_{Exploring the three retirements, abandoned education, and the imposter}

Happy Thursday! Thanks for reading Intentional Dollar — where we look at old money ideas through a new perspective.

What’s inside?

• One idea to experiment with

• Two quotes from others

• Three questions to dig deeper

• Four lines of poetry for the point

Disclaimer: This is not investment advice. These weekly posts represent my simple thoughts, a few quotes, and some questions — for educational purposes only.

_{One idea to experiment with:}

The Three Retirements:

How do you think about retirement?

The traditional view would have us think retirement is the magic age when Uncle Sam unlocks our 401(k), pension, and generously activates our paid-for Medicare and Social Security benefits. Maybe it’s a number—59½ to 70. Largely, the image is the same: work hard, save money, and pull the plug when the calendar gives stage to that special date. 

A clear problem with this traditional view is that it subtly encourages accepting suboptimal fates for long periods. Namely, staying in jobs solely for the sake of future retirement. 

I see three broad structures of retirement.

1. Traditional: save and wait for the standard retirement age to roll around.

2. Financial independence, retire early(FIRE): either drastically reduce your expenses or aggressively build an investment and saving base that covers them. 

3. Enjoy the work you do without thinking of the money aspect. Absorbed in the work for the sake of it, you never plan to retire.

Now look at your own retirement path through these structures—which one are you pursuing? 

Structure three is the most aspirational because it suggests true alignment in life. Structures one and two often involve substituting enjoyment, purpose, and passion in exchange for freedom, and they both fail to solve the meaning problem. 

When successful people sell companies, they don’t sit around at the beach—they get bored. Before long, they’re launching second companies, new projects, more work—a continued search for meaning. 

The best strategy is the one that gets us on the path to path—and fast. We trade meaning for money to one day have enough money to have some meaning. It’s a little backward, and it reminds me of the short parable of the fisherman and the businessman. 

The story goes that an astute businessman wandered to a small coastal village and saw a man catching fish. Complimenting the catches, the businessman was quick to offer advice. Scale your operations, increase your fishing fleet, move to the US, continue scaling, go public, make millions. “And then what?” asked the fisherman. To this, the businessman suggested that after a successful exit the fisherman could retire to a coastal town, catch fish, and spend time with friends and family—everything he already does. 

So if retirement is your focus—your distraction from mind-numbing, purposeless work—perhaps it’s time to rethink what it means to retire. Maybe it means accepting less money (that you can’t really enjoy now anyway) for the work you feel good about. Sustainable work. Work where your curiosities and passions align. This kind of work might not produce the largest paycheck, but it certainly provides the best returns on your time. 

_{Two quotes on abandoned education:}

What’s the typical education path? Hear the lecture, skim the book, cram the material, reproduce a best-efforts recall of the facts on exam day. We repeat this cycle for a few decades and call it education. This broken system burns us out of the learning desire. We throw our old books away and seldom open new ones. Don’t let your past educational experience ruin education on your own terms; don’t abandon the pursuit of knowledge. 

_{Three questions on the imposter:}

1. What don’t I do for fear of being an “imposter?”

2. What are the odds that the people that do these things feel the same way?

3. How can I stack little files of evidence to build an undeniable base of proof showing myself I’m no imposter?

Which question stuck with you? Questions like these are spotlights for the mind. Reply to this email and let me know which one shined light on a previously dark cave.

_{Four lines of poetry for the point:}

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Disclaimer: This is not investment advice. These weekly posts represent my simple thoughts, a few quotes, and some questions — for educational purposes only.