Some Things Require A Human
The respected press, Harvard Business Review (HBR), has a “retirement toolkit.” It consists of an ebook, handbook, nine worksheets, and four podcast episodes. As they say it, Retirement is, in HBR’s words, “perhaps the greatest and most deeply personal career transition you’ll ever make.” The transition is genuinely complex, and one of the most respected names in professional development is now selling tools for it. That’s actually worth pausing on: even the gold standard of professional development looked at retirement transition and said, this is hard enough that people need help. That was a “Wow!” moment for me.
But. But … but. Toolkits can’t do some things. I have a dozen books on retirement on my shelf, and there only a few things they can help with. Because I am stuck at the moment on something no written page can help with.
Three months ago, something started seeping up from somewhere way deep down. I wasn’t really aware of it for a while. It was a momentary irritation, but it kept coming back. And I kept explaining it away. For three months.
Then it blew up in my face, and it was clearly time to look at it directly, and I am fortunate enough to have access to a great coach that I trust. Sixty minutes later I had a realization of what it was, why it wasn’t going away, and a direction to keep working on it. I have enough now to stop explaining it away and start actually working on it. And no worksheet would ever have gotten me there.
What moved me from my stuck point was being asked the right questions, in the right order, by someone with no agenda except to help me see clearly. She noticed what I was skating past. She named the thing I had no name for. And she stayed in the room when I got uncomfortable.
Self-directed tools have a structural issue in that they presume you can self-diagnose. They presume that you can identify what you’re avoiding, what old story you’re running on autopilot, what you’ve been conditioned to want or fear or perform rather than actually choosing. For some people, some of the time, that’s true. Usually it’s not true.
Further, the retirement transition has a specific wrinkle that makes self-diagnosis much harder than usual: the structure change. For decades, your orientation came from outside you. It was the schedule, the role, the institution, the inbox. To me, that structure felt like constraint. For many, the structure also provides direction, a genuine orienting system, whether you liked it or not. In fact, about 1 in 4 retirees return to work and say the reason is social and emotional, not financial. Work wasn’t just income to them. It was structure, connection, and identity.
The average retiree gains approximately 2,500 hours of unstructured time per year. That’s not a vacation. That’s a complete restructuring of daily life with no job description, no schedule, and no one telling you what matters today.
The need for daily/weekly/seasonal structure doesn’t disappear on a retirement date. And without the structure that our careers give us, a lot of people feel unmoored in a way that’s very hard to distinguish from something being wrong with them. And here’s what makes the whole situation worse: the experience often presents as something else entirely. Depression. Low motivation. Feeling lost. A vague sense that you should be doing more, being more, wanting more.
Coaching helps with that.
The thing is, a worksheet can’t push back. It can’t ask the follow-up that cracks something open. It can’t notice what you glossed over in your own answer. That’s not a criticism of worksheets; it’s just a description of what they are and aren’t. By definition, written materials push answers at you. Many people need someone to think with them instead.
I’ve been in this transition for a year. I’m credentialed, trained, and I think about this stuff for a living. And I still needed someone to ask me the question I hadn’t thought to ask myself, and to stay present as I start my search for the answer. That’s what coaching is. It’s not information delivery. It’s wise human contact that gives you space to find your specific answers. It’s an outside perspective with no agenda.
If something has been seeping up for you, quietly, persistently, in the background, and you keep explaining it away, that might be worth thirty minutes of real attention. That’s what the FREE “A Quick Conversation” is for.
