Information Arbitrage: The Wall Street Series Part V: Moving On

"Should I leave my current job?" I've gotten this question on many occasions and figured I'd share some thoughts on this important and anxiety-inducing topic. Changing jobs, altering paths, switching careers is an exciting, dramatic and risky proposition, and certainly not one to be taken lightly. There are clearly few black-and-white answers here, though there are some. And there are certain issues you must consider that require a great deal of introspection, perspective and honesty. Being honest with yourself? This is very, very hard to do, especially when the stakes are high (with those fat Wall Street pay packages being dangled in front of you). And the stakes aren't just about money - they are about job satisfaction, being in a position where you can succeed, feeling good about your peers, and general happiness. That said, we're talking about your career, right? So hard or not, facing into your underlying motivations is really important - no, actually critical - in order to make a smart, educated decision concerning career path and long-term objectives. I know you're up to the task.

The Obvious 10% - When to Move On No Matter What

1. You are stagnating

One of my favorite sayings (which I've uttered around 3 million times) is "If you're not moving forward you're moving backward." I really believe this and live my entire life this way. High achieving, highly motivated people can't live in a state of stasis. It is a waste of time. You're not learning. You're not growing. You're not sharpening your skills. And you most certainly aren't having fun. So move on. Right this second.

2. You are positioned to fail

Motivated people like to win. And, at a minimum, they need a chance to win if they do their jobs, use their intellect and drive and execute well. There are times, however, when a situation is wired for failure. And there can be a wide range of situations where this is the case. But you've really got to analyze the situation in a cool, calm, dispassionate way in order to make this assessment. Because things have to be really, really crappy for this to true. So just make sure you are not getting emotional and too locked into a losing mind-set. Because situations that may seem bleak can, with a little perspective, look a whole lot better very quickly. And it is incumbent upon you to use any and all tools and relationships at your disposal to test your assumptions before saying you're positioned to fail, no matter what. But if after this process your conclusion is yes, then run, don't walk, out of the place to greener pastures.

3. Life circumstances necessitate a change

Somtimes non-work life trumps work, and a situation calls for a dramatic re-assessment and re-positioning of one's work life. And if this happens, there is no amount of job happiness that can change the calculus. It is what it is, and moving on becomes not about work life but about your entire life. And this is when flexibility, a hallmark of a high achiever, will help you through, painful though it might be to leave a situation that is working for you in that sphere of your life.

The Not-so-Obvious 90% - When Moving on Makes Sense - I Think?

Oof. This is tough stuff. Let me use the mechanism of a list to organize a few of my myriad thoughts on the topic:

1. You get a killer offer for a job you are really excited about

Sounds great, right? Sure it does. And it may well be. But how long have you been at your current job? Will you be viewed as a "job jumper" if you bail, putting yet another shop on your resume? This looks really lousy over time; it really does. How about non-monetary issues? Are your really happy where you are, feel good about your work, dig your peers, like your clients, and just basically have fun? How much is this worth? To properly answer this question you've got to think in terms of utility, that fungible measurement that puts every factor on an equal plane. Sure, more dough has more utility, but the grass is always greener, right? That job that looks so plum right now could turn out to be a nightmare. You're the new guy/gal with the guarantee. Therefore, by definition, you're a prima donna a**hole. Then what? So before grabbing the pen and signing that offer letter, take a deep breath and give yourself some time to make a list of pros and cons, taking into account both monetary and non-monetary factors, as well as short- and long-term goals. This will help you make a cogent, thoughtful decision. And if it turns out that your well-thought out utility function is better served by taking the offer, then take it with the knowledge that you went through the right process. A good process will always set you free.

2. Your boss is a prick

Gee, nobody has a worse boss than you, right? Bullshit. There is a place for shithead bosses like there is an island for misfit toys - except it's much, much bigger. Kind of like Manhattan. Anyway, having an annoying boss sucks, but it can also be a vehicle for your reaching out and really honing those networking skills. Let's say you are a high achiever, get paid pretty well but your boss sucks. Bosses don't unilaterally pay their minions; others generally have a measure of input, especially if you are a highly compensated individual. So, by definition, you are pretty well thought-of at the firm. Use this goodwill and network around. Get to know some of the other power brokers at the firm. Maybe they'll help you switch groups. Or maybe you'll just be in line for a bigger job if the prick leaves or goes to run something else. It happens all the time. But having a prick boss can be the impetus for looking outside yourself and becoming the networker you can and should be. And maybe some day you'll buy your ex-prick boss a box of chocolates as you step on his head while ascending the corporate ladder. That said, if you are locked into a shitty situation and nobody is willing to toss you a life preserver and help is definitely not on the way, use those newly acquired and well-developed networking skills to outplace yourself. You see, you just turned a negative situation into a positive outcome. Aren't you proud of yourself?

3. You are unhappy with your bonus

Oh, boo hoo hoo. You're unhappy with your bonus. Welcome to the club, buddy. Everyone on Wall Street is unhappy with their bonus. If you got $10 million, you're saying "What a bastard. I should've gotten $12." It's almost like a broken record. In fact, I've never met a Wall Streeter that has affirmatively said "I'm happy with my bonus." Because if they did, they wouldn't be enough of an a**hole to be on Wall Street. So, let's say for a minute that you aren't just unhappy, but you are surpremely pissed about your bonus. Ok, what now? Tell your boss that he's a cheap dick and hit the bid from B of A? Whoa, there, big fella. Calm down. Look at 1 and 2 above. Are you in a good environment but just got screwed? Does your boss lack the political capital to get you paid right? Did the overall group suck ass but you had a rocking year? All of these things can be the reason why you didn't hit your target number. So my advice to you: if you like where you are, really don't want to leave but feel you got jammed, get a cover bid, wave it in the face of your current employer but couch it in the best of ways ("I've always been loyal to the firm, loyalty is a two way street, I wasn't looking for this competing offer but got it, etc.") and see what happens. Most likely they'll come up with more dough (it will generally be a 1 year guarantee instead of the 2 year you got from the cover shop, and be a bit below the average annual comp of the 2 year deal), and you'll be able to make an educated decision. This is a game you can play precisely once; because if you try it again, you will really burn bridges and look like a total shithead. And if they overplay their hand with the loyalty card and aren't willing to come up with the requisite cash, there is only one thing left to do: bye bye.

4. You hate your job

I hear you. I really do. Sometimes it happens. But the operative question is why. You don't like the firm? The culture? Your boss? Your peers? They pay like crap? This is a hard one which requires maximum honesty. There are too many possible good and bad reasons to list. But I'd make a list of the good/bad aspects of your job and the firm in order to isolate the source of your agita, because it will become pretty clear pretty quickly whether or not you are being petty or are concerned over issues of substance. If they are substantial and you don't see a clear path towards remedying them, move on in a deliberate, thoughtful manner. If they are annoying issues but don't rise to the level of "This job and firm are hopeless," then create a plan that is a mix of personal development, seeking out a mentor and actively managing the situation in order to give it a shot. Because it is always better, all things being equal, to stay where you are. Moving is hard. It just is, even under the best of circumstances.

There is so much more to say but this is at least a start. Hopefully my dime-store advice will help a few of you out there. If there are other specific threads where you feel I can lend a helping hand please shoot me a note. And be careful out there.