LOTR: Gandalf and the Golden Girls

TL;DR: Gandalf wants to find a better balance of when, where, and how much he works. He doesn’t want to retire quite yet, but he’s ready to prioritize other things above his career now. How can he do that without quitting?

Finally, 67,000 years old. Social Security kicking in, pensions ready, Medicare on lock. Time for a grand old wizard to retire. But.. maybe retirement’s not what you’re looking for quite yet. You enjoy your work, that’s why you’ve been doing the same job at the same company for so long. Maybe you aren’t looking to stop working, but just.. change it.

You could visit old friends in the Shire, work from Khazad-dum for a few weeks, even just take a day here and there to travel to Lothlorien without having to worry about scrambling to order an eagle back to work when a crisis starts.

A bit less responsibility and a bit more flexibility would be nice.

Gandalf the Grey had begun to show his age – having fought for millennia against the dark lord and his minions, perhaps it was time to let someone else take the mantel. Maybe it was time for Gandalf to retire.

Gandalf reached out to me because folks close to him started wondering when he’d finally take things a little easier. Originally purchased for the aesthetics, Gandalf had begun to lean on his staff more and more when standing or walking for long stretches. And at 3.5 hours of runtime per (extended edition) film, they were some long stretches.

Just as work looks different for each of us, so too is retirement a very personal thing. And Gandalf didn’t want retirement to look like it did in pop culture: at this point, at least, Gandalf didn’t want to give up work entirely. Maybe someone else could shoulder the heavier burdens, but the gray wizard still wanted to be active in project planning and intended to schedule his time so he could be available during peak season; he knew the team got busiest around the same time each year, and he honestly got a lot of energy from the buzz around the office.

From our first conversation, Gandalf and I arrived at two primary steps we wanted to complete:

1. Identify what Gandalf wanted from work
2. Plan how to get Gandalf that new relationship to work

Wizards just wanna have fun

Despite the subheading here, Gandalf’s reflection on our call showed he didn’t want to fully drop his work. He enjoyed getting to work with hobbits, elves, dwarves, and men alike; he just wanted to do it a bit less. He wanted freedom from some of the obligations that America’s full-time work paradigm demands.

Let me start by relaying the picture that Gandalf painted for me of his ideal circumstance coming out of this:

• “I want to be able to work less; I’m happy to give the usual heads-up for time off, but I’d like to be able to take 3-5 months off a year”
• “When I am working, I want the flexibility to work remotely. For a time, we were all communicating telepathically, and it’s fine to have in-person meetings when I’m in town, but I want to be able to work while visiting friends and comrades across the varied lands of Middle Earth”
• “To be able to do these first two things, I think I’ll need to reduce my scope; no one would be happy with me managing a team while ‘out of office’ up to half of every year”

Great! How do we make a wizard’s dreams come true? The answer might surprise you! (It’s not magic)

How to make less and influence people

As it stood, Gandalf had a number of direct reports that he was responsible for: he had to sign off on the great eagles’ timesheets each week and tend to all the manager-ly tasks such a position required. In general, he liked working with the eagles and enjoyed his managerial role, but in reality his position was that of a player-coach: he was part manager, part individual contributor. And because Gandalf knew he wanted the flexibility in when and where he worked, and that it was incompatible with managerial responsibilities, he knew he had to ask to offload such duties.

But with a smaller scope and less time at work, we knew it wouldn’t be possible to keep the same pay scale and benefits – and that was okay! Gandalf had been saving up and didn’t intend to start burning cash, even in retirement. He still wanted to be paid for the time he worked, but he could make do on less work, less pay, and more Medicare.

In crafting a plan, I asked Gandalf to identify two particulars:

• Who are his stakeholders in this? ie: who needs convincing?
  • Supervisor
  • HR
• What do those stakeholders need? ie: how do we convince them?
  • Reasoning
  • Considerations

Crucial to this point is that Gandalf is closest to his work and his colleagues: I can’t tell him who owns a decision, though I can prompt him to consider certain folks from past experience. For example, he mentioned that his relationship with the essence of light and fire (his direct supervisor) was a good one – they had worked together a long time, and by this point it could be considered at least a friendship, even family friends.

