Leadership is all about embracing both the highs and the lows. This episode’s guest finds comfort in the impact a leader creates through it all. Dr. Tracey Jones engages in a thought-provoking conversation with Derek Kilgore, a grounded leader and financial advisor with Northwestern Mutual. Together, they pull back the curtain on the challenges and triumphs of leadership, discussing topics such as overcoming loneliness, navigating weariness, making strategic decisions about abandonment, and crafting a compelling vision for the future. Derek shares personal experiences and practical insights, emphasizing the importance of meaningful connections, intentional prioritization, and the relentless pursuit of a vision. Whether you're a seasoned leader or aspiring to be one, this episode offers valuable lessons and inspiration to help you on your leadership journey.
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Derek Kilgore - Leaders On Leadership
I am very excited because my guest is Derek Kilgore. Let me tell you a little bit about Derek. Derek is a grounded leader with a heart-centered and results-focused approach. He and his wife, Amber, live in Littleton, Colorado with their two children, Addison who is 12, and Ethan who is 10. Derek is a financial advisor with Northwestern Mutual and leads a team of 15 advisors in his office. Derek, welcome.
Tracy, thank you so much for having me. I'm so excited about our conversation.
Thank you, Derek. As I read to the folks, he is an advisor with Northwestern Mutual and that is how we connected. I am with the Center for Military and Veterans Affairs at the American College of Financial Services. I teach their CLF designation, which is their chartered leadership fellows. Derek is taking this tremendous certification because he is very serious about leadership. In the course, I'm like, I would love to have you on my show and Derek graciously accepted, so thank you again.
You're so welcome. I was excited and I think we got a lot to talk about so I'm looking forward to it.
We do. Let's get right into it. My father gave a speech many decades ago, many times. Probably his most often given speech, he was a world-renowned motivator, but he also talked about leadership. very pragmatic, very real. He talked about the price of leadership in that if you are going to be wearing the crown or the mantle of leadership, there's a price you're going to have to pay. You need to be aware of it. In that, he listed four things, the first of which is loneliness. We've all heard that it's lonely at the top, but can you unpack for the leaders tuning in, what does loneliness in leadership look like for you, maybe a time you went through it? Any words of wisdom or resources you can share with our audience?
I love the idea of being vulnerable in the conversation about these are the hard things around leadership and the things that we struggle with. I think it's so easy and tempting to write a beautiful book about all the amazing accomplishments that we've done and all the awesome trophies and look at all this stuff. That can be inspiring, but I think it often can be somewhat defeating. Let's talk about what it's like and let's build alongside each other. I love this idea.
Around loneliness, I am a very connected person and I feel very deeply. It's very important for me to have meaningful and deep relationships with the people around me. I've struggled quite a bit with the loneliness factor. People inside my immediate professional circle professional, they totally get what we're doing right. They're building something alongside, they're in another office in another state or another city and we're encouraging each other. That's amazing and helpful.
Outside of my professional world, people don't understand what I'm building and what we're doing and leading people on a large level. Especially being in the financial services world, I think people look at that as like, "Are you guys on Wall Street up there? What are you doing over there?" They don't understand. There is a little separation where the wins that I have, if we are hitting a recruiting goal or we're hitting a metric for our office or a sales target, we're so excited about that, and then I share that with people outside of my professional world and my church community or my friends. They're happy for me. They're like, "Yay, good job, Derek," but they don't understand what it took to do that and what the scale of that accomplishment is.
On the other side when I'm oh we had this amazing recruit, "He was coming in in April and then he decided to take another job and we were so bummed out because he was going to be a perfect fit for our team. It was an alignment." The curve ball, I share those heartaches and people are like, "That's a bummer. I'm sorry that happened," but they don't understand that it's a big deal. It's important to do that.
Loneliness outside of my professional world has been a challenge to fill. What I've done to mitigate that is surround myself with people who get what I'm doing. People who are building alongside, creating accountability metrics, and also encouraging relationships that say, "What are you working on? I know you were hunting that goal down. How's that working out for you?" They can do the same for me. To mitigate the loneliness as much as possible has been very helpful.
