The Inner World of Entrepreneurs: Exploring Attachment Styles.

by Chris Endersby

What’s your leadership attachment style? Dip in to discover more about attachment styles and how they can impact your relationships. Learning this will enable you to gain greater control over how you show up in the world.

In our flagship Brand Re:Ignition programme we embark on a journey with founders and business leaders to help them transform their identities ready for growth. We use a combination of creativity and psychology to make sure their newly ‘firestarted’ brands work on every level to attract more fans and forge deeper connections. 

Part of this means working with entrepreneurs on their own identity. As they prepare to grow from the founder of a start-up to step into the role of CEO of their thriving enterprise in 2, 3, or 5 years from now. 

The very first step is self-discovery. Because through increased self-awareness (and acceptance) we can reach higher levels of performance and mastery. This is where Attachment theory (courtesy of pioneers like Bowlby and Mead) plays a part, by helping us to understand how our early life experiences shape our present and future. 

How? Our formative bonds often guide how we approach day-to-day interactions and, in doing so, they go on to influence our relationships. Gaining insight into our attachment style and preferences is not just self-enlightening; it’s transformative for relations with those closest to us. But it also impacts how we do business – how we interact with our clients, employees, and partners and how we show up in the wider world.


So what’s your natural attachment style?

Let’s delve into the main attachment styles, reimagined as entrepreneur types, and explore how these impact business dynamics.


Entrepreneurial Attachment Styles:



The Visionary Leader (Secure Attachment)


Visionary Leaders are coherent and collaborative. They are adept at expressing their thoughts and feelings clearly, making them influential leaders and team players. Their conversations are marked by an openness to feedback, a balanced perspective on successes and challenges, and the ability to engage in constructive conflict without damaging relationships.

Visionary Leaders:

  • Balance intimacy with independence, fostering relationships out of curiosity rather than fear.
  • Value mutual trust and openness, leading to enduring business relationships.

How this comes through in communications:

  • Coherent and Consistent: Their writing style is clear, confident, well-organized, and easy to follow.
  • Engaging and Relatable: They tend to use examples and narratives that resonate and connect with their audience.
  • Inclusive Language: They choose language that includes others and fosters a sense of belonging and team unity.

Example: As a Visionary Leader, you confidently involve your team in the decision-making process, valuing their input as much as your own. This approach not only accelerates innovation but also cements a culture of trust and mutual respect.


  • Leverage your ability to inspire trust to build strong networks.
  • Encourage open communication in your team, setting the foundation for innovative collaboration.



The Passionate Pioneer (Anxious-Preoccupied Attachment)


Passionate Pioneers often display preoccupied and sometimes intrusive communication patterns. Their intense focus on relationships can lead to conversations that seek constant reassurance. This can manifest in business as a tendency to micromanage or require frequent updates, reflecting their underlying worries about performance and approval.

Passionate Pioneers:

  • Seek closeness but fear rejection, potentially impacting team dynamics and decision-making.
  • Can appear overly eager, which might lead to quick decision-making without thorough team consultation.

How this comes through in communications:

  • Intense and Emotionally Charged: Their messages may convey a sense of urgency or need for reassurance, reflecting their underlying anxieties.
  • Detail-Oriented: They might focus on minutiae, reflecting their concerns and insecurities.
  • Persuasive but Potentially Overbearing: Attempts to connect deeply with the reader can sometimes overwhelm with too much intensity.

Example: As a Passionate Pioneer, you might find yourself micromanaging a project out of fear that it won’t meet your high standards, inadvertently stifling creativity and innovation in your team.


  • Recognize the value of secure professional boundaries to enhance focus and productivity.
  • Channel your passion into clear, structured goals to mitigate feelings of insecurity.



The Independent Innovator (Dismissive-Avoidant Attachment)


Independent Innovators tend to adopt a self-reliant and somewhat detached communication style. They might minimize the importance of relationships or emotional needs, which can translate into a preference for solitary work or decisions made without extensive consultation. This approach can sometimes alienate team members who seek more collaborative or inclusive leadership.

Independent Innovators:

  • Value self-sufficiency and can often be seen as aloof.
  • Emphasise independence, sometimes at the cost of team cohesion.

How this comes through in communications:

  • Brief and to the Point: They favour succinctness, potentially at the expense of emotional depth.
  • Self-Sufficient Tone: They may avoid revealing personal vulnerabilities or needs, emphasizing independence and competence.
  • Practical Over Emotional: Focusing on facts and data, with less emphasis on personal feelings or the emotional impact on the audience.

Example: If you’re an Independent Innovator, you might prefer to work on projects alone, believing you can do it faster and better. This could lead to missed opportunities for collaboration that could bring fresh perspectives and innovative solutions.


  • Acknowledge the strength in vulnerability and seek out collaborative opportunities.
  • Practice active listening to foster a more inclusive and engaged team environment.



The Cautious Creator (Fearful-Avoidant Attachment)


Cautious Creators often exhibit a fluctuating and conflicted communication style. This is fuelled by a desire for close relationships tempered by a fear of getting too close. It can lead to mixed messages or hesitancy in decision-making, reflecting their internal struggle between seeking connection and protecting themselves from potential hurt.

Cautious Creators:

  • Desire closeness but are wary of it, leading to inconsistent team engagement.
  • Struggle with self-doubt and trust, which can hinder the building of stable relationships.

How this comes through in communications:

  • Inconsistent and Ambivalent: Their writing style might vacillate between closeness and distance, reflecting their internal conflict.
  • Rich in Content but Guarded: They often provide detailed information but hold back on personal emotion or conviction.
  • Seeking Connection but Fearful: Attempting to engage the audience while also showing hesitation to open up or commit to a viewpoint fully.

Example: Imagine you’re on the brink of securing a pivotal partnership for your scale-up. As a Cautious Creator, your underlying fear of rejection might lead you to procrastinate on finalising the deal, concerned that this partnership could become too demanding or lead to a loss of control. This hesitation can cause delays or, worse, risk losing the opportunity altogether.


  • Establish clear and consistent communication channels to build trust gradually.
  • Focus on personal development to overcome fears of intimacy and embrace collaboration.



Potential to adapt and grow

While we may naturally incline towards a particular attachment style, it’s important to remember that these categories do not confine or define us entirely. Our attachment style is just one aspect of our complex identities, especially in the dynamic realm of entrepreneurship. 

Throughout our lives, we learn and adapt, developing what can be termed as ‘forced competencies’—skills we may not innately possess but have cultivated over time to navigate the challenges and relationships we encounter.

These competencies allow us to connect, lead, and innovate in ways that may seem contrary to our fundamental attachment styles. Whether it’s the Visionary Leader learning to embrace solitude and reflection, the Passionate Pioneer finding balance in independence, the Independent Innovator discovering the value of collaboration, or the Cautious Creator stepping into vulnerability with trust, we are all capable of growth and change.


In Summary

As with other aspects of our personality, understanding and embracing our attachment styles empowers us to build stronger, more meaningful connections in business, fostering a culture of trust, openness, and innovation for lasting success.

For those intrigued by the concept of attachment in the entrepreneurial world, I recommend the insightful book by David Wallin, available here.


Or reach out to us here, and let’s get the conversation started.