is humility holding you back?

Q3.25 LP update excerpt

Dear Moth,

I know I’m bad at telling my own story. I kinda just make it up anew every time I’m asked and while I like the way that helps what I say feel less like a pitch, I hate coming out of many of these conversations wishing I’d presented myself better. How do I get better at telling my story?

— Humble Mumble

---

Dear Humble Mumble,

Up until around 6 months ago, I was extremely resistant to doing the work to become a better teller of my own story. Despite spending a lot of time helping others develop this skill, I felt strongly that making my story easily digestible to others would diminish my authenticity in a way that felt self-serving and wrong.

I’ve mostly gotten over that now, mainly because I realized I basically just wasn’t taking myself seriously. On one hand, I’d gotten decently far in my career without ever learning to pitch myself, which gave me the mistaken sense I might never need to. On the other hand, I didn’t feel very proud of the things I had to talk about and gave way too much detail than anyone wanted because I was so afraid of being misunderstood.

Ironically, this meant that I ended up being misunderstood by people who weren’t like me most of the time. The more the misunderstandings compounded, the more I resisted fixing the problem and took it personally. Their confusion felt like a reflection of my character instead of the obvious storytelling failure that it was.

The turning point was when I finally asked a trusted mentor for help. I presented my story to him and watched as his face twisted in confusion. Here was someone who knew me well, believed in me, and yet was completely confused by the way I was describing myself. Finally it clicked — this was a narrative problem, not a me problem. He helped me discern which details were important and noted compelling through lines he saw in my story, giving me the seeds of confidence I needed to state them out loud to others too.

Now, does it feel comfortable revealing I was hand-picked by lots of important people? No, absolutely not. It feels unnatural and braggy. But not saying it out loud was leaving me stuck in the misunderstanding mud, unable to do anything for anyone. It helps to think about why I’m talking myself up — because by doing so, I’m able to help other exceptional people spend more time doing and less time talking about themselves.

I think most of the resistance people feel to getting better at telling their story is actually just immaturity. Growing up is realizing that we’re all special snowflakes (especially in Silicon Valley) and you can’t expect others to know why you’re special unless you tell them. If you feel rejected or like you did something wrong when your specialness isn’t immediately recognized, you should probably address that belief head-on.

I think if you’re a good person, you should talk more. I also think that you should only spend time refining your story once you’ve done enough things in the world to know who you are. At a bare minimum, I hope you stop self deprecating. That’s not humility, that’s critiquing yourself before others can in order to feel a sense of control.

— Moth