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Top 5 Investing Regrets Updated

I wrote about my top 5 investing regrets in 2007. I made some unforgivable mistakes back then but have made a few more. The introspection of my previous article was cathartic. I hope this attempt is as enlightening.

Estimated reading time: 3 minutes

Too Many Eggs in One Basket

This is an extension of the “held onto High Tech too long” regret. In hindsight, I was far too invested in Nortel when I was younger.

  • Nortel paid my salary until they laid me off.
  • Initially, they paid my benefits, but I ended up paying for more later in my career.
  • Options and bonuses that were given to me over time
  • I invested in Nortel in too many places.
    • An After-Tax Savings Vehicle
    • A Deferred Profit-Sharing Plan
    • My pension, which was far too invested in Nortel as well
    • My disability insurance, as Nortel was self-insuring

I didn’t lose as much as I could.

Realize how much you are invested in your employer. Divest your investments from your employer.

Asking for What I Wanted

Too often, I settled instead of trying to negotiate better prices. This was true for many things. Some examples:

  • Insurance for my car and house. I should have spent those extra few minutes to get a cheaper rate.
  • Mortgage rates are always negotiable. A bit of time spent would have put more money in my pocket.
  • Honestly, the Answer is Always No if you don’t ask.

Invested in My Health More

Investing is working for your future. Staying in good health is the same thing. Is this an investing regret? I didn’t invest in myself, which is an important edict of investing.

Had I gone on vacation more, my perspective on life might be less pessimistic.

Your health and keeping yourself healthy is something that cannot be quickly recovered if you neglect it. Keep up the work needed to keep yourself healthy.

Understood that Time is the Essence of Investing

Time is the only variable when it comes to investing. Time cannot be recovered, but remember the mistakes you made in your youth, can be recovered. The mistakes you make later in life, time is not on your side. Don’t waste time in your life.

Planning more could have made this journey simpler. Yes, this is viewed with hindsight on full scan, but a few mistakes were made over time.

Enjoyed the Fruit of my Investments Sooner

My investment journey has been during the most significant Stock Market growth ever. Even with my blundering along, I made a pretty penny along the way. As with most of my decisions, I was lucky, but I think I should have spent a few more dollars earned. A vacation or two more might have been better overall.

Investing Mistakes FAQ

Regrets are they worth rehashing?

Looking back in life is only worthwhile, if you are willing to learn from that retrospective.

What is the most important variable when it comes to investing?

Time, it is the one variable you cannot control.

What is free advice worth?

Every penny that you paid for it.

What is the significance of Slim Pickens from Dr. Strangelove in reference to investment mistakes?

Riding your mistake all the way down to the big boom. A metaphor for my Nortel mistakes.Boom goes the High Tech Bubble

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