A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.” – Tim Ferriss
The hardest conversation I have ever had was with myself.
Tough conversations fucking suck, especially the ones when you have to come to grips with a truth that you have been avoiding and stand up to the ego that has been dragging you down.
In my opinion, a great depiction of the tension behind a tough conversation is found at the end of the movie The Notebook. After spending years and years longing to be with the love of his life, Ryan Gosling overcomes his pride and lays out his heart, finally telling Rachel McAdams that “It” in fact, was not over.
When she hears this and realizes that her mother had been hiding his letters from her and that he did love her, she jumps into his arms (in the rain of course) and they live happily ever after.
Albeit cheesy, this story shows the impact a single conversation can have on your life.
Gosling’s character in the movie exhibits something very similar to how I used to handle tough conversations. Rather than speaking up, I would bottle up how I felt, hoping for a cinematic rain scene to finally express my true self, which of course never happened.
How many relationships are ruined because of this way of thinking? How many battles lost? How many lives wasted? All because someone was unwilling to have a tough conversation. In my opinion, too many.
Perhaps the biggest tragedy of our lives is that freedom is possible, yet we can pass our years trapped in the same old patterns…We may want to love other people without holding back, to feel authentic, to breathe in the beauty around us, to dance and sing. Yet each day we listen to inner voices that keep our life small.” –Tara Brach
I was the classic case of someone who avoided tough conversations. I hated confrontation. I wanted to please everyone. No, I needed to please everyone for validation that I was great and smart, and funny. However, this way of living left me empty. I was chasing a dream I did not want, surrounded by people I did not want to be with. Why? Because it was what I was supposed to do.
Let’s be honest; you know what you need to do. You have the words you need to say to correct a problem or mend a relationship, but due to past conditioning, you do not speak up.
Why? For me at least, it was because I did not want to upset the status quo. I figured if I kept my head down, bottled up my authentic voice, and follow the course, I would break free unscathed. But the tragedy of this mindset is that is leaves you living out life on the terms of others, rather than going after what really matters to you.
To me, this is the meaning of the maxim, “the richest place on earth is the graveyard.” In the graveyard, there are millions of people who had so much to offer but didn’t. Millions of people that had so much to say, but kept quiet. Millions of individuals who had so much beauty to share with the world that never did because they lacked the ability to speak their truth, and follow their unique path.
Tough conversations fucking suck, especially the ones when you have to come to grips with a truth you have been avoiding and stand up to the ego that has been dragging you along.
The ego can destroy you. The ego has killed more dreams than failure ever has. It keeps you locked up in a prison of external validation. The ego will convince you that others are smarter. That their path is more secure. That what they say and believe should come before what you know inside to be true.
However, if you ever want to make a dent in the world, you have to be able to master tough conversations. For me, that meant I first needed to confront the demons inside, because if I could not do that, no amount of external growth would matter. So, I began having those conversations. First in my head. Then on paper through journaling. Some were easy. Stop eating like shit. Some were hard. Take a break from your friends and lifestyle. One was monumental.
Accept that you have anxiety.
Tara Brach, in her book Radical Acceptance, tells an anecdote about confronting your deepest fears and anxieties by inviting it to sit down for tea. I liked this notion, and I started inviting my anxiety to tea. I knew that to heal I had to accept my reality, and although the conversation was ongoing and took every ounce of energy I had, it started to change my relationship to my anxiety. What I once feared deeply, I now began to accept, even appreciate.
The more I accepted it. The more okay I became with the reality that anxiety, like all emotions, would always be there. Instead of waiting to be healed before I took risks, I started to step out on limbs daily, well knowing my friend would be there, and calmly inviting it for tea when it did. As I began to master my inner conversations and stopped shying away from conflict, my external life started to see changes as well.
I began to realize that the more tough conversations I had, the more confidence I gained in myself to make the right decision, which in turn made it easier to have the even more challenging talks later on. Psychologists call this the competence-confidence loop; the better you get at something, the more confidence you gain in your ability to perform the task. Conversations work the same way.
The more tough conversations you are willing to have, the more confident you will become in your ability to confront difficult, often uncomfortable, situations with growing ease.
I began to see challenging conversations differently. I started to realize that my current status in life was the direct result of the decisions I had made in the past, and if I wanted something different in the future, all I needed to do was start making better decisions now, which meant having a lot of difficult conversations.
The Power of No
When deciding whether to do something, if you feel anything less than “Wow! That would be amazing! Absolutely! Hell yeah!” — then say “no.” – Derek Sivers
There is much debate in the self-help rotunda surrounding the idea of saying no to opportunities. I will give you my two cents. Say no. Say no to everything you are not excited about. I do not care if you are just starting out in your job or if you are a busy executive. Saying no is a secret superpower. Not only will it free you up to focus on what matters to YOU. Saying no is the best way to understand who you are and what you want. A life dictated by the schedule and desires of someone else is a failed one.
When I decided to quit my first job in consulting, I had no plan. It was not preconceived. I had no other job waiting. What initiated the decision to leave was my newfound confidence in myself to have tough conversations. And my understanding of the power of no.
I hated my job, and I knew it was not what I wanted to do, but unlike the me of the past, I did something about it. During my mid-year reviews, after receiving positive feedback, the Managing Director asked me what I thought about my future in the group. Without hesitation, I replied that I saw no future in the group, and in fact, I was quitting.
That was my last day working there.
I walked out of the office scared about what I would do next, but feeling a sense of clarity from just having another tough conversation, this time with someone else. My life was starting to take the direction I wanted it to go, and all because I was having conversations that I knew all along needed to take place.
