My theme for 2019 was: live the good life. 

After a raging bull market since 2009, I’ve started to get more comfortable spending more on a better life rather than always trying to save and invest as much as possible.

2018 was a bad year for the stock market. At one point in 4Q2018, I was probably down ~$500,000, even with my relatively conservative public investment portfolio. However, we recovered tremendously in 2019. With the rebound, I figured, better to start spending our money than lose it all in the market again!

Here’s a review of my goals for 2019. It’s a really long post because I can’t help but reflect during the holidays. The beginning portion is what I wrote at the start of 2019. The italics portion is my review.

When I was in high school, I got in a lot of trouble. As a result, I often wondered if anybody would ever give me a chance at life. Because I ended up receiving multiple chances despite my screw ups, I’ve learned to be more thankful and not take things for granted. I also developed an affinity for people who also had a rough time growing up, but found a way to make things work.

The following is a guest post from Bill, a man who spent 10 years in prison before getting on the path to financial freedom. Hopefully his post will give you the motivation to stick with things when times are tough and not lose faith that everything will turn out OK in the end.

I walked into my jail cell. I heard the door close behind me. I had just been sentenced to ten years in prison. It was my first time ever in trouble and I was in shock. I didn’t know what to think.

The emotions came in horrible waves. I felt an overwhelming sense of relief at first. The night before, my attorney had braced me with the reality that the negotiations with the district attorney had not gone well, and that the state was going to be recommending 20 years of incarceration.

In court that day, the judged looked down at me in handcuffs and I heard him read his sentence in shock: “The state sentences you to ten years in prison. Due to sentencing guidelines, you will have no chance at early release or parole. Good luck to you.”

That night the harsh reality of being sentenced to 10 years in prison settled in my mind like slow mental torture. How was I going to survive it? How could I hold onto my sanity with such a horrible future ahead of me?

I reflected how I found myself in this position. I had first used drugs when I was 14, smoked a joint, and liked it. For years, drugs and parties provided an escape from my otherwise normal life, and drugs provided me a fantasy of happiness I thought was real. But that illusion was shattered after a friend left my college apartment one night after partying, overdosed, and died in his sleep.

The next morning, I was arrested and charged with “reckless homicide by delivery of a controlled substance.” I had provided some of the drugs that contributed to his death that night, and that’s all the state had to prove to convict me of the charge. 

I had gotten high hundreds, or thousands of times, but I never meant to harm anyone. It was a terrible accident. Everyone involved in the tragedy lost. I learned that when you play with fire, you don’t get to decide how badly you get burned. 

Life as I knew it was over. No one was going to fight for a comeback for me.  My life was now a mission to prove that I was a better human being than the one they threw away for a decade.

After writing The Bear Market Checklist, I thought I’d follow my own advice and do a mid-year review. The last thing I want is to get broadsided because things feel so good.

So far, this year has been solid on the financial front. I haven’t felt this good since 2007, the year before everything fell to pieces.

I truly hope all of you are benefitting from this extraordinary bull market as well. 4Q2018 was such a dicey time period. It was hard for me to imagine things turning out as well they have since.

I’ve been trying to live it up, especially now that my boy is over two years old and is able to communicate better. We’re going on more trips and doing more things in public settings.

I’m also trying to be much more appreciative of the good times by constantly reflecting on the past. The more we can show gratitude, the better our lives will get.

Here is my 2019 mid-year update.