I love that you said building alongside because I would venture probably 80% of our audience are entrepreneurs or retired once, twice, or thrice from other entities and now are already served. It's so important. You talk about building your business, especially in the financial services sector. You need to be with people who are like that because otherwise, you get somebody who may be in a 9:00 to 5:00. They can be very discouraging because the world we live in where you can only eat what you kill, it's a whole different thing. I love that you talked about get people that get you. Sometimes even your family. I can remember my dad saying, "Honey, I got man of the year." She's like, "Where's the check?" She didn't get the fact that all these things are necessary.
I'm echoing that exact thought. Align yourself with people that get you. I've got a buddy, Scott, who we met at church and he's about 20 years ahead of me. We'll talk about mentorship here in a minute, which is crucially important. He totally gets my world. He's built businesses. He's taken them public before. For me to share and for me to feel heard reduces the loneliness factor.
Align yourself with people that really get you.
That's so important because you want to quit. We all want to quit. Especially entrepreneurs, why shouldn't we quit? Why shouldn't I go back to the easy secure way? You get people who have already gone through it and they understand what you're going through. I love that. We talked about loneliness. Next, we talk about weariness. Before you came on, I asked Derek how he was and he was talking about being busy. You talked about sleep, water, rest, and all that stuff. This plays onto weariness because even in times of abundance we can get stretched too thin. Can you talk to us with everything you have going on, you're a father, you're involved in a lot of different things, and building a business, how do you day energized at top form?
We could probably spend hours talking about this subject, about effort and rest at the same time. I've learned this phrase called equipoise, which means two things at the same time. Two things that are both true at the same time but could appear to be opposite. This idea that we can have full effort into our life and also a healthy amount of rest is the ultimate challenge. I think we could all work ourselves to death. Brene Brown says, "Some people wear overwhelmed like a badge." They're proud of how overwhelmed they are. It's like, no, I don't want that, but I do want a high amount of success and a high amount of accomplishment. I want to maximize the life that God's given me, but I also don't want to burn out, be exhausted all the time, not present with my family, and not loving my wife the way she deserves.
There is a tricky balance between the two. Maybe balance isn't even the right word. I like the word harmony quite a bit, meaning some things are louder at certain seasons of my life and some things are quieter in certain seasons of my life. Sometimes the percussion set is taking a solo and it's like this crazy moment. Sometimes it's this peaceful sauna that's playing. The harmony of the pieces of my life, I work hard to do that.
Practically, what that means for me, that's been so helpful. I modeled it after one of my mentors, Ben. The quiet time in the morning is the most important time of my day. I've heard it say, "If you win the morning, you win the day." I'm typically up around 5:00 or 5:30. I try to do 30 minutes, sometimes an hour in the Bible, I'm reading and praying. Sometimes I literally just sit in my chair and be quiet because I know starting at 6:30 or 7:00, it's to the gym and then in the shower and then meetings back to back all the way through. Full productive. We're rocking and rolling all the way through, and then it's home, then dinner, then the kids, then some fuss is going to happen, and then it's in my bed and I'm going to sleep.
I know if I don't carve out the first hour of my day, there also is a tide element I think into that, meaning giving the first of your day and the first of your money to God. If I don't do that, I feel like I'm out of sorts. I work hard to compartmentalize that part of my day. Also, I feel like it gives me more freedom to drive into my day harder because I know I've already rested and I feel renewed and I'm not going to get burned out. That cycle has been very helpful for me in order to stay grounded and stay rested while also producing at a high level.
"Win the morning, win the day." You talked about it being your first fruits, that is a biblical concept. You give your best. We're republishing Ben Franklin's way to wealth, early to bed, early to rise. It seems like it's one of those constants out there thinking of financial geniuses. I love that you talked about that. It's so important. When you say balance, it's not like at any given time we can walk away from something. Balance implies something is down, but I love the harmony or the synergy or something is louder, something is a little bit lower.
I would say 99% of our guests talk about that first hour and how important that is to get your spirit fed first because that's what fuels. When you get burned out and tired, it's not your body. I know we're mere human beings. Hopefully, we know enough to take care of ourselves and get rest and stuff, but your soul's tired. Something's not getting fed.
