Carl Richards is a friend of our firm and has been for years, even before he became The New York Times “Sketch Guy.” This may well be one of Carl’s earliest drawings connecting money and emotion, but it’s still one of our all-time favorites.

While staring off into space is all well and good when waiting for a total eclipse of the sun (what a treat!), when it comes to our clients and our firm, we prefer to be a little more focused.

That’s why, shortly after co-founding Hill Investment Group in 2005, Matt Hall and Rick Hill turned to Collaborative Strategies, an independent strategic planning firm, to help them articulate the vision they had for us, and to hold us accountable for getting the job done. Lots of businesses have ideals, but not nearly as many solidify them into the measurables: What will it actually take to achieve them?

In a way, our strategic planning began before Rick and Matt even co-founded HIG, sandwiched into lunch breaks at their previous career. Today, all of us convene with Collaborative Strategies every few years to revisit our plans. We hold our meeting out of the office, where we can focus on the business at hand. Our most recent round took place in July at the Saint Louis Art Museum (so we could wax creative). There, we reviewed our ongoing focus as a firm and tightened up our succession planning in the context of our larger, multi-office team.

Now, if you’ve been reading all of our commentary, you may think you’ve caught us in a contradiction, based on a comment Matt posted last spring about our Houston office: “Opening another office was nowhere in our strategic plan.”

The thing is, having a strong strategic plan in place is not only paramount for existing initiatives. It also serves as an essential touchstone whenever new opportunities beckon. While our Houston office wasn’t specifically part of the original plan – and neither was hiring me as the firm’s first COO – the idea fit so well with everything else HIG had in mind that what might otherwise have felt like a random wager became a clear, confident choice. Similarly, our leadership team also has felt more comfortable declining several other tempting opportunities when they did not fit as well with our existing plans.

So here’s to many more years of well-structured strategic plans, with the occasional twist of serendipity to season our success.

We love Morgan Housel’s writing. Just last month we shared one of his gems and we’re back again with more because we love how he thinks and writes, plain and simple.

In Housel’s excellent post, “Getting Rich vs. Staying Rich,” he compares the real-life experiences of two wealthy investors during and after the crash of 1929. One immediately lost everything. The other shorted the market and immediately became the equivalent of a billionaire. What do they have in common? Hint: It’s got something to do with what can happen to stock speculators in a New York minute. Click here to get the full story!