I never know how to start.” This is a common complaint when it comes to facing difficult conversations, one I hear often from private clients and larger audiences alike. Toss in the reality of the past year, with its plethora of controversial topics and elevated emotions, and you have a climate that only cements our aversion to taking that first step.

As we age, we may feel even less inclined to begin not-so-smooth conversations because we may be used to our way of thinking and expect the same from others. Or, we may just not have the energy or bandwidth to deal with controversy and default to the too-often-used, “whatever.

But whether you are in your 20s or your 50s, avoiding dicey exchanges is not a particularly healthy choice. On the contrary, when we avoid expressing honest feelings, it can lead to a host of unsavoury outcomes including low self-esteem, frustration, and anxiety. That’s because the longer we hold thoughts and feelings inside, the more emotionally charged they become. It can even make us sick. Research conducted in 2013 found that holding emotions inside can increase the risk of premature death. Certainly not an ideal strategy as we face midlife and beyond.

Pros and cons of difficult conversations

So, why are we so good at avoiding difficult discussions? A common reason is that even before we utter that first syllable we are expecting the worst. According to a 2018 study, people tend to misunderstand the consequences of honesty and even overestimate how negatively others will react.

Before engaging in any form of awkward conversation it’s worth considering the following pros and cons.


  • Shifting from a victim mindset to one of problem-solving.
  • Building confidence in communication skills (in other words, learning to be comfortable being uncomfortable).
  • Allowing your opinions and feelings to be aired and heard.
  • Listening to another perspective may lead to learning something new.


  • Unexpressed feelings can manifest in different ways including anger, blame, hostility.
  • Bottling up emotions increases stress which may lead to related illness.
  • Unresolved issues will only end up taking more energy, space, and attention.

Best strategies to manage your emotions

Handling difficult conversations requires skill, empathy, and ultimately, courage. How can we change our approach to it as we age and learn to embrace – instead of avoid – self-expression?

Here are five tips to get you started:

  • Step One: Unpack the Fear

Chances are you’re letting fear-based thinking get in your way. Whether avoiding a discussion with family members, your life partner, or your boss, it can be helpful to give yourself space and time to identify the fears behind your hesitance. There could be old dynamics at play, perhaps from past relationships or workplace dynamics, that are keeping you stuck in fear-based thought patterns and convincing you that unsavoury outcomes from your past will repeat themselves.

  • Step Two: Discern between Fear Fact and Fear Fiction

The human brain is a meaning-making machine that constantly creates stories to explain its experiences, then looks for evidence to confirm those stories are true (scientists call it cognitive bias). But the internal narratives we create do not necessarily reflect reality. So, to avoid acting based on those stories, we must be able to discern between fact and fiction. In difficult conversations, it is best to stick to the facts by speaking your truth with respect and kindness but to avoid anticipating what the other person might feel or think (see Step Three).

  • Step Three: Do Your Job
Particularly when approaching a tense exchange, keep the focus on communicating your thoughts and feelings instead of predicting the reaction of the other person. It is not your job to speculate about how your words will be interpreted, only to deliver them in an honest and respectful way. Keep your comments focused on the “I” and avoid “you” statements. It’s not that you’re being inconsiderate or self-centred: on the contrary, by limiting your words to the things you know for sure—your experience and feelings—you are conducting the discussion in a way that serves both parties.
  • Step Four: Don’t Be Sorry

There is no reason to apologize for being open and honest if you are doing it in a measured and respectful way. Apologies are required when we offend someone, not merely for taking a position on an issue. They can become a crutch, something done automatically to rid ourselves of guilt or shame, even when there is nothing to feel guilty or shameful about. Constant apologizing only dilutes the meaning of any one apology, so reserve “I’m sorry” for times when they are necessary and meaningful.

  • Step Five: Say it, Then Wait

When having a difficult conversation, conversation is the operative word. Leave space and opportunity for both parties to speak openly. If you make the courageous choice to communicate honestly, say your piece and then give the other person the opportunity to process and respond. Honour the silence while resisting the urge to fill it. Expect to be heard when you are speaking (interruption and over-taking is a no-no) and then let your words take up space. If your family member chooses not to respond right away and you are uncomfortable with the silence, ask whether they may need some time to process.

Try these strategies the next time you feel the urge to clam up instead of lean in. It may take some practice, but over time you may find that honesty and transparency leave you feeling less anxious and more empowered, even comfortable in your skin. A welcome gift for your older, wiser self. But it all begins with starting.

Originally published in Crunchy Tales on April 26, 2021

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