The Ruthless Elimination of Hurry: How to Stay Emotionally Healthy and Spiritually Alive in the Chaos of the Modern World
I totally agree with that. Have you read the book, The Ruthless Elimination of Hurry?
No. Sounds tremendous.
It's awesome. The Ruthless Elimination of Hurry by a guy named John Mark Comer. It's exactly what you described is giving us space for our souls to rest. Left to our own devices, I think we would all, for a million miles an hour, everything's on fire, total chaos, always distracted, always on our phones, and there's a real effort to being restful and being settled. Check that out. It's a very interesting read. I think you'll like it.
I love the title. Thank you. You always recommend the best books. We've been recommending books since we met.
That's right.
We talked about loneliness. We talked about readiness. The next term my dad talks about is abandonment. For those of us in pet rescue or fear of abandonment, that's not the abandonment he's talking about. He's talking about the ruthless elimination of whatever it is that is sucking away the best and highest. Hurry, how do you abandon hurry? With everything that comes to you and you know you've got a million people, you're getting good ideas from, how do you stay tightly focused, singularly focused so you can channel your best into that vision that we will talk about next?
Abandonment, this is a beautiful concept. I think it comes down for me to having the courage to say no to things that are good so that I can say yes to the things that are great. I think that summarizes it. Let's break it down, but I think that's a good starting place because we all have good things in our life. We have relationships, opportunities, business stuff, coaching, "Can you be on this podcast?", and all this stuff. You're deciding, is this good or is this great? Sometimes we need to say no to something that could be awesome and very profitable and probably what God wants us to do in the end. It's not bad. It's pretty good. We need to say no to that and leave some space for something that we couldn't even think of or didn't see around the corner, comes around, and we're like, "That was amazing."
For me, practically what that means is every year, sometimes I'll do it twice or quarterly, but at least every year, I'll reprioritize the things in my life. I literally get a piece of paper out and write down, professional life, my leadership responsibilities, my family, my relationship with my wife, my relationship with my kids, my relationship with God, my responsibilities at church, this other side project I'm working on. I look at them and I ask myself introspectively, are those misaligned? Are we putting more time and energy towards the wrong thing? How much effort and energy we're putting toward each thing? Is it the right priority order?
For me, that priority is first my relationship with God, and then second my relationship with my wife, then my kids, then my professional world, and then all my church responsibilities. At times, those have turned upside down or mixed around and the reassessment helps line out what's most important. What that does for me is it allows me to go with so much more confidence to do the things I need to do because I know it's the best and highest priority. It's easier for me to say no because I know that I'm doing the thing that's the highest priority. What do you think about it?
I love when you say no to people and you have a reason for it because this is what I'm focusing on right now. People get that. I think sometimes we're like, "I don't want to let that person out." When you explain that to them with truth and say, "Listen, this is great, but right now my main focus is this. Can we reconnect in 3 or 6 months down the road?" I love that you talked about that because everybody in the CLF talks about this. When we lay out our refocus or recalibrating or are pruning away not the highest and best use of our time, we do talk about the different areas. Family, faith, financial, physical, relational, volunteer.
For the audience out there, don't try and throw it all onto one plate. Be very intentional about teasing it out and looking at specific goals. People are like, "It all links back up to the one thing." I think sometimes people try and take on too much and it's very good. Successful leaders like Derek sit down with a piece of paper and scrap up. We all do it. It's not like, "Haven't you figured it out yet?"
There is no amount of time during the year that it's not good to recalibrate your flight plan because remember, things are changing too. Doors are opening, doors are closing. There are unexpected things, an illness, a bonus, or an opportunity. Thank you so much for that. I love that you shared with the audience that you get the old-school piece of paper out and write that stuff down.
I love your comment about recalibrating your flight path. That is exactly it. You're in flight and you're like, "Let's make sure we're on track for where we're supposed to be going. Are we in the right seat? Do we have enough fuel?" Recalibrating is so helpful. I remember a time when I wasn't doing that and it didn't go good, so I thought I might share that story. It was the end of 2021 is when this happened. The business was going okay, but it wasn't really where we wanted it to be. I was turning the flywheel hard, like working a lot of hours and putting my effort and energy toward it, believing that this thing was going to take off and be amazing, but it wasn't amazing at the time. It just was okay. My wife's like, "I think you could do it. It's going to be great." I'm like, "This is hard." I'm working.
