What I’m listening to right now: Amanda Blank. Here’s a song to play when you’re not at work.

Amanda is a white-girl rapper, darling of the hipsters, and hot-girl candy for the intelligentsia. Right up my alley, right? My favorite line so far is “My rhymes are painful and fresh/My p*ssy’s tastin’ the best.”

Today, Ryan Healy and I were in D.C. for a marathon strategy meeting with a board member. The second half of the meeting was about marketing strategy. The first half of the meeting was about finding a strategy for ending how Ryan and I are at each others’ throats over subjects that having nothing to do with the company.

When the board member left the room for a minute, we had this conversation:

Me: It’s so awkward to be left in here with just you.

Ryan: It’s not awkward. The meeting is going well.

Me: Right. It could be more awkward. Like when it was us not talking in the airport.

Ryan: At least we weren’t sitting together on the plane.

Me: Yeah. I know. I changed my seat so we didn’t sit together.

Ryan: Really? So did I.

Then the board guy came back and I bitched about how a vendor we hired was doing no work, and how a year ago I told Ryan we should fire them and then Ryan told me to shut up and so I did.

Then board guy said some obvious things: Ryan should not tell me to shut up, I’m the CEO, and I should take decisive action faster.

Then we all talked more, and Ryan and I started getting along again. And we all plan the next twelve months of the company, getting excited about the community. This is how it always goes with us.

But the whole time, Amanda Blank is running through my head. Why does she say “My rhymes are painful and fresh?” Why are her rhymes painful? I ask myself this. And then I answer philosophical questions about why LinkedIn appeals more to Gen X than Gen Y. And then I go back to Amanda.

She says, “My p*ssy’s tastin’ the best.”

I have never said that. I am too shy. Even when I was her age, and I was running around in a bikini in Budweiser ads for spending cash, I would not have said that.

And this is why her rhymes are painful. Because they exude so much self-confidence. And every regret I can think of is about self-confidence.

There’s a really interesting study from Harvard, reported in the Atlantic, that I have spent way too much time reading.

The study follows Harvard students for more than 70 years to determine what makes people happy. Here is something: The fact that people are totally pulled together and focused and in Harvard has no bearing on whether they’ll have a happy life.

Here’s another thing: There best indicator of if someone will be happy in the future is if you are 47 and close to your siblings. After I read that, I started calling my brothers more often. Really.

But you don’t have to wait for your mid-forties to find out if you’ll be happy.
Look at how you frame your life now. If you frame things in a positive light, you’ll be happier later in life. The optimists win. Plus, the Harvard study finds that people get better at optimism as they grow older. And I believe that. Maybe when I have a startup at 70, I will trust myself enough to act decisively and avoid all management conflicts.

And then this becomes clear to me: I have spent way too much time in my life worrying that I was doing my life wrong. But now I see that I can change. Right now. Right now I can be someone who assumes I am making good decisions. Because we each have to make decisions. So we may as well assume they are good. There’s not really anything else to do.

Besides, no one was ever penalized for believing in herself, even if her raps were not safe for work.