Shamelessly Sincere

I think the most important skill no one teaches you is how to be shameless.

I don’t mean ‘being an asshole’. I'm talking about the willingness to put yourself out there - to fail, look stupid, and risk embarrassment - in service of something real.

This has become a bit of a lost art. Maybe the internet has insulated us, from asking the girl out in person, or from posing stupid questions about the world in public.

We live in a weird moment where everyone's terrified of being ‘cringe’. Where irony is armor. You’d rather make a joke than ask for what we need. But there is something very sincere about being shameless and willing to fail. This tweet sums it well:

To strive for success requires utter sincerity. To be sincere and truly put yourself out there you must be shameless and risk failure, embarrassment, and ‘cringe’. Some examples:

• Sending the fourth follow-up email when they haven't responded to the first three. (One of our biggest deals at Babbl came from fourth follow-up on a cold email, and yes it felt cringe when I hit send)

• Asking the basic question everyone else is too scared to ask. If you dont ask now you the friction increases, being young and naive is an advantage

• Posting your real thoughts, with vulnerability and ‘cringe’, online without wrapping them in seventeen layers of self-deprecation is an act of sincerity (and more or less it is how to grow a following).

In the moment it hits the sensitive part of your brain, it feels uncomfortable. But it’s good for you and you’d be better off knowing that and embracing it.

This graph went baby viral on Twitter recently - how "unkind truths" build functional systems while "kind lies" create dysfunction over time. It’s thought provoking (people say this is how Elon works):

Being shameless is choosing the unkind truth about yourself. Admitting you don't know. Admitting you need help. Admitting you want something badly enough to risk looking desperate.

Implicitly most people would rather fail in private than risk embarrassment in public. They'd rather not know than ask. You’d rather stay comfortable than admit they're lost. This is something I am trying to learn for myself.

Brian Chesky said this well: "Shameless people learn really quickly and are successful." He credits this as one of the main reasons AirBNB became successful:

Austin Butler too: “Somebody very close to me… I was at a party once and I was dancing and they said embarrassment is an under-explored emotion, go out there and make a fool of yourself”:

I hope that this will become more of a trend for younger people. If not that’s fine too - then it becomes more of an advantage for those who accept the challenge.

The alternative to shamelessness isn't dignity, it’s the opposite. It's ignorance. It's watching other people build what you wanted to build because they were willing to send the email and do the dance and feel embarrassed and you weren’t.

Success is mostly pain tolerance. Maybe not physical pain. Maybe shame tolerance.

The willingness to be seen trying. I hope you will try!

Peace,
Ramsey