There are people ahead of me like, "He's there or she's there, it can be built." I was right in the thick of, someone had to graph around the valley of despair. You're excited about the thing, and then it's going great, and then you go to this valley of despair, and you're like, "I'm in over my head and I'm not making the money I wanted to." The failures are stacking up longer than the successes. I was right in that moment at the end of 2021.
I then did that exercise and I realized that part of the problem is I'm giving too much of my time away to my church responsibility. I was on the executive leadership team at the church and I was putting in a bunch of energy and effort. That wasn't producing a ton of fruit, but I felt like it's good work, obviously it's growing the church. I also had some other personal things that I was doing for fun that weren't filling my cup.
It's like good or great. I think it was that comparison. I did the sheet of paper and I was like, "This is a hard decision but this church responsibility has to go down a couple of notches. I got to put my business relationship higher up, my business adventure at a higher level of priority." I talked to Amber about it and she was like, "That makes total sense."
I had a hard conversation with my leadership team at the church and I said, "Obviously I'm still in this thing and love you guys. I just need to put my focus or turn my flashlight toward this business. We're at a crucial point where we need to get out of this dip." Like you said, they were so gracious, so kind to say, "We love you. Go crush it." I felt validated in that, and then we did. We had a great year in 2022. 2023 was even better. I want to share that story for our audience to say, it's okay if it's not going okay. It's okay if it's not going the way you thought there is a path forward.
It's okay if it's not going okay. It's okay if it's not going the way you thought. There is a path forward.
I thought that you said in the thick. You're talking about this and I don't know if I should laugh or cry because I remember those days. I still have them, but I'm laughing because we've all been there. When you talk about being in the thick, that is a great point for our audience out there. That's probably a great indication for you to say, "Stop. Let's lay it out on a paper and see exactly what's going on."
The second point that I love you talking about, you said to be fruitful, not be workful or be productive, but be fruitful. I'm all for kicking down doors and making it happen, but if you've been kicking on the same door for three years, it might be time and there's something not meant to happen. Like you said, you're a man of face, so you and I both know that we're being oriented towards, there are other circumstances, blessing, and things coming into our life. Again, if it's not bearing fruit, I don't want to say quit, but be honest about that and see what you need to do.
As you said, you went to your church leadership and you were honest with them. If you are out of whack or out of balance and you have to throttle back from something, don't just ghost people. Don't just leave them wondering, "I wonder why Derek isn't so engaged anymore. I wonder why Steve stopped coming to our board meetings." Be honest with them because otherwise, that person is like, "Did I do something wrong? Are they upset?" Everybody who loves you understands time is precious. We time tied. That's so wonderful that they would be fully supportive of you, but had you not had the courage to speak truth and love with that tough conversation, they might have been like, "Why is our brother dissing us?" That's never good.
Also, to echo that point, I felt more supported and more encouraged to go into this new season because they were like, "Let us know how it goes. We're rooting for you."
They're praying for you. They can support you from another facet of your life because they know it's all congruent. When you get this dialed in, then you can come back and touch on that again. Like I said a lot of times, like you said, when you're in the thick, we don't want to let people know we're in the thick, we tend to isolate ourselves. Worst possible thing we can do. We don't want to throw out our lifelines.
Loneliness, weariness, abandonment, and vision. I can remember sitting around as a little girl listening to people like Og Mandino, Zig Ziglar, and Norman Vincent Peale thinking, "These guys are smart. How do they get so smart?" I'd hear people talk about vision. I'm like, I'm not sure if I was born with that. My father was always like, "Tracy, vision is simply seeing what needs to be done and then doing it. Otherwise, you're a dreamer or you're a doer." You don't know where you're going. Like we said, you're a busy little bee. Either/or you're dreaming but you're not putting anything to work. Your vision for your business and what's next? You are growing an agency so everybody's looking to you and you have all these different pieces. How do you own your vision for what's next?
