Landing on the Right Side of Your Ass by Michael Laskoff

This website was created not only to promote a new 2003 book called Landing on the Right Side of Your Ass by Michael Laskoff, but also as a platform for the author's raving, thoughts, prolific Questions & Answers, and other pontifications. With so much archived content, I offer the reader just a small sampling.

For several years I found great entertainment from the content that Michael Laskoff posted on AskYourAss.com/. Several of my co-workers had read Michael Laskoff book, Landing on the Right Side of Your Ass, and would quote from it on days in which we were releasing pent up energy. I happen to work at a progressive company where I am part of a team who does tailored web app development work. Our skills take us from a client who may be in the heathcare industry one month to another client the next month who has an e commerce business. We've done custom web app development for companies in finance, real estate, healthcare, or education. Since all these industires work with higher then usual security concerns, we develope customized software addressing security and privacy as well as developing apps that allow all back of the house operations to run smoothly. I like my team members who are an awesome lot with warped senses of humor. Landing on the Right Side of Your Ass has been the basis for lots of entertaining lunch break discussions.

So it was with dismay when I discovered the site had disappeared from the Internet. Recently I discovered that the domain was available, so I bought it with the goal of recreating as much of its original content as possible from archived pages. I did not want someone else to purchase the domain and re-purpose the site for something that had nothing in common with the original AskYourAss.com/ website.

Since the site will not be exactly as you remember it, please be indulgent.
Now let's take a nostalgic stroll back to the early 2000's and Michael Laskoff, the Ass of American Reemployment.

The Book: Landing On The Right Side of Your Ass

Landing On The Right Side of Your Ass is a straight-up/no-chaser survival guide for handling the misery of unemployment and moving forward to get a better job. From personal experience, Laskoff-the Ass of American Reemployment-knows that losing a job is a lot like being "dumped" by someone you love, who no longer loves you back.

Thus, the first section of his book prepares the reader to move beyond the seemingly unquenchable desire for revenge, the chasm-like depression, and the blistering terror of a future stripped of a way to earn a living.

The second section jettisons the usual Psychology 101 approach found in most career books and helps the reader make himself attractive to prospective employers through understanding a variety of issues, including: a resume is a marketing document, not a history lesson; honesty is the best policy, especially when it's flattering; people are lying to you, particularly your friends and family; and, other job search realities that no one wants to talk about.

The final section helps the reader snatch some control back in the job search and interview process; this section covers everything from separating yourself from the candidate herd to creating competition among potential employers, and winning the best job offer.

Landing On The Right Side Of Your Ass isn't for everyone: trust fund babies and those who struggle with anything more taxing than the their horoscope won't get much out of it. But if you're looking for practical job searching advice from someone who won't treat you like a high school student, then you've found the right the book. But don't take my word for it, take it from those noble reviewers at Publishers Weekly who say the following:

This realistic look at dealing with getting downsized is written by an author who has "been through this crap so many times that I can rightly and truly call myself an expert." Laskoff talks readers through the process of getting angry at those who laid them off, then through the necessity of owning up to the reasons why they themselves might be accountable. With tips on rallying support from friends and family, finding meaningful activities to pursue while job hunting and keeping up good relationships with those near and dear, this book covers just about all the issues unemployed people face. The second half of the book tackles the business of finding a new, better job, and Laskoff offers solid advice for resume writing, marketing one's skills, interviewing, networking and negotiating offers. And he reminds readers not to take the first job that comes along (e.g. "What's your gut telling you? If your tummy has you seeking the nearest bar not to celebrate but to dull the prospect of impending pain, maybe you should let this one pass."). With the down-to-earth advice in this book, searching for a new job might not hurt so much after all." (Copyright, Reed Business Information)

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About the Author

 

Michael Laskoff has been described as a high functioning schizophrenic, a dilettante, a laggard, an embarrassment to every institution that ever lost its senses long enough to admit him, and a few things that break the decency laws in 48 out of 50 states. Former employers offer a somewhat more charitable view, under oath.

