The Next Chapter

After going through The List we picked the second most challenging option – moving across state lines to the barrier islands of Outer Banks in North Carolina. The most challenging option would be moving to Costa Rica which we ruled out, at least for now. Living on the Outer Banks may not be as cool as somewhere on the beaches of Costa Rica but it sure beats staying in a landlocked city where we are now. Continue Reading

Lifestyle Deflation

Wanna date yourself? Start talking about landlines, corded phones and beepers. I had all three and spent a disproportionate amount of income on them back in the day. Every self-respecting busboy needs a beeper! Owners of the German restaurant paid me $2 per hour plus a share of waiter’s tips for a total of $5 per hour on average. A beeper cost $50 so I had to bus tables for 10 hours just to buy it . The service was $10 per month so add another 2 hours of work. Of course what teenager would ever look at this rationally? Continue Reading

Real Estate Moves

One night back in 2009 we were driving on I95 to visit family in New York. As we passed yet another cop sitting in the median I had an idea: what if I could mark a cop’s location on the GPS map and share it, in real-time, with the cars behind us? Imagine how valuable would it be to have this information as you drive? As you approached the police trap your GPS could flash a reminder to check the speed. Smartphones were becoming widespread so how hard would it be to get them all connected? I had no clue how to get that idea off the ground so I filed it under “someday” and forgot about it… A few years later I learned about Waze – an app that had this and other crowdsourcing features built-in. Google bought Waze for almost 1 billion dollars in 2013.  Continue Reading

Pura Vida 2020

Ever since our son was born five years ago I’ve been thinking about The Great Escape. Something changed at the hospital when I held him for the first time. There is a clear line – the Before and the After. Everyone said it would be life changing but I didn’t understand just what that meant, for me. I didn’t think it would be this life changing. Something clicked that made me realize what really matters in life. The job, the career, the house, the material possessions all took on a different meaning. The concept of Enough made its first appearance. Escaping the rat race became The Mission. This year we will pull the trigger on something that will change our comfortable suburban 9-5 life forever. Continue Reading

Where Do We Go From Here?

To summarize last post: feeling burnt out at work, no one knows how much time they have left, time is more important than money… At least after you have investments working for you. The only reason these conversations are even possible is because we’re slowly closing in on Financial independence (FI). Two decades of work and (mostly) smart investment decisions are finally paying off. Years of prioritizing savings over spending should soon make having to trade time for money optional. So what’s the plan? Continue Reading

Why

To understand where you’re going you need to understand where you came from. After working 16 years straight in IT I’m starting to feel burnt out. It was fun working at a consulting firm after grad school. Every 6 months brought a new client, a new challenge. I was assigned to projects in Florida and Belize during what would’ve been cold winter months back home, which worked out nicely. There was also a lot to learn as a junior IT consultant. Days were anything but routine. Continue Reading

Adult Conversation

Kids are excellent at monopolizing the time to the point where there’s very little time left to actually think about anything else. Between a full-time job, the commute, the daycare hustle and other daily chores it’s hard to find that uninterrupted moment where you can sit down and really figure things out. When we’re home, our lives revolve around our son – because we love him, obviously, but also because we feel guilty about seeing him only 2 hours during an average weekday. He is in daycare and we are at work. Continue Reading

Reevaluate

My best friend – let’s call him John – lives on Long Island, New York. Recently John hit a rough patch, deciding to separate from his wife after just two years of marriage. They don’t have kids or own a house together so it should be pretty straightforward, financially, to go through a divorce. As it often happens after a major life event, John is ready to make some other changes in his life. This story is about two small but financially significant changes that transpired. Continue Reading