From Loneliness to Connection: 5 Foundational Tips
Let's start with the basics
Last week, I shared a little about the ‘long dark night of the soul’ I experienced in my mid-30s, an all-encompassing depression that redefined my life.
That experience transformed me into an entirely different human being. The axis of my world shifted, and the lens through which I viewed others was profoundly altered.
One way it changed me was through an acute experience of deep loneliness: the deeper I went into darkness, the more I withdrew from others out of a sense of shame. The more I withdrew, the darker my experience of life became because of the isolation. It was a vicious cycle.
As I began to ascend out of the darkness, after two long and painful years, I vowed never to feel that crushing weight of loneliness again. Connection became a vital necessity and a significant focus of my life.
Much of my work now, with the Wayfinders community and my public events, is in helping alleviate loneliness and increasing connection for others. The motivation and drive for my work come from those experiences of isolation in my mid-30s, as well as the sense of alienation I felt for much of my childhood.
I’m blessed now to live a life rich with connection. It did not happen by accident. It is the result of intention, dedication, research, and practice. I live a life rich with connection because that is where I invest much of my time, much like my financial wealth will likely grow if I invest my time and money into wealth-building.
1. Recognize Loneliness as a Signal, Not a Failure
We all know what loneliness feels like. For many, it’s the gnawing sensation of being unmoored, longing for connection but unsure where to begin. It’s important to understand that loneliness doesn’t reflect our worth. It’s a signal—a nudge from our hearts reminding us that humans are meant to connect.
When loneliness creeps in, it’s easy to spiral into self-criticism, questioning why we are so isolated. I know I did - I thought there was something profoundly wrong with me at my core.
But loneliness isn’t a personal failing. It’s a natural response that evolved to ensure we seek the connections we need to thrive.
Once I learned to stop judging myself for feeling lonely, I started seeing it as an invitation to grow. Recognizing loneliness as a signal rather than a flaw opens the door to compassion and a readiness to reconnect with the world around you.
2. Cultivate Solitude as a Foundation
It’s essential to distinguish between loneliness and solitude. While loneliness can feel empty, solitude can be deeply nourishing. Solitude provides the space to reflect, recharge, and strengthen your relationship with yourself.
I transformed my alone time into meaningful self-connection by journaling about my feelings, taking mindful walks in nature, and meditating to listen more closely to my inner voice.
Not only did this help me develop more self-love and appreciation, but it also helped me to get to know myself on a deeper, more authentic level, which also informs the type of people I want to connect with.
Building this foundation of solitude can give you the strength and clarity to connect more authentically with others. Create a daily practice of intentional solitude, such as meditation, journaling, or time in nature.
Normalize being alone and content.
3. Embrace Vulnerability
Vulnerability is the bridge between isolation and connection. When I opened up to a close friend about feeling lonely and depressed, something unexpected happened: instead of judgment, I received understanding and empathy.
Later, when I started speaking publicly about my depression, many people reached out to me to thank me for sharing my story because it lowered the stigma for them around depression and mental illness; my vulnerability became a point of connection with others.
Those experiences taught me that vulnerability isn’t weakness; it’s a courageous act of showing up as you are, without pretense.
Start small—send a heartfelt message to a friend or share a thought that feels a bit tender. These moments of vulnerability can deepen your relationships and remind you that you’re not alone in your feelings.
4. Get Out of Your Comfort Zone
Growth often happens outside our comfort zones. The first time I attended a community event by myself, it felt awkward initially, but by the end of the evening, I’d had meaningful conversations and connections with people I wouldn’t have met otherwise.
Pushing ourselves to try something new—a local meetup, a hobby class, or volunteering—creates opportunities for connection. These steps might initially feel risky, but they open doors to new friendships and experiences that bring lasting joy.
5. Build and Nurture Your Village
Connection, for me, is about nurturing the relationships we already have and intentionally cultivating new ones. For me, it’s roughly an 80/20 mix: 80% of my ‘connection’ time is spent nurturing existing relationships, and 20% is spent on activities connecting me with new people.
Building your “village” might mean hosting a monthly dinner, organizing a game night, or simply sending a quick check-in message to an old friend. People are hungry for connection, so they will usually respond favourably when you make the effort.
When we make the effort to create spaces where meaningful connections can flourish, we lay the groundwork for a rich, interconnected life.
Next Friday, I’ll share 10 practical tips for “Building Your Village and Eradicating Loneliness.”
Stay tuned, and let’s continue this journey toward a more connected and fulfilling life.
Four More To Explore
Join me on Instagram, where I post short videos and daily posts about living more authentically and with more connection.
Check out my upcoming Adventures and Retreats with Wayfinders, where I take bold entrepreneurs to some of the wildest places on Earth, or consider our community membership if smaller events and workshops are more feasible.
Subscribe to my public events calendar on lu.ma, where I host online and in-person events to help people live with more soul and more connection.
Subscribe to my channel on Youtube, where I’ll be posting long-form video content about connection and authenticity.