Hate To Break It To You is a recurring feature wherein we dispense succinct home truths that everyone could benefit from facing up to, unpleasant as they may be.

This one goes out to everyone who’s ever been hella pissed off at the story of the Prodigal Son.

Life is not a meritocracy. I’ve been meaning to tell you that for a while (and it’s not as if I haven’t hinted at it before), but I recently saw Stephen Sondheim’s Assassins* and the whole theme of the ugly truth of the American Dream not panning out for everyone reminded me that, yeah, input and output aren’t always aligned.

Photo by kevinthoule

Hard work and talent and eating all of your vegetables without complaint and wanting it so much that it’s all you can think and even breathe about doesn’t always pay off. Well, what does then? Nepotism, luck, right place at the right time, cleavage, the ability to convince middle-aged women that you find them sexually desirable, sociopathy, good hair and teeth, shrewdly reading and manipulating the zeitgeist like the Wizard of Oz, ruthlessness, coquetry, singleminded self promotion, selling your soul, being all things to everyone, etc, etc. If there was a surefire recipe, wouldn’t we all be in the kitchen whipping up a batch of personal glory right now?

People who are less talented, less awesome, more venal and more vapid than you will sometimes get what you want. Ain’t that a kick in the head? Attempting to beat these folks at their own game is not only likely to prove futile, it will leave you feeling frustrated and slightly soiled. I also don’t recommend that you let resentment about this inequality of opportunity fester inside of you and warp you into a Charlie Brown sad sack or a gun-toting academic.

The conventional path to the top is pretty much gridlock as far as the eye can see. You can join the traffic jam, but forget about getting anywhere or doing anything more productive than staring at the bumper of the car in front of you for the next 20 years (not to mention feeling irrationally pissed off that they have a pair of neon pink fuzzy dice dangling over their rear view mirror). If you want to move forward, you’re going to have turn off the ignition, lock the doors behind you and start out on foot. Forget competing with the seeming golden children, you’re going to have to carve out your own opportunities, make your own map to a place that you’ve invented, hack a shortcut through the woods with a homemade machete or  start as small as launching a blog for your writing after receiving the 17th rejection letter from a major publishing house. It’s tough and there’s no guarantee of the pay-off, but if the only other option is fighting blind luck and a hoard of post-modern P.T. Barnums, it might just be your best bet. Sure beats shooting the President (sorry, Sondheim).

* Skip it, unless your John Wilkes Booth is as natty a dresser as ours was and your Sam Byck is a dead ringer for my (imaginary)  indie pop boyfriend. Heck, even then you can still give it a pass.

I promised that I’d offer a rough and ready guide to Project Guinea Pig, in which you acknowledge that you can’t predict the future, stop trying to and start diving down interesting rabbit holes as you encounter them, without thinking about how these life tangents will affect A) your personal “brand”  B) your five-year plan C) your upward mobility D) all of the above and then some.

Photo by Thorsten Becker

How To Be A Guinea Pig: A Tutorial

Get a handle on logistics

Before you can be wonderfully spontaneous and unfettered, you’ll need to do some legwork.  Figure out the minimum cash flow you need in order to maintain a tolerable quality of life. If you have the relative luxury of being able to save up for a couple of months of potential dark night of the soul expenses (like I managed to do – I’m a scrimper, no doubt), absolutely do it.  If you’re inclined to downsize yourself out of a lot of unnecessary possessions, so much the better (following whims is easier if you don’t have to load up the U-Haul first). And even if you don’t plan to relocate to a strange city to start from scratch, having the cash to pursue non-freebie flights of fancy (Fencing lessons! A weekend road trip to Carhenge!) never hurts.

Realize that it might not work out

Maybe you aren’t cut out for being aimless (maybe I’m not cut out for it, either).  Maybe you need order and structure and deadlines to sleep at night. Maybe you’ll gamely grind through the entire experiment and not feel enlightened or edified at the end of it. Maybe you’ll open yourself up to the whims of the universe and the universe will totally blow you off. It can happen. It might happen.  If you’re looking for a guaranteed miracle or epiphany,  save your money and trek to Lourdes instead.

Give yourself permission

The first hurdle is overcoming the worry about what others will think of you if you take a temporary timeout from upward mobility. Let’s try a little game of imagination. Think of your mother. Think about talking to her on the phone. Think about her filling you in on all the gossip from back home.

Can you believe that Matt and Jess are expecting another baby and they’re still not married?

You remember that Amy girl you graduated with? Well, I saw in the paper where she’s got this big time job at NASA now.

You’ll never guess who got arrested for shoplifting boxes of Sudafed from Walgreens!

How long does any of this stay in your head? 10 seconds? The length of the conversation? Two days, but only because you take a giggle fit as you pass a Walgreens on your way to work? That’s exactly how long your  information (as reported by their respective mothers) resonates for Matt, Jess, Amy and the unnamed shoplifter-cum-meth maker.

