Making Work From Home Permanent

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Before the pandemic, hustling was seen as a badge of honour. People went to cubical farms, put in long hours, swore, and got stuck in traffic during their commutes, rushed through family dinners, woke groggily to a 6am alarm, only to repeat the entire cycle again.

But then the pandemic happened, putting the pause button on everybody’s crazy hectic lives. Working from home was suddenly mainstream, not just for weirdo digital nomad types. Employees finally had more autonomy and time to themselves without their dreaded commute.

Priorities shifted, and employees started picking their family, health, or free time over a big pay-check, so much so, that 4 million employees quit their jobs in the last 6 months in what the financial media has dubbed as “The Great Resignation”.

Now, with businesses re-opening and employees being asked to go back to the office, being forced back into traffic jams just so you can sit in a cubicle prison sounds about as fun as sliding down a banister made up of razor blades butt-naked.

Unless you are financially independent and no longer need to work, you’ll have to suck it up and take it because that’s just the unfairness of life, right?


With the US unemployment rate back at pre-pandemic levels and 11.3 million unfilled jobs in the U.S, the challenge is in finding workers to fill positions, not the other way around. That means the pendulum of power has swung away from the employers and towards the employees.

Take advantage! Now’s the time to use your negotiation skills to make “work from home” permanent.

Negotiating with your boss is always a tricky endeavour, but having done this successfully when I was still working and helped coach many of my friends suceed, I have a few tips and tricks to make this work for you:

Timing is everything

Never underestimate the power of timing. If unemployment was at an all-time high, like during 2008, pushing your employer to let you work from home permanently would be a bad idea. But, if your boss is freaking out because several of your co-workers just quit, there’s an avalanche of work coming down the pipe, and they can’t possibly figure out how to meet the deadlines with the skeletal staff that’s left, their desperation is your salvation.

In a hot job market, bosses are more afraid of you leaving than you are afraid of them firing you.

Back in the before-times when I was still a corporate drone, I was able to negotiate a raise at my job by picking the perfect time to do it. It was right after my boss had just taken over the team and my colleague had unexpectedly quit. He was trying to prove that he could handle being a manager and worried about how his employee’s resignation would make him look to his superiors, and I knew it. So I scheduled a meeting with him in which I put the subject line as “To discuss my future with the company”.

I can still remember the beads of sweat collecting on my boss’s forehead and the look of sheer terror in his eyes in that meeting room. The team had dwindled down to half its size after a continuous streak of losing employees to better paid jobs for the past year.

The conversation went something like this:

Him: heavily sighs, muttering under his breath “oh here we go.”

Me: “Ok, so I know this is bad time, but I wanted this chance to talk to you about…”

Him: winces heavily, waiting for the hammer to drop

Me: “…my promotion.”

Him: Huge sigh of relief “Oh thank GOD! I thought you were quitting!”

We both walked out that day with a big smile on our faces and I had landed a promotion on the spot. And it was all thanks to timing.

Prove You can Benefit the Company by Working from Home

One of my favourite laws from the book The 48 Laws of Power is: “Appeal to People’s Self-Interest, Never to Their Mercy or Gratitude.”

In this case, trying to get your boss to let you work from home by telling them how loyal, hardworking, or a team player you are doesn’t work. Or trying to get them to feel empathy for you by telling them how stressed or mentally overworked you are won’t work either. Never ever used the word “unfair” or other equally emotional appeals.

Appeal to their self-interest instead. Make your bosses’ life easier by making them look good in front of their superiors.

One way you can do that is to show how much money you’d save the company by working from home. Instead of having them pay for Wifi, electricity, office space, you’d be taking on the burden by paying for it yourself at home. That results in tens of thousands of dollars in savings for the company.

You can also prove you’d be more productive and increase their revenue by eliminating that wasteful commute, which can now be used for working. Assuage your bosses’ fears of you slacking off by giving them weekly updates. Prove that working from home is a no brainer by showing how this situation benefits the company.

Leverage, Leverage, Leverage

When I first started working, I didn’t understand office politics so I wasted a lot of time trying to prove I was right and arguing over stupid things that didn’t matter.

Then I discovered the book Secrets to Winning at Office Politics.

This book opened my eyes to realizing that office politics isn’t about justice or fairness. It’s about playing a game. Acknowledging that office politics are rarely fair and it’s not about just putting your head down and working, changed my whole perspective.

The number one lesson I learned in this book is about how to “leverage.” Instead of waiting for your boss to see how hard you’re working, and then getting irritated that they won’t even let you work from home, you use leverage against them by getting multiple job offers and use it to extract concessions.

Sometimes you don’t even have to have the offers in hand for this leverage tactic to work. In fact, when I worked as a contractor straight out of university, my boss kept dragging his feet in turning it into a full-time position. Every time I would bring it up, he would reply with “We’ll discuss this some other time.” After my 3rd request went ignored, I had enough and started taking my fate into my own hands.

I started applying for jobs and I made sure he knew it. I would leave my resume in clear view on my desk, I’d have open on my browser when he stopped by. And when I started getting interviews, I would deliberately schedule it during work hours so I could block them off in my public calendar.

