I hope you’re having a beautiful day. ♡
We’re celebrating another ¤ JohnnyO Gratitude Day! ¤

Worst Case Scenario
I am on the cusp, the cusp of greatness. But then, greatness is such a curious thing.
I say it often, and it comes from both my martial arts training and my experience as a soccer player: “If you have to think, you are too late.”
I have also heard it said that being underestimated is an underestimated Superpower.
Sometimes, not knowing what you don’t know, and consequently overthinking things, can be an advantage. You don’t know all the obstacles, so you just make it happen.
So given my experience and my long-term track record of envisioning concepts and businesses long before they became a reality, and, in fact, watching major deals in which I was involved in happen without me, witness Realtor.com and Rocket Mortgage. It would be no surprise if the same thing happened again.
But the beauty of this day is that the writing prompt has given me the privilege and opportunity to reframe my mindset and prepare a pilot’s checklist before I am cleared for flight. I do know that I will need stellar teammates/crew members.
To summarize quickly, I have been working for some time now to redefine and reimagine different types of real estate ownership and financing vehicles so we can all live together, work together, eat together, and support the multi-generational entirety of our communities.
I have personally achieved considerable one-off, individual successes over the years going all the way back to the eighties: one deal here, another there.
But now I have the opportunity to present to the University of Denver. In this opportunity, we would take existing student housing and convert it into as many as 90 2-bedroom units, designed for multigenerational occupancy within each unit. This is a profound opportunity.
When I can negotiate and assemble the team to put this deal together, it will not only be a monumental real estate transaction for me and everyone involved; it will set a high bar for social change for Universities across the United States.
Now, to the prompt. What could possibly go wrong? How about an acrostic! Everything! Ten letters in the word and ten different shitshow deal-breaking scenarios for each letter.
Let’s start with the fact that my recent portfolio is only trees and parks. Beautiful trees, in lavish parks. But living in those trees and parks as a member of the unhoused community is not exactly a line item on my resume. Or is it? Talk about a reframe!
But let’s not dwell on the negative; what could go right? The fact that I even have the opportunity to discuss such an endeavor, much less close it, states that in no uncertain terms, “My God’s got me” on this, my 2107th day of Sobriety. 3 sevens is 21. How about that?
From Rick Rubin, The Creative Act, A Way of Being
“If you have an idea you’re excited about and you don’t bring it to life, it’s not uncommon for the idea to find its voice through another maker. This isn’t because the other artist stole your idea, but because the idea’s time has come.”
So, reframing my thinking, attuned thought by attuned thought, the opportunity to TRY and make this deal at this stage of my life is a blessing beyond my wildest dreams.
I will show up each day and do my best to be my best, at 68 years young in my “rewirement”
I will act as though being underestimated IS MY SUPERPOWER.
I will step in the box, adjust my gloves, and hit it out, baby — after all, it is October.
If I don’t succeed, I will know I did my best. I will enjoy the privilege of knowing I planted at least some of the seeds that brought this magical social change to fruition, the greatest service and self-care I can imagine.
Blessings to you all.
-John Olander