Stories about Software


8 Career Tips That Don’t Require Competence

A few weeks ago, I posted my spin on the MacLeod Hierarchy and promised to follow up with a post addressing the kind of vacuous, non-strategic career advice that is often given in Buzzfeed sorts of formats.  I started, then, to type this post, but realized that a bridge of sorts was needed.  So I indulged a digression wherein I described the corporate idealist that typically solicits and follows this sort of advice.  (That post also became pretty popular, with a number of requests to pre-order my upcoming book, which you can now check out here on leanpub).  Now, having described the corporate idealist and his willingness to overwork in exchange for useless status tokens, I can go on to be clearer about why so much of the career advice that you tend to hear is so, well, frankly, dumb.

I started to write this just from anecdotal experience, including various comical, ham-fisted self promotion attempts that I’ve watched over the years.  But then I thought it’d make more sense to go out, do some research, and synthesize my experience with actual advice offered in these “Linkbait for Idealist” articles.  This is a list of the ones that I read as reference material.  (As an aside, I also stumbled across a few that offered fairly sensible, decent advice for how to advance meaningfully, so it is actually possible to find advice that isn’t silly)


That last one provides an interesting segue.  You might be tempted to sharpshoot me if you read that bullet, pointing out that I was misrepresenting what they meant by “don’t be too smart,” and that’s fair.  But here’s the thing.  Corporate opportunists are the sorts of people that catapult themselves to the very upper levels by doing exactly those “silly things in the office and not [getting] caught.”  For each of the bullets below, I’ll explain why the advice is really targeted for (clueless) idealists and then discuss what an opportunist would do instead.  While I have not yet delved into the opportunist archetype, suffice it to say that this advice is NOT for the faint of heart and risk averse.  Corporate opportunism is, as Venkatesh describes in the Gervais Principle series, a high stakes game of creating “up or out” situations that result in dizzyingly fast advancement or a need to move on.  Opportunists are like sharks that always need to keep moving, and so their reaction to idealist advice will seem dangerous.

But it’s not so much that it’s dangerous.  It’s just more a well calculated risk and one that always keeps their rational self-interest at the forefront of their decision making.  Idealists are content with long-tail, deferred gratification narratives that assume the ends will eventually justify the means, where the means involve lots of self-flagellation and brown-nosing.  Opportunists ascribe much more to the “bird in the hand is worth two in the bush” wisdom and are not going to be content seeming ‘proactive’ at meetings for 10 years in the hopes that someone will eventually reward their commitment to proactivity with an office.

1. Be a Team Player

I might as well start with the most nebulous and banal piece of idealist advice out there, which is “be a team player.”  This could probably mean anything from “play nicely with the other children” to “take one for the team, and by one, I mean all of them, forever.”  Usually, though, what this actually means is, “pay your dues and eventually you’ll be promoted by default.”  Think about scenarios where you’re being asked to be a team player.  “Hey, can you come in on Saturday to get this feature into this release?”  “I know that Bill is hard to work with, but please, just be a team player and see if we can’t all get through it.”  And, so on.  Career advice to be a team player is akin to the advice that fraternity pledges and NFL rookies receive: put up with the hazing for long enough, and you’ll eventually get to do it to people sitting where you are now.

The Opportunist Play: You’re not a team player.  You’re a team leader and trend setter, but the company has yet to figure this out.  Size up and be aware of interpersonal dynamics and be friendly and agreeable with those around you.  The idea isn’t to seem like some aloof hermit, but rather not to rely on blending in with the herd.  Have to come in on Saturday?  Fine.  Skip next week’s TPS reports or whatever and spend that time instead figuring out and fixing why the team had to come in on Saturday.  Go to the boss (or whomever) and say, “here’s a thing I did that’s going to save man-hours in the long run and give us back our Saturdays.”  The team player thing to do is make the best of the Saturday thing with pizza.  The opportunist thing to do is change the game.  It’s your Saturday that you’re getting back — other people getting theirs back as well is just an ancillary benefit.

