Never Retire - Organized Spontaneity

The ultimate life and money goal: structure that allows for freedom

After a really great two-week trip to Italy with my girlfriend, it’s nice to be back.

As we reenter the groove of life in Los Angeles, I intend to step up newsletter posts—free and paid—going forward.

At the same time, I plan on writing more about travel—often as it relates to personal finance—on Medium. Expect a Medium post about that later today or tomorrow. You can subscribe to receive notifications of my Medium articles here.

This newsletter installment focuses on a thought I had during the aforementioned trip.

I tend to be a highly organized person, in terms of efficiency and having a detailed plan/schedule. I’m like this day-to-day as well as in special circumstances such as travel.

Over the years, I learned about the fine line between rigidity and spontaneity.

While I will never give up being organized, I function better when I establish structures within which I can be spontaneous. We’re all probably best off doing this with our money and in other key components of life.

This spontaneity within structure—or organized spontaneity—comes off in two key ways.

One, the most obvious.

You create a framework, be it for your day, your money, whatever, that allows for changes over time and on the fly.

That’s really the goal of any Never Retire strategy.

Ideally, you want to be in it by choice or, at the very least, you’re embracing the necessity of working in retirement (or whatever your situation looks like).

You also probably require a methodical approach to money management (maybe pots of money) to successfully satisfy your wants and needs now and going forward. At regular intervals, you move money into your accounts to take care of what has to happen today and the things you want to have happen tomorrow.

However, within this there’s wiggle room.

Wiggle room to, as one example, take money from the emergency fund to make a modest upgrade to your rental property. This decision triggers stepped-up deposits to replenish what you deducted from your emergency fund, if necessary.

You can go on all day with scenarios specific to your circumstances, but the general rule is you absolutely can earmark money for one purpose and—thoughtfully—use it for another.

It’s a bit like having a plan when traveling.

Each day in Italy, my girlfriend and I had a clear idea of what we wanted to do. We’re not the tour types for the most part, so this consists of saying we want to hit this neighborhood and this or that restaurant, along with walking or public transit directions for how to get there.

However, as the day unfolds, we let the day take us where it takes us. Without the structure, this spontaneity, at least to me, would feel more chaotic than free.

If this makes sense, the second point probably will as well.

It can be healthy to completely blow off your plan occasionally.

In the day-to-day, you might leave your house with no other thought than taking a long, meandering, aimless walk. You’re not working or doing chores, you’re just walking. As you set out, you end up wherever you end up.

Doing this every once in a while has helped me put organization in its proper place in my life.

This trickles through to personal finance strategy.

For example, I don’t spend a ton of money on clothes. I tend to dress reasonably well (I think), however I almost always buy on sale or at thrift stores and I don’t tend to buy expensive brands.

That said, there’s this relatively expensive coat I have my eye on. One day, the time will be right and I’ll buy it.

Dropping the cash on a coat I don’t need isn’t part of my ongoing plan with money. Other discretionary purchases (mainly travel) are, but the coat and things like it aren’t.

But it’s okay to throw structure out the window to do something like this—whatever something like this is for you. Because, in a weird way, it can help you stick to the larger plan a vast majority of the time.

It’s akin to however you blow off steam during your day or, on a larger scale, once in a while. You release pressure so your head’s in the right place to stick to the plan.

If you never allow yourself these deviations, you run the risk of your plan—your organization—turning into a miserable rut.

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It’s good to be back. As always, thanks for supporting my work as a freelance writer through this newsletter and on Medium.

I appreciate it.

Rocco