How I’ve Failed at Friendship — and What I’m Learning

Four personality "quirks" that have surely caused friendship with me to be challenging. Here's what I'm doing to help improve.

With Friends in the Swiss Alps

As mentioned yesterday, I don’t think I’ve always been that great at friendship.

My propensity to be selfish,

my focus on achieving and being the best,

my fear of being vulnerable, and

my default of stinginess have created conditions in which, well, I imagine people have found friendship with me to be challenging.

I said I was going to say more about those today, so here we are. But I don’t just want to unpack each of my… issues… I also want to try and be helpful (to both myself and any others who struggle as I do). So after each “Challenge” (meaning, things that make being friends with me challenging), I’m going to say a bit about what my Invitation to growth is.

Because I really do want to be a better friend. There are some amazing people in my life, people I’m lucky to call friends. And I want to do right by them.

So here we go…

Challenge: I Can Be Self Absorbed

Living alone has brought this particular issue into unavoidable clarity. It may be slight exaggeration, but I can sometimes go an entire day without interacting with or even thinking about another person.

Whether it’s because I’m locked in to certain projects, or overwhelmed with work stuff, or wallowing in self-pity (for the aforementioned living-alone thing), I know that I can sometimes be way too focused on my self, my needs, and my wants.

Is there a spotlight? I’d love to be in it, thanks.

Is there an award to be given? I’m assuming I’m being considered, right?

Is there an hour of availability in the calendar? I’ll do something for myself.

I could go on, but you get the point. I can be selfish. I can care more about my thing than your thing. I can prioritize my comfort or my entertainment over what you want.

Invitation: Look for Who I Can Love On

One of my favorite things to do (and it’s odd to say that because it is simultaneously true AND something I don’t do enough of) is to cheer on, encourage, support, and love on my friends.

Sending them texts to congratulate them on achieving some goal.

Calling just to check in because they popped in my mind.

Asking if there’s a way that I can amplify or support a project they’re working on.

Looking outside myself and focusing on supporting the efforts of other people (rather than using that energy on more me me me) is one way that I can help to sand off the rough edge of my propensity toward selfishness.

Challenge: I Can Be Achievement Oriented

As a fabulous Three on the Enneagram, my thirst for achievements is nearly unquenchable.

To explain that last sentence I’ll say it like this: at my core I do not believe that I am worthy. Worthy of love, worthy of care, worthy… at all, really.

As a hack for this perceived lack, I have learned to find love (or, more accurately, respect and admiration) by being great at things. By producing stuff. By achieving.

When I win, or when I make something cool, or when I get recognized for some success it (momentarily) fills the hole in my heart. I feel worthy. Like I matter.

This unhealthy remedy, even if entirely understandable—meaning, of course I am this way—was a strategy I developed to survive early on in life. However it has some pretty gnarly side effects. Not least of these is the ways in which I can commodify relationships and see them as stepping stones for my own success.

I’ve no doubt that people in my life have felt used by me in the past. (Again, my urge to not be seen as a monster wants to immediately follow that up by saying, It wasn’t intentional! I’m not out here TRYING to use people!)

But on some level my intent is irrelevant insofar as the impact it’s had on people. Because I’m keenly aware of my own internal drive for winning and success and achievement, I also must then be honest about how I can sometimes see people (aka, relationships) as means to get to my end.

Who do you know or have access to that, if I play my cards right, I might someday get to know as well?

What kind of skill or competency do you have that might help aid me in my pursuit of accomplishing X, Y, or Z?

You have access to resources that I do not, but if we become friends then maybe you’ll share with me.

My incessant drive to achieving and success can sour my relationships when I turn them in to a means to an end.

Invitation: Do Things That Can’t be Won (Alternatively: Stop DOING Things)

While it strikes me that one path of growth might involving being more than doing, that also feels a bit unattainable at times.

Therefore, what if my invitation is to look for things I can do that cannot be won? Where there is no such thing as “being the best” (I know, it sounds boring… but I’m sure it’s good! ;)

This summer I decided I wanted to get back in to camping. I have not been camping since my divorce, so for my 43rd birthday I bought myself camping gear: a tent, a stove, an air mattress, a hammock, and so on.

I think it’s hard to “win” at camping—though don’t kid yourself, I’m still low key trying to be good at it, I can’t change my stripes that much. But the larger point remains. As I sit by the fire or swing in a hammock I am mostly just… existing.

I’m both doing (camping) and being (just chilling).

Doing things that cannot be won might help, over time, to adjust my orientation away from the success/achieve/be-best-at mentality. My hope is that as I get more comfortable with my self in this regard (meaning, being okay with who I am even if I’m not crushing everything), this will help me in my relationships because then I will be less focused on extracting something from people.

That’s the hope, anyway.

Challenge: I Can be Afraid of Vulnerability

Connected to what I just wrote about not feeling worthy and feeling like I had to be GREAT ALL THE TIME in order to be loved, my underlying goal for most of my life has been to NOT be human.

Humans make mistakes. Humans hurt people.

Therefore, I must be super human.

Being super human also gave me the illusion that I could control how people viewed me. If I was awesome all the time then you had no choice but to think I was awesome.

This should come as no surprise, but never being vulnerable with people makes them not only not think you’re awesome, but also kinda slowly they stop trusting you.

If you’re around someone who never makes a mistake (or at least acts they don’t), and if they never share about their struggles or the failures, then you naturally want to stop sharing your weakness and issues as well.

This makes closeness very, very challenging.

I have no doubt in my mind that many of my friendships over the years suffered, as the years went by, because of my fear of being vulnerable with them. My initial charm might’ve drawn them in in the beginning, but charm can only take you so far.