This nature-phobic fool was raised in the Pine Tree State, a.k.a. Vacationland, a.k.a. Maine. When he was just 17, the state assembly passed a resolution encouraging Laskoff to move away. Although non-binding, it was nevertheless delivered by state troopers in full riot gear.

Laskoff was educated, if you can believe it, by two venerable institutions, the University of Chicago where he received a B.A. in political science and Harvard Business School where he briefly met people who are actually successful; none of them recall meeting Laskoff.

After receiving something approximating an education, he launched himself at the business world, over and over again, with the same kind of determination and success enjoyed by General George Custer at Little Big Horn. Thus, he’s managed to blow himself up, both with and without help, as:

  • A very junior investment banker
  • a staff monkey at a very large entertainment company
  • the head of marketing at a record label so small that you’ve never heard of it
  • the global brand director for the failed internet spin-off of a big-ass publisher
  • the chief marketing officer of a major retailers ill-fated foray into the web
  • a sort of consultant for a big, global consultancy
  • a corporate wonk with P&L responsibility for a small, public telecom company

After leaving the sanitarium, Laskoff spent the second half of 2002 amassing enough blackmail material to convince the nice people at Three Rivers Press to publish his book, Landing On The Right Side Of Your Ass, which will help the unemployed get back in the working saddle just as soon as it’s published in January, 2004.

Laskoff is enormously grateful to be married and living in the center of the known universe, also know as New York City.

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This Week's Ask Your Ass -

Newsletter #9

Volume #9 -2003

Q: I'm a web designer who lost my job about a year ago and has since managed to make a decent living as an independent consultant, although nothing like what I made before getting laid off. Recently, one of my clients has offered me a job. Compared to my current situation, the money is almost as good, the benefits better, and the security definitely greater. Do you think that I should continue go it on my own or take advantage of this relatively rare opportunity?

A: It seems to me that you're really wrestling with the notion of risk. Right now, you're living with uncertainly because you don't know what the future holds: maybe it's wonderful and you'll prosper, or perhaps things will dry up and life will become altogether less pleasant. Until now, you haven't had a choice so such speculation wasn't terribly helpful.

Now that you've got options, you need to ask yourself what you really want from your professional future. If you prize your independence and can handle the uncertainty, than you're already living the dream. Stay focused and build your business. If, however, you crave more stability and predictability, than you need to carefully consider the offer that your nice client has been kind enough to make you.

Realistically, I can't tell you whether or not you should give up your independence, with all its potential risks and rewards, to become an employee, with its stability and predictability. But if you ask yourself what you want out of your professional existence and what you're willing to risk getting it, you can probably provide yourself with the answer. So give some thought as to what you want from the future, and then trust your gut to provide you with the right answer. If that doesn't work, you can always flip a coin.

Volume #9

Q: How do you feel about the thought of interviewing for a job that I'm pretty sure I'm not qualified for? On the one hand, I really think that the position may be too senior for me. On the other, I haven't exactly been blown over with opportunities and hate to waste one. What do you think?

A: f there's no way in hell that you've got the skills or experience to tackle the available position, I wouldn't bother. Without such things, you'll have nothing to say and be forced to suffer through a boring, pointless meeting. Such an encounter will drive you to drink but accomplish little else.

But let's assume that you might have what it takes to do the job: by all means go and check it out. For starters, you've got the time. No matter how busy you're keeping yourself on the search, you're missing the point if you can't accommodate an interview. Equally, the reality of the job is usually different than what's advertised. So don't assume that you know what the position actually requires until you get this information directly from a knowledgeable interviewer.

Finally, great candidates don't grow on trees: they practice hard to refine their interviewing skills. But no matter how hard you drill and rehearse in front of a mirror or friends, there's nothing like doing it in a live setting. So even if the job

 

Newsletter #81

Volume #9 

Q: My employer, a multinational company, has a statistically significant record of unfair and perhaps illegal treatment of older employees. Hundreds of ex-employees have filed complaints with the EEOC, which has thus far taken no action. After 25 years with the company, I have recently suffered several minor incidents of verbal disparagement regarding my age. Also, I recently received a poor appraisal based on biased, subjective observation even though my business results exceeded target. I worry that the only reason I am still employed is that I have critical skills. My questions are: 1) what defensive measures can I take to prevent being fired besides continuing to retain skills critical to the business and to deliver excellent results; 2) what can I do to build a solid case for a possible age discrimination complaint while I'm employed; and 3) if terminated, how can I receive my severance package without signing away my legal rights?

