How to do things: Just do it!

I get asked a lot for tips on how to "break into the biz" as a tennis writer or tennis journalist. As I have always considered myself more of the former than the latter, I usually pass on questions about the latter. But I got the question again this morning on Twitter and it dawned on me that I usually pass on questions about the former, too. It's not that I don't want to help. I do! I just...

...knowing how to answer the question would imply that I somehow already have the answers. And I really don't. I don't feel entirely qualified to give advice on this because I think my practical advice is not good advice for many people. Everyone is different, we all come from different circumstances, and we're all dealing with different situations. So no, I can't give you a roadmap on how to get paid writing about tennis. Poll 10 different people in the press room for their origin stories and you will get 10 super-crazy different roads to glory. One man's yellow brick road is another man's highway to hell.

But I do have some conceptual advice. This is how I've approached my life and my various career paths, and it's worked out ok so far. And I think it's pretty universally applicable (hopefully) so maybe it can help.

1. Be honest with yourself.

This is not easy. It may send you into an existential crisis that ends with a bottle of whisky and lots of "meaning of life" chats with an innumerable number of strangers at bars. But it's very important and here is why.

Assuming you are a generally ambitious person, and I do think we are all ambitious in our own ways, there is a thing that you want. Maybe it's being famous. Well respected. Rich. Famous, well-respected, AND rich. Maybe it's just being happy. Feeling free. Finding yourself. Happy, feeling free, AND finding yourself. We all want things. That's ok! The wanting drives you forward. Don't apologize for the wanting. Unless what you want is to break the law and hurt people, in which case, maybe go back to the drawing board.

In my experience, people aren't often honest about what they want. Parental pressure, peer pressure, familial pressure can have something to do with that. Like, telling my Asian parents that I just needed time to "find myself" was a really selfish fucking thing to say considering they were immigrants and busted their ass to put me through school and get a professional degree and make an exorbitant salary. Telling my co-workers that I really wanted that promotion seemed the thing to do because, well, didn't we all want that promotion? I didn't give a shit about getting promoted. But I wasted quite a few years believing that I did. Because I wasn't honest with myself.

Being honest with yourself is important because no matter what you do for a living or where you are in life, there will be times when things are really hard. Much will be asked of you. And when you're tired, anxious, and really stressed out, things can get super clouded in your mind. "Why am I doing this? What's the point? Why do I care?" These are the questions that will keep you up at night and cause you to self-medicate and you can nip them in the bud if YOU ALREADY KNOW THE ANSWER BECAUSE YOU'VE BEEN HONEST WITH YOURSELF.

In the course of deciding to switch careers, it took me about eight months to get to the point where I was honest with myself about what I wanted out of life and what I wanted/needed in a career. It was very hard. I was not entirely happy all the time. I once burst out crying in the elevator going to my office one morning because I was so overcome with dread and sadness of having to go to work while at the same time being incredibly frustrated because I didn't understand why I all of a sudden hated it so much. My best friend stared awkwardly as I snot-cried into a bowl of clam chowder the day I made my decision to quit, knowing that it was the right decision but never being clear as to why.

But it all finally made sense once I got my head sorted and realized that all the things my old job provided -- money, security, prestige, cache -- were not things I cared about in the slightest. None of those things made me happy. I thought they did. I was wrong. Maybe they did make me happy at one time. But they didn't anymore. What I wanted and what I needed was room to breathe and be creative. I basically went from being a type-A lawyer to sounding a lot like a hippie, and it took me a while to accept that because augh gross hippies are terrible. But once I did, every decision I've made ever since has been super duper easy. Because I know what I want out of life now (kinda -- it's always a work in progress) and it has nothing to do with accomplishments or milestones.

That works for me. It may not work for you. But the concept remains the same. Just be honest with yourself.

2. Just do it.

No, Nike is not paying me to say that although I will take any swoosh bucks that come my way no questions asked. This is probably the closest thing to practical advice as I can offer. People ask "How do I become a tennis writer/journalist" and my gut response is always "I don't know. Just do it."

This has never been a difficult thing for me. When I was a kid and I wanted to know something, I went to the library, pulled out the encyclopedia, and I read about it. I didn't sit back and wait for a teacher to teach it. When I was in my third year of law school -- i.e., the most unnecessary year of law school -- it dawned on me that even though I loved movies, my historical knowledge of American cinema was pretty crap. That day I printed out the AFI Top 100 list and marched down to Blockbuster, and every week I watched 6-10 movies off that list.

It was great. It also tells you how strenuous the third year of law school is. So dumb. Law school should be two years with a year of interning. Fix it, ABA.