We could spend lots of time talking through this subject because it's so powerful. I think I have struggled with vision early in my career. For me, what I struggled with was believing that big things were possible. That was hard for me. We came from a modest income and lifestyle. Both my parents worked their whole life. They were moderately successful. We didn't go without by any means. I paint that picture because in the financial services world, some of the people who've been here for 30 years and have built tremendous businesses, they're wildly successful. The amount of income that they're bringing in is a pretty big number.
When I say I struggled with believing for big things, that's what I mean. It took a lot of effort and a lot of faith for me to be like, "No, I am deserving and worthy of running a successful practice, earning a healthy income, making a big difference in people's lives, and being present for my kids and for my wife." Believing that took a lot of effort. I don’t want to start there because it's not easy. It's not like you roll out of bed and go like, "I'm going to be the next Disney. I'm going to make this humongous." That doesn't happen. It takes a lot of effort to build a vision. Do you have comments on that?
Leadership: I am deserving and worthy of running a successful practice, earning a healthy income, and making a big difference in people's lives.
No. It's funny because one of the things in the CLF was guys how to write your vision and how you're incorporating that, so no. Keep going.
Some practical things that helped me quite a bit. One, I had examples to follow. I had people that I could look up to, buy a cup of coffee, meet with, sit with, buy lunch, and visit with them. Just ask them about their life like, "How did you get there? What is your life like? What are you struggling with. What's going good?" That way, it's not this abstract idea. It's like, I don't want everything that Mike's life is like and I don't want everything like Rachel's life, but I want a little bit of that. That seems pretty good. Her life is pretty cool. It helps you believe more if you can see and meet people who are ahead of you. That takes some humility to go, "I'm not where I want to be but I'd like to be where you're at in 5 or 10 years. Can I buy you a cup of coffee? I'd love to hear."
They're always so honored. They're always like, "I'm still trying to figure it out and you think you want to be like me?" It's always a great connected moment, back to loneliness, helping mitigate that. You then get to use parts of their life as an example on how you want to build yours because if you've never seen what an amazing and tremendous life is like, it's easier to see it from someone else already having it been done, and then you can start to build it yourself.
I love that. To reverse engineer. I love that believing that big things are possible for you. Derek, I know you say your parents were moderately successful but they raised and had you.
I don't mean to downplay my parents. They're amazing.
I'm kidding. I'm just looking at like, "Your parents must be so proud of you." I'm so proud of you and I'm just your acquaintance.
I appreciate that. I had one other thought. Here's a practical idea. I have a vision document that I use typically once a year. I have almost all of my advisors use it on a regular basis. It has the categories of life. This isn't like a hard and fast rule, but generally speaking, the categories of someone's life, spiritual, physical, emotional, financial, relational, and professional as well. Those areas are pockets of someone's life. It's helpful to own this document, write out 2 or 3 sentences of what that part of your life looks like in 24 months. Sometimes 10 years is too far, and I think 6 months is good but you want to stretch it a little bit, so the 2 to 3-year mark works well.
The cool thing is you write it in first person. It sounds like, "I am a loving and present husband and I treat my wife with respect." All these amazing things that you are. "I'm running a successful business and earning this income and I'm impacting my clients in this way. I am a physical body is strong and I sleep well at night." The more detailed, the better, and then you have a literal document, you put it on your wall, you read it, and you're reading the picture that you've painted of the life that you're building.
It helps as a true north to go, "Why are we working so hard and why is it worth the fight?" You then read the document about what your life is going to look like in 2 or 3 years and you go, "Yeah, that's what we're doing. That's who we want to be. That's what we're building. That's what we're going to." That has been tremendously helpful.
We covered loneliness, weariness, abandonment, and vision. Anything else that you want to talk about on leadership, because then I want to talk a little bit about what you do?
Real quick, an advice I would give everybody across the board if they're willing to listen is have somebody who's pouring into you, walk alongside someone who's at your same stage, and always be pouring into someone else. If those three things in your life are happening at every stage, you're more better off than less. You're more doing it the best way than not.
Have somebody who's pouring into you, walk alongside someone who's at your same stage, and always be pouring into someone else.
It's so funny you said that because I can remember 6 years ago when I met my husband. Of course, I was coaching and like you, we pour a lot into people. I remember he looked at me and said, "I read books so I get it. I have my faith, I get it." He's like, "Who's pouring into you?" I remember thinking, I think we overlooked that. Most of our audience are probably like, "Really, Tracy? I didn't." I think it goes without saying be very intentional because that keeps you from getting stagnant. That's the way it's supposed to be to keep that regenerative cycle.
