Courageous Living Might Break Your Heart a Little
Have you ever thought about courageous living and why it truly matters?
My sense is that most of us don’t spend much time musing on courageous living. I certainly didn’t, until a few years ago when I discovered poet David Whyte’s essay about 10 Questions that Have No Right to Go Away.
The timing was good. I’d reached a difficult moment, coping with a series of life transitions that were happening one on top of the other. Whyte’s questions helped, and also inspired several clients to pause and ponder their own complex transitions.
All of his questions are valuable and full of insight. But the one that I keep returning to is this: Can I live a courageous life?
Whyte defines courageous living as “the measure of your heartfelt participation in the world.”
(He also notes that the root of courage is the French word couer, meaning “heart.”)
Here’s what he says about courageous living…
Human beings are constantly trying to take courageous paths in their lives: in their marriages, in their relationships, in their work and with themselves. But the human way is to hope that there’s a way to take that courageous step—without having one’s heart broken. And it’s my contention that there is no sincere path a human being can take without breaking his or her heart.
Whyte’s essay reminds me that we can’t trace the arc of our lives going forward.
Of course, the courageous path does regularly bring heartbreak. Nevertheless, we are routinely convinced we should be able to (or wish we could) avoid the heartbreak.
That makes sense, considering the internal and external pressure to know where we’re going and what we’re doing. If you listen closely you’ll hear the undercurrent: that you’re more likely to succeed (and bypass heartbreak) if you have a predetermined plan for your life or goals that are smart and focused.
To be sure, there’s nothing wrong with being planful, smart, and focused, but it’s unlikely they will save us from heartbreak along the way.
Many times, when you feel responsible for figuring out all the details of your courageous path before you take the first step, the experience feels more like confusion than courage. The result: worry about what you overlooked and why things aren’t going as planned.
No wonder we keep looking for ways to take courageous actions that won’t break our hearts.
Yet, when we allow ourselves to stop and look back on our lives with a bit more compassion and grace, we might see that our stories are filled with examples of being courageous. We might get a glimpse of our own heartfelt participation in the world in more personal ways.
I know this to be true, because I experience it every week in my work as a therapist. Again and again, people find themselves at the edge of their next courageous step…
Leaving or staying in a difficult relationship. Venturing out alone to start a business or other endeavor. Making major life decisions on behalf of aging parents. Stepping back from the grind to heal and regroup. Starting therapy or embracing self-care. Letting go of waning friendships or moving out of isolation. Giving in to creative whispers or walking away from confining structures. Retreating from toxic family dramas. Questioning beliefs that no longer seem to make sense.

At the same time, courageous living means so much more than the path ahead or life’s complex experiences.
Quite often courage is born in the small moments of day-to-day living. While we tend to see courageous choices as large and impactful, they are just as likely to show up as unexpected insights and ahas that unfold gradually over time.
- the boundaries you set
- the moments of speaking your truth
- day-to-day challenges and decisions
- commitments to your well-being
- stepping back from the urge to mend what’s broken
- stopping, breathing, and accepting what is
Courageous living moves us toward more engagement with life and a wider range of emotions.
Still, you might be wondering…is there any way to take the courageous path and leave the heartbreak behind?
David Whyte says no, and I agree.
There’s immense heartbreak in these lives we lead—from the quiet pricks of regret to the often overwhelming weight of grief. And yet, if we erased the pain wouldn’t we also have to erase the joy, the possibility, the growth that came with the heartbreak? As well as the discoveries that will come after?
In this way, heartbreak is evidence of our capacity for deep feeling, resilience, and love. Ironically, it’s also part of what makes life worth living. And certainly, we wouldn’t want to miss out on having lived.
However, I do think David Whyte’s essay left something unspoken.
It’s this: human beings are tremendously wise and resourceful.
Although the human way may be to hope that we can live with courage and without heartbreak, in the small quiet moments our deepest wisdom tells us otherwise. And even though our hearts may break in the midst of courageous living, we possess a powerful capacity to heal and make it through to the other side, where possibilities often arrive that we couldn’t see before.
I’m not talking about backup plans, although they may be helpful. I’m talking about the inner work of being with and being in the journey.
Maybe a better way to explain it is to reach back to an old question that often gets asked during times of transition:
What would you do if you knew you couldn’t fail?
It’s not a great question, so let’s improve it with some of Whyte’s words:
What courageous path or choice would you follow in your life if you knew you’d bypass heartbreak?
Still not a great question, is it? Because deep down we know that denying our fears of failure (or success) won’t get us very far.
Ultimately, your deeply embedded wisdom understands the fears that show up when you’re trying to live courageously.
Failure (felt or anticipated) doesn’t have to hide in a back room. It can be welcomed into the light of day.
Contrary to what you may have experienced or been told, there’s no shame in fear of failure (or failure itself). Your fear is a natural response that has its roots in biology. Furthermore, naming it and normalizing it creates a resilient platform for courageous living, with less worry and more acceptance about about what you may encounter along the way.
When we start releasing the belief that we can or should know the outcome of any courageous path we step on, we create safety.
And when we enlarge our capacity to find some grace or growth or insight in all possibilities, even those that may break our hearts, we create self-compassion.
Because–we don’t have to get over our fears by denying them, we can instead move through and with our fears by acknowledging them and exploring what’s on the other side.
And even if your courageous choice goes as planned, even if your are “successful,” heartbreak may still emerge in ways you couldn’t have anticipated: being uprooted, feeling out of your comfort zone, shifting relationships, discovering it’s not the choice for you.

Maybe it’s time to ask ourselves a different question about courageous living.
Here’s the last reframe, again inspired by David Whyte’s lovely words:
What courageous path or choice would you make if you knew that you could not only heal from the heartbreak and pain that may come with courageous living, but also discover something on the other side of it that is beautiful and unexpected?
Personally, I’ve come to believe that our deepest fears aren’t really about the failures themselves. Most of us have experienced and eventually moved through disappointments and perceived failures. Then, it’s easier to accept that courageous living won’t necessarily mean one success after another.
But the heartbreak that can arrive in the midst of making our way on the path? That’s hard and I understand not wanting to re-experience it. When we are in that place the courageous way through is to hold ourselves with compassion, reassurance, and a reminder of who we are at our core.
*****
Courage is what love looks like when tested by the simple everyday necessities of being alive.
-David Whyte