A: This question caught my attention for two reasons. First, it’s a well-articulated example of the difficulty facing many Americans when they hit 50. Instead of being rewarded for their long contribution, they’re too often driven out of the very companies that they’ve faithfully served. Second, I mostly hear from people who have already lost their jobs, but you’re being proactive. That’s both rare and impressive.

To begin, let me reinforce what you already know to be true: the EEOC will not come to your rescue. Under the current administration, I don’t think that this well-intentioned organization gets to do much of anything beyond tabulate complaints, and even then, they have to promise not to upset anyone. (Employee rights tend to lose out to the corporations that fund political campaigns.)

Diatribe dispensed, let’s get to your questions. Answer One: Nothing. If you stay valuable and contribute to the company’s profitability, then you’ll likely stay employed longer. The kicker, unfortunately, is that many companies are willing to sacrifice excellence to save a buck in the short-term. That can and will cost you your job. Answer Two: Document everything. The more that you write down, the more evidence that you’ll have if and when you need it. This won’t save your job in the end, but it will hopefully allow you to negotiate a better exit package. And finally, Answer Three: you can’t. It may be called a severance package but it’s actual a transaction in which you trade your potential legal recourse for money – nothing more, nothing less.

And so, my suspicion is that you’re doing everything right. All that’s left for me to do is to observe that while you love your job, it doesn’t love you back. So go find yourself a more deserving employer. Believe it or not, you’ll be happier if you do.

 

Newsletter #86

Volume #86 -2004

Q: My wife and kids have moved to another state to allow one of the kids to pursue high-level, specialized athletic training not available here. My job, which I can't stand, keeps me from moving, and I am the sole support for the family, making just around $100K. I've been conducting a long-distance job search for almost three years, but to no avail. Should I keep trying to do a long distance search or quit, move, and look locally? We'd probably have to liquidate one of my two larger retirement accounts to do the latter. We're feeling desperate and ready to do this. Advice?

A: I’m not going to tell a man supporting a family to quit a job. And I’m also not going to tell him to continue to live in agony – doing a job he hates far from his family. I don’t want to be responsible for either prolonging your personal misery or urging you to abandon a job that will be difficult to replace

I do, however, have an observation coupled with a piece of advice. With respect to the first, I’d argue that you’ve already decided that you’re ready to leave your job, even without the certainty of a suitable replacement. (Who could blame you after three years?) But because you don’t want to be accountable for the decision, you’re looking to external sources to force your hand. This approach, unfortunately, prevents you from planning and executing a clean exit. Thus, you risk leaving under less than ideal circumstances, which could make your impending search more difficult.

So here’s the advice: do what you need to do, but do it thoughtfully. If you want to leave your job, carefully present your boos with the reason why you need to leave and provide him with a plan for ensuring an orderly transition. For example, give three or four months of notice and suggest ways that you can help identify and train your replacement. Such helpful actions will allow you to leave a wake of good feeling behind you, which will go along way toward ensuring good references. And with not many $100k jobs out there, you’re going to need every advantage you can get.

Volume #86 -

Q: I have been out of work for the last two years due to personal/professional reasons. It has now become impossible to explain this gap to headhunters and approaching companies directly has been of little/no help. I am 35 years old with a reasonably good ten-year career, but terrible people/networking skills. In the past, I inadvertently burned a lot of bridges, which I regret now. Now, I’m losing confidence and feel terribly depressed. How should I bounce back?

A: If you can’t figure out how to help yourself, start by helping others – volunteer. Take some of those reasonably good skills of yours, and put them to use helping some worthy cause. This will not only help your self-esteem, it will provide you with a source of good references. Both of these will help re-energize your job search and tangibly demonstrate your desire to be productive again.