2. Dress For The Job You Want

This was probably the most common piece of advice, and it’s a real blue-chipper, due to how non-controversial it is.  All of these authors probably throw it in there when they’re at 6 out of 7 required bullets and “don’t be audibly flatulent” seems a little too “goes without saying.”  So, why would I consider “look nice” to be bad, idealist career advice, when it’s just life advice that applies to anything, anywhere?  Well, exactly because of who takes this advice.  It’s people with shameless, naked careerism but who also have to google “how to get ahead at work,” making earnest notes, muttering, “oh, wear nicer clothes than other people — that’s gold!”  Winning the war to dress the sharpest when you’re the only one fighting that war is a clear calling card of someone destined for lower middle management and nothing besides.  That’s who behaves that way — don’t mimic them or you’ll wind up smashing into a pretty low glass ceiling that you can’t fathom.

Think of it this way.  Who wins by taking this advice?  How you dress is a form of low information signaling that helps someone like a boss make a decision about you when you’re not really worth much attention.  So, the scales for a promotion will be tipped in your favor as a snazzy dresser when the opportunists discussing the promotion say something like, “well, I’m not really thrilled about either one of these people, but Jones… I dunno, seems more managerial, somehow.  I guess him.”  If you approach promotions like climbing on an escalator and waiting your turn, this is perfect.  On a long enough timeline, when you’ve been snazzing it up for decades, you might wind up marginally promoted as the least bad interim choice.  If they’re weighing your wingtips as part of the promotion consideration, what they’re not saying is that you’ve added so much to the bottom line that it would be foolish not to promote you, and the no-brainer promotions are what you really want to target.

The Opportunist Play: Be comfortable, presentable, and unremarkable.  Dressing wholesale like a scrub and sticking it to The Man is a passive aggressive pragmatist move, so you certainly don’t want to do that.  That’s the archetype that triggers insufferable HR-led meetings about what is and isn’t considered sweatpants.  Just as you don’t want to wear a tux to the company bowling outing, you also don’t want to be known for sloppiness.  What you want to be known for is an ability to be strategic.  Wear your jeans (or minimum casual-ness clothes) most days to indicate that ho-hum office drudgery is not of special importance.  Dress noticeably more nicely when you have client meetings or other such occasions.  Your idealist counterparts won’t be noticed in this situation since their attempts to add value to the organization via ironed shirts just fade into the background eventually as never-ending, non-strategic careerism.  You will be noticed, since you don’t normally dress that way.

If I’m a strategic power player thinking about who to bring with for important interactions with other departments or important clients, I don’t want to bring Steve Urkel (the kid who idealistically sought status via cluelessly overdressing for social situations).  This sort of person is going to be, at best, a non-factor, and, at worst, a braying, posturing distraction.  I want to bring the person with that sizes up the subtleties of the pending situation and makes intuitively correct decisions about all manner of details, including the best approach to dress and accessories.

3. Speak with the Voice of the Organization

This has long been one of the tactics that I find most amusing.  The most obtuse version of this that you’ll see is a line level employee that, after some amount of elapsed time with the company, starts talking about management decisions in the first person plural, particularly to newer people.  “Did you hear about the new summer hours schedule, Jane?  We really want you to feel like you’re living life more in the summer.”  If you’ve never heard or seen someone acting like this, you’re missing out.

I have no idea what prompts people to do this.  I usually hope that it’s some kind of extremely poor understanding of social dynamics among the pragmatist set and that they’re referring to “we” as the lower managers and line employees, inclusive.  In other words, I hope they’re doing it in kind a mushy, one-worlder, “let’s all enjoy the summer together, mmkay?”  That’s my hope because the alternative is that they have adopted the Gepetto strategy of career advancement and they hope that, if they just pretend and wish really, really hard on a shooting star that their wooden doll line-level position will turn into a real-boy manager position.

The problem with this approach isn’t just that you remind everyone in sight of the iconic, hopeful dork running to catch up with a group of jocks and saying, “so, bros, what are we doing tonight,” only to be laughed at.  Because, while the pragmatists (and possibly other idealists) find you ridiculous, opportunists aren’t jocks — they won’t tell you to get lost.  What they’ll do instead is recognize that you’ve just offered, for no reason whatsoever, to be the deliverer of all bad news.  If you want to play Dwight Schrute and insist on being a (useless) conduit of information between the boss and the peons, they’ll let you have at it any time they need to announce a salary freeze or an unpopular new dress code policy.  What they won’t do is let you have at it when it comes time to announce promotions — those will be done in official one on ones, of course.

