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I’ve been fortunate, to get a look under the hood at the lives of the conventionally successful.

Before we get into tactics for discretionary spending, it’s worth thinking about what our spending might bring us.

What’s the strategy? Where are we trying to get to?

Thinking back to last week => if you think about my childcare spending with this in mind… it makes much more sense. I wanted to maintain my ability to explore nature and create space for a little serenity.

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My first boss was a very successful investor. He repeated his success multiple times, with different teams, across a long time horizon. I use what he taught me, every day of my life. A favorite quote:

It’s the first five million that makes a difference.

You’re going to read that line in your own voice. You’re going to overlay your own values. To understand, for myself, I had to watch what he did for a number of years.

He loved what he did and he didn’t like to be told what to do. He was living in London, with two kids, in his early 40s, with limited interests outside work… what money brought him was the freedom to leave any situation he didn’t like. To be his own boss.

Related from another self-made mentor, talking about a family member with cash flow, who left a successful firm, at a very young age.

Nobody ever goes back.

So, if your financial chase means you are beholden to your boss then you’ve missed out on a key benefit

• the ability to control your own schedule
• the ability to walk from unreasonable demands

Once you realize the underlying need, you will be able to address it with far less money than you think. The entire point of my financial writing.

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What do successful people do when they’re not being successful?

My first boss used to read about accountancy! He’d head off on vacation with a large stack of Accountancy Age (or whatever it was called) and work through back issues. His partners got a kick out of that. If you wanted to learn about financial fraud, he was your man!

My lifestyle aspirations are a better fit with the smart folks I met through sport. There are a lot of high-achievers in masters athletics.

What did I see?

Mastery, novelty, competition, adventure, peril, connection, shared suffering… ideally, combined with heart beats in nature.

Adventure, beauty, variety – there is a ton of it within 90 minutes of my house.

No balance sheet required.