If you’ve spent most of your life in medicine, chances are you’ve always had a plan.

Undergrad. Medical school. Residency. Fellowship. Practice. Each step built on the one before it, with clear goals and a system with clear guidelines and expectations. Even when things felt uncertain, the structure helped you find your footing.

Thinking about retirement? How's that feeling? I'm guessing it feels a little… off? That makes total sense.

Retirement isn’t a solo endeavor,  it's a team sport. For all the talk of independence and freedom, the truth is the quality of your retirement has everything to do with the people you share it with. Think of it like a team sport where each player contributes to the whole, and the experience is more gratifying when you share both the challenge and the reward with each other.

I’ve spent much of my career helping others navigate life transitions. I’ve seen executives redefining their path, individuals facing all varieties of uncertainty, and organizations managing change. But it wasn’t until I began approaching my own transition into retirement that I fully understood the weight of this question:

What happens to our identity when we step away from the work that has defined us for decades?

For physicians, that question can be especially complicated.

As you approach retirement, are you inclined to look for an advisor? A coach? Are you a “just give me the plan” type of person?

At Retire Artfully, we pride ourselves on guiding clients through the practice of retirement. Now, this might seem like “semantics” but bear with me as I explain why the language matters and how it can help define what we offer as you transition to this new and exciting phase.

Retirement is often described as the “freedom years”—a time to relax, travel, explore passions, and reclaim your time. The thought of being on a “perpetual vacation” may sound awesome at first but there's a stark difference between planning for two-weeks of time off and planning for 30 years of “play”. But perhaps the most not talked about subject of retirement is the invisible expectations that come from others the moment you step out of the workforce.

I had the wife of a couple tell me, “I married him for life, not for lunch.” Her point to me was that when her husband retired, he needed to find something to do during the day.

Retirement often brings relief, excitement, and the long-awaited chance to reclaim your time. But for many couples or households, it also brings an unexpected guest: tension.

One of the most powerful questions I've used in an executive coaching session is “Does your calendar reflect what you value?” It’s true. Our time is often a reflection of our priorities, our habits, and sometimes… our autopilot. Retirement gives you a rare opportunity to take back your calendar—and make it mean something.