LIVING OFF DIVIDENDS & PASSIVE INCOME

As someone who’s struggled with finding meaning in life, I can understand the frustration young high schoolers feel when they ask me what they should be doing with their life. Unfortunately, I never have a good answer.

But now thanks to Penelope Trunk, I can direct them to this page and get them off my back:

There is no other way to figure out where you belong than to make time to do it and give yourself space to fail, give yourself time to be lost. If you think you have to get it right the first time, you won’t have the space really to investigate, and you’ll convince yourself that something is right when it’s not. And then you’ll have a quarterlife crisis when you realize that you lied to yourself so you could feel stable instead of investigating. Here’s how to avoid that outcome.

1. Take time to figure out what you love to do.

When I graduated from college, I was shocked to find out that I just spent 18 years getting an education and the only jobs offered to me sucked. Everything was some version of creating a new filing system for someone who is important.

Often bad situations bring on our most creative solutions. And this was one of those times: I asked myself, “What do I want to do most in the world, if I could do anything?” I decided it was to play volleyball, so I went to Los Angeles to figure out how to play on the professional beach circuit.

I spent my days on the courts, and late nights at the gym, and in between, I worked odd jobs in bookstores. And then I realized that the other thing I wanted to do was read. I had been so stifled in school being told what to read all the time. It was thrilling to be able to read whatever I wanted.

I wasn’t making very much money. Sometimes I couldn’t pay rent, and my landlord hated me. And sometimes I couldn’t afford to wash my clothes and I pretended that bikinis never get dirty. But, in fact, you really don’t need much money to figure out what you love to do, you just need time and space and a willingness to keep yourself busy until something sticks.

2. Take time to figure out what you can get paid for.

It took me a few years to navigate the arcane hierarchy of Southern California beach volleyball, but I finally played on the professional tour. For a summer. And what I found was that I am not nearly as competitive as the top players. I was, at one point, ranked 17, but I can tell you that I never cared as much about my rank as the other women.

What I did excel at, though, was winning sponsors, which, on some level, is what professional sports is all about anyway. I always had better sponsors even than women higher than me in the ranks, and I won partners and trainers by dint of my ability to attract sponsors.

But the truth about professional volleyball is that it is a really tough life. The eight hours a day on the beach starts getting old, and so do the Budweiser commercials I did (totally not fun) to manage to scrape together enough money to support myself.

So I thought to myself: Who is using the skills I have to make money? And I landed on marketing. And I had this boyfriend who was going to hire someone to do marketing at his Internet startup, so I volunteered to do it for free, to get something on my resume. And then I got a job.

3. Watch people around you to figure out who is happy.

I ended up having a pretty big job at a Fortune 500 company running their web site. Don’t get me wrong. It was the earliest days of the Internet, and it actually took more people to redesign my blog recently than it did to launch that Fortune 500 site in the early 90’s.

But anyway, I started climbing the ladder and tons of people wanted to mentor me, to help me get to where they were. And they told me they were happy, but when I watched them, day in and day out, I realized that the people at the top of the ladder were not nearly as happy as I had expected them to be. They tucked their kids into bed from their phones at their desk. They were overdressed constantly and they had hair-trigger tempers for topics that seemed inconsequential to me.

So I went to where coolness seemed to be: At startups.

Now that I’m on my third startup, I can tell you with certainty that if you looked at my life you would not see that I am happy. Running a startup is really high risk and really difficult, and entrepreneurs work longer hours than anyone else. But I’m almost always there to eat diner with my kids, because I control my own hours.

So the final step of finding out where you should be is looking at everyone’s life with a clear lens. Adult life is really hard. Finding out who we are, and finding someone to share our life with, and having kids and still having a life, and being able to pay for all of that: Impossible, really.

So you look around and see who is doing what part of that well. And you pick the sacrifices that they made. Because no life is perfect, but all lives have some things to offer. Be clear on what you’re choosing and what you’re giving up, and don’t pick anyone’s life if they tell you they have everything: they’re lying.

But if you’re already out of college and still don’t know what you want to me, may I suggest considering an MBA at top Business School?

If you found this post helpful, consider donating to my coffee fund!

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