It’s been a long journey but I’ve had to really come to grips with not only my own fear of vulnerability, but also how that reluctance in me has caused the people in my life to pull back as well.

Invitation: Authenticity and Honesty

One time years ago I preached a sermon at Sojourn Grace Collective in which I publicly acknowledged my innate complicated relationship with “the truth.”

I’ve learned this is true for many Enneagram Type Threes. It’s not that we outright lie, per se, but we might have no qualms with massaging the truth a bit. Whether it’s to spin something so that we still look good, or, avoid being fully open so that we don’t look bad.

Either way, it’s not great. I don’t love it.

My growth edge, as I move toward becoming a more vulnerable person, is to practice being authentic and honest—first with myself, and then with others. (This post is a big effort toward this practice, btw)

Sometimes this is being honest about how I really feel. Which of course requires that I learn to feel my feelings; then name them; then name them out loud with honesty. In years past I haven’t said how I really feel about things because maybe I’m afraid of hurting someone’s feelings, or I’m afraid of confrontation, or I’m afraid of just owning up to the fact that I’m human and things bother me.

Nowadays I practice (or I try to, anyway) a kind of radical authenticity even if it makes people uncomfortable. This isn’t an excuse to be rude, I don’t buy that garbage (you know, when people “Just tell it like it is,” as though they get to say their opinions without repercussions). Kindness still matters to me.

But as Brene Brown teaches, clarity is kindness. That applies to feelings, too. Be clear about how you feel, that is kind.

I like to think that my attempts at being more authentic (with my issues, my weirdness, my weakness, my humanity) and more honest (with my feelings and my needs) has helped to improve my friendships over the years.

But I’ve still got a long ways to go.

Challenge: I Can be Stingy

My final “quirk,” to put it kindly, is how stingy I can be.

Stinginess comes from a scarcity mindset. It believes that there isn’t enough to go around. It believes I have to quickly and firmly get what is mine otherwise I’ll be left with nothing.

Stinginess is a fear that mana won’t arrive tomorrow. Sure, today may be taken care of, but that’s just today!

Stinginess is a form of the aforementioned selfishness inside me. It comes from a place of believing that no one else is thinking about me, or concerned about me, or going to take care of my needs so I better make sure I’m covered.

Because if I don’t, know one else will.

Example: I can be slow to grab the check sometimes. Not just because I’m poor and probably can’t afford to pay for everyone, but because I’m afraid I will always be poor and so don’t waste what little money you have now!

I have a friend name James, and while James was never rolling in the dough he almost ALWAYS paid for whatever he could whenever he could. I watched him grab the check (literally and metaphorically) over and over again, even as I knew it was beyond his means.

I fricking envied that man. Still do.

I’ve never made much money. Always at or below a Living Wage. So on a very practical level, my “stinginess” makes rational sense.

But it has created a culture of stinginess within my very being.

I don’t think you can just say, “Oh I’ll only be stingy with my money,” and not have it impact other areas of your life.

Stinginess leaks. We can be stingy with our time, our attention, our love.

Um… not sure why I wrote “we” in that last sentence. That’s me avoiding vulnerability.

Let me try that again.

I can be stingy with my time.
I can be stingy with my attention.
I can be stingy with my love.

In addition to, of course, how I can be stingy with my finances.

Invitation: Claim and Practice Abundance

It seems obvious to say but the antidote to scarcity is abundance. Well, obvious and scary. To me anyway.

Abundance sounds lovely in principle, but deep down I’m not sure I believe it. Or rather, based on how I live, my actions would reveal that I do not believe it.

But in theory, as a concept, I am ALL IN on abundance! I think there is and always will be more than enough. Somehow. Some way.

Some of the most generous people I know are also the most wealthy people I know, and I’m not sure that’s an accident. While the assumption might be that they are generous with their resources BECAUSE they have great wealth, the older I get the more I wonder, what if they have great wealth BECAUSE they are generous people?

I talked about the culture of stinginess that can live inside a person… er, um, that lives inside me… and I think it’s even more true the other way around. Generosity is a culture that lives in people.

While I can’t inflate my bank account overnight (therefore practicing abundance with my money may not actually be possible at the moment), what I can do is look at the list above (time; attention; love) and start to practice a culture of generosity with those things.

I believe there is enough time, more than enough. So I can give some away to my friends.

I believe there is an endless supply of attention. I don’t always need to focus it on me or my things. I can give that away.

And I KNOW there is a never ending flow of Love. Being stingy with Love makes NO sense considering the supply. Holding back my love is only ever a result of fear (of getting hurt, of not getting loved back, etc), it has nothing to do with me not having “enough” of it.

Closing Thoughts to My Friends

I don’t know how many of my friends read my newsletter. And of those friends, I don’t know how many have been friends of mine for a long time.

But if any of you are out there I guess I want to close by saying I’m sorry.

I’m sorry because I know that my tendency to be selfish, my propensity to focus on achieving things, my fear of being vulnerable, and my stinginess very likely made it so that I wasn’t a great friend to you.

Just know that it was NEVER about you, it was always ME. (Which sounds selfish, but that’s not how I mean it, lol).

It was MY fears, MY insecurities, MY undealt with childhood trauma that caused me to treat relationships like stepping stones to my own advancement, or, as one-way streets where you shared your humanity and I responded with my awesomeness.

If you hung in there with me, even in spite of my lack of friendship skills, you’re a saint and God bless you.

I’m hopeful for this next stage in my life, whatever that looks like, because I think the above four challenges are all things that not only am I absolutely aware of, but they’re things I’ve been actively working on for a while now.

Hopefully, ten years from now, I’ll feel differently about my rating as a friend.

Until then, I have some notes. (They are above :)

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