The Opportunist Play: Just don’t do this.  In fact, do the opposite.  Opportunist play is up-or-out, so you’re actually better off remaining aloof and talking about the company as “you guys” or “them.”  It conveys the subtle impression that the company has yet to convince you that it knows what it’s doing, and you’d be surprised at how much more effective cultivating this worldly air can be toward your goals than pushing your high chair up to the grown-ups table and asking that someone “bwing you a beer.”

4. Come In Early and Leave Late

Sigh.  This piece of advice is up there in frequency with the “overdress for success” canard, and more frustrating by far.  The reason that it’s frustrating for me, though, is deeply philosophical.  It implies that value to the organization is about presence rather than, well, value to the organization.  Most corporate office jobs these days are some form of knowledge work, and, yet, we value the same thing that would be valuable in a Walmart Greeter — being there physically.

Now, most of these advice pieces are self-aware enough to realize that they should at least pay lip service to work quality.  This one says:

Hear that? It’s the sound of your fellow readers frantically scrolling down to the comments to whine, “It’s not about how much time I put in at work, it’s about the quality of work I do!” That’s a valid point. Quality is more important than quantity. Know what else is completely true? As long as the quality’s there, the quantity helps too.

The message here is essentially equivalent to the “dress sharp” one, wherein punctuality is meant to give you a little edge when your work is indistinguishable from the competition’s. In this light, he’s saying, “do good work, but then give yourself an edge to the tune of, say, an extra half hour per day.”  He concludes in a self-congratulatory tone, saying that putting in 15 extra minutes on either side of the day to make it seem like you love being at work is “not a bad return” on your time.

Welp, Nate, master-boss-impresser, let’s do some quick math.   At a 100K salary, 15 minutes twice per day is 2.5 hours per week or 130 hours per year, for a grand total of $6,500 per year for the market value of this time.  Now, if you wear a lot of collared shirts and pump in a lot of extra hours and enthusiasm, you might just net yourself a 5% COLA instead of the 3% ones those 8-hours-on-the-nose suckers get.  That’s right — by investing only $6,500 in time, you can make a cool extra $2,000!  You’re right, Nate.  It’s not a bad investment — it’s a horrible investment.

The Opportunist Play: Opportunists spend their time strategically, and this may mean spending a lot of time at the office.  Creating the alignment of circumstances that allows for meteoric success typically involves a significant time investment.  I’d be a hypocrite to tell you to work 40 and not a moment more after a life in which I’ve probably averaged 60 hours per week of what would generally be considered work.  But what I wasn’t doing was religiously giving a company an extra 20 per week because I might get a slightly larger raise some day.  I was building my resume, earning a MS at night, forging relationships, learning new skills, building a portfolio, and so on.  And yes, I was sometimes investing my time in key efforts to ensure their success — but always to achieve a positive sum outcome for myself and a company, and not to “convince my boss I’m in it for the love of the game” or some such idealist claptrap.

You want all of the benefit of this with none of the sucker-hood?  The opportunist play is simple.  Come in to work an hourly early and watch Pluralsight courses.  Stay an hour late and write blog posts.  Do that for a few years, and you’re giving your company its 8 hours and you’ve invested in yourself and you’ve even beaten Steve Urkel at his own game, without actually playing.  After all, it’s not like your boss is going to walk in for an early meeting, notice you in your chair, and double check that you’re busily setting up status appointments or six-sigma-ing people.  Of course you’re doing something valuable — you’re physically present, aren’t you?

5. Speak Your Mind

These articles are long on pithy advice and catchy quotes, so I’ll offer one myself.  As Abraham Lincoln said, it is “better to remain silent and be thought a fool than to speak and to remove all doubt.”  One of the most common things that you’ll see in the budding idealist is a desire to charge in and make sure everyone knows they have opinions and information… about everything.  I guess the thought is that, come promotion time, your boss will remember that you exist… or something.

It’s surprising how many people over-share in situations with realpolitik implications.  They explain why they were late when nobody noticed.  They describe how they’d phrase the VP’s power point slides differently when no one asked for their opinion.  They brag about bits of gossip from management just to show their coworkers that they know.  And the list goes on.  They prattle.  And thoughtful opportunists (or spiteful pragmatists) listen, take the information, and put it to their advantage somehow.

