How Many Hoops Are You Willing to Jump Through?

By Ann Douglas

My friend Jen went through a series of 25 interviews before she was ultimately named editor-in-chief of a major consumer magazine. That’s a lot of hoops to jump through in the hope of landing a job—but, then again, it was a pretty nice job, complete with a rather droolworthy salary and a skyscraper office with an amazing view.

But what if the job you’re applying for doesn’t offer the potential for that kind of payoff—or at least not anytime soon? How many hoops are too many to jump through when you’re applying for a part-time or contract freelance writing gig?

It’s a question I started mulling over recently, after stumbling across a rather over-the-top writer/editor recruitment ad on a marketing agency website. Not only did the company in question expect writers and editors to bring “intense joy, abundant love, and infinite gratitude” to the job application table. They also expected them to “pay their dues” by going through a rigorous, six-step job application process, one that involved…

  1. submitting a sizzling résumé (“If it’s boring, liven it up,” the company advises)
  2. pouring through the company’s corporate and community websites and submitting written feedback on “the parts that spark your interest”
  3. being explicit about what you have to offer the company—and submitting an “authentic” mini-bio as opposed to spewing out a mash-up of career achievements (“We don’t care if you were published in The New York Times unless it changed your life and is your proudest accomplishment,” the company warns)
  4. writing a short story about something “non work-related” that made you feel good about yourself recently
  5. explaining “what joy and celebration look like for you” (because “joy is imperative” at this company) and, finally,
  6. “saying something nice” in your e-mail to the person in charge of vetting job applications for this company because “she deserves it.”

I don’t know about you, but this strikes me as an awful lot of hoops to jump through in order to have a shot at part-time, contract work (although, to be fair the advertisement does indicate that there is the potential of the job “growing into a full-time role” within the company).

So how do you go about deciding just how many hoops you’re willing to jump through in order to apply for a particular freelance writing opportunity and when it simply makes more sense to walk away?

For me, it’s a matter of weighing the potential payoff against the time and effort involved in applying, while also factoring in the likelihood that I’ll actually be successful in landing the job:

I also consider whether I’m likely to be able to re-use any of the materials required for a particular pitch when crafting similar pitches in future. In applying for this particular position, I’d likely only be able to re-use two out of the six elements required (my “sizzling” résumé and my “authentic” mini-bio): the other elements would likely languish untouched on my hard-drive forever. Frankly, that’s kind of a waste.

Other considerations that show up on my radar screen when I’m trying to decide whether or not to apply: how badly I want or need the work right now (which means taking into account everything from whether or not this is my dream job to how healthy my bank account balance is looking these days) and how likely it is that I’d be happy working for this particular company over the long-term (if they want me to jump through this many hoops at the job application stage, what are the odds that they’re likely to be high-maintenance every step of the way?)

I don’t think it will come as any surprise to you to learn that I decided to take a pass on applying for this particular job.

It’s not that I didn’t find the job intriguing.

I did.

It’s just that, as a busy freelancer, there are countless other opportunities competing for my time, energy, and attention on any given day—and when I factored in the number of hoops I’d have to jump through just to be considered for this opportunity—well, I simply couldn’t justify the time, energy, and attention involved.

Now I’d love to toss this out to you, Story Board readers: How do you go about deciding when it is—and isn’t—worth your while applying for a particular freelance opportunity (or non-opportunity)? And what’s your best advice to other freelancers who want to enjoy a reasonable return on the time, energy, and attention they invest in pitching?  


Ann Douglas is the author of numerous books about pregnancy and parenting including, most recently, Parenting Through the Storm (a guide to parenting a child who has a mental health, neurodevelopmental, or behavioural challenge). She is @anndouglas on Twitter.


Posted on April 8, 2015 at 9:00 am by editor · · Tagged with: ,

7 Responses

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  1. Written by Lori
    on April 8, 2015 at 2:34 pm
    Reply · Permalink

    For me, it’s when I have to submit so much work for their application that it looks like the application process is really a call for free content. They should be asking for my own samples, at least at the beginning. If their process included writing something fresh after they’d whittled the applicant pool down to the final five, for example, I’d certainly be okay with writing something new for them and would even welcome it: it would give me the opportunity to show them how my writing fits their exact needs.

    • Written by editor
      on April 8, 2015 at 2:55 pm
      Reply · Permalink

      Very good point. When a company is asking you to do a bunch of free work before they’ve even hired you, it shows that they don’t consider your time to be valuable. Doesn’t really inspire much confidence that it’s going to be a solid, respectful working relationship once you get hired.

  2. Written by Christine Peets
    on April 8, 2015 at 2:55 pm
    Reply · Permalink

    I’m with you, Ann. I’d have to look very carefully at what the ROI (Return on Investment) would be on this. How much time would I have to invest in putting together the material they want, and preparing for an interview (if I got to that stage.) What would be the likely return to me? If it’s a gig I really want, and I think it could turn into some really good work for me, then I’d likely go for it. If not, I’d take a pass.
    I’d also have to consider what other applicants might be submitting–who I’d be “up against” and weigh my chances–compare my experience theirs.
    It’s a crap shoot, but sometimes it’s worth going for it.

  3. Written by George Butters
    on April 8, 2015 at 3:30 pm
    Reply · Permalink

    Many moons ago, a successful freelance writer gave me a bit of advice in the early days of my career:

    “Go through the open doors.”

    They’re not always easy to find, and they’re not always easy to recognize.

    Eventually, you’ll learn to differentiate open doors from brick walls. Sure, there can be real benefits to climbing over a significant obstacle, but make sure it’s worth the effort or you’ll end up with a permanently flattened forehead.

    And as he added: “That’s easier said than done.”

    But if it was easy, everybody would be doing it.

  4. Written by Tracey L. Anderson
    on April 8, 2015 at 3:59 pm
    Reply · Permalink

    If the job doesn’t leave me with an excited feeling in my gut when I read it the first time, then I am not interested in jumping through any hoops.

    The number of hoops I will jump through is directly proportional to my enthusiasm. Even then, though, it would still have to be a job I stood a reasonable chance at getting, and a reasonable number of hoops.

  5. Written by Virginia Heffernan
    on April 9, 2015 at 6:44 am
    Reply · Permalink

    Strive to reach the point when you don’t have to pitch anymore because the jobs are coming to you. Pitching is a crapshoot that depends on factors largely beyond your control: timing, the editor’s mood that day, the publication’s financial state, etc. Instead, become sought after using a combination of writing quality, expertise and reliability.

    (Hoops aside, that ad is just downright creepy. A job in Pleasantville? No Thanks)

  6. Written by Morty
    on April 17, 2015 at 6:33 am
    Reply · Permalink

    I had a laugh when I read the point:
    “2.pouring through the company’s corporate and community websites”
    That should be “poring.”
    I guess the company does not care about grammar, spelling, etc. –as long as there’s “infinite gratitude”!

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