Beyond that, I strongly suggest that you review your network to see who might be helpful to you in the search. Most people – even those who have burned some bridges – overlook potentially useful contacts within their personal network, either for reasons of pride or laziness. After two years of being on the employment beach, you can’t afford either.

Finally, and perhaps most importantly in your case, practice your networking skills in advance. To do this, you’ll need to plan a campaign based on a careful and controlled presentation of your professional past and potential contribution to an employer. In Landing On The Right Side Of Your Ass, you’ll find very detailed information on how to go about this, and I suggest you pick up a copy if you haven’t done so already.

Collectively, these activities will accelerate your job search and help with the depression. But if you continue to have a problem with the latter, get yourself some help of the therapeutic variety. Depression after all, will keep you unemployed, and that’s not something you can afford – literally or figuratively.

 

Newsletter #110

Volume #110 -2005

Q: The managing director (MD) who I reported to is with the overseas headquarters will not provide a reference. And since I was in charge of the US operation, there is no one here I can ask. I can’t prove that the MD was 'nuts', and although I feel 'screwed, sold down the river, etc.,' I have to take some responsibility for my undoing regardless. I let it happen, even if unwittingly. Am I finished? I've had one decent interview with a very favorable e-mail reply to a thank you, and then nothing. I am sure it was the reference or lack thereof issue.

A: You know that your former manager won’t provide you with a reference, so work around it. Get other people within the company to speak on your behalf, or ask former consultants/contractors to do so, or cobble together a ‘panel’ from previous jobs. None of these solutions will work all the time, but you don’t need 100% success; you just need to get one potential employer over the hurdle.

In addition, you should spend far less time guessing about the reason that you haven’t received an offer from one particular organization. Companies slow down, put on hold, and stop candidate discussions for more reasons than you can possibly imagine. For example, that employer you were so excited about may have found a better person for the job; or, the budget environment may have changed, resulting in a hiring freeze. Of course, neither of these may have happened, but the point is you don’t know and probably never will. So don’t waste your time trying to be clairvoyant. Instead, focus on finding a creative solution to your reference problem and keeping the prospect pipe full because those are the kinds of actions that will get you employed.

Volume #110 -

Q: I was fired seven weeks ago: my supervisor attributed it to “tension.” Other supervisors have told me that there were rumors of an inappropriate sexual relationship existing between my former boss and me. So, to spare his reputation, I got canned. This same guy told me not ten days earlier in a review that my job responsibilities would be expanded! What am I supposed to tell interviewers?

A: I’m not a lawyer, so I can’t give you legal advice. But if you really think that you were wrongly discharged solely on the grounds that your boss was attracted to you, then you may want to find out what legal recourse you have, if any. But before you start counting the award money, give your situation a hard, dispassionate think.

Consider that rumors whispered to you by other supervisors may have nothing to do with why your employment was terminated. Compound this with the reality that most companies prefer to be vague when discharging employees, so as to minimize the probability of a lawsuit, and it’s easy to see how the non-specific “tensions” might cover a litany of legitimate reasons. So unless you were sleeping with the boss or he’d openly propositioned you, you’ve got no substantiation that rumors were your undoing.

Incidentally, even if you weren’t sleeping with the boss, it’s worth noting that an overly familiar relationship with him could easily raise the ire of your co-workers. That doesn’t mean that your boss wasn’t also at fault, but generally speaking, it takes two to tango. So if you were being too flirtatious, or allowing him to be that way with you, you may want to consider changing your behavior in the future to prevent a re-occurrence. (That may sound unfair but managing messy situations is part of the reality of employment.)

As to what you should say in interviews, I’d recommend that you avoid this line of discussion all together and find a way to put a more positive spin on the events that led to your separation. (If you don’t know how to do this, then certainly pick up a copy of Landing On The Right Side Of Your Ass.) Talking about this sort of “tension” makes you sound like trouble, so you’ll have to draw upon your creative resources to come up with something a little more gratifying. And if that requires being a little creative with the truth, so be it. The important thing is to learn from your current situation, and if you’ve made mistakes – and I’m not saying that you have – don’t repeat them in the future.

