The Dream Purchase That Woke Me To Financial Reality

“Be careful what you wish for, you just might get it.” This phrase used to really bug me. It seemed meaningless and pessimistic. Then, I made a dream purchase and I understood because it led to my financial awakening. 

It was a crazy four months. I achieved something I’d always imagined doing. Then, I was consumed by a crushing paralyzing pressure. That feeling of despair led to changes that have made my life better than ever. 

While the above may seem dramatic, I can vividly remember each point. After all, it was only three years ago. 

You see, I did something financially stupid – I bought a vacation home. Stacked on top of owning an already ridiculously large house. Leaving me with virtually no money in the bank.

I trace my pursuit of financial independence back to that moment. Next week, I’ll publish the financial reality of my dumb “dream purchase.” Today, I’m going to focus on how my life has changed as a result. 

I think of this financial awakening in three phases:

• The Dream 
• The Despair
• The Decision 

The Dream

At some point in my chidhood, I decided owning a vacation home was a sign of financially security. As a child growing up poor, I was in awe of families who “went to the mountains” on weekends. In college, I had friends who would just invite me on a whim to go stay with them in a family member’s vacation home. It seemed the ultimate freedom.

My partner, TFI, had a similar concept of vacation home ownership. Having gone to private school, the kids with all the power had families that owned second homes. It was a sign of status. Something her low middle-class family never achieved.

I loved the idea of letting family members use a vacation home I owned. I wanted them to experience something we’d never collectively had. I dreamed of letting my mom, who had given up so much for us, use it whenever she liked. Combine that with a flawed belief that all real estate is an investment, and it was inevitable we’d end up with one.

Knowing what I know now, several years later, it’s embarrassing to admit. We bought a vacation home.

I’ve talked before about our saving grace during our lifestyle inflation period: We were dumb, but we weren’t reckless.

Thankfully, that was mostly true here as well. We saved for a solid downpayment. (Ironically, this period of saving was our first step toward controlling our spending.) We bought in partnership with another couple, and we considered potential for rental income. 

I’ll talk more in next week’s post about the mechanics of it all, but the end result was this: Two career, formerly broke educators, had a beautiful vacation home in a desirable location. We could even reasonably afford it.

Dream achieved. No longer a poor kid – I had arrived.

So, how does that turn into a financial wake-up call?

The Despair

(An Important Note – I feel incredibly lucky that my wake-up call was the result of a dream financial situation. As a child, I saw my mom struggle with money and know what real despair is like. My wake-up was nothing but a problem of privilege.)

At first it was exactly the dream I imagined. It felt truly exhilarating to go to our vacation home. I was able to let my mom use it. We had a list of family and friends we offered open weekends to. We’d budgeted accurately for the purchase and costs. It was set-up to bring in extra rental income.

The high lasted about three months. Coincidentally, during that time work also ramped up. The vacation home became an important monthly escape from my reality at work. We loved the location and peace we felt there – still do. That was never the issue.

While saving for the vacation home, we’d had significant extra money sitting in the bank and I’d felt almost financially secure for the first time in my life. Now, we’d depleted our savings and most of our extra income went to owning the home. Money felt tight again. The feeling of financial fear from my childhood grew strong again.

Still, my wife and I started talking about where we’d buy another place. (Yes – another vacation home!) Friends who’d stayed at the vacation place started asking us to include them in our next purchase. 

One day, our partner in the home called to talk about another real estate purchase. He’d “run some numbers” and thought we could make good money on this other vacation purchase. (We weren’t “making money” on the current one. A vacation home isn’t an investment.)

I hung up the phone and looked around the office I didn’t want to be in. (Work really sucked at the time.) Suddenly my future was clear.

I’d have a life with everything I wanted, but I’d rarely enjoy it. I’d be comfortable, but financial obligations would keep me working until well past normal retirement age. Worse, it would require me to stay in a high-stress job that I sometimes hated just so I could maintain the lifestyle. 

My life would have short periods of escape during which I was incredibly happy and free. Most of it though would feel like a trap – or at the very least a grind until I got to the next escape moment. 

My job would shift from a mission I willingly undertook to something I did only because I had to. I’d seen far too many educators reach that stage. 

The family I knew I’d have to support financially would become part of the trap and an obligation I’d resent. In short, everything I valued would become part of the trap.

I was living the American dream. And I didn’t see a way out.

The Decision

Now, this story is nothing new. It’s almost cliche for an early 40s professional to suddenly feel trapped by the reality they’ve created. (There are lots of unbearable novels and movies about this.) For me, it wasn’t about family or relationships. Or even my job. I liked those things – even the job (mostly.)

For me, it was all about my financial reality and loss of choice. I’d worked myself into what seemed like a street with only one way forward.

In response, I (also typically) started trying to figure out how I could get rich quick. Was there a way I could escape the trap simply by outearning it? 

I spent several weeks, desperately researching. I even considered some of the “investment” proposals other clueless friends were putting forward about real estate. I was a smart guy – maybe I could make the perfect investment.

It’s probably lucky that we’d just put most of our available cash into the vacation home, because I had no money to play with recklessly during this period. Instead, I started reading.

Somehow, probably because of the word millionaire, I stumbled onto a book called “The Automatic Millionaire”. Three years later, I don’t consider the book a must read of personal finance, but it gave me an important anchor and framework at the time.

It helped me to two important realizations:

1. Stop thinking short term. I could build a path to financial security over time. This stopped the despair.
2. We were earning plenty, we just needed to be purposeful. This gave me hope and purpose.

This was the moment of financial awakening. I poured myself into reading personal finance and financial independence books. I discovered financial independence blogs. Over a period of months, I worked on my wife and hoped she’d see our reality as I did.

We decided, together, to change our approach to life and money. We built our first financial independence plan. We’d get to financial independence in 14 years. A long way out, but still before most of our peers – certainly before I’d thought possible just a few days before.

It was a new world.

Now

It’s still motivating (and embarrassing) to think of that moment when I achieved a dream and then suddenly felt trapped. My financial awakening.

We still own the vacation home. Our initial partnership agreement had a required minimum holding time. We still love using it and have taken steps to mitigate the financial impact. The reality is, it’s probably a small financial plus at this point. We’ll definitely consider selling it after the holding period but it’s not inevitable.

I wouldn’t do it again, but I don’t regret it.

We have transformed the way we approach our money. We’ve reduced our housing costs, set financial goals that have gotten tighter and more aggressive each year, and achieved a seven-figure net worth. 

Life is pretty good. Our money is under our control. Rather than feeling trapped, I feel empowered. I know that work is on my terms.

“Be careful what you wish for, you just might get it.”

I understand that phrase better now. I got my dream. Then realized I didn’t really want it. But it’s led to something even better. It woke me to a nightmare reality that has now changed back to a dream.

How about you? Have you ever achieved a goal and realized it was the wrong one? How did you respond?

Or have you had your own financial awakening? If so what caused it?

Next: How We Are Buying a Vacation Home Without Spending a Fortune