“Adrian, I don’t know why I can’t just stop,” Maya said, wrapping her arms around herself. “Financially, I know we’re fine. But I keep telling myself I should keep working.”
Her husband, Daniel, gently smiled. “She says that word a lot lately…should.”
They both laughed, but it was the kind of laugh that carried a little exhaustion underneath.
After decades of helping doctors, Maya had reached what I call the Retire-ish zone. That in-between stage where the numbers say yes, but your heart hasn’t caught up yet. Their spreadsheets looked great. Her Prof Corp was healthy, their debt gone, kids grown and their savings structured across all five of my retirement “buckets.”
So why the hesitation?
Guilt is a huge block for doctors
“I love what I do,” Maya said. “I’ve trained so long to help people, but the waitlist of people to see just keeps getting longer. We want to look forward to the next stage of our lives, but it’s really hard to think about leaving my patients.”
I nodded.
I’ve heard some version of that same sentence from dozens of physicians over the years. It’s the same guilt that comes from decades of being responsible — for patients, for staff, for outcomes. You’re wired to solve other people’s problems. When the problem becomes your own future, you don’t quite know how to diagnose it.
“Let me ask you something,” I said. “If one of your patients came to you exhausted and said they were afraid to slow down, what would you tell them?”
She smiled, knowing where I was going. “I’d tell them to listen to what their body is saying.”
“Exactly,” I replied. “The same principle applies to your finances. You’ve built the capacity to choose. The question now isn’t can you retire, it’s how you want to live.”
We spent the next hour mapping out what her Retire-ish life might look like. Two days a week at the clinic for another year, one day the following year, then full flexibility after that. Daniel was already picturing them hiking in the Italian Dolomites next summer.
As we talked, I could see it happening — that subtle shift from fear to excitement. The conversation changed from “I should keep working” to “I want to keep contributing — just differently.”
That’s when I leaned in and said, “You know, the word should is really just guilt in disguise.”
Maya laughed. “So, what do I replace it with?”
“Try want. Every time you say I should, ask yourself, Do I want to?”
Replace the word SHOULD with WANT
That’s what Retire-ish looks like. Not a finish line, but a shift.
The word should is really just guilt in disguise.
When you stop should-ing yourself? That’s when retirement really begins!
Enjoyed this article? I’d love to hear from you! I’m always interested in hearing about the unique financial situations doctors have. Send me a note! And please check out my newest book, Retire-ish: What Doctors Need To Know Before They (Sort Of) Retire