Sure, I was afraid that I might not find a job or that I had just thrown my career away, but something happens inside of you the moment you start living your truth, it is an inner confidence that you will figure it out. And you know what, I did.
One simple, but tough, method of practicing this is by committing yourself to talking to one stranger a day, beyond just hellos. Ask them what the most important lesson they learned from their father was. Ask them what their favorite meal to make is. Ask them anything that goes deeper than the casual. The hardest part will be approaching them, but just tell yourself that you will never see this person again and who cares if you embarrass yourself. Plus, you will hear some amazing stories.
Be Steadfast in Your Decisions; Flexible in Your Approach
Stay committed to your decisions, but stay flexible in your approach. – Tony Robbins
Within days of leaving my previous job, I was on a plane to NYC for a final round interview with a startup, my dream job at the time. I nailed the interview and received the offer that night. I knew this meant that I would need to leave my girlfriend and friends to move to a new city where I only knew a few people, but something deep inside me said it was the right move.
The following week, my now fiancée and I discussed the offer in detail and what it meant for our relationship. Having this conversation was big for us. We had vaguely talked about our future in the past, and I think we both knew that we wanted to get married, but we had never gone deep on the notion of what to do if one of us moved.
Would she come? Would I deny it to stay close? These were all questions we had never discussed, so over dinner, we talked, and ultimately I told her that I would only take the job if she agreed to join me in NYC. A sentence I never thought I would ask her, but one she happily agreed to.
Flash forward twelve months, we found ourselves again having a similar conversation about relocating. New York was not for us at that point in our life, and we wanted to transition somewhere else, and the only place we wanted to be was Chicago.
We had all the common fears. We had just moved from there, shouldn’t we give it a chance? Would we be able to find a job? Would people think we failed? Would we be able to sustain our new lifestyle?
Like most fears, none of them came true. Yes, we had just moved to New York, but one day spent living a life not aligned with your purpose, is one day you will never get back, and we internalized that belief and knew we had to make a change. Gratefully, we had the ability to move, which I understand not everyone has.
What is important to note is that the decisions and the conversations you have are not the end all be all. Life is fluid. There will be things you cannot control, and things that you will change your mind about. If you are stubborn, unwilling to allow yourself to be pliable, you will find yourself living a life that was created out of pride. Be steadfast in the end goal, but flexible in the approach. We realized this and made a move and couldn’t be happier.
Nothing is harder than having an intimate, tough conversation with someone you love. The fear of hurting them is so intense that you often just forgo it. However, by doing this you cause far more pain than you save.
Another method to grow your skill is something I learned from Noah Kagen. He calls it the coffee cup challenge. The premise is to walk into a random coffee shop, order your drink of choice, and when you come to the register ask the barista if you can have your drink for free. Do not give any explanation. Just ask and see what they say. It will be way harder than you think.
Firewalk the Fear
“The greater danger for most of us in not that our aim is too high and we miss it, but that it is too low and we hit It.” – Aristotle
Before my fiancé moved to New York, a time came for another serious, and tough conversation. We needed to answer the all-important question, were we right for each other long-term?
I knew that I was going to marry her, but I had never seriously thought about it. Moreover, if she was going to move away from her friends to be with me, I wanted to be crystal clear. In the past, we had had some serious, deep conversations, but rarely intentional ones about what we wanted in life, and more importantly what we did not. I think I feared these conversations because I did not want our relationship to change. I did not want to lose what we had, or even worse, what if we realized that we wanted completely different things in life?
However, I knew that it would be better to discover our differences now than in twenty years. So, I got a pad of paper and wrote out every question/topic that I could think of to ask her.
We went out to dinner; I brought the notepad. She had no idea. We talked. We laughed. We discussed. However, we ended the meal more connected and secure in our relationship than ever before.
I proposed a couple of months later.
I honestly believe that if I had not had that conversation, our relationship would be half as good as it is now, but luckily we did, and the growth between us has been exponential. Failing to have conversations because you do not want to upset someone is a real fear, but one that is often unfounded, and even if it is the case that you upset them, wouldn’t you rather know that now?
You only get one life, don’t spend another minute with people who are not 100% for you and your purpose.
Whenever you go out to eat, try to ask if you can have an add-on or a side for free. Usually, they will just say no, and you will go on with your meal. However, the fear that swells up before asking is like fire walking an actual tough conversation and will condition your brain not to run away.
Keep It Small. Make it Stick.
“Reality is merely an illusion, albeit a persistent one” – Albert Einstein
If you cannot tell your waiter that he messed up your meal, you will never be able to tell your husband that you are completely distraught with your marriage. Having tough conversations is a skill. Moreover, like all skills, it needs to be practiced before it can be mastered. You would not expect a novice athlete to compete at the Olympics, so why would you expect yourself to have the biggest conversations in your life if you have never practiced?
Start small. Get the easy wins to build the confidence to move on to tougher conversations.
The opportunity to listen to the voice inside is constantly there, but a lifelong conditioning to follow the norm can crowd it out. So, to amplify this voice, you need to practice it daily. Cultivate opportunities to speak your truth using the methods above.
Or let me know in the comments what tactics you use to get better at having tough conversations.
Either way, start having tough conversations. Stop waiting for the rainy day to release the tension, and express what is wrong. You get no dress rehearsals. Your life is the main stage. You only have one chance to live. You have the power. No one is going to do it for you, so get out there and start giving yourself permission to live well. Goddamnit!
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