Here’s How to Quit Your Boring Job in the Next 12 Months

Tim Denning

Write an unconventional resignation letter.

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Giving the middle finger to a boss is a lot of people’s secret childhood fantasy.

I’ve had my f-you moments at work too. I’m sure you have. It surprised me to learn that in a recent study “64% of employees say they will leave their job … mostly because their employers fail to ‘engage them.’”

Quitting a boring job in the next twelve months isn’t so taboo. Here are the three steps to doing so, based on my past and potential future attempts. It’s not what you think either.

1. Set a date.

Plan the moment. Think about possible dates. Think about what you will do after you quit your job. Setting a date locks you into following through on your promise. The worst that can happen is you plan to quit your job, do it, regret it, and go back into the job market and get a regular job again. Not so bad, huh?

2. Write the resignation letter.

Sit at home late one winter’s night. Open your laptop. Start with the email subject line.

“<Insert Full Name> Resignation Letter — this email will subtly enhance your perspective of <Inset Company Name> and uplift your day.”

The email subject line gets your brain into a flow state. Add the email recipients: your bosses’ boss, and HR. That’s all.

Start the email by stating the emotion of what’s about to happen. “I write this letter with a lot of emotion and plenty of tears.” Instead of putting your boss under the next bus. Instead of talking about everything that went wrong. Instead of making other people sound dumb so you can feel smart. Instead of writing an email disguised as an f-you … don’t. Resist the temptation for rage. Use discipline instead.

Write about the bonus you got. Tell them how you didn’t deserve the entire bonus you were paid because you failed to achieve your KPIs. Tell them how you’re going to donate your bonus to a good cause in your soon-to-be former employer’s name. Remind them that doing the right thing is always the right thing — the first lesson.

Talk about the fulfillment issues you faced at work. How every time you made a promise to a customer, you felt like you were lying to them because you couldn’t give them what they needed. But don’t blame your employer. Instead, blame yourself. Talk about what you could have done to fix the issue.

Layout a plan you could have come up with — you could have gone on LinkedIn, messaged the right people, and attempted to recruit them so you could fulfill your customer’s promise.

Write about how recruiting people through job ads is a thing of the past and you did nothing to influence your employer to try other avenues. You could have used meetups or live events to find the right people. Damn it, your close friend Chris runs one of the biggest meetups in tech in your area, and you didn’t even call him to help your company. But you would have if you had your time over.

Mention the 4-day workweek your employer gave you. Tell them how you used the extra day to write online and try to inspire people. Tell them how grateful you are that they allowed you to do that. Tell them there is a lot about the employee experience that could be improved, but this is a step in the right direction.

Make them feel inspired, not deflated.

Then talk a little about what you learned. Mention the polite woman you met in your last job. Talk about how she told you that you could be a leader when you didn’t believe you could. Talk about how working with her could light up a thousand Christmas trees. Once you’ve written about her finest work qualities, then get to the difficult part. The part about where you messaged her one day while at work and she wasn’t there anymore.

Write about the moment when you discovered she died unexpectedly as a young 30-something with a new husband, and with dreams of motherhood.

Talk about how that ripped your heart out. Write about how you attended her Youtube funeral because of a pandemic. Then insert a sentence that suggests she is guiding you through this moment right now, from up above.

Write about how your operations guy at the company, hated you when you joined two years ago. Tell them how he refused to work with you. How he left you in the lobby to work, and wouldn’t even buzz you through the door so you could work on level two of the customer’s office.

Talk about how excluded you felt. Then write what you did about it. Mention the coffees you had with him. Talk about the speeches you gave to him. Talk about how you thought about quitting many times because of him.

Then write about that night.

The night the two of you stayed back in the office with a single customer. The night you broke your no-drinking rule and poured yourself a glass of wine so you could bond with him. Explain the story he told you and the customer about teaching his kids the power of kindness while holidaying in Bali.

Then talk about the day before the start of the pandemic. Talk about when you wanted to pay for bottles of water on your company corporate card. Talk about how he said no. “These small businesses are about to go through the fight of their life. Paying a little extra for bottled water is the least we can do. Perhaps it will give them a little hope.”

Emphasize how it was always the little things with him. On the outside he appeared to be a grumpy man. On the inside he had a heart of gold. Talk about how you eventually learned to work with each other. How you overcame your differences and blended two different ways of working.

Mention how you’re now close. How you defied the label of ‘enemy’ and became good friends. How you’re always looking out for each other. Write about how you changed minds while being at work.

Get into your proudest moment. Talk about breaking into the department of a large enterprise. Write about how they hated your company and made fun of you. Add in the conversations you had with each customer for context. Don’t filter out the insults or the language. Let them see what you saw. Talk about what you did to change their mind.

Highlight how you emailed a person you knew in the company. Tell them how they kept emailing you back and saying “I can’t help you.” Tell them how you begged them to help you. Talk about all the follow-ups. Explain how you felt rejected and stupid for even trying. Explain how one day you got an email back saying “Alright, I’ll introduce you.”

