What to do when your heart is not in your work

As a teenager, my friends nicknamed me “Dr. Kiley”. Whenever they were confused or depressed, or struggling with relationships, I was the one they sought out for advice. I think it was because I was willing to listen with curiosity and without judgement. Also, I didn’t say much back then, which was helpful because mostly they just wanted to feel seen and heard.

Nowadays, people still seek me out for advice, but it’s more specifically about their work. Mostly, they want to talk about how their heart is not in it and they are questioning what to do next.

Our relationship with work is similar to any other kind of personal relationship in that it reflects how we are showing up in the world. And just like intimate relationships, we can fall into work unwittingly. We may unknowingly choose work to compensate for our wounds or “make decisions out of fear disguised as practicality”. However, there comes a time when being in a loveless relationship is no longer enough. The natural desire to experience joy and passion in our work starts to supersede the choices we once made out of the need to feel safe.

If I were an advice columnist, letters from the working lovelorn would read something like this:

Dear “Dr. Kiley”,

I’ve been enduring a long-term relationship that’s never really satisfied my soul. I got into it out of necessity. It wasn’t really a good match from the beginning. There was no spark. No real connection. But I carried on anyways because I didn’t believe there was something more enlivening and more meaningful available to me. Now that years have gone by, I’m no longer willing to deny the yearning in my heart. I want to be in love.

The thing is, I’ve invested so much time and energy into this relationship, I’m afraid if I leave, it will have all been for nothing. I’m afraid I don’t have what it takes to start over. If I’m being honest with myself, though, my real fear is facing the unknown.

However, something deep within me knows I am deserving of more and that there is a relationship that will allow me to be all of who I am and truly express myself in the world.

I believe it’s time I trust this inner knowing and make the big leap. Do you have any advice as to how to make this transition easier for everyone involved?

Hopelessly Unfulfilled


It used to be common that people would choose their work for reasons other than love. But the consciousness on our planet has changed, we have changed. What is emerging now is the call to live from our hearts. We are the generations bridging the separation between work and love.

Even when there is no love in our work, it is still unnerving to venture into uncharted territory. In our hearts, however, we know we have no choice but to make the journey. The choice we do have is how we undertake the journey. What I would write in response is this:

Dear Hopelessly Unfulfilled,

All you have lived has not been for naught. You have gained so much clarity and insight from this relationship. You’ve learned more about who you are and who you are not. You’ve learned to listen your inner knowing and to trust your heart. Give thanks for your experience and carry all this goodness forward with you into the next phase of your journey.

Rather than a “big leap”, perhaps you can make the journey in smaller, more incremental steps, savouring each one as you move along your ever-evolving path. You can trust your inner guidance, in the form of inspiration, to show you the way.

Indeed, the unknown can feel scary. Instead of perceiving it as a dark empty void, think of it as a light-filled space where all potentials exist, and you are consciously choosing to play in it.

Before you commit to something new, however, my encouragement is for you to take some time to reflect deeply on all that you are and consider what you’d like to bring to your next relationship. Then, what’s next will emerge from your sense of self-worth and true desire, the foundation of all fulfilling relationships.

I know you know this, and I will remind you anyway – you are worthy and deserving of big love. Go for it.

Believer in Big Love


My “advice” for falling in love with work

By claiming your desire for a more loving relationship with work, you’ve already taken a big, bold step. To continue your journey:

See work through the eyes of love
Our past experiences can taint our perceptions of work itself. Many of us carry old beliefs and stories that hinder us from inviting a more loving relationship. Take the time to identify, acknowledge, and release those limiting beliefs. It is also a powerful exercise to write a new, more loving story of work. These actions welcome new possibilities for your work.

Keep your heart open
Even though you may have been hurt in the past by a painful or toxic relationship with work, it is essential to keep your heart open. Your willingness to stay open and feel everything (both the “good” and the “bad”) is the key to accessing your inner guidance. Your inner guidance wants only to lead you to the fulfillment of your true desires. You can trust yourself.

Nurture your self-love
You were born into this lifetime with extraordinary strengths, gifts, and talents. You may not yet fully recognize them, but you do have them. Since you were born, you have lived an extraordinary life through which you have gained tremendous insight and wisdom. Who you are and what you have lived has so much value. When you recognize your worth and treat yourself with care and compassion, you will be ready for the love of your life to appear.

Play the field
There are many work potentials available to you, which would provide both love and money (you can have both). Before you make a big commitment with any one new relationship, take some time to explore your ideas and dream up new possibilities. They might lead you to an even grander experience that you cannot see from where you now stand.

Let the world receive your love
Work is not just about you as an individual, it is a reciprocal relationship with others. It is the container through which you share your love with the world. You have so much to give and the world is starving for it. When you create work that allows you to be yourself in service to others, not only do you fall in love with work, you fall in love with life itself.


Even though I offer up these nudges as a way to help you discover a loving relationship with your work, these days, my work is not as much about dispensing advice as it is about helping people connect with their own hearts. I know that as long as you trust your heart, it will lead you to the most beautiful love relationship with work you could ever want – the one that allows you to be and to express all of who you really are.


If you’d like to create a more loving relationship with work, join the “Work: A Love Story” Workshop.
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