6 Habits of Happy Retirees
6 habits of happy retirees.
BLUF (Bottom Line Up Front):
I used to think this job was all about investments, rates of return, market volatility etc…Its not. In a decade of helping people get into (and more importantly stay) in retirement I have noticed some common things my happiest retirees do like:
- Eliminate the unexpected
- Focus on their health
- Outsource
You can skip my pontifications if you like to the 📽️👇.
I have conversations every day with people at every stage of their financial lives.
Encouraging young savers to forego that cup of coffee and invest the $14 it costs to get time and compounding interest on their side.
Talking my near-retirees through market ups (ok, mostly the downs.)
Checking in with my retirees about that stage of life that they worked, saved, and invested to reach.
Over hundreds of conversations I have discovered that the things people talk about change.
Younger investors are focused on the money, an “escape hatch”, and planning for growth, tax efficiency, and individual investments. But underneath those conversations I pick out that what they are really worried about is:
“Am I doing the right thing”
“Am I on track”
“I am so busy I don’t have time for this (or know what I am doing)”
When I talk to my clients who are kicked back on a beach or visiting their grand kids on vacation I have discovered that the conversation has shifted from the dollars and cents. Given the right tools, I have very few clients who live the retired life they want knowing the money will be there.
In talking to retirees all the time (getting a glimpse into where I will hopefully be…one day…) I like to find out some common themes around what makes the retired people happy. I have noticed 6 things happy retirees have in common 📽️👇.
The basic theme among the most successful retirees are things that
- Free up time
- Free up head space
- Decrease worry
- Increase confidence
Watch the video below to learn about these habits and try and incorporate them into your overall financial plan.


In all my financial plans I often recommend things 95% of people aren’t familiar with. This is because 95% of financial planning is run by Wall St, who wants to convince people that “the institutional research we do blah blah…buy and hold…don’t catch a falling knife…” will get you to the finish line. And, to be honest, over a long enough period of time…it probably will.
When it comes to the tools you can use to do things like reduce unnecessary risk, lower your tax burden etc… here is my belief about the BEST investment available, and it isn’t what you think.
The truth is…there is no one best investment 🤯 . I know, statements like that are why I will never retire. I probably have half the clients I could but have happier clients than most, because I believe people deserve honesty, and not a sales pitch.
Ok, I told a half truth. The best investment is the one that accomplishes your goals. The best investment is the one that does the job you want it to do.
All stock jocks think their “propriety portfolio” will make you rich overnight 🛥 while ignoring that something ridiculous like 95% of active portfolios underperform a passive index 😥 .
Everyone in real estate will tell you that as soon as they “get to 100 doors” you can help them pick our the color of leather interior on their new G5 🛫 (and then interest rates go from 0% to 10% and the market tanks.)
“Can’t go wrong putting 100% of your money in annuities” says your buddy who was hired at an insurance company right out of business school.
The truth is that all investments do different things, at different times, and have different strengths and weaknesses. Every investment vehicle is different and all have their purpose (except Variable Annuities, I will die on this hill).
Want tax free growth and safety: Roth fixed income
“But I want to use my money before I am 59.5”
I get it, I want my cake but also to eat my cake.
This is why the best financial plans and portfolios have all different tools at their disposal, and why I don’t push one solution, or shy away from another. At the end of the day the point is to have the right tools to build a financial plan that will grow in the sunshine but protect us from the rain.