I stopped working a corporate job but I seem to be busier than ever. There seems to be an endless list of chores and things I need to do so I decided to write and share some of those things here.
Home De-cluttering & Remodel
Home de-cluttering seems to be an endless activity. I have a two story residence with 5 bedrooms and they were all full of “stuff” and no matter how much stuff gets tossed it never seems to be enough. My plan for 2027 is to be a lot more aggressive with tossing and giving away things.
My wife and I worked this past weekend to try to clear a closet and a bedroom. I donated about 50 lbs of clothing that no longer fit me. I tried on a tuxedo I bought in 2016 and I’m swimming in it now. Going to take it to the tailor to see if it can be salvaged along with some other very expensive suits. With my weight loss I’ve shrunk 5 inches on my waistline and dropped to shirt sizes. We also got rid of hundreds of books. We got $75 at half-price books for them.
After de-cluttering I need to remodel the upstairs of our home. New decking, flooring, painting and maybe upgrade the light fixtures.
Travel
I had an amazing time traveling Europe for 3.5 months in 2026 and I want to repeat that experience in 2027 and perhaps be gone for 6 to 9 months. I’d love to be gone the whole year but with the remodel and other things I need to get done it probably won’t be possible. For 2027, I am tentatively planning on traveling throughout Asia but I haven’t booked a single thing and it’s subject to change based on geo-political risk and cost.
I do have a trip booked to the Eastern Hemisphere for December to meet up with family for the holidays.
Hermes and AI Agents
I plan on continuing to use my Hermes AI agents to help improve the travel planning. Right now, my agent generates a very detailed spreadsheet for my travel including a Master Plan, Schedule, Day-To-Day Activities, Visa requirements, Weather, Safety Summary (scams, terrorism alerts, etc), Restaurant options, Tickets-Pre-Buy, Transport Rules (airlines luggage size limits, weights, etc), Budget tracking, Maps. I am working on integrating my credit card portfolio, hotel chain status, and other related information as well to get a total holistic trip planning agent. Quite frankly, it’s like having a team of full time travel advisors at my beck and call for pennies a day!
AI agents are saving me literally hundreds of hours of work each month. Since I will be traveling a great deal in 2027, I will also add some additional Robby angles to this blog. I know some of you don’t like AI generated posts but I have been finding them fascinating and insightful.
I also have other AI agents doing lots of different things related to my investment portfolio, health, and property searches overseas but I am not ready to post anything about those activities here and I probably won’t anyway since they are not personal finance related.
Rule of 55 Cash Out
I will fund some of my activities by cashing out my 401k in 2027. I will do this in early 2027 to mitigate as much of the tax liability as possible. I have a calendar appointment for January 3 to do just that and then wait for the checks to come in.
Health
I plan on focusing on health and wellness. Now that I’ve lost 50+ lbs, I feel much lighter and happier. I don’t get exasperating climbing up stairs nor after walking long periods. My back problems and pain have been significantly reduced and I’m not sure if that’s from the weight loss, zepbound’s anti-inflammatory effects or a combination of both.
Waiting For The Disaster
Lastly, I am planning and waiting for the disaster. The periods in my life that were going so well always seem to have a sudden negative event to jolt me from my happy place. In 2001 it was the dot com crash, in 2007 it was the great financial crisis then 2020 COVID. These traumatic events seem to happen every six years and we are all right in the zone. It’ll probably be the AI bubble imploding or maybe some geo-political event like larger war outbreak or supply chain disruption. I certainly don’t want anything like that to happen but I’d rather anticipate one than get blindsided for the 4th time. This time around, my investment portfolio is very well hedged and I have enough funds to last me a while.
Share The Wealth
Have you prioritized 2027 yet? Let me know in the comments.