Are You Carrying Someone Else's Insecurities?

Welcome back to the 39th issue of Disrupting Conversations!

Have you ever thought about what insecurities you bring into your conversations? Where they originate from, and why? You know, the need to validate yourself through sharing expertise, the hesitancy on asking really meaningful questions, referencing important people you know, or places you’ve been, or that people pleaser in you.  

This week, I’m going to share an important experience I had with a client—how they struggled to ask what needed to be asked because past experiences and present-day insecurities got in their way. I’m also going to share one of my own life experiences and lessons to help you realize that you always have a choice in how you show up. 

In the end you’ll realize that having good disruptive conversations that benefit the prospect, client, your teammate, and you do require an evolving sense of awareness and a willingness to let go of experiences and patterns that don’t belong to you, but that you may have internalized as your own along the way. 

The read will take you 5 to 7 minutes, but I think it will be worth it. And for those looking to transform their own conversation patterns and performance, I’m sharing a select opportunity—more details at the end of this newsletter.

– Dan

Breaking Sales is my podcast to connect with those who are ready to break free from the chains of old sales methodologies that don’t work.

Title of Episode: Episode 163: What Are You Really Running From?

🎙️When we label a situation as "hard" or "uncomfortable," are we responding to genuine challenge or inherited fear patterns? In this episode of Breaking Sales, Pam and I explore what's really happening in our minds during those pivotal moments where we feel compelled to validate ourselves or retreat into old insecure habits.

We break down practical strategies for moving past your insecurities and habitual reactions, so you can show up fully present in every interaction. Because until we understand what we're carrying with us, we'll keep allowing those old patterns to influence our performance in conversations.

Are You Carrying Someone Else's Insecurities?

In a recent conversation dissection review with a client (we will call him Mike), we were breaking down his interaction with a top prospect. There was an important moment in the conversation where Mike needed to dive deeper with the prospect on what they would “risk” or “gain” if they decided to make a partner (relationship) change. It was a pivotal point because the prospect needed to fix and improve their strategy, but was struggling to move beyond the loyalty biases they were feeling about the current 15- year relationship. 

Mike knew that the “risk vs gain” question would help the prospect think more objectively about change and gain some clarity on what was more important- the loyalty or the prospect’s business- but Mike’s need to be liked and his propensity to be a “people pleaser” took over. In the end, the prospect decided to do nothing different.    

So what happened next? Mike did some important reflection and realized that this need to be liked and/or “people please” stems from some past experiences that he had growing up. Moving forward, if he was going to be better for himself and his prospects and clients, he was going to have to reconcile the root cause of this need. 

Through the years, I’ve learned that past experiences and patterns are often what hold us back when it’s time to feel and show confidence in our conversations. 

I’ve learned that we all carry experiences and patterns with us into every single interaction and relationship we invest in. These patterns often stem from childhood experiences, early career setbacks, or relationships that shaped our worldview. These patterns can manifest as an underlying need to validate ourselves or prove our worth, avoid meaningful questions for fear of perceived conflict, and in general put others on a pedestal and sell ourselves short.

This need for validation usually springs from some form of insecurity. The fascinating part? Many of these insecurities aren't actually our own—they're handed down to us. Maybe it was a parent's survival mechanism, a teacher's limiting belief, or a mentor's fear that was unconsciously passed along.

💡 Let me share a personal example. Growing up, my mother was perpetually in survival mode- the glass was always half empty. Whenever I experienced a setback or failure, her response was always the same: "I’m sorry, son- nothing good ever happens to a Lappin." It was her way of coping, her survival mechanism kicking in. Furthermore, if it was just our luck, there was no need to take accountability for what had happened. 

Years later, I realized something profound: this wasn't just a way of rationalizing life- it was a baton being passed from one generation to the next. Her parents had instilled this mentality in her, and she was unconsciously attempting to hand it to me and my brother. 

But we have a choice regarding how we run our race with or without the baton. We don’t have to inherit the experiences and patterns from our parents or others. We can choose to let them go. I chose to set that baton down. 

But to do that, we must recognize them for what they are.

Think about it: How often do your attempts to validate yourself actually serve the conversation? When you feel compelled to demonstrate your expertise or share an impressive connection, is it advancing the discussion, or is it addressing an inherited insecurity?

When you choose to hold back a question that might cause the prospect to reflect and think a bit harder, but would also help them debate change more objectively, whose needs are you serving? 

👉 To have truly powerful conversations—the kind that build trust and create real connection—we need to take stock of what we're bringing into the room. What insecurities are we carrying? What inherited patterns are influencing how we show up?

⏰ Ultimately, these insecurities will surface in our conversations, often in ways that undermine our effectiveness. They can prevent us from listening deeply, asking meaningful questions, or being truly present for the other person.

The path forward isn't about eliminating insecurity entirely—it's about recognizing its source and making a conscious choice about whether to let it into our interactions. 

👉 You will never be able to control how another person shows up or reacts in a conversation, but you can control how you show up. We all have baggage, but one of the greatest gifts we can give another person is to leave our insecurities at the door.

It’s funny, I’m often an unpopular client with some of our marketing and brand partners because I refuse (limit) the use of “call to actions.” My philosophy may be flawed, but I’m a believer in having a genuine approach to attracting clients, and it should never be a 24/7 message or ask. As someone who invests time into reading or listening to our material, I’m sensitive to the experience you have. 

That said, I will cut to the chase. I'm opening two coaching spots for professionals committed to finding and tapping into that next level of performance. Typically, if and when I add clients, I do so exclusively through referrals, but thought I’d open it up to our broader audience.

If any of the following goals speak to you, it might be worth speaking further about: 

• Sell more and earn more

• Stop the feeling of chasing the sale, number, and day

• Minimize insecurities that hold you back

• Learn how to ask powerful and meaningful questions

• Feel more confidence selling to upper executives

• Overcome your prospects biases

• Reduce decision maker uncertainty and delay

You can contact us by emailing Ashlee at [email protected].

Thanks for reading!

Want to know more about the work I’m doing? Follow me on LinkedIn.

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