Then the interviews started rolling in. A few here and there turned into an avalanche until I was spending more time away from my desk than behind it. All of a sudden, my boss panicked and put together a full-time offer for me. Ironically, by that time it was too late. The jobs I interviewed for were way better than the one he offered me, so I leveraged my existing salary to get the new company to exceed it, and I turned my old boss’ full-time offer down. I now had a better job, less work, and I was making more money. Leverage for the win!

Leverage was also used successfully in publishing and renting as well. I got one of the most sought-after New York literary agents because I had multiple offers from other literary agents to represent me. And during the pandemic I was able to lower my rent by 15% by leveraging other rental offers I had to my landlord.

Leverage is one of the most powerful tools you can use to make your work more flexible.

Even if you don’t have a job where you can work from home, you can still use most of the tactics above to challenge your employer and improve your work situation. Start applying for jobs that allow working from home. Start scheduling interviews at your desk so your boss notices. The more signs that you’re thinking of leaving for a job that allows working from home you drop, the more you’ll scare your boss into giving you what you want.

Or failing that, consider retraining for a career with more flexibility and lets you become location independent. Like this bartender turned coder, or nurse turned developer. The more location independent your job is, the more you can enlarge the gap between your earnings and spending, and the faster you can become financially independent.

What do you think? Have you successfully negotiated a more flexible situation at work? If so, how?

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19 thoughts on “Making Work From Home Permanent”

  1. Excellent points !
    It’s unfair comparing cubicles/commuting to razor bannisters. I think FIRECracker owes an apology to all the razor bannisters out there for casting them in such a negative light.

  2. The best part of your story is when better opportunities cane your way. I tried getting a transfer to a part if the country I wanted to be in three times all to no avail because of one difficult Managing Director who could never give a convincing argument other than he wanted people in the office and geographically within sight. Sometimes you have to vote with your feet.

    1. Same situation. Wanted to relocated from HCOL area back to the Midwest to be nearer to family. Was a no-go until I gave my notice. Management then said, if it is about money, we’ll give you a raise to stay and you can still relocate. Needless to say, I turned them down. Best decision of my life!

  3. Long-time reader, first-time commenter!

    Thank you so much for this article!

    Leverage is exactly what I’m going for now. My company wants me to return to the office two days/week starting in May, with a full-time return anticipated. During the last two years, most jobs in my field have gone fully remote. I’m applying like mad and filling up my calendar with interviews. Hopefully, I will have at least one offer I can accept if my boss won’t budge.

    I hate having to do this but my employer leaves me with little choice. Return to the office like Covid disappeared and gas isn’t $5 gallon – yeah right! Not if I don’t have to.

    1. Amen to that! Fortunately, my current employer understands that folks have been 100% remote for over two years and managed to get the job done. Our team has the option to go back to the office 100%, a hybrid option and a WFH permanently option except for team-building exercises and mandatory department meetings, of which so far only one has been scheduled and it is a fun team event outdoors golfing (lunch included!) 😀 The good employers know that they have to pivot or they will lose talent. Hopefully your employer will recognize your worth so you don’t have to leave.

  4. I’m so glad you posted this, Kristy. After two years of working remotely (and getting more done than ever while not having to deal with the nightmarish commute or general office stupidity), all of a sudden my company is trying to make some noise about getting us back into the office “at least 60% of the time.” Yeah right! I don’t want to go back and I know I’m not the only one who feels that way. My manager is thousands of miles away from me. Everyone I work with is either across the country or across the ocean way over in Europe. So there’s no point in going back. Maybe I need to get a few interviews and offers to remind the powers that be that remote work is here, and it works, and it’s awesome…

    1. Its amazing how companies act as if they haven’t had distributed teams all along. Fundamentally whats the difference?

  5. I transitioned to 100% remote because I didn’t want to go back to work and risk getting sick or really want to talk or look at any one of my coworkers TBH.

    I think I was a lot less tact in my approach though. I just interviewed until I got a job offer that was 100% remote (but would require a lot more work than I was doing now) and I just used the job offer to threaten my manager.

    At that point it was they approve it or I quit. They approved it so I stayed so I can do less work.

  6. I accidentally did this. The company wanted me to move to Office City after a year and a half remote. I scheduled a meeting with my boss to ask to stay remote and talk relocation details if not. A coworker just happened to quit shortly before that meeting. I thought I’d have to negotiate – not after that!

  7. Working mostly from home towards tail end of my career, is nice. However, I’m very lucky to have an office job. This conversation doesn’t work for millions of the front-line workers in hospitals (even those professionals), restaurants and walk in stores. We should be careful to feel so victorious…as a result of this work from home choice…for office workers.

    Some of my siblings are envious because they work as hospital pharmacist, physician, patient intake for pediatric cancer patients, etc.

    I’ve signed in to work only 1 day / wk. at office. I am very lucky to work with a hardworking team where we do trust each other to pull our weight and pump out quality work.

  8. May I please have your permission to use this wording in future negotiations when I’m offered an option that I don’t like? I can respond with: That sounds “about as fun as sliding down a banister made up of razor blades butt-naked.”

    Should I use a graphic cartoon that I can hold up while I utter this (in case the StupidVisor doesn’t understand what I’m talking about me and is staring at with what Gunny Sergeant Highway–Heartbreak Ridge, Clint Eastwood–calls the “I just [had sexual relations with] the neighbor’s dog look”?

    Thanks in advance,

    Dan V
    Taipei, Taiwan

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