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When You Know You’ll Never Retire, The Hardest Part Can Be Acknowledging Your Situation

Never Retire Checklist: #2

Rocco Pendola
6 min readFeb 3, 2024
Source: Author / Barcelona, Spain

For many people who end up Never Retiring and living the semi-retired life, very little of meaning happens in the early assessment phase of your situation.

Because we’re conditioned to do everything in our power to maintain the status quo.

The status quo has a way of maintaining itself, especially in our personal finance.

For me, it looked like this —

  • As I noted in part one, I knew I needed to make changes to my money strategies and lifestyle. I just didn’t know where to start and what to do.
  • Everywhere I looked, the prevailing remedy to not having enough cash saved for retirement was to run the basic math on how much you have saved, your time to retirement and how much money you’ll need in retirement. This calculation spits out a number — how much you need to save each month to reach your goal.
  • Instinct says if I have been unable to execute this strategy for close to 20 years, it’s illogical to double down on the very same strategy for the next 20. Middle age — maybe the most pivotal point of our existence on Earth.
  • We all face stigma and feelings of failure when we can’t seem

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Rocco Pendola
Rocco Pendola

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