This year I finally admitted I’m not the climb-my-way-to-the-top type I was when I first started writing. Probably this happened a long time ago, and I was in denial. After all, so much of my identity was wrapped up in being a higher performer.

But I look at the most popular posts of the last year, and I see the change.

I remember when my agent said she could get me a $100,000 book deal to write about Generation Y. I thought, “That’s not me. I’m not even part of Generation Y.” But it was me. I just didn’t see it.

And now I see that the most popular posts are about admitting that life is not turning out how I expected. I don’t have any posts in this list about being king of the hill. But I do have a lot of posts about coping with adjusted expectations. And, based on your comments, it seems like we are adjusting together.  Thank you for doing that with me. Read more

Each of us is only as effective as the questions we ask. So understanding the process of asking good questions is essential to our success.

1. Ask questions about what you care about.
A great example of the importance of questions is the  Justice Assistance Grant which gives states $400 million to fight crime. The JAG board asks for data  on how many arrests were made and how much property was seized  – questions that inadvertently encourage states to add to unacceptable rates of incarceration in the US. Read more

You know authenticity is how you connect with people, but it’s hard to know how to gain authenticity. Just wanting it does not increase it. Also, our perception of what is authentic changes. For example, five years ago, when social media was new, authenticity was transparency. Today, with most things feeling transparent, authenticity is something more nuanced. Read more

I try to never do New Year’s resolutions. Statistically speaking they’re the path to failure. If you are committed to doing something big, you’ll do it now.  Also, in December people have a sense that time is running out, so they do things carefully and methodically. In January people have a sense that it’s a new year and there are twelve fresh months and I think that leads to delusional BS about how much we can get done.

Read more

I sent this post to my editor and he said to me, “This is not a blog post. This is a breakdown.”

So fine. It’s a breakdown blog post. But it’s a plyometric breakdown. Do you know what plyometrics are? I learned about this when I played pro volleyball. It’s a way to train your muscles to respond fast. You get your jump to happen in a more explosive way by training your muscles to react faster to shock.

Plyometrics are key to any elite training, even elite-level breakdowns.

Step One: Hate as many people as you can, all at once. Also, hate yourself.   Read more

The world of entrepreneurship is typically one of black and white. Magazine covers are full of people who have given up their lives to grow a billion dollar tech company. And the phalanx around those people are the entrepreneurs who want to sell a big company themselves. Which means long hours, huge tradeoffs, and participation in a hard-core boys club.

In that view, entrepreneurship is only for an intrepid few. They are young with no responsibility, or they are rich, with a huge paid or unpaid support system. But I think there is a much more broad way to think about entrepreneurship.

Here are four models for entrepreneurship that no one talks about. See if you find something that’s a good fit for you. Read more

You are not going to make more money by focusing on income. That’s a way to make small, temporary change. You need to make big changes in your approach to your life in order to make big changes in your financial path. Here are four ways to do that.

1. Stop hoping people will pay you to do something good for the world.
You do not get paid to save the world. You get paid to compromise. There are no jobs where you get paid a living wage to learn and do good and live consistently with your values every second of the workday. Those are volunteer jobs. The farther you get from this all-encompassing goodness, the more you get paid. Read more