Seeking stories of professional boldness.
June 2, 2014 4:06 PM   Subscribe

I'm looking for real examples of people who made bold, honest, and somewhat risky moves in a job situation and saw positive results.

What I'm talking about is E.g. writing a cover letter saying "I don't have any of the skills or qualifications you specify in your ad, but I'm perfect for this job and let me tell you why." Or emailing a company and saying "The way you're currently doing X, Y, and Z is counter productive/awful/looks like crap and I can fix it for you!" Or demanding respect from a superior who takes you for granted. The kind of move you might make out of frustration if you've been following the supposed rules for years and getting nowhere, but one that could backfire by branding you a weirdo/loose cannon/naive idiot.

I'm looking for actual instances where this sort of action had a positive outcome, either for you or someone you know, or for examples you've read about and can describe or link to. I am not looking for stories about telling your boss he's a jerkface or quitting a job in an outrageous way or yelling at anyone. Nor am I looking for extreme examples like a high school kid sending 500 chocolate cakes, one for each employee of the university he's applying to, along with his SAT scores and essays. (Entertaining as those stories can be.) Preferably, the person in the anecdote will be a job applicant or freelancer or a worker in a low-level, less powerful position, and not a bigwig.

Thanks in advance!
posted by ocksay_uppetpay to Work & Money (12 answers total) 18 users marked this as a favorite
I was working as a part time security guard in an office building. My future wife kicked me in the ass to do something with myself. I saw a job posting for an intrusion analyst, so I read as much as I could about security, and wrote the most arrogant cover letter possible because I was a college dropout that had a shittastic resume. I talked a lot about how I read the stuff on my own, and how I tinkered with security tools on my own to learn them.

It worked. I got a phone call. I got a first interview. At the end of their interview, I asked if there was anything the hiring manager thought I was weak on. He said the specifics of a certain technical package. I RTFMd, and when I made my thank you call, I said "hey, I read up on that, and I'm serious about doing this job."

It worked. I got a second interview, and met the hiring manager's boss. Our conversation was about what we were doing to get ready for the holidays (we were just before Thanksgiving at that point). I knew I was golden when I didn't get a single real question.

Indeed, I was hired. I was in over my head for about a month. Then I got in the groove. And I started excelling. And in two years, I was the technical lead in my department.

I don't have any delusions that I was actually that hot a commodity when I first got hired. I was motivated and cheap, and the company had an immediate opening. A lot of it was luck. But I made the most of it.

And 10 years later I'm still kicking ass at this. All because of my wife and one very arrogant cover letter.
posted by bfranklin at 6:04 PM on June 2, 2014 [3 favorites]

Also, I should note (because it's not clear), I did have some nominal intrusion analysis knowledge before my binge reading when I applied. I wasn't BSing when I said I did this stuff on my own; I just added a heck of a lot to my limited toolkit between applying and that first phone call.
posted by bfranklin at 6:08 PM on June 2, 2014

I have a friend who had an interview for a prestigious fellowship. She thought some of the questions asked were weird and suggested the interviewers hadn't really read her application thoroughly. Near the end of the interview she decided she wasn't going to get the fellowship anyway, so she told them exactly what she thought of their application system, of their interview questions, and of their organisation. None of those things were positive. She rang me right after the interview and told me she thought she had probably been downright rude and insulting to them.

She got the fellowship. They said they admired her confidence.
posted by lollusc at 6:45 PM on June 2, 2014 [1 favorite]

In the mid 90s, one of my cousins (who'd dropped out of junior college and lived in his parents basement) got a minimum wage data entry job at a small company - just reading government reports and entering the data into a minimalist DOS program.

He decided he hated the DOS program he was supposed to use. He ordered a PC with a credit card, taught himself how to program, and wrote a better, faster version of the data entry program. He showed it to his bosses, and was immediately hired to be the computer support person for the company, and his first job was to implement the data entry program he'd just written.

Within two years he was vice president of the (growing) company in charge of tech.
posted by overhauser at 6:59 PM on June 2, 2014 [1 favorite]

Sometimes I think it's just about having the audacity to ASK.....

