I want to live in a different city every 30 days

For 20 years, I've been putting nuts in the tree. I've been doing it because, just like you, someone told me to. "Make sure you save for the future, young man," some random person said. So I did. And like you, my vision of retirement was as foggy as the minds' of a bachelor party leaving Vegas on a 7am flight.

Let me take you back a bit. When I figured out soon-to-be-Mrs. Planner was the person for me, I began to save for an engagement ring. Make fun of me if you want (I'm a ginger, I'm used to it), but having a significant purpose propelled me toward my goal. Saving thousands of dollars as a college student wasn't exactly easy. I was a plumber's assistant. Picture me 20 years younger, a wee bit manlier, and about 40 lbs lighter. I made good money and I saved most of it. I was 100 percent motivated by my desire to buy soon-to-be-Mrs. Planner a ring.

There was no inner-struggle.

I wan't wishy washy. I wasn't conflicted. It was on. Done deal. It was just a matter of time.

Retirement planning never feels that way, especially when you first start saving for retirement. It seems, well, like an obligation, if not a speculative bet on living past 50. Short of knowing it's the right thing to do, there isn't much pleasure in saving for an event which is decades away. Truthfully, I get much more pleasure funding my children's 529 college savings plans than I do my own retirement. I'm motivated to give them the same debt-free college experience I had. I visualize it. I can almost feel the future satisfaction. It's visceral.

Until about four or five months ago, saving for retirement felt like nothing. But one day when I was on a flight to who-knows-where, it hit me - when I retire I want to sell my house, downsize by 75 percent, pack a couple of suitcases, and live in wonderful places around the world with Mrs. Planner. I want to live as a Tuscan, in Tuscany for a month. I want to live as a whatever the hell you call someone who lives in Santorini, in Santorini for a month. These aren't vacations, they're my life.

Wakeup whenever people in that area wakeup, go have the local breakfast beverage, and live modestly experiencing the culture. Then after a month or so, peace the hell out to the next place. Swing back to where my kids live every once in a while as needed, and experience live as a modern nomad, absent possessions. I've done a bit of math, and I think we could do it for $3,500-$4,000/month in today's dollars.

This vision of the future has FINALLY brought purpose to my retirement preparation. In order for me to live my vision, I must payoff my mortgage prior to my kids' going to college, pay for their college outright (because it's important to me), max-out my retirement accounts religiously, and save non-qualified (non-retirement) funds because I plan on living this vision well before the age of 59 1/2 (when I'll gain access to my qualified retirement accounts).

Some people think freedom is having a bunch of money. After the last 20 years of digging into tens of thousands of financial lives, I've determined that for me, freedom is not needing money to live the life I want to live. Retirement is no longer just a long vacation in my mind. It's a chance for me to experience cultures from around the world with my best friend. The same best friend I worked in a plumbing shop for.

I'm not wishy washy. I'm not conflicted. It's on. Done deal. It's just a matter of time.