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Let’s Talk About Hard Things

Let’s Talk About Hard Things by Anna Sale

Emotionally charged issues like death, sex, money, family and identity are never easy to address, but the benefits of doing so outweigh the costs. Anna Sale a political journalist and the creator and host of the podcast Death, Sex & Money provides guidance for having high-risk conversations with intention, kindness and consideration.


  • Having forthright conversations about death, sex, money, family and identity is notoriously difficult.

  • Magic words that alleviate or erase the pain of losing a loved one don’t exist.

  • When talking about sex, be clear about your needs despite the risk of embarrassment or rejection.

  • Honest talks about money go beyond dollars and cents to explore values, status, opportunity and security.

  • Hard talks with family members are fraught because family dynamics are resistant to change.

  • Constructive identity conversations acknowledge differences while seeking commonalities and connection.

In the absence of religious or social support, individuals must devise their own strategies for dealing with loss and adversity. One tried-and-tested approach involves reaching out and sharing your thoughts and feelings with others.

“When tensions are high, a single conversation has the potential to solidify a relationship into a lifelong bond, or to send it spiraling toward doubt.”

Magic words that alleviate or erase the pain of losing a loved one don’t exist.


Nothing you say to someone who is grieving a death will heal his or her aching heart. Yet this fact of life is not an excuse to say nothing

Grieve with the bereaved, bear witness, express love and share remembrances.

Sharing memories and stories with someone who is dying, and memorializing those who have passed, honors your history and gives voice to how much you will miss each other. These conversations, while difficult, become lasting and precious memories. You may fumble for the right words, but sharing grief thwarts the isolation and loneliness of a great loss.


When talking about sex, be clear about your needs despite the risk of embarrassment or rejection.

Sex conversations require you to put your needs into words, while also listening to what your partner craves. This is emotionally risky, as you expose yourself to the possibility of embarrassment, guilt and rejection. You might discover you and your partner are incompatible, or that the conversation leads to more questions. However, talking plainly brings problems into the open and provides a chance to work through conflict.

Sex worker and performer Ty Mitchell recommends starting with a question borrowed from LGBT culture: “What are you into?” This question prompts a conversation about what you want and expect – whether it’s a casual hook-up or long-term relationship – and what your partner might need.


Financial psychologist Brad Klontz categorizes people’s attitudes toward money into four personality types: “money vigilance, money worship, money avoidance and money status.” Your type affects your financial choices. When people in a relationship have mismatched approaches to money, problems arise.

Discussing each other’s positions and exploring how your background, experiences and upbringing influence your view of money can bring deeper issues to light. Once you’ve addressed these issues, you can talk about them openly and shrug off the emotional baggage.


Ideally, family surrounds you with love and support, and it provides a protective buffer from the outside world. Unfortunately, in many cases family relationships give rise to hurt, built-up resentment and contempt. Conflicts are almost inevitable

Finding the right time for a hard family conversation is essential. The years may take the edge off conflict or, conversely, give resentments time to fester. For example, when the sister of radio station personality Yesi Ortiz struggled with drug abuse, Ortiz took custody of her sibling’s six children. When the eldest boy turned 21, Ortiz had trouble relinquishing control or giving him the space to find his own way. In retrospect, she wishes that she had listened more to what he needed, withheld judgment and spoken to him as an adult rather than a charge – skills she developed as the other children grew older.

Relationships often evolve and establish new boundaries through incremental conversations, as filmmaker Desiree Akhavan learned when she came out as a lesbian to her conservative Iranian family. At first, her parents were devastated. But with time and through many conversations, they accepted her lifestyle and welcomed her girlfriend into the family


Attorney Liam Lowery, a trans man, approaches identity conversations cautiously but openly – particularly when it’s with someone unfamiliar with gender identity issues.

Hard talks about identity dynamics are personal and intimate. They get to the heart of how you see yourself and others.

Finding out about other people’s family histories is an effective way to move beyond stereotypes and discard assumptions. Sharing personal histories allows people to see the nuance and detail of what makes each individual special and highlights the similarities of the human experience.

“Identity conversations are about creating space for differences – differences that are layered with power and pain – in the hopes of creating a feeling of connection, or at least a sense of peace with the distance that remains.”

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