

I pride myself on my self-deprecating humour. It works for me in life and even in this blog. But the startup scene is a different beast. Everyone's juggling a million tasks, pitching to investors, and chasing elusive funding. It's like a competition to see who can take themselves the most seriously, even when burning a mountain of cash on a dream with returns being a hypothetical number in the future.

Who am I to judge, though, because I'm pretty much in that same category? I'm juggling so many to-do lists about work that people in the team have probably forgotten. I am chasing elusive investors and living on a prayer that money hits the bank soon. Laughter seems to have disappeared from me. I'm just barking orders at everyone to move faster, even if they're already going at a fast pace.

Tell you what, it's incredibly difficult to laugh at me these days in all these scenarios.

The Pitch Deck that Looks Like a Dream (Or So We Think): We poured our heart and soul into creating a perfect pitch deck. Every slide was crafted with so much thought that the idea of cracking a joke while talking to a partner or investor feels criminal. It's like if I make fun of it, they'll be able to see the gaps I can see.

Fear of Lacking Gravitas: That word, "gravitas," has given me nightmares since I joined this sector, and it still does. When the grey was finally showing up in my hair, I thought, finally I can look serious. But, I decided to experiment with an (admittedly ugly red) burgundy colour, and now I've gone indigo on top of it. I can't joke around now because I might be misinterpreted as lacking gravitas and not having what it takes to create this awesome platform.

The Competition Conundrum: I constantly get the "Have you checked out so and so?" question. I say yes, but they're a website, and we're creating a platform. The partner or investor will tell you it's all the same. Now, how do I joke and tell them they're not techies and don't understand the difference between creating a Facebook or Amazon versus any other standalone site that sells books or whatever? Everyone and their mother is considered a competition depending on how you perceive the app. If I say that, they might think I'm delusional because how can I talk about conquering and disrupting the world?

The Operations Dilemma: They say "When the cat's away, the mice will play." Not true in my case. They've been working, but I want more, a lot more. The funders are looking at just us because we're so important in my head, so we need to be bigger, better, faster, and always moving! Yeah, the orders keep getting barked, and the chill person who laughs at herself and believes in non-violence resorts to every violent form of communication to get work done.

So, what can I do in this situation? I don't know. I've seen some of my former bosses break the ice with a perfectly timed joke to ease the tension or humanize the hustle. Come on, who else can talk about having a cannula on their hand and going to raise funds the next day? The absurdity of what I did in May while on antibiotics and collapsing every time I came home could help break the tension, but who wants sympathy? Maybe I could try a joke about not understanding convertible/non-convertible notes because I failed finance in my MBA (yes, I was one of those who got a 3 in both FIN 1 & 2), but then they might look at me as super inexperienced and green.

Guess I'll just combine all of this and practice because I don't have the skills to be a super stand-up comedian like Vir Das but my authenticity goes a long way. A touch of self-deprecating humour about the absurdity of the startup world might be just what the doctor (and the team, and the investors) ordered. Forget the gravitas, I doubt my indigo hair is going to help any of that anymore.?

Any ideas on how this is done? I am getting too serious and me being serious is the death knell for me. How do you look for humour in your jobs, startups, and lives? Pointers and stories are all welcome because I definitely need a couple of laughs on this sweaty Monday morning and so does the world.