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The high cost of success: exploring Craig's loneliness

Updated: Jan 24

Loneliness: A choice, an illusion, a friendly reminder.


Very few gay men seek out and then read articles about loneliness unless they’ve come to the realisation that they’re lonely. The stigma and shame we feel is real, and it takes a lot of courage to even engage with the subject.

I’m proud of you for opening this article. I recognise and admire your courage. Now that you’re here, let’s start getting you connected to yourself, those most important to you and to your community.

This is the next article in an ongoing series where we're exploring loneliness as a lived experience from others in the global gay and queer community. If we are to de-stigmatise gay loneliness, then we must know that there are other gay and queer people thinking experiencing loneliness like we are. I'm here to have The Loneliness Guy as a forum for that to happen.

Enter Craig Cassey. If you’re unfamiliar with Craig’s work, he’s an intuitive life, business and sex coach whose mission is to empower his clients to get out of their own way and on track to create a life they love. Check his website here and his Instagram here.

You’re here to read Craig’s words and experiences of loneliness. Writing about loneliness and sharing our reflections with the world is never an easy thing to do. I want to honour Craig’s courage, curiosity and his beautifully human story.

This article was published on Ngunnawal country. I wish to acknowledge and respect the Ngunnawal people’s continuing culture and the contribution they make to the life of Canberra and the surrounding region. I would also like to acknowledge and welcome other Aboriginal and Torres Strait Islander people who may read this post.

~ Phil

* * * * *

As an entrepreneur and recovering perfectionistic workaholic, loneliness is no stranger to me. In fact, it’s been intertwined with my understanding of success since I was a child.

Growing up I was both a premier track athlete at my school and an openly gay teen. The faster I ran in track, the more I realized how succeeding as an athlete could keep a vulnerable to being bullied gay kid protected. Who was going to go after the star athlete winning your school medals?

But my excellence in track offered a hurdle I wasn’t expecting. The faster I got, the more my training occurred away from my team. The less time I got to spend around my friends. The more distant I felt even whilst sharing the same common goal. My friends who trained together got closer, where I got closer to my goals by training alone. At least, my athletic goals.

It seemed to me back then, the better you got at something - the less you related and could be friends with others who weren’t on the same path.

I find this is a common narrative with my present day clients who eventually realize that their old friends might not match their new life as they take leaps towards a truly authentic vision of themselves. Or at least, they can no longer rely upon just having things in common to be the glue that holds them together.

And this can feel like loneliness. Heartbreak.

Pursuing a true professional desire at the cost of social desires.

But it doesn’t have to be that way, trading friends for success.

I simply accepted back then that the better I got the less I’d have in common with old friends and frankly, stopped trying. This also limited my risk because the more I expected to be alone, the less close I got with others and the less heartbreak I would experience when leaving them on my upwards trajectory.

Less risk. Some success. More loneliness. And the desire to connect still persisted.

But I ignored the part I played in all this and my desire for more connection. Instead of creating new ways to connect with people I actually cared about, I chose what felt the easier option and stopped putting in the effort to build something that could last even if the building blocks looked different than they used to.

Loneliness was a choice I chose repeatedly. So was creating new ways to connect. But it didn’t seem like it back then. The subconscious has a weird way of ruling what possibility we see for connection and does its best to choose the past of least resistance for us.

I take this lesson from my father who I love and who loves me deeply, albeit - in entirely different love languages than my own. While I am a words of affirmation and physical touch kind of guy, my father communicates love in time spent together and providing a life, gifts of support for my interests.

For part of my childhood I questioned whether or not my dad loved me, when to him it was obvious. How could I not see his love based on the time he spent or the track shoes he bought me? But for me I was waiting for a hug or the direct words I love you from a man who wasn’t taught or used to expressing affection in such ways.

Even inside of what I now know to be a loving relationship between father and son, I felt lonely because my subconscious didn’t let me see the ways he did love me. Loneliness was an illusion my subconscious wanted me to relate to as truth. Connection is no different, and the wildly successful individuals I work with experience this same breakdown in their marriages or families all the time.

I find for clients and myself alike we all have rules or expectations for how connection should look. These expectations keep us feeling lonely in relationships that really are filled with love once we open up our eyes to the many forms of connection being offered. And the more ingrained these expectations and relational patterns were from our youth, the more disrupting they require today. It requires putting down a mentality of right or wrong, and instead looking with curiosity at how connected we might actually be.

It also means welcoming loneliness not as a dark pit we’ve fallen into and can’t escape from, but as a friend reminding us that we have desires that aren’t fully fulfilled. Often by our own doing.

My friend loneliness tells me when I want more time together and also tells me when I’ve gone too far off on my own without touching base with loved ones.

Loneliness also teaches me when I’m leaving my comfort zone and reminds me that while I could go it alone, I no longer have to. That my success and my safety coexist alongside some really delicious relationships I’ve nourished intentionally with time.

My loneliness also informs me when my relationship life cycle with certain friends is coming to an end. Truth be told, we can almost always create connection where there are people. It doesn’t take much. But when others are not committed to the same work, it is only reasonable for our bodies to suggest finding others who are and with whom you can create the relationships you desire. So in those moments when I feel repeatedly lonely with once friends who feel like acquaintances, I make the empowered choice to release those relationships.

Who knows. Maybe they’ll come back! Maybe they won’t. But in a world where scarcity is not my mindset, and loneliness is not my fear, I’m too focused on creating the life I want to worry about repairing every relationship that no longer is for me.

To me loneliness now is both a feeling and a thing I have a relationship with.

I’m reminded often that I’m the creator of my own experience and that loneliness, if it persists, is a choice I’m choosing into somehow that I too can change.

I’m also aware that often when I am feeling lonely, it is in fact an illusion. A ruse my survival mechanism or subconscious is using usually to keep me from being vulnerable with others. In those moments I practice opening my eyes and heart and remind myself, I’m not as alone as I feel. It’s safe to share and connect how I yearn to be connected with.

And lastly, loneliness is a friend. Perhaps not the friend I hit up when I’m ready to dance until 4 am. But a friend nonetheless who has wisdom to share and love to give. Even if it comes with a few heartbreaks along the way.

* * * * *

Craig - a HUGE thank you to you for sharing your loneliness story and wisdom with us. There's a rich depth of reflection which I know was tough to tap into. It's always a privilege to receive someone's loneliness story, and I love your courage.

Reader - you may need some help after reading this article. Please, reach out to your partner, a friend or someone in your orbit who you know is trying to put themselves into the world just like you are. That could be me through my mentoring services. That could be a therapist or a counsellor – including a crisis counsellor. That could be a coach. It could be a combination of all.

Be sure to check out this page if you need help.

Let's have a chat with Craig about this wisdom-filled article. Join us for a coffee and a chat in the upcoming episode of my podcast for gay men ‘Connection over Coffee with The Loneliness Guy’ from Thursday 8 September 2022.



Important notice: All views expressed above are my own/the authors and are intended to support, challenge and inspire gay men to consider the issue of loneliness and increase awareness of the need for authentic connection with themselves, with others and their communities as an antidote to chronic loneliness. They are not intended to, nor should they, replace the advice of a licensed helping professional. Please consult the Services page if you feel that you need the services of a licensed helping professional where you are in the world.

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