I can’t say I’ve ever had “5 year plans” and even I did, facts on the ground change so fast, my plans would change.

I’ve been working since 1996. But without going into ancient history, in 2008, I had spent the last 9 years at my second job, became an expert beginner, been divorced for two years, and had 5 mortgages between my home and two rental properties that were underwater by about a $250K.

I was also teaching fitness classes part time to make up the gap - that was suppose just be a hobby.

Then my plan was to get out from under all of that mess. I didn’t know how or have a timeline. But it started with getting a job where I could get exposed to modern development practices (done after 3 months and a lot of prep work), stopped teaching so much (just kept my favorite classes where my friends were), and walked away from five mortgages and wrecked my credit (everyone was doing “strategic defaults” back then).

One thing I didn’t “plan” for was to meet and marry my future wife and become a father to pre-teens by 2013. I’m still married, boys are grown. That by itself changed my goals.

By 2013, I was still about 25% under paid even for an enterprise “senior” [sic] dev in Atlanta and still digging myself out of my financial mess while supporting a family.

My goal by then was to develop the soft skills and hard skills to be a team lead - again no timeline.

Then in 2016, my goal was for us to move and work for a much better paying tech company after 2020 when my youngest graduated from high school. Even that changed to I would rather just not move and get into customer facing cloud consulting (not staff aug) after 2020 when I thought I would have to travel a lot (who could have predicted a worldwide pandemic??).

Well both fell into my lap in mid 2020 - customer facing cloud consulting and BigTech and I didn’t have to move when I got a job at AWS working in Professional Services. I didn’t even know the department existed. Again not planned.

2020 my plan was to work for Amazon for four years, pay off debt, save some money and work for a smaller consulting firm. I knew three months after I got there that I definitely didn’t have the stomach for BigTech long term. This was the only 5 year plan that worked out more or less as I wanted (staff consultant for a reputable mid sized company).

Even then, I never thought in 5 years, we would decide to sell our house in the burbs, downsize and move to state tax free, much better weather Florida