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Prompted by Mark’s thread I’m having a bash, although I’m sure that this will be a subject that’s been covered before.
Having lived experience to wherever you’re at now and with the superpower of hindsight (not to be spent on putting every cent you theoretically had in 1980s and subsequent into Apple) what are the key things you’d say to your younger self at say the following points:
i) Starting out in the serious working world at age 21ish
ii) Into middle age and pre-retirement working life at say 45-50
iii) On the cusp of retirement or making the decision of when to go
iv) 5 years into retirement
Be like a gator and keep it snappy 😉
My responses so far
i) You’ll probably stick at this job/career longer than you think so don’t worry about job security and having cash on hand – be a bit bolder in putting funds away for the long term.
ii) Don’t dither – start shaping what you want out of the remains of your career now. It’s no good getting the better counter offer when you’re handing in your retirement notice.
iii) There’s never the perfect time but there’s a point in which the present value of not being tied to work exceeds the marginal security/enjoyment from further work. Decide what goes into that value and commit.
A wise old Irishman once told me “We’re here for a good time, not a long time”
The older I become, the more I know that’s the truth.
Great prompt—hindsight really sharpens perspective. If I could speak to my younger self:
At 21: Start saving earlier and automate it—time in the market matters far more than timing it. Build good health and discipline while energy is high.
At 45–50: Be intentional. This is the decade where complacency can quietly erode options. Shape the next chapter before circumstances shape it for you.
Near retirement: Run the numbers, trust them, and remember—time becomes more valuable than income past a certain point.
Five years in: Focus on purpose and health as much as finances. Money gives freedom; habits give fulfillment.
“time becomes more valuable than income past a certain point.”
Excellent sentiment!
Just keep on going. Work hard at what you’re doing each day, and it will work out OK. Don’t overthink it.
For about 18 years I performed a somewhat hazardous occupation while my family grew from just me to a spouse and 4 kids = 5 dependents. During that time I carried about $650K in term life. Looking back, I should have had much more life insurance during those years. I was healthy, term life was cheap, and had I ended up in a “smoking hole”, my family would have been a whole lot better off. Fortunately, I didn’t need life insurance then, but I knew a few who did and some were well insured, others not so. The spouses of the well insured had a great deal of flexibility regarding where to live, how they lived, educating their children, etc. If you have a spouse or spouse and children, term life is a great deal.
Take really good care of your body! It’s the only spaceship you’re gonna get for all your trips around the sun.Don’t allow yourself to get overweight. Exercise often. Eat reasonably. Because if you don’t take care of yourself when you’re young then you’re gonna require someone to care of you when you’re older. And the. you won’t be able to enjoy your money!!
Save as much as you can after you start your first job at 22 or 23 years old generally after college. What you save at 22 years old can easily become in 56 years each dollar can become $160,000 if untouched and invested in the S&P 500 fund. Small amounts are most meaningful from when you are YOUNG, COMPOUNDING does all the work. Best tip an 80 year old can give you.
Fill your retirement savings buckets first, with that task set on autopilot. After that, feel free to spend and enjoy the rest.
Your integrity matters more than you think. Never abandon your morals for quick personal gain.
There is something of value in each and every person. Find that value, and learn to embrace esch person as unique with differences to celebrate.
Forego the investment newsletters, avoid individual stocks, and embrace index ETF’s. That is all. Stay Calm, Stay Well, and Carry On!
Save more, starting yesterday. Budget better, as in do it this time.
Exercise more. Listen more.
Talk less.
I don’t fit neatly into your age brackets. I made three decisions in my twenties that would have led to a radically different life if I had chosen the other path. I can’t advise my younger self, because I have no idea how the paths not taken would have worked out. I am sure I wouldn’t now be living in a CCRC in NC. I would advise her to start saving earlier, but I would enthusiastically endorse her decision to retire at 53.
I spent most of my 20s in grad school and got my first “real” job right as I turned 30. So my path was not typical.
Mid-career: This is where I started getting serious about managing money—it helped that I received an inheritance the year I turned 45 and that we were both finally making decent money. I’d tell myself “it’s not too late to make good choices and set yourself up for the future.”
Approaching retirement: I just went through this, so I’d say “Run the numbers, and if you feel like you’re psychologically and financially ready, DO IT. Your remaining time is more precious than anything you could buy.”
I only retired in July, so I have no five-years-on perspective.
Just curious, have you experienced any change in your spending habits post-retirement? This is one area of concern for me.
