They called me a lovely person, always ready with a compliment or a helping hand. When I stood up for myself, I found out who truly valued me.

For years, I was known as the “nice guy” in the entrepreneurial world.

Everyone liked me and I liked everyone – a mutual admiration society, if you will. My business partners and employees knew me as a man always ready with a compliment or willing to lend a helping hand. It wasn’t until my 42nd birthday that I realized this persona, this image of congeniality, was more of a shackle hindering my growth than a virtue propelling me forward.

In the world of startups and venture capitalism, where cut-throat competition is the norm, I found myself constantly bending over backwards to maintain my “nice guy” image. The cost? My own satisfaction and the success of my ventures.

The day I decided to stand up for what I truly wanted — in business negotiations, in employee performance reviews, in every aspect of my entrepreneurial journey — was the day everything changed. Conversations were no longer sugar-coated. Business meetings became less about maintaining harmony and more about attaining goals.

Some people didn’t take it well. Business partners who once smiled at my every word suddenly showed their true colors.

Yet, despite the initial shock and discomfort, this transformation felt liberating. I began to understand that being liked by everyone wasn’t as important as respecting myself and my dreams. The journey of self-assertion wasn’t easy, but it was necessary and enlightening.

Now, having weathered this storm of self-realization, I look back at the transition from being the ever-accommodating entrepreneur to an assertive leader. It’s like shifting gears from being perpetually stuck in the friend-zone to finally asserting your feelings and intentions without any inhibitions.

The fallout? A clear demarcation between people who valued me for who I am versus those who merely enjoyed the convenience and comfort of my agreeableness.

In the following discussion, I will share my experiences since that pivotal decision and the lessons I learned about the importance of standing up for oneself, even if it means ruffling some feathers along the way.

Embracing the courage to be unliked

The transition from being the “nice guy” to a more assertive individual wasn’t sudden. It was a slow, deliberate process that started with a simple realization – my desire to be liked was stifling my potential.

I remember the first time I had to stand up for myself. It was during a negotiation with one of our business partners. Until then, I had always been the one to compromise, to avoid conflict. But this time, I held my ground. I knew that the terms they proposed were not in the best interest of my company, and I made it clear.

The reaction was immediate and shocking. The smiles disappeared, replaced by looks of disbelief and, in some cases, outright resentment. It was uncomfortable, but it was also incredibly liberating. For once, I felt that I was truly standing up for myself and my business.

From that day on, I started setting boundaries in every aspect of my entrepreneurial journey. It meant having difficult conversations and facing uncomfortable truths. But it also meant learning who truly valued me – not just as a “nice guy”, but as a leader and an entrepreneur.

In the following section, we’ll delve into the widely held belief about the importance of being liked in business relationships and why my experience has led me to a different conclusion.

The fallacy of universal amiability

The world of entrepreneurship often paints a picture in which likability is the key to success. It promotes the idea that if you’re affable, if you’re the kind of person everyone likes, you’ll have an easier time building connections, securing deals, and growing your business. But my journey taught me otherwise.

Being universally liked, I found, often meant compromising on my own needs and aspirations. It meant swallowing my ideas and opinions for the sake of maintaining harmony. It meant undervaluing my worth just to keep everyone comfortable. In essence, it meant sidelining my own success for the comfort of others.

I’m not suggesting that being pleasant and approachable is unimportant. No, far from it. But there’s a vast difference between being a genuinely good person and being a people-pleaser. The former involves respect for others while maintaining your own dignity; the latter often results in self-sacrifice and frustration.

In the following section, I will share how I navigated this delicate balance – how I learned to assert myself without becoming obnoxious or aggressive; how standing up for myself led to healthier business relationships and personal growth.

Asserting myself without losing my authenticity

Navigating the fine line between standing up for myself and maintaining my authenticity was a challenge. It meant redefining the way I communicated and interacted with others. But, it wasn’t about becoming ruthless or insensitive – far from it. It was about developing a stronger sense of self-respect.

The first step was to recognize my self-worth. I started acknowledging my skills, my ideas, and the value I brought to the table. This laid the groundwork for me to assert myself in business conversations without feeling guilt or apprehension.

Next, I learned to communicate more assertively. Instead of keeping quiet or agreeing just for the sake of peace, I began expressing my opinions and ideas clearly. Not everyone liked it initially, but over time, people started respecting my honesty and straightforwardness.

Finally, I made it a point to set clear boundaries.

This meant saying ‘no’ when necessary and not allowing others to take advantage of my willingness to help. It showed my partners and employees that while I was still the same person who valued kindness and respect, I wasn’t going to let anyone undermine my worth.

These steps may seem simple, but they require courage and determination. If you’re in a similar situation, remember that standing up for yourself doesn’t mean you have to change who you are – it means respecting yourself enough to ensure others do too.

Taking a holistic view of self-assertion

Looking back at my journey, standing up for myself in the entrepreneurial world was more than just asserting my worth in business meetings or negotiations. It was about breaking free from the societal expectations that had held me back and moving forward with more purpose and direction.

I took responsibility for my situation. Even though I wasn’t to blame for the way others behaved, I recognized that how I reacted was entirely within my control. This mindset shift increased my personal power and helped me navigate other challenges in life.

I learned to think for myself. I started questioning the societal norms and expectations I had unconsciously internalized. This helped me live life on my own terms and align my actions with my true nature.

Here are the key points I found crucial in this process:

  • Acknowledging dissatisfaction or struggles without resorting to blind positivity.
  • Understanding external influences and societal conditioning.
  • Pursuing personal ambitions and desires, not externally imposed ones.
  • Breaking free from societal expectations to seek self-empowerment.
  • Dedicating time daily to practice self-improvement techniques.

By embracing this journey of self-exploration, you can reshape your reality and empower yourself to assert your worth without losing your authenticity.

If you’re looking to further enhance your self-awareness, I highly recommend the defining your values exercise by Jeanette Brown, a renowned life transition coach. It’s a valuable resource that helped me clarify what truly matters to me.

You can find it here.

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Justin Brown

Justin Brown is an entrepreneur and thought leader in personal development and digital media, with a foundation in education from The London School of Economics and The Australian National University. As the co-founder of Ideapod, The Vessel, and a director at Brown Brothers Media, Justin has spearheaded platforms that significantly contribute to personal and collective growth. His deep insights are shared on his YouTube channel, JustinBrownVids, offering a rich blend of guidance on living a meaningful and purposeful life.

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