Back in 1868, my ancestors made the decision to seek out new financial opportunities in another part of the country. They set off from the small town of Independence, Missouri on a treacherous journey to the Willamette Valley in Oregon. Along the way, they encountered all sorts of economic perils and fiscal woes. With the help of some of my friends in the personal finance blogosphere, this week’s Carnival of Personal Finance showcases the journal of my great-great-great grandfather and his family’s trek along the Oregon Trail in search of a better, higher-paying life…

March 1, 1868

Our financial situation is starting to look pretty grim here in Boston. There are more and more bankers popping up every day, and I’m getting absolutely killed by these online savings accounts that offer ridiculously high interest rates. I don’t know how they do it! At first I thought it was all just a scam, but it looks like ING Direct really offers 4.40% APY.

The situation has only been complicated by the fact that Emma was laid off from her job at the bakery. We’ve been going three months now on just one income, and that’s proving to be a difficult thing to do with three kids to feed. Barely able to make ends meet, we’re not keeping any of the money we earn. Sooner or later, we’re bound to break the cardinal rule of sound personal finance by spending more than we earn!

So we made a decision as a family to try our luck in a new place. I did some research and found that I could be making a lot more money out West. Not only that, but there are more family-friendly workplaces, and there are even municipal bonds effectively yielding 7.12% APY!

We’ll be setting off for Independence, Missouri in a couple of days. And from there, it’s on to our new home in Oregon. We know the journey will be hard, and it’ll definitely be a test of our financial cunning to make it across half the country through wilderness on just $1,600, but I think we can pull it off if we work together as a fiscally responsible family.

March 30, 1868

We’ve finally made it to Independence. If only the trip to Oregon would be as simple as the one from Boston to Missouri! We’re planning to roll out with the next caravan of settlers destined for Oregon tomorrow. In the meantime, it’s off to the General Store to pick up some supplies.

March 31, 1868

As much stuff as we bought at the store, we should only be grocery shopping once a year! We ended up spending almost three-quarters of our funds, but we’re fully loaded with supplies, we have a wagon with 20 oxen ready to go, and we have enough clothes, food, and spare parts to make it to Oregon and back again.

I’m a little suspicious of that store owner, though. For instance, the store had a special on oxen where they were 25% off. Fortunately I found out before buying them that the 25% off also applied to the oxen–they only had three legs! So I decided to go with quality over price and opted for 20 four-legged oxen.

And the whole time I was in the store, there was an employee following me around and taking notes. It was rather creepy, but afterward I found out from another customer that the store was tracking customer traffic to improve sales data.

We only have about $400 left to our name, but that and our load of supplies should be enough to get us to Oregon. I’m going to turn in early tonight to prepare for the first day of the journey tomorrow.

April 1, 1868

Our first day on the trail, we met another family originally from Chicago. They had bought a house in Chicago, but it had lots of previous claims and was uninsurable. They’re upset they didn’t look up the claims history on the property before they purchased. So they sold the house, packed up, and started heading west instead.

April 3, 1868

I decided to buy a mattress for the wagon, but I think I got ripped off. Then again, I don’t know the first thing about how to buy a mattress. Oh well. At least our ride will be a little more comfortable.

April 11, 1868

We’ve arrived at the Kansas River crossing. The ferry operator is gouging us poor settlers, but there’s no way I’m coughing up five bucks just to cross the river. Besides, it’s only a few feet deep, so we’ll just ford it.

April 12, 1868

Heh. Oops.

April 14, 1868

I learned how to use Quicken 1868 to update our wagon maintenance records. Quite handy!

April 17, 1868

Tom, our oldest son, is suffering from student loan debt. He should have returned that extra loan money he didn’t really need to pay for college instead of spending it. Now if only there were an easy way to pay back student loans…

April 22, 1868

We’re almost to Fort Kearney. Today we met a couple who’ve been together for years and have children but aren’t married. At first, I suspected they didn’t marry because of the advantages of a couple remaining unmarried, but then I found out they were brother and sister and couldn’t legally get married in their home state and were heading to Oregon to see if they could get the job done there.

April 23, 1868

We made it to Fort Kearney. While we made camp, somebody offered to trade us some Apple stock for an ox. I told him no because I heard investing in Apple may not be such a great idea right now. While Apple is a socially responsible company, I feel they’re simply too overvalued.

April 27, 1868

I’ve been thinking a lot lately about what things will be like once we make it to Oregon. Sure, it’s still months off, but a guy can dream, can’t he?

I think the first thing I’ll do is change jobs. Maybe I’ll become a money manager, one who people can trust. And maybe I’ll be able to reach our Roth IRA contribution limits, possibly even end up saving 12% of my salary for retirement. And for once, we’ll start to accumulate savings instead of living paycheck to paycheck. Yes, that would be quite nice–to be able to secure my retirement without stress or worries.

May 2, 1868

Emma’s suffering from high credit card debt. I offered her some tips to help avoid and manage credit card debt in the future, but she refused them. So we rested for four days instead; from what I hear, that seems to cure just about everything.

May 7, 1868

Well, we made it to a big rock that looks like a chimney. While we were there, we talked to a man who was selling oxenless wagons. Apparently they run on some sort of mechanical engine. I doubt the idea will take off, and I suspect this guy is just an affiliate for some crazy entrepreneur getting paid for each product he sells.

May 16, 1868

A thief stole 48 bullets from our wagon. Stupid punk.

May 17, 1868

That thief came back again and tried to steal more bullets. This time he only stole two of them–the ones I shot into his leg. I don’t think he’ll be bothering us anymore.

May 22, 1868

Haha, stole your journal!

