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The 3 biggest leadership obstacles

| by Matthew Fretwell

Like many people in the business world, I have extensive experience in leadership. I’m a self-motivated, entrepreneurial, multi-tasking person. I’m currently a director of a leadership coaching network (and coach), a pastor of a revitalized church, a director of operations for a global church planting network, a doctoral student, and a family man. I was a restaurant owner and executive chef for over 20 years. Needless to say, I know about leadership and obstacles.

Here are three of the largest leadership obstacles, I have observed.


Time is the number one obstacle. News Flash: There are 24 hours, seven days a week—no more, no less.

When making business decisions, time can be used as a weapon, or become a major detriment—we’ve all been there.

But, the obstacle is not time management, it’s our view of time. Time is a measure of success. We sometimes gauge success by how fast we reach our goals.

Goals and time correlate. Effective leaders must set goals. Period. A leader without goals is only a manager.

For instance, I made a goal to be a head chef by age 24; I did it at age 23. I pushed for executive chef by 27, did it by 25, then owner by 35, I did it before 30. In each of these set goals, time was a factor, but not an obstacle. An obstacle is something in the way—a factor is an influence.

I used time to motivate me to achieve my goal—not vice versa. Biblically, think Caleb, 85 years young, and he faced his toughest battle. But, it was his goal to possess the land (Joshua 14:10–12).


I view myself as an everyday guy. I’ve had money, I’ve lost money. I’ve coveted money (confession), and I’ve loathed money (usually, when I lost it).

Answer this question: If you had an unlimited amount of money, how would it change your goals or leadership style? The answer provides a truth to your passion, drive and self-motivation. If money “changes everything,” you’re not passionate about your leadership goal(s). Money is a tool—not the goal—if it is, you have a misconstrued view and will find this out the hard way.

I’ll use my past as an example. Early on in my career, I took a lower paying job because it provided the title that I needed. In reaching my leadership level and goals, I had to place money on the sacrificial altar. It worked.

I forfeited a better paying job—for my goals. I did not allow money to dictate my life.

When leaders are focused on money—it’s an obstacle. It fogs decisions, wrecks relationships, and hinders goals. Remember, it is the “love” of money that is the root of all evil (1 Timothy 6:10).  


For many leaders, prioritization will either make or break you.

Effective leaders are strategists—prioritizers. As it has been said, if something is important, you’ll make it happen. When your smart phone lights up, you either answer it, or you don’t—prioritization! Do you really want to talk to your mother-in-law, right now? Don’t answer that (pun intended).

Everyone prioritizes…from what we wear, to which item we put on first, to when we’ll eat.

When a leader fails to strategically prioritize, their ship will drift with no one at the helm. As a sea captain utilizes a navigational chart, he strategically maps out his course. So too, a leader must strategically map out tasks—what’s important?

Most of my restaurant-owning days were brutal, especially on the days when I was cooking and prepping. I had to strategize my priorities. A food item which took several hours to cook caused prioritization. But, while the item was cooking, I was performing other tasks in payroll, scheduling, or finances—keeping a watchful eye on my food.

Prioritization is not about multi-tasking, but strategically ordering things of importance—whether a daily task or life goal. When a leader does not prioritize—things gets hi-jacked.

I’ll leave you with this—If you don’t make a decision, life will make one for you.

Matthew Fretwell

Matt Fretwell is married, has three daughters, is an author, revitalization pastor, national director of operations for New Breed Network, and leadership coach. Matt holds a doctorate from Southeastern Baptist Theological Seminary in Great Commission reproducible disciple-making strategies. Matt also writes for Church Planter Magazine and interviews well-known evangelical leaders on his discipleship podcast, The Wretched & The Wrecked.

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