In my case, not really. We did some traveling this summer, but we were traveling regularly before I retired. We’re socializing more because I have the time and energy for it, but it’s mostly low output—think neighbors coming over after dinner for cards, listening to music at the local winery while getting dinner from a food truck, stuff like that.
One thing I’ve been musing about is my evolving relationship with my wardrobe. I live in California where it’s fairly warm 9-10 months per year, and I’m bored with my spring/summer/fall clothes—but I also can’t bring myself to buy new stuff because I don’t have to go to work. So I think that will be one expenditure that will decrease, not that it ever was a huge one for me anyway.
I met Dianna when I was 16, in the McDonalds parking lot, we became great friends. Recently, Dianna sent me a picture from her 21st birthday party. She was smiling, standing over her birthday cake. Next to her, seated in a chair, was a long haired, drug dealer looking dude, sipping from a long neck bottle of beer; that would be me, though I never sold drugs (unless beer counts, in that case I deserved to suffer Pablo Escobar’s fate).
By age 21, I had already been engaged in serious full time work for a couple years, working on a side load beverage truck. If I could have talked to that kid, I might have told him that there’s no way you can do that job for another 44 years. You should stay in school, get an accounting degree, and start your own tax prep business.
By the time I reached middle age, the advice given by me, to me, at 21 had begun to sink in; no further input was necessary. I was making plans for my escape, not only from the brutal job, but from a failing marriage as well. (I might mention that my old friend Dianna had introduced me to my 1st wife. I do not hold it against her. But I digress…. again). By age 50 I had ended the marriage, given birth to Dan’s Tax Prep, and met a wonderful girl.
On the cusp of retirement, I may have told myself to increase my fees, which would have enabled me to sell my business for more money.
Today I am five years into retirement, and the only thing I can tell myself is that it’s a good thing I can’t go back and tell myself a damned thing, because there is no place in the world that I would rather be.
I can hardly remember my 21-year-old self. Obviously, I’d compliment him on how awesome he looks. I already owned a home and had a retirement account. I think I would encourage myself to contribute more to the retirement pot and try to pay down the mortgage quicker. But honestly, I probably would have ignored the advice in favor of beers and partying.
By my mid-forties, I had already been running my own business for nearly twenty years. Truthfully, I don’t think I would have given myself different financial advice. But on the personal side, I would have strongly advised the reverse of my early twenties—much less work and more play.
Moving on to my mid-fifties, the decision to sell up and retire was pretty simple for me. My retirement accounts were well funded, and by this stage, work was simply getting in the way of life. Cutting the cord was sweet relief.
At the risk of being criticized, there is nothing I would change.
I entered the workforce at 18, I stayed with one company nearly 50 years. I retired when I decided it was time.
I married my first girlfriend and was activated on active duty in the army a month after we met and were separated for nearly two years, except when I came home on leave for two weeks to get married. Who does such a thing and have it be so successful?
I achieved every career goal I set for myself at age 18 although it took a bit longer than I would have liked – until I was 63.
Between always saving, use of a 401k, employer contributions, equity pay in the last few years of my career and a pension- based on those 50 years – we are financially independent and are in a position to help others, especially family.
We do whatever we want to do in retirement, but at 82 and 86 we are slowing down. Perhaps I wish that was not the case, but that is life.
We drove across the country three times and visited over 45 countries in retirement.
In short, we are incredibly grateful for our life and retirement. Every time I look back at where we started, basically at the bottom in a MW job with no college, I ask how did it happen, how and why have we been so fortunate?
Bbbobbins,
Excellent post!
As to your last point. Towards the last 5 years of my wife’s professional career she didn’t want to leave the job she was in for about 20 years. For years she had not been happy with the new management. She knew she would go back to only two weeks of paid vacation (or holiday as you would say) which is standard for newbies in US.
I finally convinced her the extra week off is not worth it if you hate your job the rest of the year. She left that job and found a job at a non profit CCRC for relatively well off retirees. She loved the culture of the residents and the staff. She once again felt challenged at her job and was enjoying work again. COVID ended her career early as she was going to retire that November.
I recently did some primary research reading a CCRC book that was recommended in a post, and spurred by Cathy’s and others statements that great facilities have 7-10 year waiting lists. I filled out a form sketching out or finances for the facility and lo and behold apparently preliminarily we have enough assets to qualify to live there. My wife always said we could never afford to live there as only rich people could afford it. So either we are “rich”, or even “average” people can live there.
