Dealing With “The Impossible” At Work

The novel Catch-22 by Joseph Heller is a “satirical critique of bureaucratic operation and reasoning.” The book is famous, unique and hilarious, but the term “Catch-22″ itself has become more popular than the book it came from. The phrase may seem old and obscure, but it’s still part of the English lexicon, and it’s been used most recently in popular TV shows like Lost and The Office.


  1. A situation in which a desired outcome or solution is impossible to attain because of a set of inherently illogical rules or conditions.
  2. A situation or predicament characterized by absurdity or senselessness.
  3. A contradictory or self-defeating course of action.

Unfortunately, Catch-22 situations are a common occurrence in the workplace: If two managers have differing plans for a project, they might ask their employees for two completely different outcomes. If a poorly written policy contradicts an existing one, employees will be forced to break one rule by following another. When people say they’re being “asked to do the impossible” at work, it may not be an embellishment. Consider the following examples:

  • You can’t get a job without work experience, and you can’t gain experience without getting a job first.
  • To save money (and trees), your company institutes a new policy mandating that all documents be printed on double-sided paper. As the keeper of such files, you are instructed to throw away any single-sided submissions and reprint them…to save paper.
  • Your supervisor wants the written copy for your next marketing brochure to be “edgy, creative and different,” but also requires you to stay within the bounds of industry standards and your company’s rigid style guidelines.

Solutions, Not Excuses

So, how does one approach one of these absurd “Catch-22” dilemmas? Should you just try to work around the problem? Rarely are these issues single, isolated incidents. They are usually creatures of habit, and a temporary, “band-aid” workaround will look like a sloppy job and land you in the same exact predicament later. If there is truly no acceptable way to do the work, you have to show your colleagues what’s hindering you. Your peers and your boss don’t always have time to understand the details of your dilemma, and unless you point out the predicament, they’ll assume that you’re mishandling some straightforward work through your own laziness or lack of ability.

But, don’t point out the problem without offering a solution to resolve it. If you only point out the problem, it will sound like complaining, making you the bigger issue to deal with. Your boss and your co-workers want solutions, not excuses or grumbling. Offer some sensible ways to resolve the dilemma, and you’ll instantly transform yourself from a griping, disgruntled employee into a savvy efficiency expert. Rather than getting the typical “I feel your pain” empathy from your colleagues, you’ll get what you really want – a permanent fix to a frustrating problem.

Catching The Big One

“Catch-22” quagmires aren’t always small, tedious problems; some have been lurking unchecked for a long time, and they’ve been allowed to grow into gigantic monstrosities. Maybe your overly-ambitious company is perpetually planning new projects, and never leaves any time to actually complete them. Maybe your company’s attempt to “branch out” with new products is rendering their old products obsolete, resulting in more work and less revenue. These types of quandaries, regardless of size or scope, are never too big to fix. In fact, they might be too big not to fix. As long as your solutions to them are sound, you can show off your problem-solving skills on a grand scale. Fixing a company-wide crisis will always win you more praise than fixing an accounting bug or a problematic paragraph in the employee manual.

Are there any risks that come with taking on one of these dilemmas? Yes, sometimes. Pointing out one of these problems might expose a co-worker’s oversights. Suggesting that you have a better way to do the job might look like a challenge to the status quo. But, in almost all cases, the risks are worth taking. They don’t call it “sticking your neck out” because it’s easy and risk-free. Remember, a good company will always be receptive to potential improvements, and if you’ve got the perfect solution, it will be hard for even the most stubborn supervisor to dismiss. It’s far riskier to ignore these kinds of problems, and allow them to hinder your own performance, and that of your company.

Catch-22 situations happen all the time. While they are by definition “no-win” scenarios, there is a still a good and bad way to handle them. Don’t be the “complainer” or the “whistle-blower.” Instead, find the fix and the gumption to pitch it to your peers. Most importantly don’t let these conundrums defeat your positive attitude and ruin your day, week, month, or career. If Joseph Heller can make them funny, then surely we can laugh about them.

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Peter is Vice President of Digital Marketing at an investment holdings company in Washington DC and Co-Founder at True North.


  1. AirWeb on the 21st May

    This article has a good beginning but needs to have some real-world examples please.

    • Peter North on the 21st May

      Hi Airweb.

      I tried not to get too specific with my examples. I didn’t expect any readers would want to hear the particulars. If only my colleagues had the same interest!

      One real-world problem I run into has to do deadline-based freelance work. After agreeing to a scope of work, a price and a deadline, clients will sometimes ask for project additions and a quicker completion date. Asking for more work to be done in less time is “inherently illogical.” Additionally, If we spend valuable time renegotiating the terms of the job, it will inevitably take longer to finish. So, it’s not just absurd and illogical, it’s also “self-defeating,” as the client delays the completion of the project in an effort to expedite it.

  2. Tristan Rineer on the 21st May

    @AirWeb: How’s this for a real-world example?:

    I had a client last year that “absolutely had to” have her website created and online by a certain date. My company came up with design options, and she selected the one she wanted, told us what to change, and we re-presented the updated design. It was approved as being “perfect”. Then, we were told that before the site could be built, we had to design the perfect logo to go with the design we made for her website. Although we already had the “perfect” site design, and could have tweaked the logo later, she kept approving & then changing her mind on the logo aspect until the deadline for the site was less than a week away. Then (after a long period of time saying “Don’t start building the site until the logo is perfect”), she said that we took too long on the “site design” and she didn’t want to use us anymore.

    We could have had her site implemented within a couple weeks or less, but instead of letting us do that, she went with another company (who had to come up with their own design because she hadn’t authorized the release of our design, or paid for it). The site took over 3 months to be completed by our replacements, and the only good looking part of the new site is the part her replacement company stole from our original design.

    The Catch 22: “Get it done by (X) time, but don’t start until I approve the least important detail… which I refuse to make up my mind about.”

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