My Top 5 Leadership Regrets

This is a public confession of sorts. While the past cannot be changed, the past can teach us some lessons for the present that will impact the future. While I have reserved this for my top 5 leadership regrets, it is not to say by any means these are my only mistakes or regrets.

  • Not being a “Respectful Rebel.”

I just got done working on a message I will be speaking to youth that I titled “Respectful Rebels.” Come on, doesn’t that sound awesome??! All my life, I have only heard of “rebellion” in the negative sense, and yet there is a lot in this world that I find myself wanting to rebel against. It dawned on me as I was working on this message that Scripture actually holds up many positive examples of rebels. David verse Goliath, Daniel and his friends, Moses verse Pharaoh, Jesus, His disciples etc. We seem to only discourage negative “rebellion” however!

But as I thought about many of these, something else struck me. They were not just “rebels” but “respectful rebels.” They were courageous, but calm. I also think of Martin Luther or Rosa Parks and how the civil rights movement was a “rebellion” but a core aspect of it was the “respectful non-violent” philosophy.

Respectful Rebels. Rebellion is often not only not wrong; it is sometimes right, good and necessary. The issue, and my problem, and thus some of my biggest regrets, have been not combining “rebellion” with respect. I can’t say I regret much of what I have rebelled against that many just go along with in not wanting to make waves, but I do regret my attitude not remaining respectful in many cases.

What if however, parents began not merely speaking negatively against the “rebellious teenage years” but worked to channel teenage rebellion in positive and respectful ways? I don’t think I’ve ever really heard (nor have I yet preached this clearly) a sermon encouraging believers to be “Respectful Rebels” in appropriate situations.

  • Becoming angry, bitter and letting frustration influence everything.

This might be my biggest regret of all. I have left several situations on a bad note like this. Again, as with rebellion, anger is not always wrong, but sometimes very right. Jesus got angry over injustice. He gets upset over lukewarm believers. He made a whip out of cords, overturned tables in the temple and drove out all those abusing and taking advantage of the genuine hearts of worshipers. He called out religious hypocrites. God gets angry over evil, in fact He hates it. Therefore anger has it’s place.

But Scripture also warns us not to sin in our anger or remain in our anger. I fail on both counts more than I would really like to admit. Whether with my kids, my wife, the church I pastored, or even now in situations or with people in various settings, anger (in it’s negative and destructive sense) is still a battle for me. Regardless of whether the anger is justified or not, I have more regrets in either sinning in my anger (through words or attitude or action) or stewing in my anger, resulting in depression or frustration being expressed. It’s an area of my life I am still seeking greater victory in.

  • Lacking “People Discernment” that led to ruined witness and trust.

This is another area where I have had a particular weakness in, especially when emotionally vulnerable. I have trusted certain people whose character I should have questioned or others warned of/sensed red flags. Because of trusting, confiding or too closely associating with people like this at times, I have been influenced in wrong ways, burned relationships and damaged trust and testimony. Scripture warns:  Do not be misled: “Bad company corrupts good character. (1 Corinthians 15:33).

I have both been guilty of this, but also been on the other side of seeing others doing this. It leads to pain and problems for those who lack discernment and those affected by that, especially when leaders fail in this. Whether hiring the wrong people or associating too closely with the wrong crowd, it never ends well no matter who you are.

  • Not taking enough time to simply “be” with people without trying to “drive results.”

I admit that if I don’t see the “purpose” in something I struggle. Whether that be simply “having fun” or “hanging out” or just spending time with people, family, friends or relaxing, I get antsy. I want to accomplish something of eternal significance, see results or make progress in measurable ways.

I am not there yet in this, but God has been really working on me in this area lately by changing my mindset of what “purpose” is or “progress” looks like. Sometimes just being or resting is the most productive thing that can be done! I also don’t want to be a “slave-driver” only concerned with results as a leader, but become more of a “servant-leader” who looks to come alongside of others for their sake. Looking back this has led to some regrets of wishing I’d have spent more time simply with people or family or staff.

Well…that’s my confession for the day! What are some of your top regrets?

Oh…one more “bonus” regret: E-mail is the worst way to communicate anything that might be perceived as “negative” or is sensitive of nature. I have sent way too many e-mails that have led to misunderstandings or hurt…or sent while still upset and thus regretted after sending.

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