May 24, 1868

The thief stole our journal, but we got it back. Increased pace to “faster than thief can walk.”

May 27, 1868

Today, we ran across a rich family making the journey to Oregon. They mentioned how they had sold off some of their stock and donated the proceeds to help out displaced Indians. I told them that it’s much better all around to donate appreciated securities directly instead. Upon hearing this, the family was quite distraught, so they gave away all their clothes, too.

June 1, 1868

I remember when I first became a banker. I really wanted to take my time deciding my future career, but someone told me not to waste too much time thinking about my first career choice. And here I am, 15 years later, still a banker. I should’ve been a carpenter instead.

June 6, 1868

Another wagon collided into ours and damaged our wagon tongue. The other driver’s insurance is paying for a rental wagon while they try to recondition our wagon tongue instead of just replacing it.

June 12, 1868

Another frugal-minded traveller we encountered today passed on 25 tips for saving money. But when he mentioned how much money we could save if we used public transportation instead, I pointed out that we were in the middle of the freakin’ wilderness.

June 14, 1868

Sam has cholera. We successfully negotiated down the price of his doctor’s bill, but next time we’ll probably just amputate. Or is that another disease I’m thinking of?

And fortunately the generic prescription he needed was only $4 at Wal-Mart.

June 21, 1868

Went hunting. Shot two deer. They were rather pale for deer, but they were still quite tasty.

June 27, 1868

The wagon caught fire and we lost most of our clothes. But that’s okay; it’s so hot out that clothes don’t do us much good anyway. And yes, I’m journaling naked.

July 4, 1868

Happy Independence Day! I am continuing to celebrate my independence from pants this week because it’s still very hot.

Emma’s credit card debt is getting worse. I found out today she hasn’t been reading her credit card statements. How can someone spend $400 on knitting yarn??? Come on! I don’t see any sweaters made out of gold around here…

Even worse, she’s been paying off her smaller card balances first instead of focusing on those with higher interest rates. I think she’s been reading too much Dave Ramsey.

Once we reach the next fort, I’m planning to submit Emma to the No Credit Needed Network so she can start tracking her debt reduction goals.

July 9, 1868

We bumped into a family that wanted to trade for baby formula. We had store-brand formula to offer which we think is just as good, but they weren’t interested. Oh well. That just means more formula for me!

July 15, 1868

I set up a bill-paying simplification strategy. Now we pay most of our bills online automatically, though it’s a bit hard to get a decent internet signal out here in the mountains… in 1868.

July 20, 1868

Time is flying and we still have far to go. Worse, we have little money left. If only spending time were as easy as spending money!

July 23, 1868

Thanks in part to our impending financial crisis, Emma seems to be building a better relationship with money. She’s learning more about our money and how to make wise financial decisions, and she’s starting to realize that personal integrity is more important than buying stuff. She still has some trouble overcoming some of the myths of saving money, but I think we can work on that.

August 1, 1868

A Shoshoni guide offered to take us across the river in exchange for three sets of clothing. When I told him that we only had three sets left but I didn’t mind giving up the one I was wearing, he took us across free of charge.

August 5, 1868

We’re getting really low on funds. Hopefully we’ll be able to buy a home with zero down payment in Oregon. And once lots of people start moving to Oregon, the property value of our home will skyrocket, and we’ll take out a HELOC and buy a Porsche if they’ve been invented by then.

Then again, once we get to Oregon, we’re going to be pretty darn broke. Maybe we should wait to buy.

August 13, 1868

We’re running low on food, so we may have to take drastic measures to save money on food. Maybe we’ll organize a pot luck at the next fort.

August 17, 1868

I finally enrolled us in a health savings account (HSA). Now I can pay for Sam’s snake-bite medicine with pre-tax dollars.

August 21, 1868

We’re practically down to our last dollar. Once we get to Oregon, we could invest what money we have left, but I wonder how long it will take for our money to double.

August 22, 1868

Our freaking brilliant daughter Jill traded 200 pounds of food for a Beanie Baby. I don’t care how much the thing is worth; you can’t eat a Beanie Baby, Jill.

August 23, 1868

Jill has a broken leg. We’ve increased the wagon’s pace to “faster than Jill can hop along.” Beanie Baby. Grr…

August 30, 1868

We’re almost to the Barlow Toll Road. I’ll gladly use the few dollars we have left to pay the toll rather than raft down the rock-filled Columbia River.

September 5, 1868

So much for buckling down on debt! Emma just spent the last of our money on a Ralph Lauren wagon cover. Looks like we can’t afford the Barlow Toll Road anymore. I sure do hope nothing happens to my spendthrift of a wife while we’re rafting down the dangerous river instead of taking the nice, safe toll road…

September 7, 1868

Rollin’. Rollin’. Rollin’ down the river…

Heh. Oops.

September 12, 1868

Tom and I have made it safely to the Willamette Valley in Oregon. Of course we’ll miss Mrs. Spendaholic, Miss Beanie Baby, and Little Mr. Sick-All-The-Time, but I still can’t help but feel that things are finally looking up.

The first item on our list is to find a nice plot of land to call our new home. Fortunately there’s no need for a land survey for our home; we just pick a hill and it’s ours!

September 27, 1868

So… as it turns out, the only folks who are making it here from Missouri are all the bankers. Right now, Willamette Valley has 690 bankers, one carpenter, and nobody else. As a result, the average home price in Willamette Valley has jumped to $2 million. Tom and I have decided to pack up again and head south to California. We hear housing is cheap there, and they don’t even expect very high housing prices there anytime in the next couple of centuries!

Next week’s edition of the Carnival will be hosted at Journey to Financial Freedom.