Find Someone Who Knows Their Sh*t, Then Shut Up and Listen


It’s odd when you think about it: We were smart enough to know we needed someone with more experience in this area than we had, but at the same time we were dumb enough to throw almost all of his advice out the window.


Quick Note: Things are going well on this New York business trips in terms of me keeping up with the posts. The bad news is that I don’t have my art software and/or tools with me, so you get no fancy images at the top of the post today. I’ll add them retroactively when I get home this weekend.


We are very fortunate in that my wife and I have an Uncle who has been a Financial Advisor for the better part of 50 years. About two years before we hit our financial crisis, we reached out to him and asked for help in getting things in order. I think we had realized that we had kept the debt monster in the closet for far too long, and it was about to kick down the door and eat us in our sleep.

Our Uncle is a fantastic human, and so not only did he agree to sit down with us, but he agreed to provide long-term guidance free of charge.

Think about that for a moment: A person who is financially sound –wealthy in fact– with a healthy list of very successful clients, was 100% willing to provide guidance to us at absolutely no charge, and do so with no set end date. We could use him until we felt secure.

Pretty baller.

So we met with him and he started to advise us on a financial strategy. Up until that point, our investing knowledge consisted solely of blindly throwing money into a 401k each month and not much else. He started teaching us about diversification, opening up a Roth IRA, building a stock portfolio, and more. He also told us that we were making some silly mistakes with our money, such as throwing all of our cash into a vacation, versus saving part of it, even if it meant putting the vacation off a few months longer.

This man told us how to kill the monster in the closet.

We then promptly went out, ignored all of his advice, smothered ourselves in BBQ sauce, and laid down in front of the closet door and patiently waited.Read More »

A Fun Approach to Being Broke


“So this blog serves the purpose of creating what I feel is valuable entertainment, but it’s also a coping mechanism for me of sorts. After all, if I really stop to think about the fact that I have  OVER ONE HUNDRED THOUSAND DOLLARS in credit card debt, I’ll probably just pass out. However if I think about having that same amount of debt, but then see a cute little drawing of a guy with a shovel… It can’t be that bad right?”


First things first! As you can see, I’ve removed the stat tracker from the top of this post showing how much credit card debt I have remaining, and I have instead moved it over to the fancy new graphic on the side bar to the right over there.

I felt like it was cluttering up my posts to have that sucker at the top of each post, and since the numbers really don’t move from day to day, it was often just a stagnant piece of information that felt better served to the right.

As I was making the little graphic of the dude with the shovel on that chart, I got to thinking about whether or not my approach to debt is the right one. I don’t mean in terms of what I’m paying and where, but more in terms of the fact that I’ve created a semi-sweet, light and fluffy blog about effectively being broke.

I pepper the tops of posts like this one with fun little illustrations, and then spend several hundred words talking about just how close I came to losing my home and putting myself and my family in a really ugly situation. It can be quite the contrast!

Humor has always been a defense mechanism for me. When I get nervous, or when I am put in tense situations, I tend to crack a lot of jokes… usually of a self-deprecating nature. It’s something I’ve done since was a kid, and continue to do often as an adult. So if you ever happen to be in a situation with me where I am obviously desperate in my attempts to make the group I’m with laugh, chances are it’s because I feel WAY outside of my comfort zone.

I was up in the mountains once and had a guy pull a revolver on me and two of my friends. True story. We were driving up to a keg party in the mountains, and as we crested up over a hill in my pickup, there he was on horseback, pistol drawn, pointing it directly at my face. He then told us that his son had put his pickup in a ditch about a mile up the road and needed to be pulled out. The gun was just a “motivator” as he called it. To make a long story short, I was so scared and cracked so many jokes as a result that by the end of the night both the son and the father were standing at a campfire with us drinking beers and laughing.

Again… defense mechanism.

So as you can imagine, when it comes to writing a blog chronicling the really dumb situation I put myself in, I try to find to add some levity.Read More »

In the Hole

Hi, my name is Dave Johnson. Let me begin the very first post of this blog by saying that I don’t even have enough money in my pocket right now to pay for the premium hosting for this blog. That’s around $3 bucks a month for those of you wondering.

The kicker? I make well over six figures a year.

If that sounds hard to believe, let me double down on the craziness for just a moment.

Three weeks ago we were at a high school lacrosse game. My son plays lacrosse in grade school, and we were asked with a group of parents to turn out with our young players to support our high school team. We love the sport, so we made the commitment and attended with our kids.

At the game, a group of parents had set up a concession stand to sell simple snacks to raise money for the lacrosse club. One of the items they had for sale was pizza by the slice. $2.50 per slice. What a steal!

And yet my wife and I were too concerned about finances to partake. We bought our son a single slice and we waited until we got home to find something else to eat. We couldn’t bring ourselves to spending $5 dollars on a slice of pizza on a six figure income, because we weren’t even convinced we could pay all of our bills that month.

How in the hell does this happen?

I’ll get to that in future posts, but I wanted to establish a baseline of where I’m coming from on this journey, and I want anyone reading to know that they’re not alone if they feel the crippling weight of debt and financial distress. My realization of just how bad things were came around 6 months ago (I’ll get to that in a future post), and there have been times where I have wanted to curl up into a ball and lay there until the banks came and took the roof from over my head.

That’s a difficult post for me to write and allow you to read. It’s demoralizing. It’s embarrassing. It’s shameful. It’s also a wake-up call for me that if I can get into a financial hole like this one, a lot of people like me can too. I’ve never been arrested, I’ve never so much as had a speeding ticket. I am a married father of two who tries really hard to give his family everything they could ever ask for, and in doing so I made some really stupid decisions that got me into this hole. With every credit card I took it was like a bank handing me a new shovel and saying, “Those others look a bit worn down. Try this bad boy on for size!”

So if you’re like me, standing in a pretty deep hole with more shovels than you can hold right now, keep checking back in. I’m going to figure a way out, and I hope you pick up some tips of your own along the way that help you to do the same.

I’m tired of this hole. It’s lead to nothing but callused hands less and less sunlight.

Time to dig out.