The time I was asked to resign

It was the Spring of 2007. I wanted to move to Oregon for personal reasons. My employer at the time asked me to come up with a 12-month plan for them to continue operations in the event it took a while to find my replacement. We set my last date of employment, at which point I’d be laid off from the company and given a severance package.

As a normal part of my approach to IT I had already:

  • Documented all of our infrastructure, applications, and processes (whether manual or automated)
  • Automated a lot of our processes
  • Managed all of our vendor agreements
  • Tagged and cataloged our physical and logical assets
  • Created an emergency response plan in case of my sudden illness, absence, or death and sent a digital copy and hardcopy to our primary services vendor

I spent a week building an index for all of that information and re-negotiating some services agreements. I also negotiated a couple of vendor proposals for monthly services contracts for IT maintenance and outsourced technical support. I bundled everything together into a digital archive and printed a hard copy organized in a 4″ D-ring binder.

But… there was a problem.

OK, two problems.

First, I really loved this place and the people. Second, frankly, I wasn’t having any luck finding a new job out in Oregon. I had to come up with a new exit strategy.

On the last day, my boss called me in to formalize the layoff. I said I have a better idea – instead of a layoff that involves paperwork, severance pay, unemployment and so on, how about I resign and I contract with you on a monthly retainer to perform a set of services and provide X deliverables on Y schedule? This was a win-win: I’d get to move across the country and keep a steady income, they’d get my expertise and experience until a replacement could be found. We spent the afternoon and went into the early evening working out the deliverables and schedule, the financials, the contract and getting it signed by legal, and otherwise finalizing everything.

Finally, my boss says with a smile, “So it’s almost 7 pm. I’m beat. Are you going to resign or what?”

I handed my boss an envelope and said, “Yup, here you go, I’m officially resigning.”

“Good. Have a safe trip and call me Tuesday morning once you’re settled in and back to work.”

“You got it, boss.”

“I’m not your boss now. I’m your customer!”

“Not until Tuesday, you aren’t!”




For those wondering, the envelope contained two letters. One was a short, signed statement of resignation. The other was a personal note to say thanks and express my gratitude for having such a great manager and mentor.

I wound up on retainer for nearly a year. When we finally found my replacement, my boss joked “I can’t believe it took so long to get rid of you!” I flew back for a day to officially say goodbye to everyone, closed out that chapter of my life, and moved on to the next one…

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