Tough Conversations (Life)

Why You Need to Have That Conversation – and How To Do It!

What is a ‘Tough Conversation’ (TC)?

A TC is the one you don’t want to have. In fact, the best TC for you is probably the one you haven’t even thought of having.

Take a minute now – what’s the hardest conversation you can imagine having? And with whom? What is it you’re holding back? When you’ve got it….keep reading….

It’s also a conversation that can transform your relationships, and set you free.

OK – But Give Me Examples…

  • “I’ve hated you for leaving me”
  • “I’m angry at how you treat your children”
  • “I stole $2,000 from you 20 years ago”
  • “I’m in the country illegally, and would
    like to apply for legal residency”
  • “We’ve never said ‘I love you’ in our
    family, and I love you”
  • “Will you marry me?”
  • “I’m not enjoying our sex life”
  • “I had an affair five years ago”
  • “I really gave you a hard time at school/that
    old job – and I’m sorry”
  • “I should have told you I have an STD
    before we had sex”
  • “I’m in love with you, and am scared
    of threatening your marriage, but more afraid
    of hearing you don’t love me”
  • “I’d like to feel acknowledged for all
    the hard work I do”
  • “I know I abused you sexually, and I
    apologize from the bottom of my heart”
  • “I love you so much it scares me. And…I
    think your ears are really big and can’t stop
    thinking about them”

How Do I Know I Need One?

Well – are ALL your relationships great? With your partner? Your family? Your boss and staff?

If they are anything less than wonderful, chances are you have something ‘withheld’ – that once expressed could set you both free.

Or you may have some far more obvious clues:

  • you’re angry at someone
  • you’re avoiding someone
  • you’re embarrassed or ashamed of something
  • you feel guilty or incomplete about something
  • you’re scared something will be found out
    one day
  • you’re scared of their reaction
  • you’re worried about the consequences of the
  • when you imagine the conversation, you feel

And the best clue of all: You probably don’t want to have the conversation!

This is a sure sign that your system is avoiding something.

In a nutshell – you probably haven’t had the TC yet because you’re afraid of the outcome; that you’ll lose something or feel VERY uncomfortable.

Another great clue is that it’s been more than a year, maybe even TEN YEARS, and it still comes up in your mind every now and then, or now while you’re reading this post.

Why Should I Have This Tough Conversation?

Shouldn’t it be buried? Isn’t the past just the past?

The answer is – if you have absolutely no charge on it – if it doesn’t come to your mind when you sit down to think about it – then it may be unimportant.

But if you feel any stored guilt, any anger, any sadness, any love – in fact anything that is unexpressed – then better out than in.

The TC’s (Tough Conversations) show us where our barriers are – where we’re most scared. Now if you want to live your life in the sandbox of
your comfort zone…well …you’re on the wrong site 🙂

But if you’re committed to constantly pushing back your boundaries – breaking through barriers to feel new realms of joyous flowing self expression – to live a life without fear – then have the

Other benefits include increasing your ‘vibration’ so others want to be around you, getting more deeply related to the person you’re having the
conversation with, and setting an example for others.


The Effect On Others…

It’s also amazing the effect it can have on the other person. My brother called an old girlfriend to say “I’ve been thinking about how I broke
up with you, and I want you to know it wasn’t your fault”. Turns out she’d had several guys in a row break up with her, and it meant the world to her to hear this. My brother – the penniless student – got off the phone and said
to me: “That experience was worth $5,000 to me”.

Some people justify not having the conversation by saying “I’ll just move on”, or “It’s enough that I know about it”, or “It might upset them”. In my experience, having the conversation in your head isn’t enough (unless they have died, and then, we write a letter). It’s in the speaking it to them that transformation occurs for both of you.

And another benefit: Imagine how fearless they might be once they’ve seen you set an example. Your courage can ripple out and change the
. I’ve had people say: “You know, after you called me, I started thinking. And I picked up the phone and called…”

The Risk

Now I’m not guaranteeing you or they will like the results. In MY experience, and in the experience of my clients, the outcome has ALMOST ALWAYS been positive in some way. However, the outcome may be even worse than you feared. And if it is, I say that’s the outcome that was meant to happen – and you had been distorting it/avoiding it byholding back. Time to trust and let the universe flow where it will…

Perhaps this is a good time to say having Tough Conversations can lead to bankruptcy, divorce, law suit, prison, death, or even worse. The spiritual warrior realizes this, puts truth and love above all outcomes, and takes what he or she gets with grace. As always, you’re fully responsible for any actions you take as a result of reading this newsletter. In fact, that’s kind of the point!

If having this conversation could have legal or medical consequences, I recommend consulting a lawyer, doctor or other appropriate professional first so you know what you are dealing with.

Couldn’t It Hurt Them?

It’s true you have a responsibility to speak with compassion, and to speak responsibly. i.e. Take responsibility as much as you can for what you have done, and avoid blaming.

It’s also true that no matter how compassionately or gently you share the truth – the other person may feel pain. And again, I say that’s not necessarily a bad thing – maybe that’s what is meant to happen. Plus – in my experience, it usually does more good than harm.

It’s important to note that it’s very common to use ‘It might upset them’ as an excuse for wimping out.

If you truly believe they may be damaged in some way by this conversation, please work with a coach or get the advice of a trained professional to ensure your wording is responsible – this can make a huge difference.

Hint: If you’re still blaming or judging them in any way – work with a coach to get over it first!


7 Steps to Having That Tough Conversation

Step 1) Choose someone you don’t feel 100% wonderful or complete with, but would like to.

Step 2) Identify the truth/core of what you want to express. If you were to die today, but could pass a message to this person to clean up anything left incomplete, what would that message be? (Working with a coach can
help you get to the core of this, and ensure you are taking responsibility instead of blaming.)

Step 3) Identify the worst outcome you can imagine

Step 4) Accept that possibility of this happening. Can you get right with that? (Let go of the thing you were holding on to e.g. money,
being right, staying out of prison, not upsetting someone)

Step 5) Remember it’s OK to feel uncomfortable – even terrified. Your vocal chords will probably  still function. The greater the fear, the more you have to gain. The chances of you dying are normally quite low.

Step 6) Remember it’s actually possible to have fun with this. After all – it’s better than any rollercoaster you can imagine. You are truly living….

Step 7) Pick up the phone or set up that meeting, share honestly, and let the Universe decide what’s next.

* * *

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Post Your Story

What’s the toughest conversation you’ve ever had? Did you have a good result? Either for you, for them, or others?

Share with us your success story in the comments below!

Want to Hear Coaching on Actual Tough Conversations?

Listen to me coach daring people on having some of the most difficult conversations of their lives.

Fugitive son on run from the law asks for safe harbor, and mother has to decide what to tell him!
(actual role-play at 12 min 40 seconds.
Note I made a big assumption before the role play, and should have recommended she seek legal advice. Hey – I was young! 😉

Beautiful Father-Daughter Breakthrough
(Dad asks how he can change, and she doesn’t hold back!)

Client faces a terrifying conversation to save a friendship

Client wants to feel more loved by her Dad

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