The Opportunist Play: This is probably the hardest one to describe succinctly, but the best rule of thumb is, “don’t speak your mind unless asked, and maybe not really then.”  By all means, exchange pleasantries and collaborate with coworkers, but mainly listen.  When people complain about coworkers, confide about plans, blather about strategies, etc, listen and sympathize, but don’t reciprocate.   Speak your mind when your words can carry actual weight in the form of organizational outcomes.  In other words, if you’re in an all-hands meeting about whether to take on a new 20 million dollar client that’s a poor fit, don’t bray loudly about the company principles from the back of the room.  Keep your mouth shut until you’re in a closed-door meeting where you’re being asked, in earnest about your opinion on the company’s strategy.  And if that “until” never comes, so be it.  Do good work, prove your value, and you will be asked at some point.

6. Ask For More Responsibility

This is an odd one that I read about a few times rather than one that I’ve actually seen.  But if people do this, it strikes me as the pinnacle of corporate idealism.  “Hey, boss, I was just thinking that I don’t have enough stuff to do, so I was wondering if you could expand my responsibilities.”  What I assume is being referenced here is the general notion in the corporate world that an employee’s responsibilities may be expanded as a trial of sorts for a potential promotion.  For instance, a developer maybe asks the manager of the department if he can start doing the things that the architect typically does, such as performing code reviews and sitting in requirements analysis meetings.

On the surface, this seems like a fairly rational thing for all parties.  The quid pro quo is that the employee puts in extra work for free in exchange for the company giving him an audition for a higher paying gig.  The thing that strikes me as idealist about this approach to advancement isn’t the tradeoff of extra time for opportunity, but rather the idea of asking for an audition.  This immediately frames the relationship as one where the idealist should be disproportionately grateful (golly gee, Mr Scroodge, you won’t regret this!)  It’s a tradeoff — not a favor.

The Opportunist Play: Don’t ask for anything.  Just start solving problems.  When you’ve solved enough of them, there will be a pretty straightforward case for advancement and increased responsibilities.  If you want to start doing code reviews, just start doing them in your spare time, even if you don’t tell anyone.  Run static analysis and make bullet-proof cases as to where you as an official reviewer would have caught bugs or saved time.  Go lay this out for your boss.  You’ll be doing code reviews starting next week.  And, in up-or-out opportunistic fashion, if you’re not doing code reviews next week, it’s time to move on.

7. Act Like a Boss

A lot of career advice pieces have bullet points that say something like, “be a leader,” but what people hear and what they seem to convey is, “act like a boss.”  And you can hardly blame them for this miscommunication when “be a leader” is book-ended by advice like “dress like your boss” and “work crazy hours.”  The idealist path to advancement is mimicking your boss, so doesn’t it stand to reason that what you ought to do on a new team is start ordering people around right out of the gate?  Heck, if you can get away with it, invent a position for yourself that walks the fine line between “insubordination” and “no one will bother to contradict” (ala Dwight Schrute, the “Assistant Regional Manager/Assistant to the Regional Manager”)?

I wonder how people like this imagine their impending promotions are going to happen.  There’s something very cartoonish about this, like Bugs Bunny dressing up as a woman and Elmer Fudd not recognizing that he’s talking to a rabbit instead of a human female.  Are the opportunists running the show expected to be meeting and saying, “wait, I thought he was already a director — he clearly dresses like us and orders people around.  Someone get an org chart and fix this oversight forthwith!”

This approach is the epitome of the kinds of pyrrhic career victories that idealists tend to win.  Acting inappropriately like a boss is a move that sacrifices any semblance of likability at the altar of upward mobility.  Opportunists may hold their noses and promote you to a line manager position, but they certainly won’t want you running around in their circles because you’re unpleasant without any redeeming strategic acumen.  You’re the perfect candidate to absorb any discontentment from the pragmatist set in perpetuity.

The Opportunist Play:  Opportunists aren’t bosses — they’re more akin to entrepreneurs.  If you want to maximize your career prospects, don’t get distracted by vanity perks like being able to get away with bossing people around.  I saw a great quote that I can’t find to attribute, so I’ll paraphrase to the best of my recollection.  “When a manager speaks, I know that he’s important, but when a leader speaks, I know that I’m important.”  Be a leader.  There’s power in winning the hearts and minds of people in the organization.

