How Much Self-Work Is “Enough” Before Entering a Relationship?

As we continue our exploration of relationships, I was reminded of a question I was once asked on The Listening Well podcast: “Is the greatest predictor of relationship longevity how well you know yourself before entering another relationship?”

For those of us committed to self-growth, it’s easy to agree: understanding our triggers, emotional baggage, preferences, family conditioning, and inner narratives is crucial for healthy connection.

And yes, the more we understand and manage ourselves, the more likely we are to build stronger, more fulfilling relationships.

But here’s the nuance I would like to bring into the conversation: when are we ever truly “ready”?

Can we only bring our best self into a relationship once we’ve reached a certain threshold of self-awareness?

Or is it possible that being in a relationship is what helps us grow, stretch, and evolve the most?

Self-work undoubtedly lays the groundwork, but relationships are often where the real transformation happens.

What do you think?

Watch the short extract above and share your thoughts with us, in session or by replying here. We would love to hear from you.

Why not take this opportunity to do the work with your partner and bring a new depth to your relationship? We so rarely carve out dedicated time to have the essential conversations that truly nurture connection and intimacy.

Our Relate With Love workshop, held on the 6th to 8th June 2025, at the peaceful Swiss Club in Singapore, is designed to help couples explore these foundations in a supportive, guided environment, building not just understanding, but emotional closeness and lasting change.

If you are single, or if your partner isn’t ready or willing to join just yet, this experience is still for you!

You’ll gain valuable tools, insights, and practices that can create profound shifts in your personal life. And often, those changes will have a ripple effect on your relationships too. Growth starts with you, and we are here to support you in that journey.

Whether you are single or in a relationship, if you are feeling uncertain about your next steps or have questions about your relational patterns, our retreats, therapy sessions, or intensive programmes offer tailored guidance and insight. You'll gain clarity, address concerns, and discover ways to deepen intimacy whether with a current partner or in preparation for future connection.

Explore our different offerings with a quick call with our team to understand the benefits of each programme.