I'm family friends with these two sisters, one of whom is pretty by-the-book and quiet. The other one....well, she's more...uh...colorful. But she also has more trouble navigating social situations and life in general. I've often thought she might be a high functioning autistic.

Well the older girl was just out of college and looking for a job (she was a Fine Art major or something) and one day they saw a famous fashion designer at Starbucks. And by famous, I mean *iconic*. A brand unto himself- synonymous with classic American luxury.

The quiet, successful girl likely wouldn't have done anything on her own...because she's not one to make waves. But this was once instance where the younger girls inability to understand social norms actually served her really well.

She went right up to the guy and said "See this necklace? Isn't it great? My sister designed it. She's over there. You should really hire her."

So he did.

Since then, she's worked in a variety of prestigious jobs in the fashion industry that most others would cut off their left arm for.

All because her little sister plucked up her courage and went to bat for her that day.
posted by ChickenBear at 7:41 PM on June 2, 2014 [3 favorites]

The trope about working your way up from the mailroom is common, but finds an excellent real life example in the story of superstar music producer David Geffen, who lied about his college credentials but was able to intercept the damning transcript because he worked in the mailroom.

PBS tells that story in their episode of American Masters on Geffen.
posted by Kakkerlak at 8:41 PM on June 2, 2014

When I was 24 or so, I interviewed for a freelance position. As the interview came to a close, I was asked what my rate was. I said 40. The guy said, how about 25? I laid my head down on his desk and sighed, and then, without getting up, said in my most I've-had-it-with-everyone voice, how about 50? The guy laughed and hired me. At 50.
posted by january at 8:48 PM on June 2, 2014 [1 favorite]

I'm a senior book editor at an art museum. I got my job by applying for a position that I had no direct experience in (writing/editing for the development/fundraising department of the museum -- I had a writing/editing background, and an art gallery background, but knew zero about fundraising for a nonprofit arts institution) but wrote a good enough cover letter that it got me a first interview, then a second interview. I didn't get the job, but I impressed them enough that they asked if they could put me in the pool for freelancers for the publications department (where I really wanted to work anyway).

A month or so later they called and asked me if I was interested in a 6-week freelance gig that was mostly administrative/research-based. I said yes, and within a few days saw that what the project needed was basically an assistant editor, at which point I essentially announced that that was the job I'd be doing (even though I'd never edited a book before). They kept extending my contract over the course of nearly a year, at which point a full-time position opened up in the department and I was officially hired. That was about 13 years ago.
posted by scody at 8:49 PM on June 2, 2014 [1 favorite]

(Oh, and this is the book that I basically talked my way into editing.)
posted by scody at 8:52 PM on June 2, 2014

Here's another vote for just having the gall to ask. I was a lowly part-time editor at a digital publishing company. A new, high-profile project was coming and all the workers were abuzz. The work would be far more interesting: whoever was chosen would get to write, not edit, and the writing needed to be funny and clever.

All my colleagues hunkered at their desks, whispering to each other that they hoped to be the one chosen for the job. I found out who was in charge of the project, walked into his office, introduced myself, and said, "I can do that work. I've written for that audience before," neglecting to mention that it was all unpublished. He blinked in surprise and said, "Okay. How much?"

Some unhappy people spread nasty rumors about me but that one 2-minute conversation got me onto a trajectory that ended with me owning a business that I can run from anywhere in the world. I get to write as much as I want, too.
posted by ceiba at 6:07 AM on June 3, 2014 [1 favorite]

When I graduated from college in 2003, I wrote to the CEO of a large company explaining why I should start a sustainability program for them (though I had no experience). A month later, I had a meeting with him, and he hired me. Passion and vision go a long way. I've had somewhat similar experiences at other points (once telling a company what I thought they should be doing differently, and once convincing another company to hire me without specific experience for a particular role).
posted by three_red_balloons at 7:19 AM on June 3, 2014

David Geffen. Well, not honest, really, but effective
posted by IndigoJones at 12:21 PM on June 3, 2014

« Older Possible minunderstanding with SSI back pay......   |   Flipping my job from one field to another - again Newer »
This thread is closed to new comments.