Thrillable Hours: Vance Woodward, Lawyer and Traveler

Vance Woodward

Thrillable Hours - Careers for Lawyers Q&AWelcome back to Thrillable Hours,  my interview series about alternative careers for lawyers

The latest in my series of Thrillable Hours interviews is from Vance Woodward, who worked with me back in 2001 when we were both summer associates at Paul Weiss in New York. A few months ago, Vance wrote me on Facebook to say hello and let me know that he was also quitting his job to travel for awhile, starting a blog in the process. Like many travel blogs, his site is part travelogue and part personal musings – in Vance’s case, about psychology, engineering and science. I think his background in science makes the site, and his viewpoint, different and as a former colleague I was (ahem) thrilled to have him as an interviewee for this series.

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What made you decide to leave full-time private law firm practice and work on a shorter contract / consultancy basis?

Well, I didn’t like my job very much! But, honestly, I’m not quite “there,” yet. In other words, I haven’t earned a dime since I left my firm job. But I think that’s a good thing because I can write about what I’m doing as it’s happening. Some context: It was 2009. I was 34 year old and 8 years out of law school. I was a litigator, had never been to trial, and wanted desperately to graduate into being a trial lawyer. I really wanted to go to trial, lots of trials. Yet, trials were rare, that being the nature of my practice area: corporate / commercial litigation. Virtually everything settles. On top of never-go-to-trial problem, I had the usual reasons for being miserable with firm life: boredom, no appreciation, firm politics and emotionally stunted colleagues.

The more significant thing for me was overcoming obstacles. Granted, my final act of leaving wasn’t all that difficult. When I left my job, I had no spouse, no kids, no mortgage, no debt, and some savings. In short, it was pretty easy to just take off. I realize that a lot of people’s situations are more complicated than mine was. But on the other hand, I did get myself to the point where I could leave. I had saved my money and so on. And I did have my own little things to overcome. For instance, I have been through two marriages that never would have allowed me to do what I’m doing now (nothing particular about the girls, but rather the inertia I felt). I bought and sold real estate at a loss (something I’ve seen lots of people be psychologically unable to do). I have blown money on impossibly stupid things (that’s a a whole other story – ed. WE WANT THIS STORY).  By facing these things and working to overcome them, I pushed the scales in favor of leaving my firm job.

What do you find fulfilling about your travels that you lacked in your firm life?

Traveling makes me happy in a few ways. For instance, it feels great to leave my mental crap behind. As I leave for travels, a cloud lifts away. It’s as though, by physically leaving an area, all my problems get shifted into the distant past. In addition, it is one thing to have a sort of intellectual understanding that we live on a planet with zillions of interesting countries and cultures and people and food and so on. It is something a lot more visceral to experience those things with your own senses. And traveling shows me how similar we all are. From watching and reading the news, you’d get the impression that the entire world is lousy with disaster, crime, drugs, disease, terrorism, starvation, death, poverty, misery … did I say disaster? You’d get the impression the rest of the world is utterly mad. But that impression is absolutely wrong. There are lots of happy people all over the place, and the world isn’t filled with miserable chaos. It makes me happy to see that the world is mostly a happy place.

I didn’t get any of that from firm life.

Vance Woodward
Vance on his travels, in Tikal.

Do you have any advice for professionals who are interested in leaving private practice but concerned about what is out there?

As I mentioned, I’ve made the leap, but I haven’t quite started flying yet. This is what I did and have been doing to overcome my concerns with leaving my law firm job:

  • I succeed by failing (or try to, anyway). In other words, I set ridiculous goals. Here’s an example. I was interested in film production a few years ago. So, I bought about ten books from Amazon and set out to read them. Why ten books? I bought ten because, if I bought only one book, I might not read it. But I’d feel really dumb if I bought ten books and didn’t read a single one, right? And that’s why I did buy ten books. Even if I failed to read all of them, I’d be sure to read some of them. As it turned out, I read about five or six of the books right away. Sure, it would have been cheaper to buy one book, and less shameful to not read it. That’s why I bought ten. Incidentally, one of the film books that I read was an autobiography by Robert Rodriguez, a movie director. In it, he says something like, “I figured I’d have to make about ten bad movies before I’d make a good one. So, I just got to work with the idea of getting those ten bad movies out of the way so that I could start making good ones.” It’s another example of succeeding by failing. For people wanting to change their life, I’d recommend setting some ridiculous goals.
  • Next, I read and learn stuff. I read things to reinforce my desire to change, to learn tools for changing, and to let go of an avid desire to accumulate goodies. There were a few books in particular that kind of pushed me over the edge: The Singularity Is Near, by Ray Kurzweil; A Brief Guide to World Domination and 279 Days to Overnight Success (both by Chris Guillebeau and both free); and The 4-Hour Work Week by Tim Ferriss. I read these shortly before I made the final decision to go on my own. And I started following a few of blogs, like yours and Chris Guillebeau‘s, which have motivated me in the same way. At the same time, I found out about Kiva and The Khan Academy. It absolutely blew me away that people younger than me were doing such amazing things. Those websites inspired me to leave the humdrum and start looking for something fulfilling to do with myself. Nowadays, for life-change / reject-materialism motivation, I also follow Karol Gajda’s Ridiculously Extraordinary, A Guy Named Dave and Erica Douglass’ site. Either way, there are plenty of blogs with free and terrific motivational and educational content.
  • I understand that a lot of people might not have much time to read. In that case, I’d recommend a small project: put down the news, the entertainment literature, the TV remote, and the PS3 for a while. With the extra time you now have, read change-your-life books and blogs for a while. Set a target. Say, do it for four weeks, or do it until you complete ten books. It’ll be easier to start if you look at it as a short-term project. You can always go back to the TV and whatever else afterwards, if that’s what you still want.
  • That brings up my next point: I trick myself. Like I just said, I might undertake a project, telling myself it will be smaller than it is really likely to be. I didn’t actually do this, but I might promise myself that skip all my distractions until I have finished reading ten change-your-life books. But really, I’d be doing this knowing that this is the kind of habit that I’ll need to keep up essentially forever in some form or another. It’s the idea of: “How about I just go to the gym today. It’s just today.” Or, “I’ll just go one day without a drink or cigarette or 1,000 calorie frappy whappy. It’s just one day.”  You could say it’s a matter of focusing on what’s happening in the here-and-now when it comes to undertaking big changes. Here’s another way that I trick myself: I like to imagine the worst case scenario and then mock those fears and hangups. Part of my goals are to start up my own solo practice while having plenty of time to work on other things. And I don’t have a single client yet. Here’s the thing: I don’t tell myself it’s all going to be alright and that everything is going to be okay. Instead, I tell myself that I’m going to have to hustle for clients 70 hours a week for a whole YEAR before I get even a nibble. Actually, it’s going to be worse than that. Everything is going to be a complete disaster. I’m going to lose everything: all my savings, my friends, and my sanity. I’m going to become a toothless drunk, sleeping in the gutter next to 7-11. And then aliens are going to kidnap me. Maybe I’m nuts, but doing that seems to help me realize the truth: that everything is going to be okay. I’d recommend doing this to others. Outdo yourself. Imagine the most ridiculously horrible outcome you can. And then go after your goals anyhow. In short, trick yourself.
  • Last: I DO something. Anything! We all know there’s a circular feedback between your inner and outer self. A bad attitude leads to bad decisions, leads to worse attitude and so on. But the reverse is also true. The only trick (there’s that word again) I’ve figured out to this problem is to just … just … DO something. I force myself to start moving in a direction. Whichever way you go, momentum always builds. I’ve started two blogs in the past. And the first entry is always the toughest. It seems so significant. It’s embarrassing to just put something out there. On my current blog, my first entry says something like, “Hi, I’m starting this blog about my life and what I’m doing. I hope you like it.” My goal was (and is) to provide high-quality useful content about the technological singularity and changing your attitude. And I started with “Hi”! Obviously that first entry didn’t qualify as high-quality useful content. But it started the ball rolling. If somebody wants to stop moving down and start moving up, I’d recommend doing something. Write down a list of things you want to do and tape it to your TV. Read the back cover of a change-your-life-book. Go for a walk and think about what you want in life. Go exercise. Eat a healthy meal. Choose water instead of a Coke. The point is to get headed in the a direction. Momentum will build.
Happy Robot
Happy Robot is happy.

How did your legal education inform the way you see the world today? Do you still identify yourself as a lawyer?

I think my most important lesson is that reality is pluralistic or dualistic. I took chemistry for my undergraduate degree and was accustomed to the idea that precise questions have precise answers. Even in the arts subjects that I took, like sociology and anthropology, this attitude seemed to be common. Or at least that was my attitude. Spit back the “correct” answer contained in the textbook, and all is well.

Law school was different. In law school, exams are more about the analysis than the answer. That’s where I really discovered for myself that there are few if any absolutes in the world. Sure, some answers are more correct than others. But few things are absolute. I know that’s kind of abstract. It’s not concrete – “I learned a good work ethic”. But it deeply affected me. Because of it, I think I’m less cynical, and the world makes more sense to me.