In identifying his supervisor as a friend, we had a great footing! Step one here would be getting them on his side for this: HR was going to be the real balrog here. Gandalf would need the essence of light and fire’s help to get HR’s approval for this new working arrangement – after all, they’d have to sign off on his new pay structure to get this all going. Gandalf would need HR to confirm in writing “YOU SHALL… PASS”.

To align Gandalf’s manager to the shared goal, we wanted to demonstrate that we’d already considered how it impacted them and we are asking them how to make it work. The first point shows we’re trying to make this as little work for them as possible; but the second point is key, because by asking for their help, we’re effectively bringing them in as someone we’re working with rather than against to solve this problem.

After some reflections, we boiled down the key asks we’d be making of the essence of light and fire (and ultimately, of HR). Importantly, we’re highlighting what would be different from present state, vs what would remain the same, to show the extent of the ask. See below:

• Be able to work remotely when there is not a need to be in person
• Increase time off to ~3-5 months per year (unpaid beyond existing PTO allotment)
• Reduce scope to match new work schedule

Subscribed

The essence of light and fire’s got mail

With all the above identified, the key to starting this process off right with Gandalf’s manager was crafting a message that aligned them toward the same goal: giving Gandalf the flexibility he needed in this new phase of his life, while ensuring the company still had what it needed.

To that end, we decided to write up an email – although Gandalf had considered broaching the topic over drinks, it felt better to open the conversation in a complete overview, then dive into the details live later on. Here’s the message he sent:

Hello The Essence of Light and Fire,

To cut to the chase, at this point in my life, I am looking to spend more time with those I am close to; to do that, I want to work with you to see how we can reduce my scope and make it possible for me to take more time away from the battlefield.

I have laid out a summary at the bottom of this email, but want to walk you through the details. I know this is a big ask, and I want you to tell me what you need from me to make this happen – first and foremost, thank you for always being so supportive of me and the great eagles. I want to make this as smooth a transition as possible; I love this work and want to continue, just at a different scale that makes sense given my current situation.

With my friends’ great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-great-grandchildren having children of their own, and as I’m approaching 70,000 years of existence, I am considering how I can spend more of my time with mortals. I absolutely want to continue the work we are doing here, but I want to shift that balance towards enjoying Middle Earth over time working to defend it. To that end, I have two main goals here: more flexibility in when I work and more flexibility in where I work.

That is, I would like to shift my schedule to have 3-5 months of time off per year and to be fully remote unless it is expressly necessary that I be in person. This would give me the flexibility to have more free time and more time working near creatures of the world.

I am of course aware that this would mean a significant change in compensation and benefits, and I am prepared for that. At this point, I want to work with you to see what you need and how we can make this happen – I have already thought through some of the details below, knowing that this is not an insignificant ask I am making of you. I am here to work together on this, and I so appreciate your partnership in making this happen.

Thank you again,
Gandalf

Summary:AsksBe able to work remotely when there is not a need to be in personIncrease time off to ~3-5 months per year (unpaid beyond existing PTO allotment)Reduce scope to match new work scheduleReasoningI want to be able to visit my friends’ descendants’ descendants and spend extended time with themI want to continue working with you and the team. I love this work; you know I do.As I’m in my “golden years”, I want to be able to spend those years with a balance tilted more towards personal relationships than it has been so far in my careerConsiderationsLogisticsI would continue to give notice of time off per current expectationsI would still be working during peak seasonWe would need to identify how my scope would be reduced and where that responsibility would goWhat would pay tracking look like?“Per hour” vs. “per project”?PayContractor/consultant vs. salary?I understand benefits would be impacted, and I’m prepared for thatI am prepared for a reduced total compensation to match the scale of my reduced daysBudget cuts may lead this to be a helpful move for the company overallPeopleI know we need to consider the optics of me shifting to remoteWhat approvals do we need to make this happen?What do you need from me?

From there, Gandalf and I could reconvene to game-plan those live conversations – will Gandalf get to retire? Who ate Deb’s yogurt from the break room fridge? Find out answers to this and more on next week’s episode of Gandalf and the Golden Girls!

(Or at least more work-themed installations of LOTR)