I wanted to learn guitar in college. So I went out and bought one and taught myself how to play. I keep trying to learn how to draw. I am terrible at it. But every few months I dust off a box of pencils and try again. One of the items on my bucket list, which I can't cross off because I travel too much at the moment, is to take an improv class. I think I would be terrible at it. But I just want to try it. Because who knows? I think it's important to give yourself the opportunity to surprise yourself. Thinking you know your boundaries is a pretty arrogant thing and dumb thing. You are capable of so much more than that.

The point is, don't wait for opportunities to come to you and don't sit on your butt and expect your fairy godmother -- as fabulous as he may be -- to instantaneously turn your life around. Whatever it is you want to do, just...do it. Start a blog. Buy a camera and start taking pictures. Post video-shorts on YouTube. Record a song on Garage Band and post it on Soundcloud. Get some friends together and record a podcast. Decide to commit a TV show and every week write your thoughts about it. Whatever. Just do it.

I really loved this quote from Abbi Jacobson, who is one-half of the AMAZING duo behind my new favorite comedy show Broad City. They started at the Upright Citizen's Brigade in NYC and weren't getting cast in shows or offered parts. Their response was not to sulk about it and just keep waiting for someone to invite them in. They made a web series that starred themselves. It was great. That got picked up by Comedy Central and now they're basically changing the comedy landscape being hailed as feminist icons. It's not that dissimilar to what happened with Tina Fey and Amy Poehler. They found it hard to get cast in things. So they wrote their own show and cast themselves in the lead. I think this is a particularly important thing for women, minorities, and young people to keep in mind.

"People wait for someone else to tell them it's ok to start doing something, or I have to be allowed to do this," Jacobson said. "No, you just have to start. It might not be 'the thing', but that thing will lead to the next thing and the next thing. No one will give you permission."

If you want to do something, be prepared to bash down a few doors. Don't expect to be invited in. No one will set the table for you. I grew up in the Riot Girl era and, at least musically, that's what it was about. Want to be in a band? Start a band! Wait, you don't even know how to play guitar? Who gives a shit! Start your band! It sounds so simple but it oddly doesn't occur to everyone. And yeah, you might suck! But that could be the spark that leads to the next thing that needs to the next thing.

And never EVER let people telling you you suck stop you from doing what you want to do. Fuck those people. They are terrible. Whenever you start something, you will suck. That's just normal. You just started! But you will get better. And then you will dominate. And then you can laugh at all those stupid people's faces.

Or you can be a mature human being and be cool with them. I am not a mature human being but that's another way to go so I've been told. To each their own.

So yeah, a few years ago I started a blog about tennis. It was very juvenile. It was also pretty different. I wasn't trying to write the way professional writers write about tennis (to be fair, I wasn't trying to become a professional tennis writer either. I was just goofing off on the internet). I wasn't trying to sound like anyone. In that way it was easy to stand out. From there things started to take off. So much of it was luck and good fortune. A lot of very nice people who I owe so much to encouraged me and validated me along the way. That meant more to me than anything else.

But it never would have happened if I just sat around thinking about being a tennis writer instead of, you know, actually putting pen to paper and being a tennis writer.

3. Be good.

This one is difficult because it implies that I think that I am awesome. Trust me when I say that is not true. At the same time I figure I don't suck at what I do because honestly, you can't fool people for that long.

My best friend and I used to have this whole thing about describing people as "Value Adds". A lot of people are good at what they do. More than adequate, in fact. But the question is always "Does this person add value?" You guys know what I'm talking about. Think of your last social gathering. You know those people who were there who were perfectly nice but totally forgettable? Like, nothing would have changed whether they were at the party or not? They are NOT value adds. Don't be those people! Add something to the dynamic. Be one of those people who when the party is over everyone's like "Oh man, did you talk to Jamie? How great was s/he? I want to hang out with her/him again."

How does that whole analogy or whatever translate to being a tennis writer? Simple. Be good at what you do but also don't be like everyone else. People are looking for unique voices. Anyone can write a match recap or write a predictions post for a Slam. So if you're going to do it, do it differently from everyone else. Otherwise, regardless of how good you are, you'll get lost in the static. Take risks and execute confidently. If you receive constructive criticism -- emphasis on CONSTRUCTIVE -- listen to it. Strive to learn and get better. Be confident enough to believe in your talent and humble enough to know you do not know everything. Find a mentor. Ask questions. Again, show some humility. You can't do it all yourself.

And whens someone helps you, thank them and pay it forward. Sorry if that's cheesy but one thing that has crystalized for me in the last six months: No matter what you do it's always a team effort. You may not always acknowledge or see the team, but they are there supporting you and rooting for you. I could totally write another 750 words that would include a really elaborate Avengers analogy, but I will spare you the details.

So there you go. I hope this is helpful in whatever you do.