Friendship is not a luxury, it’s a necessity. But how do you navigate the messiness of friendship? And how do you overcome the challenge of loneliness as a leader?

Loneliness in Leadership & the Messiness of Friendship [Friendship Series]

Subscribe to the podcast here

This post contains affiliate links, which means if you choose to make a purchase via one of the links, we will receive a commission at no extra cost to you. This helps to support the costs of running the podcast and blog.

We’ve talked before about building healthy relationships and we’ve discussed marriage, but we haven’t really tackled the issue of friendship on the podcast. Today we’re kicking off a new series diving into the topic of friendship in leadership.

And along with friendship sometimes comes the issue of loneliness. Loneliness is one of the biggest challenges leaders face, but a lot of times we don’t know how to talk about this or who to talk about it with. 

In today’s conversation, Holly and I share sharing our honest experiences with loneliness as leaders and the messiness of friendship in our lives.

Dealing with Loneliness:

Holly and I each share examples of times that we have felt lonely in our leadership roles. For me, this has taken place mostly in my role as a pastor’s wife. For Holly, she’s experienced it in her workplace setting when she transitioned to a leadership role.

We also discuss how we have handled the loneliness, both in positive and negative ways. There have been times that I have put too much weight on my relationships (either my marriage or my friendships) When those relationships have had challenges, it has forced me to recognize that God should be me first and foremost relationship that I look to for fulfillment. 

We also discuss how loneliness tends to trick us into thinking that we are the only one who has experienced a particular situation.

“Loneliness is one of the biggest tools that Satan will use to destroy our ministry,  destroy our lives, if we let him.” – Esther Littlefield

We also chat about the fact that expectations also can set us up for failure because we have a false ideal of what our relationships should look like.

The Messiness of Friendship:

Holly and I discuss what our friendship journeys have looked like throughout our lives.

Holly shares how expectations affect the way we perceive our friendships.

“The expectations of friendship and what we’re going into it looking for have a huge impact on how those friendships are built and what they will look like.” – Holly Cain

I share how I have experienced different phases of friendship throughout my life, and that it has been hard for my to recognize that friendships don’t necessarily stay long-term.

“Friendship is not static. It doesn’t stay the same. But in my idealistic expectations, it does.” – Esther Littlefield

There are 2 key ingredients for developing friendships: intentionality and vulnerability.

Vulnerability is a willingness to talk about the hard things and share the hard parts of your life.  It can be tricky, at times, to determine how much to share as leaders.

“In any kind of friendship, someone has to go first with the vulnerability. If the leader isn’t doing that, then it’s going to be hard for other people to do that.” – Esther Littlefield

Friendship with God

We talk about what it looks like to be friends with God. It’s challenging to see God as your “friend” because He’s not a physical being that you can go have coffee with.

We noted that if we are relying too heavily on our human relationships more than our relationships with God, that’s where things can get unhealthy. 

I shared that there have been times when I have been too dependent on my marriage or my friendships to fulfill me, and when challenges have come in those relationships, I’ve been forced to ask myself, “Is God enough for me?”

Holly shared how her spiritual growth was intricately connected to her friendships. So she had to figure out how to focus on her relationship with God apart from her friendships.

Challenges Leaders Face in Friendship:

Obstacles that leaders face in building friendships:

  • Intentionally making the effort to seek friends
  • Seeking out like-minded leaders to befriend 
  • Time
  • Work commitments
  • Risk

“The beauty, when you can get to the place where you have a good friendship with someone, far outweighs the risk of someone not replying to you.” – Esther Littlefield

Moving Forward with Friendship:

Friendship is messy. And what we see online or in our minds eye is often this ideal of what friendship has to look like: 5 friends walking arm in arm, perfectly dressed and always smiling with no conflict ever. But this is not reality.

A big part of what we have to do as leaders is let go of expectations around friendship.

“Stop convincing yourself that you are missing something.” - Esther LittlefieldClick To Tweet 

Loneliness and friendship as leaders


How to Have Better Friendships

Stay Connected:

Subscribe on your favorite podcast app. Click here to find all the options where you can find the podcast.

Join our Purposeful Leadership Facebook group! In the Facebook group, we can chat about what you need as a leader, what your challenges are, as well as celebrate the wins. This is a great community to learn and grow together. We want to get to know YOU.

[convertkit form=5179709]

Other Ways to Connect with Esther and the Christian Woman Leadership Podcast:

Pin it for later:

Loneliness in Leadership & the Messiness of Friendship [Friendship Series]