Outside of the house’s front window my green Chinese Vespa knockoff leaned over on its kick stand gleaming under the San Diego sun. The dining room table where I sat fingering the label to my beer was full of paperwork. I’d orchestrated a complex and huge logistical masterplan for my months long trip through Europe and Asia. Trains picked. Hotels booked. Flights purchased. Little did I know at the time that this would lead to me to retiring in my forties.

My wife and I just quit work a few days prior and we were set to go on a trip that would start in Madrid and end in Tokyo. I’d no idea at the time, at the age of 27, that I’d actually set in motion a plan to retire in my forties. It was this trip, this quitting work, this planning and executing a grand plan to make it happen, that set the ball rolling and led me sitting here typing at a keyboard on my blog today.

You see, the trip never truly ended in Tokyo. Instead, the seed to give up bowing down to American consumer culture society and “normalcy” had been gently inserted into the fertile tissue of my mind.

I remember lamenting to my father about how difficult it was to get my Russian Visa. Of all the people in my life who thought I might be a little crazy for this plan of mine, my father was at the top of the list. Quitting work was bad enough in his head down hard working baby boomer eyes. But to purposely strive and pay good money to visit a country, who for my father’s entire life had been the enemy, must have seemed insane to him.

“Why do you want to go to Russia so badly?” He finally asked me.

Why did I want to go?

I had no clue why this country called so strongly to me. Growing up I had a huge National Geographic map plastered on the wall by my bed. Each night I would stare up at it and my eyes would pull themselves of their own accord, towards that hulking land mass with the black print Soviet Union across it. It felt so mysterious. And the mystery only grew after learning more about the world.

How could a country be so massive that it could swallow up the world’s greatest armies in both the 19th and 20th centuries and spit them out defeated and beaten? Who were these people who defeated Hitler? Who did away with serfdom and monarchies in exchange for communism? Who could produced a writer such as Tolstoy? A leader today such as Putin?

Why did it draw me?

I didn’t have an answer. And wouldn’t have an answer till I was standing in the middle of the Red Square in Moscow with my wife.

It was then, in that frozen square in January of 2011, that felt all of the weight and anxieties of planning a giant trip, quitting work, questioning my rationality, finally melt away. I’d succeeded. I’d saved money, quit work, and made it happen myself. As I stood there in that square I saw that old National Geographic map on my childhood bedroom’s wall and the tiny black star that signified Moscow. A speck amid the mass of land on the far side of the world. There I was.

The feeling of accomplishing a long standing dream is like no other. It was so great that when that trip ended, my wife and I quit work again in 2012 for another trip.

In 2008 I lost everything. This is the year that I got laid off in the wake of the Great Recession, lost my apartment, broke up with my live in girlfriend, spent 6 months in jail, and essentially hit rock bottom. I’d gone from having what I thought was a budding career, a life where I could take care of myself, to having to move back into my parents home to get back onto my feet at the age of 25.

Hitting bottom at the age of 25 opened my eyes. While that was the worst year of my life, it turned out, in retrospect, to be the best year for many reasons.

I needed that fucked up year.

I needed to see what lay on the other end of the choices I’d been making at the time; four concrete walls, a cell mate getting 50 to life for murder, a realization of who visits you or takes your calls while locked away from society. I needed to get rid of everything in my apartment, throw away my precious goods that couldn’t fit in my storage unit, put my life into rubber bins and boxes and close the door and lock it away.

More importantly, losing it all at 25 allowed me to see that you can start over if need be and still be successful.

Because in reality I hadn’t lost it all, I’d lost enough.

Enough to claw my way back. My small money tree was withered and near death, but hung onto enough life that I could nurture it back and allow it to blossom to what it is today.

Retiring In My Forties

So here I am again, this time at the young age of 39, with plans to pack it all away again in roughly two years time; this time for good. For some context, our reason for FIRE is full time travel. So for us, FIRE means time to leave and fulfill that long standing dream my wife and I have spoken about for years. It means retiring in my forties.

It’s been 10 years now since I’d taken my last long trip where I quit work to travel. 10 years straight of working and commuting. And in that time I’ve purchased a house, had two kids, and cultivated a successful career. I live in a wonderful neighborhood. My housing costs for my single family home is incredibly cheaper than the current going rate of two bedroom apartments in my town. I’ve been able to invest heavily into a raging bull market for the past few years. I’m healthy (for the most part)–I’ve since had some more health issues that have made me question everything and made me re-evaluate health coverage in retirement.

I’m extremely grateful for my current situation. I know what I have is not easy to come by. I have a good thing going at the moment.

So why even consider giving up daily life in America to go travel? Why not just FIRE and chill at home instead of travel and having to pack my things away and pull the kids out of school?

I have what I need. Seeds of doubt are slowly creeping up around me as I stop and take a mindful look around at what I have.

The bigger question is what happens when we stop challenging ourselves because things are comfortable and we’re afraid to disturb that comfort? I used to negatively judge people who I felt were trapped in their comfort bubbles, unwilling to take on change or difficult things. People who I might have judged (wrongly or rightly) have settled on a middle ground. Neither living to their true potential nor suffering unduly from taking a big risk.

Now I feel myself being hugged by the comfort bubble. I feel myself considering what if I just settle for what I’ve achieved in my thirties. What’s wrong with that?

Nothing of course. Except that I may have to deal with myself decades from now and feel a giant rock of guilt or regret land on my chest. I’ll never know what could have been.

In the past, the goal when I’d stepped away for extended time to travel was always to come back and work. This time it’s much different. There’s more to lose if I fail, since two young lives depend on the decision to retire early. This is why my attitude towards an FI Number has evolved over time (this fellow blogger who has since stopped writing, changed my mind on this by a comment he once made to me) into needing an FI Range. There’s no magic FI number that will turn some light green for me. There’s only a range, a mean level of confidence. Like the ocean tides, I only need to ensure I’m aware of the ebb and flood, have a chart handy and course plotted.

At any rate, the light is red at the moment. I don’t have enough to put in my notice at work. But I have enough that I don’t ever need to save another dime for retirement if I choose to just work and live the “normal” 9-5 life another ten or fifteen years.

With markets trudging along sideways, I’ve found myself looking less at my net worth. Reading less about finance. Writing less. Reading more fiction. Sailing more. Focusing on my day job more. I care less about money and more about today.

I’m still investing heavily. Near 50% of our net income is being put into VTSAX, VFIAX, VFWAX, and VSGAX.

Is 2025 still the year I’ll retire? 2026?

I don’t know. But in any case, the war against worrying about money is turning in my favor.