1. They don’t secretly demonize or idolize money. A happy investor recognizes two sides of the same coin: that they could want all the money or resist money. Either way, they’ll be caught in the same web. They realize money will elude them if they shun wealth. Conversely, they’ll never experience the benefits if consumed by accumulation. There is a dance in which they must participate, embracing moments of greed and moments of disgust. But, they don’t become them nor do they reject them. Push one side away and we’ll need to contend with the other. That’s the nature of the market place.
2. Judgement free. The happy investor has realized the difference between case study and keeping up with the Jones’. Comparison by case study offers insight to unchartered territory and the complete picture. Case studies might be available through earnest research or professional advice. Conversely, judgement (various forms of “why or how did they/can they afford that?”) merely stirs negative thoughts and emotions. It takes us further away from “I don’t know, and I don’t need to know.” Happy investors have a striking capability of not needing to know.
3. There’s an unattached plan. This type of investor values both a game plan and flexibility. They know life throws curveballs and no prior decade in hindsight remotely matches how they projected. Their goal keeps them moving each day, but they aren’t married to it. They see the value and pattern to life: order, disorder, reorder, no matter how chaotic. Not everything needs defined, but they do need to be directionally accurate.
4. Their expectations don’t continually increase. Happy investors experience ‘radical gratitude’. Increasingly, the ordinary is just as awe-inspiring as something typically labeled breathtaking. Because of this, spending less than they earn comes naturally. Keeping the goalposts from moving is a hard one. In practice, automation is their friend. Salary deferrals, automatic savings plans, committed savings plans for variable compensation, etc. But to remain happy as a long-term investor, all signs point back towards making peace with the ordinary.
5. They know why they’re striving for more. The hedonic treadmill eventually wins unless we’re clear (and comfortable) with our reasons for striving. Not to deny the instinctual acquiring trait: after all, we must acquire food and shelter. We might say accumulating has become apart of our evolutionary make-up. There’s a reason for their acquiring, however. Their things serve them, not the other way around. This requires serious personal inventory, or we become servants to accumulation and hoarding. The inventory process also never really ends.
6. The work they do is to spread love or remove barriers to love. If this is too wishy washy for you, here’s what it looks like in practice. What they do is secondary. How they do it is primary. Garbage pick-up, lawyer, investment banker, C-suite leadership – doesn’t matter. The focus is on being a bridge, and in so doing, their colleagues, employers, and customers reward them.
7. They show their family the same patience they gave to the people who paid them and work for them. At day’s end, the people who provide them unconditional support aren’t taken for granted. The reward is a fuller life and not feeling like you’re on an island during professional and personal ebbs and flows. In practice, a small step towards patience for these investors is compassion. Before something goes dismissed as trivial or “other”, there’s at least one small pause to feel their support system’s discomfort.
8. They end their day forgiving themselves where they inevitably fell short on the steps above. These traits are a narrow path to walk. Accordingly, happy investors aren’t shy to apologize and also don’t waste time with guilt or shame. They mess up a lot.
9. They get some sleep.
10. Rinse, repeat.
Now, go do this for 10 years.
Thanks for reading,
 Credit the phrasing “Order, Reorder, Disorder” to the Center for Action and Contemplation and Richard Rohr