Who’s Your Mirror Friend?

I spend a decent amount of time envisioning what I'd like my future to resemble, sometimes (unfortunately) to the point where the pondering excessively delays the enacting of said future.

I begin by distinguishing between needs and wants. Being a dirtbag at heart, the needs are few.

Next I factor in how I'll need to modify my needs to meet the needs of those I love, since that whole bachelor who could live in a youth hostel has not been my reality for the last decade and a half.

Some of those considerations in no particular order:

• I'd like to develop mastery of a creative form: music, sculpture, visual art, carpentry, literature? Still figuring it out.
• Once it's safe to resume, my wife and I would like to explore traveling 3-6 months per year during the empty nest stage of life - still a decade away.
• I'd like to preserve a home base in our high cost of living coastal California neighborhood - not the typical retiree strategy, but we've found a community of friends here and put down roots.
• For the first year of that empty nest aggressive travel, I'd want to rent out our home. This trial would help determine if we could either downsize to a smaller home or rent a condo nearby and still feel comfortable. Experience with family has shown that by the time it becomes obvious your home is too big, you tend to be too old to have the energy to downsize, so I want to get out ahead of this.
• When I leave medicine, there would be value to those I love in retaining the illusion of producing income, even if the math would not necessarily require it. Direct real estate investment would offer an intellectual challenge while providing the desired cover from charges of becoming a vagabond.
• Maintaining a vagabond lifestyle would be entirely compatible with managing real estate. I could develop a competence and the ability to manage it remotely while traveling is appealing.
• One more bonus: real estate investors anecdotally seem to retain acumen well into old age. A mental fitness dividend?

This fantasy future excites me, but has needed for some time to be tested by a more reality-based thinker. Fortunately, a fellow finance geek who also happens to be a long-time mentor in medicine generously stepped up to the plate last week.

My friend spent an hour and a half prodding, poking and otherwise stress-testing my ideas. Revealing these tentative plans for critical review by a trusted friend was not easy, but this friend has a track record of providing sage counsel at different points over my career.

An additional bonus: he retired in the past year, making his insights all the more valuable.

Fortunately, he concluded that my processes seemed sound and the plan passed his sniff test.

As my exit strategy from medicine begins to take shape, holding the plan up to a mirror friend has been a critical piece in giving form to what my Act Two will entail.

Can you think of a mirror friend you'd ask to serve in this role as you plan your future?