Of course, you might forget about leadership (and certainly bossiness) altogether and simply focus on making the value that you provide to the organization both large and visible.  If you do this, leadership responsibility will come looking for you.

8. Self Promote

Keep a binder full of your accomplishments so that at career-review time, you can remind your boss of all that you’ve done.  This is pragmatic advice for an idealist career track.  Unlike some of this other nonsense, this really does make sense, but taking it means that you’re aiming low.

If you’ve never been a manager, let me explain to you just how intense the spotlight effect is that you experience at review or one-on-one time.  You’re sitting there talking to your boss, assuming that she’s well aware of what you’re doing on a day to day basis.  Unless she’s managing only you, I assure you that she’s not.  If she’s managing a bunch of people, she’s sitting there with a great poker face at review time, relying on you to remind her what you’ve done over the last year with the exception of one or two things that stand out.  So, if you can quickly remind her of what you’ve done, that’s good, right?

Well, sure, if we assume that she has trouble remembering what you do.  But if that’s the case, you’ve already lost the opportunist game, and you’re on the idealist track of looking snazzy and being known as the office early bird to earn promotions by default.  Look snazzy, get in early, and talk a lot about how awesome you are.  And most people who take this advice to heart take it to heart way beyond just being prepared to talk about accomplishments in a salary review, so “look snazzy, get in early, talk about how awesome you are” becomes a daily affirmation.

The Opportunist Play:  Self promoting quickly makes you insufferable to your colleagues and to the opportunists controlling your career alike, making it a short-sighted play.  Forget about self promoting.  In fact, make a rule that you are not allowed to do that at all.  It’ll be liberating.  Instead, the only thing that you’re allowed to do is get others to you-promote.  When you start to strategize about how to get people who matter to sing your praises, you’re well on your way to opportunist-land.

In The End

The nature of being an opportunist is not necessarily to be a mercenary, but rather not to lose perspective in setting and pursuing your goals.  The mistake that the idealist set makes over and over again is to get themselves into zero-sum traps where diminishing returns arms races set the tone for their lives.  In other words, they’re gunning for the messy, gooey center of middle management where organizational outcomes are pretty hard to measure, so they find themselves competing against peers in situations where the judges have no idea what any of them are worth.  It’s in this context that “who puts in the most extra hours, dresses the best, and uses fancy words the most” starts to have significance, and it’s in this context that idealists lose all perspective and start competing ferociously to lead the pack in these useless categories.  And, of course, it’s with an intended audience of these people that these types of empty calorie career advice pieces are written.

Pragmatists don’t go combing through LinkedIn to figure out how to get ahead because they’ve given up on meaningful advancement without ceilings.  Opportunists don’t go combing through LinkedIn to figure out how to get ahead because they’re defining how to get ahead in real time.  So that leaves only the idealists, alone in an echo chamber, giving and receiving advice to make sure that their professional headshot is what appears next to the word “default” in the dictionary.

Think of it this way.  “Throw elbows and mace anyone that gets in your way,” might be good advice for getting the deepest discounts at Walmart on Black Friday.  But if you’re in a position where that’s good advice, you should probably reevaluate your priorities in life.

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Aaron Duty

Good advice all around on how to avoid letting other people run your life. I wish I had had the opportunity to read this a few years ago.

Erik Dietrich

Glad to hear that you see benefit in it, and it’s good for me to know that I’m not ranting my way completely out into left field 🙂

Geoff Mazeroff

Many good points — some of which I don’t fully agree with (or maybe they make me uncomfortable because it makes me question my schema for how the working world functions).

Related to #7, I remember reading this article about charisma — http://lifehacker.com/how-to-develop-your-charisma-and-become-more-likable-1673988208. There are people that you enjoy being around because they make you feel better for having interacted with them.

Thanks for sharing your thoughts!

Erik Dietrich
That was a really interesting article. I’m not sure whether I’m personally doing much of a job at being charismatic in my day to day life, but the “curiosity mode” that accompanies not knowing something as a confident person struck me. Early in my career, that wouldn’t have been true of me, but now it’s definitely true in more recent years. When confronted with some arcane language rule that I don’t know, I don’t for a second try to cover up my ignorance. Instead, my demeanor is essentially along the lines of, “oh, that’s interesting, go on…” If some sort… Read more »