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Leaving a Long-Time Career? Write a “Dear Job” Letter!

By Rosanne Ullman March 05, 2024 Mindset

Shortly after Karen and I decided to launch a business together, she put some temporary brakes on it. Whereas for me this next stage was just a pivot in direction for my freelance writing career, Karen felt she couldn’t open the door to our new venture until she closed the door on her old one.

She’d devoted heart and soul to software testing for 33 years, and she was having trouble transitioning out of that industry. She thought she might achieve closure by writing a farewell letter to her career. She wanted to make two things clear to her profession: they had a good thing going together, and here’s why it’s necessary to break things off.

This “Dear Job” letter worked very well for Karen. Writing it all out provided her with a sense of relief, as if she’d flicked the pain of separation off her shoulder. And if she’d been the only one to read it, she says that would have been good enough.

A Farewell Letter Gone Viral

But she wasn’t the only one – far from it. Karen’s international reputation as a seasoned expert in her field had earned her an impressive LinkedIn and Twitter following.

She’d been quiet on those platforms recently, so people took notice when, seemingly out of the blue, she posted a link to her explanation of what was going on with her.

The points Karen made resonated within her industry and beyond it. She was showered with comments, tweets and emails. People shared the link, and within two weeks it had attracted more than 13,000 views.

A newsletter in the tech field asked permission to run the farewell, and she even received two job offers in case she wasn’t serious about dropping out.

Most important to me, of course, is that Karen’s focus is now on our new business, Home Memoir. She’s relaxed and so glad she wrote and published her letter.

You can achieve this same closure if you’re leaving a career. Just write it all out! Based on Karen’s letter, here’s how you can structure your farewell:

Introduce the Matter

Give a little preview of what this letter is about. Karen wrote, “In tech (and perhaps in most industries these days), no one will be giving me a gold watch to say thanks and to send me on my way, so I am doing this for myself.”

The Good: Why You Were Together So Long

Karen broke her good memories into two parts – the specifics of benefits inherent in a successful career in her industry, and then the growth she experienced that she could apply to other types of work and to her personal life.

The first part included perks such as travel, flexibility, and intellectual satisfaction. The second covered triumphs like overcoming a fear of public speaking and learning to stand up for her ideas in a male-dominated profession.

Why You’re Leaving

Things were good for decades, so what changed? Like Karen, you may want to cut down the long hours or acknowledge that your passion for the industry has begun to soften. Maybe it’s begun to feel like a first chapter in your professional life, not the whole book.

My favorite sentence in Karen’s letter is: “I used to be one of the young ones, and I was young for a long time and then I wasn’t.”

What’s Next for You

You don’t have to rub it in, but it’s only fair to inform your career about your plans, right? Software testing was a surprise career for Karen, who has a degree in journalism and figured she’d probably be a newspaper reporter or work in some related writing position.

Although she did blog for trade journals in the tech field, she wanted to delve full-time in writing and publishing.

Close on a Note of Gratitude

Karen used her final paragraphs to thank colleagues. It was important to her to wish everyone well.

Karen’s not looking back. She turned down the job offers and uses her days to write, exercise, spend time with family, and build our business – exactly what she wants to be doing now.

After writing your own farewell letter – whether just as clarity and closure for yourself or as a vehicle to share your thoughts with a wider audience – you may find yourself relieved, open, and ready to face your next step.

Let’s Have a Conversation:

How long have you been in your career? Are you sensing a shift? What might that shift be? How do you plan to make your transition? Would writing a “Dear Job” letter be something that could bring you closure? Please share your thoughts and let’s have a conversation!

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Great article, and I could not have read it at a more appropriate time. I am in similar place to Karen and loved her quote “I used to be one of the young ones, and was young for a long time, and then I wasn’t.” Hah, how did that happen??? Gathering my thoughts for my own “Dear John” letter, giving tribute to all the great people I worked with and “missions” we accomplished, and outlining new priorities and plans.

The Author

Rosanne Ullman has a long freelance writing career. She is the author of the children's picture book The Case of the Disappearing Kisses, an admin for the Facebook group "Grammar Matters," and the creator and instructor of the Write My Memoirs Grammar and Writing Course.

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