 



 

More Background On AskYourAss.com

 

Introduction

At the intersection of wit, wisdom, and workplace trauma, AskYourAss.com once stood as a digital lighthouse for the disoriented and disillusioned, guiding job seekers with blunt honesty and biting humor. Originally launched as a promotional platform for Michael Laskoff’s 2003 book, Landing on the Right Side of Your Ass, the site evolved into something far more culturally significant: a candid forum where unemployment was not just a personal misfortune, but a universal punchline—and a shared, survivable experience.

While the website eventually faded into internet oblivion, its legacy endured in the minds of a loyal user base—many of whom credited the site and the book with helping them regain control of their professional lives. Today, the domain has been lovingly resurrected by a fan intent on preserving its original content and quirky spirit.

This article explores the fascinating history, cultural impact, and ongoing relevance of AskYourAss.com and its irreverent guidebook to professional reinvention.


Ownership and Origins

The brainchild of Michael Laskoff, AskYourAss.com was first launched in conjunction with the release of his book Landing on the Right Side of Your Ass (Three Rivers Press, January 2004). Laskoff, an Ivy League-educated marketing executive with a penchant for self-deprecation, created the site not only as a marketing vehicle but as a public confession booth, satirical soapbox, and advice column.

The site featured archived newsletters, question-and-answer segments, and excerpts from the book, all delivered in Laskoff’s sardonic voice. His brutally honest takes on unemployment, toxic bosses, mid-life crises, and career pivots resonated with thousands.

The domain disappeared for several years—its absence mourned by longtime fans. Recently, however, a former fan and web developer acquired the domain with the aim of restoring as much of the original content as possible using archived pages from the Wayback Machine and personal collections.


Location and Proximity

Though digital in nature, the heart of AskYourAss.com lived in New York City, where Laskoff resided during the creation of the book and the website. His worldview was unmistakably urban, shaped by years of high-stakes business dealings in Manhattan’s skyscrapers and the emotional whiplash of multiple layoffs.

His humor often evoked the fast-talking, no-nonsense cadence of a New Yorker who had learned to cope with professional devastation by leaning into it.


About the Author: Michael Laskoff

Laskoff’s biography reads like a comedic resume of corporate misadventures. He described himself as:

"A very junior investment banker, a staff monkey at a very large entertainment company, the head of marketing at a record label so small that you’ve never heard of it… a sort of consultant for a big, global consultancy… and a corporate wonk with P&L responsibility for a small, public telecom company."

A graduate of the University of Chicago and Harvard Business School, Laskoff's career was marked by repeated high-profile implosions. He turned these setbacks into teaching moments for others, embracing his failures as a source of authority on what not to do—and how to recover when it all goes wrong.

He ultimately published Landing on the Right Side of Your Ass after a turbulent 2002, during which he convinced Three Rivers Press to publish his irreverent survival guide. Since then, he has also served in various executive roles in health tech startups, though his current projects are less publicly documented.


About the Book: Landing on the Right Side of Your Ass

Landing on the Right Side of Your Ass is structured in three pragmatic parts:

  1. Emotional Triage
    Laskoff compares being fired to being dumped by someone who no longer loves you. He explores the emotional fallout—revenge fantasies, depression, fear—and validates these feelings without sugarcoating them.

  2. Job Search Reality Check
    He dismantles conventional job-hunting advice. To Laskoff, resumes are marketing tools, not biographies. He warns against advice from well-meaning but clueless friends and emphasizes flattering honesty over humble truth.

  3. Taking Control
    In the final section, readers learn how to seize back control in job searches: how to interview with confidence, create employer competition, and evaluate offers not by fear but by fit.

Praised by Publishers Weekly for its no-nonsense approach, the book was described as:

“A realistic look at dealing with getting downsized… written by an author who has ‘been through this crap so many times’ he can rightly call himself an expert.”