We figure we will put our names on the waiting list when we turn 70 assuming that by our eighties we might require or prefer that living situation. But not without doing our due diligence first however.
I don’t know how old you are, but if there’s a place you like and can afford I would get on the list sooner rather than later. There are a lot of baby boomers aging into CCRCs. Also, you will get more value from moving while you are still active – you can take advantage of the activities and make friends. Typically, when you get to the top of the list you don’t have to take the first available apartment/cottage, but you’d need to check that.
Thanks for the input Cathy, but I think we will still wait till 70 as both of us are still very healthy and active. Plus we are not claiming Social Security until 2028, so won’t have any true regular income except my small (<1K) income to put on our application until then.
PS, we are well ware of waiting too long as well as my parents would not make the move to a CCRC and ended up in assisted living in their mid eighties, with mom years into Alzheimer’s, and Dad soon after entering losing his ability to effectively communicate due to developing Lewy Body dementia. They did not have sufficient time to make friendships before the decline so were sort of socially isolated.
I think it depends on location. There is a CCRC near us and several years ago I inquired about pricing. Back then the entry fee was $700,000 and the monthly fee was $7,000 for two. However, if you wanted a small apartment the fee was a bit less. I can’t imagine what the fees are now. They kept 10% of the entry fee, but no interest was paid on any of it while they held it.
I just called our local CCRC The entrance fee is now $975,000 if you want 90% returned, less if you only want 50% returned. That’s for a small cottage. The monthly fee for two is $8,000. But includes all living expenses including home cleaning and most meals.
Which is no more relevant to David, living, I believe, in New Hampshire, than the knowledge that a studio at my CCRC in NC has a 0% refundable entry fee of $81,000 and a monthly fee for one person of $3,174. A second person is $1,401 in all units. The 90% refundable fee would be $153,900.
It depends on many factors, obviously including location. You have information, which you have posted multiple times, on precisely one CCRC in a notoriously high cost of living area. Why do you think that is relevant to the hundreds of other CCRCs with different pricing structures and different facilities in other parts of the country? Also, how much are houses going for in your area? Most people pay the entry fee with the proceeds from selling their house.
In any case, David has done his initial research and the cost of the CCRC he is considering is apparently not a barrier for him.
Ye gads calm down. Didn’t I say it depended on location? I was merely providing some information which is just one data set. And by the way, no waiting list either, I could have the cottage now.
by the way, at least one in NH is not way off from NJ
At Havenwood Heritage Heights, residents pay anywhere from $1,740 to $5,336 for independent living. Compared to the New Hampshire average of $3,537 per month. And that is for a small apartment.
Why are you shouting? In what universe is $3,537/month “not way off” $8,000? That’s over $50,000 a year. And BTW, the absence of a wait list is a red flag.
As to your last sentence. The facility Dick mentions is in our capital city of Concord, about a half hour from us. It is a very large complex with multiple levels of housing. It is a non profit with an excellent reputation. It is another facility that we will investigate and consider putting a deposit on in three years.
Glad to see you have choices. My “last sentence” referred to Dick’s comment that he could move to a cottage at his neighborhood CCRC “now”. The absence of a wait list suggests both that prospective residents have found problems and that the facility may be headed for financial difficulties. An empty unit generates no revenue. You want to see an occupancy rate in the high 90s and plenty of prospective residents. In NC an occupancy rate of 90% or below triggers a legal requirement for greater operating reserves.
That is not the case with this facility. It has been around for many years and has an excellent reputation. It’s a program of Lutheran Social Ministries of New Jersey (LSMNJ), officially opened its doors in 1998. It was named Best Senior Living Community” by U.S. News & World Report
When our CCRC opened two years ago, all 174 of the apartments were spoken for but 10 of the 46 villas were vacant. All of the villas are now occupied so we have moved from 95% occupancy when we opened to 100%.
Cottages/villas are the most expensive units and from getting to know the villa residents it is clear that, in addition to being able to afford a high priced unit, they view living in a villa as retaining more of the independence they had before they moved to a CCRC. Thus, I don’t think you can make any inferences about the financial health of a facility simply because it has one or more available cottages.
May depend on the facility and how long it’s been open. The wait time for cottages at mine is longer than the one for apartments, possibly because there are fewer of them.
My main point, at the beginning of this discussion, was that the price for just one form of accommodation at just one CCRC is not much use on its own. There is far too much variability.
Exactly the case with the facility I mentioned.