But what about what you think of yourself? Even if you can dismiss others’ fleeting judgments, what about all of your internal expectations, pressures and unmet potential? How will you ever look at yourself in the mirror if you bail on your biorobotics PhD to tour dive bars throughout the Midwest with your half-assed jam band?

Think about it this way –  Is the PhD making you happy or are you still battling the nagging fear of not doing or being enough? If you’ve condemned yourself to carrying around an albatross of guilty inadequacy, why not do so while having the time of your life grooving to Phish cover songs? I kid. Sorta. My point is that  if you’re doing everything “right” according the Young & Ambitious playbook and you still feel dissatisfied and unfulfilled, can changing courses and pursuing a more “selfish”  trajectory actually make you feel that much worse? I’m gonna call BS on that one.  If it’s a question of damned if you do and damned if you don’t, why not opt for being damned while doing something that gets your motor running vs. being simultaneously damned and dejected?

Set a time limit

This serves two purposes. It provides a little structure, especially for those us who get angsty at the idea of endless ambiguity. Secondly, it forces you to dive into the deep end, instead of splashing around in the kiddie pool with your water wings on. You’ve only got a finite amount of time (in my case, a year to possibly remake my life in the image of a Gillian Welch song ) to cram full of as many adventures, detours, false starts, mistakes, object lessons and anecdotes as possible. There’s no time for dithering, just doing.

I was recently quoted in a National Post story about the social media dimensions of  Toronto (largest city in Canada for those not in the know) mayoral candidate Adam Giambrone’s sex scandal. If you found my site through those channels, welcome!  You can click here to read my original take on the imbroglio and its lessons for the rest of Generation Y.

This site, Generation Meh,  focuses on personal and professional development guidance for twenty/thirtysomethings (i.e., the quarter-life crisis set) delivered in the form of pep talks, common sense primers and tough love beatdowns.

To help you get acquainted, here’s a small sample of what GenMeh is all about:

Generation Manifesto

Expiration Dated: Of Lost Luggage And Missed Connections

You Aren’t Going To Change The World And That’s Okay

Melissa Melanson and I have known each other for years. A few months ago, I suggested she write a guest post for GenMeh. Circumstances have changed since then and that topic is rather dated, but when she pitched me on the idea of providing relationship guidance from her former legal perspective (and just in time for Valentine’s Day!), I happily took her up on it.

P.S. No, I haven’t forgotten; I’m currently putting the finishing touches on your guide to the aimless life.

P.P.S. Interested in writing a future guest post for GenMeh? Drop me a line and we’ll see what we can do.

Photo by Francesca Tronchin

Marriage Advice From A Former Divorce Lawyer

When people find out that I practiced family law for a few years after law school, they get this uncomfortable look on their faces, like I said that I umpire cock fights or make my own hotdogs from scratch. They know that it happens, they know that it’s ugly, but they’d rather not think about it. I admit that part of the reason that I no longer practice law is because of the ugliness of marital breakdown, but it really wasn’t all doom and gloom. Change is inevitable and I was happy to help people navigate a difficult period of their lives. I also feel that I have benefited from the experience. I have never been married, but I have been up close and personal at the end of numerous unions. Eventually, you start to notice patterns. Some things are just obvious. Basically, if it could get you fired from a job or arrested, it’s a bad sign for your marriage. What I gleaned from my unique perspective on marriage is a little more subtle than that. I learned (and will gladly share with you) the kinds of things you  wish you could tell someone before they got married or before their happily-ever-after  fell apart.

The marriage has a better chance of succeeding when both people are adults

Think about the person you were when you were 18. How different is he/she from who you were at 22? 25? 30? Maybe you are the rare exception who was fully formed at a very young age, but most people are completely transformed by experiences like post-secondary education, living on your own and travel. Realistically, you might never fully know who you are or what you want out of life, but people grow and change considerably in their early adulthood. Before you commit your life to another person, it’s preferable to get your own life sorted. The complement to this is you shouldn’t commit to another person before they have their life sorted out either. While it’s true that people can grow apart after years of marriage, you can do a lot to avoid a situation where one partner outgrows the other if you’ve both already done most of your growing before the I do.

If your whole life revolves around you, you’re not leaving much room for a partner

The world is made up of givers and takers and the adage that marriage involves give and take is true. Relationships aren’t always equal, sometimes one partner is more demanding, sometimes, you take turns. Marriages seem to suffer, however, when the needs of one partner are never considered. After all, no one wants to play a supporting role in a movie about their own life. It doesn’t make you a bad person if you walk through life without asking what he/she wants and what makes him/her happy, but I’m afraid it does make you poor spouse material.