AskYourAss.com: What Made It Unique

1. “Ask Your Ass” Advice Columns

These Q&A newsletters were the site's soul. Visitors submitted job-related questions, and Laskoff answered with deadpan honesty and surprising depth. Whether it was dealing with age discrimination, agonizing over taking a lower-paying job, or surviving toxic workplace rumors, Laskoff's responses offered tactical advice with emotional resonance.

Examples:

  • “What if my boss is spreading rumors to cover up an affair?”

  • “How do I explain a 2-year employment gap when I’ve burned all my bridges?”

  • “I hate my job and live apart from my family—should I quit and risk everything?”

2. Cultural Commentary

Laskoff wove biting political commentary into his work. He was openly critical of the EEOC’s ineffectiveness under the Bush administration, observing that corporations that fund political campaigns often had more influence than individual employee rights.

His skepticism about institutions—whether corporate HR, headhunters, or the publishing industry—gave the site its edge.

3. Humor with Grit

What made AskYourAss.com stand out was its refusal to sugarcoat. Laskoff’s humor was black, brash, and brilliant. He gave people permission to be angry, confused, and even a little desperate—but also demanded that they keep moving forward.

His sign-off line might as well have been: "You’re not crazy. You’ve just been fired. Now get your ass in gear."


Audience and Popularity

The site’s audience was primarily:

  • Mid-career professionals navigating layoffs and reinvention

  • Disillusioned MBAs and ex-corporate execs

  • Freelancers wrestling with the gig economy

  • Young professionals tired of hollow career coaching

The Ask Your Ass newsletter was widely circulated via email groups in tech, advertising, and media circles. At progressive companies—particularly in software, healthcare tech, and digital media—it became a kind of watercooler read. The site was especially popular during the early 2000s when massive layoffs from the dot-com bust had left tens of thousands of white-collar workers unmoored.

Entire teams at custom web development firms reportedly quoted Laskoff during lunch breaks. Some even described his writing as therapeutic—comedy with practical utility.


Awards and Press Coverage

While the site itself did not win any formal web awards, the book received praise from respected media sources:

  • Publishers Weekly commended its “down-to-earth advice” and refusal to coddle the unemployed.

  • Reed Business Information lauded it for balancing practical job search strategies with emotional support.

The book was featured in career transition workshops and reading lists for corporate outplacement programs, albeit often with a disclaimer: “Contains strong opinions and sarcasm.”


Cultural and Social Significance

AskYourAss.com was more than a humor site. It helped normalize conversations around:

  • Unemployment stigma

  • Mental health during job loss

  • Age discrimination

  • Workplace harassment and retaliation

  • Burnout and career reevaluation

In many ways, it was an early precursor to today’s career subreddits, job-search memes, and irreverent LinkedIn posts. Laskoff’s bold tone anticipated the content revolution now thriving on platforms like Medium and TikTok.

It also arrived before terms like “toxic workplace” or “career trauma” had entered the mainstream. In short: AskYourAss.com made it okay to laugh at the wreckage—and then get back up.


The Resurrection and Archival Project

The current version of AskYourAss.com is a labor of love. The anonymous fan and web developer who bought the domain did so out of fear it might be repurposed into something irrelevant or exploitative.

Using content preserved in old hard drives and internet archives, this new version is being slowly rebuilt to capture the voice and vision of the original. The curator urges visitors to be “indulgent,” as the site won’t be exactly as they remember it—but the spirit is unmistakably intact.


 

In an era when digital attention spans are measured in seconds, AskYourAss.com remains a fascinating relic—irreverent, brilliant, and refreshingly human. It’s a time capsule of post-dot-com disillusionment, packaged in gallows humor and guerilla wisdom.

But more than nostalgia, the website offers a message that remains painfully relevant: Losing your job isn’t the end. It’s just another bad date with capitalism—and there’s always another one around the corner.

So if you’re currently sprawled on the wrong side of your professional ass, don’t despair. Fire up the archives of AskYourAss.com, laugh a little, cry if you must, then dust yourself off and get moving. Michael Laskoff wouldn’t have it any other way.

 

AskYourAss.com