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Ray Gesualdo
Loose change

Penny Smart, Pound Foolish

February 3, 2024 | 3 Minute Read | Category: Process

I’ve been thinking about the phrase “penny smart, pound foolish” a lot lately. If you’ve never heard it before, it’s an older British phrase that refers to someone who makes smart decisions with small amounts of money but makes poor decisions with large amounts, e.g. clipping coupons obsessively but buying a house far outside one’s price range. I find this phrase much more generally applicable though, particularly in the context of how I spend my time at work.

I’m a staff architect at Salesloft which means I have both the opportunity and responsibility to focus on high-leverage, high-value work. My role gives me a lot of latitude regarding what I focus on, and it’s easy to find a million little things I could fix or improve. I sometimes wonder if what I choose to work on is going to make a significant impact in the organization.

Is the answer to stop focusing on “little things” and only focus on “big things”? Well, yes and no. The trick is figuring out which little things will accomplish those big things in the long run. One of the phrases my wife and I quote back and forth to each other whenever we tackle a large problem is “How do you eat an elephant?” The answer: “One bite at a time.” The biggest, most important tasks can and should be broken down into smaller units of work.

The greatest agent of change is consistent effort over time. This is both exhilarating and terrifying. On one hand, if we’re highly intentional and choose the right small things, the size of positive change we can affect is massive. On the other, if we are not intentional and choose poorly and haphazardly, we will actually make things worse. Therefore we must be highly intentional about the work we choose.

In his book Great By Choice, Jim Collins recounts the first successful expedition to the South Pole. The expedition leader – Roald Amundsen – had his team travel 20 miles every day no matter the weather. This “20 mile march” as Collins dubs it is the radical commitment to consistency that ensures progress regardless of circumstances while also preventing over-exertion or burnout. In short, consistency took Amundsen’s expidition where literally no human had been before.

All of this ties back to an architect’s mindset: determining direction (intentionality) and defining incremental steps to get there (consistency). A 20 mile march is meaningless if there isn’t clear direction. Similarly, a clear goal with no path laid out is just a dream, not a reality. It takes intentionally prioritizing the incremental work that consistently drives toward a clear goal. If we do that, we can be both “penny smart” and “pound smart”.

The greatest agent of change is consistent effort over time.

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