Remember that even if it doesn’t last forever, life will go on

Clients would often ask me, “Are you married?” and upon discovering that I was not, would ask if my line of work had created a distaste for the institution. I normally wouldn’t provide much of an answer (we’re talking about your life here, buddy) but one day a woman in her early thirties asked me, and she was the kind of the person that I was really rooting for –  a sweet person who had married a not-so-sweet man. I wanted to give her hope.So I fed her a line, which in retrospect wasn’t really a line at all, but something that I truly believe. I told her that working with people at the end of their marriage certainly has made me more cautious, or at the very least informed, about making such a commitment. But that’s not the end of the story.

The nature of divorce law where I practiced is such that you meet people when they break up to draft a separation agreement. At that time, they’re a mess, their whole life has collapsed around them. They then have to wait a year after they separate before they can get a divorce. A lot can change in a year. People would come back stronger, happier and often would have met someone else. They could not believe how much better their lives were, and after seeing what a disaster they had been just a few months prior, sometimes I couldn’t believe it either.

Marriage doesn’t come with a guarantee. All you can do is make the best choice you can, and recognize that just like in every aspect of our lives, we sometimes make mistakes. But even coming from my former line of work, if I haven’t ruled out marriage entirely, doesn’t that say something about its inherent risk-worthiness?

-Melissa Melanson

This time last week I was frantically attempting to track down my movers in order to reclaim my meager truckload of possessions. Since then, I’ve set up my new apartment, figured out how to use a cordless drill, had coffee with one of my neighbors (and attempted to avert my eyes from his vast collection of vintage erotic fiction) and promised another that I’d never get drunk and crash into his door at 3:00 AM (apparently, the former occupants of casa de JMH couldn’t really hold their liquor), but that I would play Scrabble with him (with the warning that I’m hella competitive), checked out the coolest coworking space ever, volunteered at a bake sale for Haiti, plotted an Olympics-related hashtag revolution, subjected myself to one of Estee Lauder’s social media makeovers and walked, a lot.  And I did it all for you, dear readers. Well, kinda.

For the last six months, I’ve been doling out the exhortations, entreaties, pep talks and tough love beatdowns here on Generation Meh, so it’s only fair that I tangibly put my money where my mouth is and prove that I do indeed live by my own rules. After all, how disillusioned would you feel if you discovered that I was actually an up and coming accountant at PriceWaterhouseCoopers who had recently bought a fabulous high-rise condo with her lawyer fiance (met him sophomore year at Brown, natch)? And that we had just adopted a chocolate lab puppy and were into wine tasting and lazy brunches at the most buzzed-about downtown hotspots? Yeah, I thought so. Fear not, as nothing could be further from the truth. The mangy, stuffed E.T. doll currently taking up residence on my poorly-assembled IKEA coffee table (complete with shellacked recipe cards I bought for 79 cents at Goodwill) can attest to that.

See? Told you so.

Nope, instead you get an ambiguously-careered someone who just landed in a city four and half times bigger than the one she’s lived in for the last six years, who rented her apartment sight unseen and who knows exactly two people in this metropolis. She has no clue what’s going to happen next and is surprisingly cool with that.

As you can tell from the themes of the previous two posts, Gen Y isn’t exactly top of the class when it comes to balancing the big picture perspective with the day-to-day details. In fact, a lot of us are all forest all the time, damn the trees. We’re so busy fretting about the future and how we fit into the jigsaw puzzle of a grand scheme that we lose sight of the day-to-day potential for mini memories, pocket-sized epiphanies and other tiny bursts of humor, pathos, drama and serendipity. These things count, too. They matter. They’re cocktail party fodder, potential best man toast anecdotes, Twitter updates, texts to your best friend, cheap coffee product commercials. And by being so focused on the overarching plan (What is it? Should I have one? How do I get one?) and obsessed with meticulously  timing our lives’ milestones so that we don’t end up on the wrong part of the bell curve, we take these moments for granted, assuming  we even notice them at all.

I’ve decided that it’s high time I give these moments their due and start living out all of GenMeh’s collected wisdom in true guinea pig fashion. In fact, when people ask me why I’ve moved, I flash them my best manic pixie dream girl smile and  tell them it’s supposed to be an adventure and an experiment. And I mean it. I don’t know what’s going to happen next. If you told me that in six months I’ll be living in Reykjavik after eloping with a dude I’ll meet after standing behind him in the Starbucks line tomorrow or that, before 2010 is out, I’ll be putting the finishing touches on my vegan bakery and artist co-op in downtown Burlington, VT, I would have to believe you.  When you leave the door wide open, you really never know who or what (for better or worse) will walk through.

And guess what? I’m not independently wealthy, I’m not a maverick risk taker and I hate ambiguity even more than the next person, so you know that if I can tackle the challenge of being okay with plan-free living, I will surely handhold you through the process in convenient bullet-list form in my next column.

Stay tuned.