But yes, I still identify myself as a lawyer. I’m not really rejecting the lawyer thing so much as I am rejecting the stuck-in-a-situation-I-don’t-like thing.

What do you see for yourself in the next five years?

I want to do something valuable for the planet, something that I enjoy doing anyhow. And I’d like to support myself doing it (make a little money).

Specifically, I see myself running my own plaintiff-side legal practice, maybe focusing on IP or class actions, but definitely focusing on trials! I’ll be running my own coffee shop, and wine shop, and tanning salon, and laser-hair-removal center, and fitness center. I’ll have published my autobiography and several info-products on things like the technological singularity, changing your life, and changing your attitude. I’ll be writing my blog on the same topics, making a positive impact on a few people’s lives. I’ll be running a website that provides free, high-quality, continuing-legal-education training. I’ll be running a new type of online dictionary / grammar that promotes artists and their works. And I’ll have a website that displays old yearbooks. (Feel free to steal any of those ideas! I have a few other “secret” website ideas that I’ll keep to myself for now.)

My initial response to your question was to say something like, “Oh, well, I see myself being an entrepreneur.” But I kind of have to follow my own advice and set some ridiculous goals, right? Besides, I want to set a good example. Now that I told the world all my goals, my gawd it would be embarrassing to end up back in someone else’s law firm again, miserably toiling away! Let’s see if I can succeed by failing.

That being said, even if I crash and burn with all the stuff that I want to do, I can always go back to practicing in a law firm.  As a worst-case scenario, it’s really not bad at all.  I’m admitted to practice in New York and California, and I’m a patent attorney.  So, I reckon I’d have lots of options.

What do you have to say to those who tell me lawyers can’t have fun?

Racing Lure
Racing lure, but what happens when you catch it?

Well, yeah, that’s kind of a problem for a lot of us. It makes me think of a scene from … I don’t remember which movie now. Maybe it’s Snatch. Anyhow, the protagonist is narrating off-screen about dog racing. The dogs chase after an artificial rabbit that flies along in front of the dogs. And the narrator tells us that, once in a while, a dog actually catches the thing, which utterly ruins the dog. Lawyers are a little like the stunned dog, standing there dumbstruck because the thing in our mouth isn’t what we thought it would be. The good news is, unlike the dog, we can leave the track anytime we want and go play in the park.

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In his previous life, Vance was a corporate commercial litigator and patent attorney.  Vance would never want anybody to know that he aspires to be a gun-slinging, swashbuckling, benevolent space pirate.  Arrrrrr, matey.  Right. Currently, Vance is traveling throughout Latin America, diving, practicing Spanish, blogging (about the technological singularity, the future, philosophy, and his travels), podcasting, and writing a couple of books.  His goal for each book is to earn at least ten smiles, regardless whether anybody actually reads the book.  

6 thoughts on “Thrillable Hours: Vance Woodward, Lawyer and Traveler”

  1. Another great interview! I am reading more and more of Chris Guillebeau’s stuff and really enjoying the inspiration. Love the stories of all these lawyers who left to pursue other interests in their lives!

  2. Just came across this series and now I’m working my way back through the archives. I love his approach to failure and it’s something that we all can learn from. Worst case scenario, it’s likely we aren’t going to die trying to do something different, something that we love, so failure along the way just opens our eyes to what doesn’t work so that we can get close to what does.

    Thanks for doing these, Jodi! *high five*

  3. I was struck by this quote from Vance’s Daily Journal piece: “I think this is a problem with lawyers in general: No matter how much money they make, they keep thinking they are poor.”

    I’ve read stories about bankers that tell a similar tale, ie they complain that the guy down the hall is making $20 million and they’re scraping by with 10. What was your experience with that, Jodi?

  4. I had the pleasure of meeting Vance on his travels on the tiny Caribbean island of Utila – one of the Bay Islands of Honduras. We were completing our Dive Master course. I found his chats about his history fascinating.

    I loved this interview. I particularly like his take on dealing with disasters by tricking himself… I too have been using this technique to some degree for many years. For example, if I do not have high expectations of a future event then I am not so let down if the worst case scenario happens or the event is a disaster. You can look forward to something but not have over inflated ideas about how something will be.

  5. I laughed at your analysis of the our homeland westerns news networks. All they give us knowledge of everything bad that is happening in the world. People have enough crap in their own lives, to hear about the rest of it, but they continue to pile on that devastation.

    They know that good news often isn’t as shocking as bad news.

    As you call it ‘firm life’ – that is a little bubble/ goldfish bowl. That is simply of snippet of life in a country. Most people know nothing about the rest of the world – is it fear that stops them from becoming a traveller and leaving this life behind?!?

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