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Leadership is Messy. It Always Has Been!

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Leadership can’t fully be taught in a classroom. Many leadership lessons must be learned on the field, and that process is often messy. Consider the pastor with a wayward church member who needs to experience church discipline. Straightforward enough. But what if that member is also the church’s largest giver, and the church is way behind budget? Or perhaps an employee has been disrupting the rest of the staff and needs to be confronted. The problem is that she is also the company’s leading salesperson and her father is the chairman of the board. Leadership would be much easier if everything were black and white, but it rarely is.

When leaders face problems, there are usually multiple factors at play. Every choice carries the weight of potential consequences. Some people will applaud the decision, while others will be irate. Certain issues involve timing. Acting immediately may produce enormous pushback and opposition. Waiting for a year might allow things to cool down. On the other hand, opposition could become more organized and outspoken over time. Which is the best choice?

My wife and I recently celebrated our 40th anniversary. We considered taking a trip to various exotic locations. I suggested Hawaii or Europe. But Lisa, being who she is, wanted to wait on those destinations until we could bring our kids and grandkids with us. (Apparently, an exotic getaway with just me does not have quite the appeal it once had!) Nevertheless, I pivoted and suggested we go somewhere where Lisa would not feel guilty about not inviting the grandkids. As a result, we checked some things off of my nerdy historian bucket list.

I have always wanted to go to Virginia to visit the homes of former American presidents. I also thought it would be relaxing to drive through the Virginia countryside. Lisa was game, so we visited Mount Vernon, Monticello, and Montpelier, as well as Ford’s Theater where Lincoln was assassinated, The Battlefield of Bull Run, and the Smithsonian. It sounds like a high school field trip, but it was a lot of fun. In preparation for our trip, I read a 900-page biography of George Washington (affiliate link) by Ron Chernow. I know. I’m a hopeless romantic!

I came away with many impressions, but this one in particular was at the forefront of my mind: Leadership is messy.

Four of the first six American presidents were slaveholders from Virginia. They all knew the practice was morally wrong and wished the institution would end, but none of them abolished it. Why?

Slave Quarters
The Slave Quarters at Mount Vernon

One obvious reason is that their livelihood depended on plantations being run economically. They owned extensive numbers of slaves. They were also in great debt. Washington fought his entire life to make his plantation profitable. Being away for years at a time while leading the Revolutionary Army or serving as president didn’t help. Thomas Jefferson was in such debt that his home was sold to cover his financial obligations after he died. James Madison feared he would run out of money. His wife, Dolly, had to sell their property at Montpelier upon his death and died impoverished.

While self-preservation is the motive here, we ought to keep the context in mind. Today, politicians typically become rich while serving in office. We would be hard pressed to name present-day politicians who chose to surrender their wealth and property by doing the right thing politically. That is not to say these presidents were right, but simply to point out that the decision was complicated.

The southern leaders who knew slavery was evil agonized over ways to wean the South off of slaves without throwing the entire South into destitution. At the time, the North’s economy no longer required slaves, so emancipating them was not a financial sacrifice like it would have been in the South. 

There were also political considerations. Southern politicians were fearful that the new nation would abolish slavery and bankrupt the South. Southern states were clear that they would secede from the union if slavery were abolished. People at this time did not primarily view themselves as Americans, but as Virginians, Georgians, etc. Men such as Washington believed that it was more important to hold the infant nation together than to divide it so soon in its history. Interestingly, even John Adams, who was from the North and not a slave holder, could not envision how abolishing slavery could be accomplished politically at that time.

It seems clear from their correspondence that the Virginian presidents feared civil war was inevitable should they free the slaves. History indicates that they were correct in their assessment. Lincoln, who ultimately addressed the issue head on, was assassinated for his efforts. We must remember also that Washington had fought a six-year war against the British for American independence. Many Americans had died in the conflict. He, for one, was ill-prepared to plunge his war-weary nation into another conflict immediately, even if it was for a noble purpose.

Jefferson’s Library

So these early politicians bided their time. They assumed that more and more Americans would recognize the evils of slavery and that it would eventually become easier to discard. The founding fathers largely believed that the infancy of America was not the right time to address its most polarizing emotional issue.

From our vantage point, it seems clear that these educated, brilliant men could have found a way had they been willing to pay the price. Of course, hindsight is always clearer. We enjoy 250 years of history and science from which to draw our conclusions.

So what is our takeaway? Leadership is complicated! Rarely does a decision impact a single issue. Few problems are black or white, even when an important moral issue is involved. This truth ought to incite us to do our homework diligently and to seek godly counsel. We ought to be cautious in making decisions until we have examined all the issues and fervently prayed for God’s wisdom. Not every leader is driven by pure and noble motives, but many truly desire to do the right thing. It’s just that doing good can be more complicated and costly than it first appears. Leadership is messy.