Convey the adulation you felt in that moment. Talk about how you prepared for the meeting. Talk about how the presentation went. Then, tell them how there was radio silence. No next step. No “we’d like to work with you.” You were back to step one again. Write about how you repeated the process over and over, getting slightly closer each time. Then you got the email you didn’t expect. “We’d like to proceed.”

Those four words were all it took to put your company back on the customer’s key priority list. First you changed a colleague’s mind, then you changed a customer’s mind — all through persistence and a belief in yourself.

Write about your perspective on work. Mention the health scare you had all those years ago. The lump they found. The thoughts of what it would be like to die as a 20-something-year-old. Talk about why that makes you live like Peter Pan and feel carefree. Talk about how that carefree attitude sometimes causes you to say the wrong thing at work.

Use the courage you’ve got in reserve to let them see who you really are one final time.

Then get to the hard part of the story. Tell them how they didn’t know when they hired you that you were fired from your last job. Tell them how you felt ashamed to be fired and didn’t really know why.

Tell them how you shared the story on LinkedIn and then hid from the world for weeks after. Tell them how it was the hardest thing in your career you’ve ever been through. How your ego took a beating. How you left the building that day and broke down crying in the middle of the street after resisting the overwhelming temptation to do so. Write about how you came home and told your partner and felt like you were a terrible “provider.”

Then get into the gory details. The part where you tried to get another job. The part where you told all your old colleagues you’d have another job in under a week. Then how after a few months you kept having to make excuses about why you weren’t “snapped up.”

Explain how you rolled up to job interviews and got rejected. How you prepared, put on a show, got great feedback, and then got ghosted. How people you used to work with stopped taking your calls.

Then get to the section of the story where one colleague defied the trend. Talk about how he invited you to work from his company’s office so you’d feel like you belonged to society again and didn’t feel like such a loser. Then talk about the mentor who flew from interstate to hang out with you, and gifted you tickets to a live event with a well-known motivational speaker.

Write about how you sat in the first row of the event, and saw two of your old direct reports from the job you were fired from, sitting three rows back. Talk about how you were there alone but tried to pretend you were okay, when on the inside you were a broken human desperate for someone to care about what had happened to you. Attach the selfie your mentor arranged for you to have with the speaker, to the resignation email.

Write about how that silly selfie made you believe you could rebuild your life again.

Don’t forget to add in how you got the job you are about to leave. Talk about how the two of you met. How you worked together in sales and acted like cowboys. Talk about what it was like to get promoted, do the job for a while, and then step down and give her your job so you could return to the job you loved with the farmer who was looking for a wife.

Write about how surprised she was to be given the opportunity. How you didn’t want anything in return. Talk about how she thrived well beyond your expectations and became a female leader in tech because of that job.

Add in how you lost contact for a while, then you met for coffee when you lost your job. Describe how your coffee catch-up had no agenda. Mention how she offered to see if there was a job for you at her new employer.

Talk about how even though she tried, it didn’t work. Then get to the meat of the story. The part where she put her career on the line and followed up for you daily so you could have a new opportunity. Write about how you felt cared for in your career for the first time in a long time.

Get to the good part. The part where you got the job at this company you are about to resign from. Reflect on how it’s strange when you do something without any selfish intentions, the universe pays you back handsomely.

Then write the end of the resignation letter. “I know you probably won’t read this and that’s okay. It took me a few hours to write and it was worth it. This company has been extremely good to me and this letter is the least I can do.”

End with — “I will be around for the next 4 weeks if you’d like to chat. I will ensure an in-depth handover is done with the commercial team, and will remain available after the 4 weeks notice period is up, in case something pops up that neither of us could have predicted.”

Finish with thanking both people for the opportunity before hitting send on your resignation letter.

A resignation letter shows who you are.

When you add in the problems you encountered in your job and how you overcame them, take responsibility for your mistakes, find the good in your colleagues (terrible ones too), avoid shaming anyone, decide to leave on a positive note, have the humility to reflect on your flaws, and turn the major events of your job into lessons, something strange can happen.

Your employer can end up reading your resignation letter and wanting you to stay to take a promotion and solve the problems you eloquently explained and attached possible solutions to. That’s the power of offering solutions and taking responsibility in life and work.

Make your story positive. Talk about lessons. Don’t shame anybody. Avoid a rage quit.

3. Save up money.

In the months prior to quitting your job, you want to ensure you have saved up enough money. When I quit my job, I didn’t realize how quickly my savings would evaporate. Unexpected expenses seemed to crawl out of the dark closet like boogie monsters in the night.

Money in the bank equals less stress.

Quitting a job takes a huge mental toll. Excess money equals a good night’s sleep during these uncomfortable times. Sleeping well gives you the energy to fight another day when you no longer have a safe job.

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Aussie Blogger with 100M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship www.timdenning.com

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