Exactly.
So important. Derek, you're talking about your job as a financial planner. I'll tell you out there for our audience, the more I interact with these people, if I had to do over again, listen to Derek talk about his vision. If I had to do over again, I would've signed up. I would've found Derek and been one of his advisors and helped him grow his business. For anybody out there looking, it's such a tremendous opportunity.
I know what it did for my father, Charles. He had no education, he had nothing, but it is an industry that you'll help people mitigate the risks in life, build for their dreams, and build to take care of those that they love. Like you said, you get to build whatever you want it to be. Yes, it's hard work, but what isn't? I marvel at what you're doing and the gift that you do for other people and helping them achieve financial wealth and most of all security.
I appreciate you saying that. I love that comment. You can build it however you want. I came from a culinary background, so years ago, I was a chef. I didn't even go to finance at college. I worked in the kitchens for almost ten years and have a culinary degree, and then realized that I want to do something more significant. It's been an uphill battle, no doubt, but I just share that story to say, this is not a well-educated Harvard grad that needs to have a finance degree. It's like, if you want to build something, help people, and make a difference in other people's lives, it's a tremendous career.
It is, and my dad didn't even have a high school diploma. I'll tell you what, the company you're working for, Northwestern Mutual, nobody trains better than that. They will not let you fail. That's what's a beautiful thing. Derek, what was the thing at culinary school? Had you heard about this? For our audience out there that may be at a point where they're like, "What's next?" I have a couple of friends midlife that I'm talking to and I'm like, "You need to look into this industry." What made you make that pivot?
I was running a catering business that was mildly minus is how I would describe it. That's not a word I know, but it's like less than mild. Again, I'm working my butt off doing this thing and it wasn't working. It was like not doing what we needed it to do.
Yeah, I know.
That was on its way in a folding fashion, and then my advisor tugged my sleeve and said, "Derek, I think you'd be good as a financial advisor." Honestly, my first thought was like, that's a nice compliment, but I don't know anything about financial planning. That is not in my wheelhouse. I'm not even understanding why you're asking me that question.
I then unpacked. It's not about how beautiful a portfolio you can make or how great at math you are or algorithms, it's about connecting with people and a lot of effort, but building relationships and wanting to build something yourself, wanting to be an entrepreneur, and wanting to grow something. You can learn the tools and the skills of financial planning. You can learn how to build an insurance tool. You can learn how to build a financial plan. You can understand how Roth taxation limits work. You can learn the skills, but the hard around building something and helping people was what drew me to the business.
Leadership: It's not about how beautiful a portfolio you can make or how great at math or algorithms you are. It's really about connecting with people.
Derek, now that we mention that, how do people get ahold of you? Is there a preferred manner?
Yeah, sure. You'll put my email and probably my website in the link. Best way is to click that and check out my website. I'd love to connect and always up to chat.
To our audience and Derek, thank you so much. I got a lot of great notes. The way you say things, you got me laughing and reminiscing about my own personal journey. What a joy to have you share with our audience about what it takes to pay the price of leadership. We wish you so much more success. I know you'll achieve it.
I appreciate that very much. It's been awesome hanging out with you. Thank you.
You're welcome. To our audience out there, thank you so much. If you like what you heard, please hit the subscribe or share button. If you do us the honor of a review, we would be so thankful. Share this with other people. Share this with your friends. I know your leaders, you hang out with a lot of leaders that are maybe looking at how to pay the price of leadership to encourage and inform them. Always remember, you're going to be the same person 5 years from now that you are now, except for 2 things, the people you meet and the books you read. Make sure they're both tremendous. Thanks so much everybody. Have a tremendous rest of your day. Bye.
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About Derek Kilgore
Derek Kilgore is a grounded leader with a heart-centered and results-focused approach. He and his wife, Amber, live in Littleton, Colorado, with their two children, Addison, 12, and Ethan, 10. Derek is a financial advisor with Northwestern Mutual and leads a team of 15 advisors in his office.