A clear demonstration that not knowing what you are doing and taking risk may not always lead to financial disaster, but not recommended

I have been pondering for a week whether or not to post this out of concern it will be misinterpreted – I have experience with that. 

As Jonathan once told me,  “those who are financially prudent will most likely enjoy success, even if events don’t always go their way.” That’s it for me, mostly prudent and very patient. 

Is it always necessary to follow all the “rules,” to be precise with every financial decision you make, or to agonize over every detail or calculation to find financial success however defined?

None of that is bad, of course, but if you have made mistakes as I have, if you threw caution to the wind at times as I have, if you did it your way, all is not lost. 

Here is my point. Sometimes the end can be better than the means appear to justify with time and good fortune on your side. Just keep at it. 

I have been writing and commenting on HD for several years and based on the extensive feedback I receive including those darn down arrows with red numbers, my views, my actions, my suggestions are often viewed as  – how shall I put this – not normal, unconventional, wrong and at times misunderstood as if I was urging others to do as I do – never the case. 

The fact is you probably should do nothing financially the way I have – except be patient and never give up.

Looking back on my life from my first job at age 18 and considering the financial actions I and then we have taken as a couple compared with conventional wisdom, we should not be in the financial place we are today. 

Instead I am living proof that financial success is possible even when you don’t always know what you are doing and have minimal interest in finding out except through life experience. 

It may be that sticking to the basics, trial and error – and an absence of uncontrollable misfortune can get you where you want to go. Not a recommendation though.

The basics are well known. Live below your means, avoid debt as much as possible (absolutely no credit card debt), avoid lifestyle creep, save and invest from your first job and never stop. I didn’t obtain a college degree until I was 35 so minimize that advantage.

I didn’t job hop, but stayed with one company pushing through a variety of vicissitudes, nepotism, backstabbing and corporate games. There was a price to pay, but also significant rewards – eventually. 

I didn’t retire until age 67. I very much liked my job until then. As it turned out my last five years were by far my highest earning years and also generated significant amounts of stock compensation. And then there is the pension based on all those years working and the last five years earnings.

No financial advisor, no planning a retirement lifestyle or even thinking about it. I still hope to visit Monte Carlo someday though. I did none of the well advised, conventional stuff financially or on the road to retirement some of which I advised others to do. 

I bought a second home (with a 9-3/4% mortgage) just before the real estate market collapsed, the year before our eldest child started college. 

Connie and I began collecting SS at my FRA while I was still working. 

We didn’t have a Roth 401k.  I never considered Roth conversions as I felt the payback time too short given I didn’t have a roller-over IRA until 2021 at age 78. I did invest heavily in municipal bond funds, but never bothered to compare the tax-free interest rate with net taxable returns- tax free just sounded appealing. Today those funds are 17% of our portfolio – I am surely not investing for growth. 

I was talked into purchasing two small variable deferred annuities decades ago when I was in my forties,  but stopped contributing as soon as the penalty period was up. Could I have made a better investment? Very likely, but I don’t think about that. The more important thing is we still have them with a combined value of $265,000, and still earning tax deferred. 

I converted all my restricted stock and stock options into shares when they vested. It could have been cash, but I put it at risk. Now my former employer stock is too high a percentage of our portfolio – another questionable decision, but oh those dividends. If the company goes kaput so does my pension and we will be living off the tax-free interest and less than optimum social security – I say in jest.

So where has this literary labyrinth taken us? Nowhere of significant interest to anyone except perhaps to give hope to others just as detached from financial reality as I was – am. 

No doubt an unnecessary caveat for regular HD participants, but please don’t assume I am suggesting a strategy to follow. Just be patient, approach finances in a way that is comfortable for you – never give up the journey.