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Chapter 1: Awakening (con’t)…The Bike Ride

Updated: Mar 1, 2022

Welcome to one of the craziest rides of your life. You have awakened to realize your dreams will best be met by starting (building or changing) your own business. You have begun deepening your understanding of what it takes to be an entrepreneur. And now for one of the hardest parts, you must continually put yourself out there!

The act of putting yourself out there can be one of the most challenging and consistently draining parts of the journey. These difficulties are present in my own journaling and consistently come up in my conversations with other entrepreneurs. So, how do you maintain the emotional bandwidth needed to put yourself out there consistently and authentically? Despite the rejection, in spite of the unanswered emails, even though there are crickets after getting positive feedback about your idea.

Understanding Your Emotions

The first step is to accept the fact that you are an emotional being. We are all emotional beings. This can be hard. Many people have been taught to burry their emotions since childhood. Most of us have learned that positive emotions like joy are better than negative ones like anger or sadness. Either way, there is a good chance you have some emotional work to do to succeed in your entrepreneurial journey.

Karla McLaren said it best in her book, The Art of Empathy, “emotions are action-requiring neurological programs. They’re not positive or negative, glorious or shameful, right or wrong; they’re action-requiring neurological programs.”

Learning this has been one of the most freeing parts of my entrepreneurial journey. Before I learned the purpose of emotions I was one of those people that got upset about feeling mad. Adding insult to injury, my emotional wellbeing would spiral out of control and inhibit my progress.

It is crucial that you learn to feel to your emotions without shaming yourself. Listening without judgement helps you to identify the emotion you are feeling. It also helps you deal with the emotion appropriately. As an entrepreneur you will often feel fear that, if you listened to, will stop you from doing what you must. Fear has it’s place for keeping you safe but there is no imminent danger to your survival with the mere act of putting yourself out there.

Reconciling with Your Vulnerability

Starting a business is inherently vulnerable. Like emotions, Brené Brown shows us that vulnerability is not a bad thing, even though society has likely taught you otherwise. In fact vulnerability can be very constructive. Being vulnerable does not mean that you shout all your indiscretions from the rooftop for all to hear. It is about having the courage to show up authentically.

The heart of your business, what makes it unique, is your vulnerability. Instead of stuffing it, own it. That quirky weird thing about you, share it don’t hide it from the world. I know, this goes against everything you have been taught. We are taught to fit in, be normal, and not rock the boat.  Normal isn’t where connections happen and it certainly does not inspire people to buy.

Let me be clear. I am not saying you need to be self-effacing. Sure, people want to hear about those genuine moments of your life when you fell on your face, and how you got back up.  Sharing those stories will enable you to connect with other’s in real and meaningful ways.  But that does not mean they deserve to hear your story.

Vulnerability can be incredibly painful and it can be ridiculously rewarding.  That is why I have learned that it is important to reconcile with your vulnerability.  Prepare yourself, show a little compassion and acknowledge, “I am being vulnerable here, and I can live with them knowing this about me!”  Go on to ask, “what is the point of my vulnerability?”

Sharing the timeline from my journals is by far the most vulnerable thing I have ever done.  Years ago, except for the people really close to me, most people did not know that I journaled.  It is a very private practice after-all.  So, why now am I sharing this piece of myself?  Because my journals are a gift, they provide a glimpse into my deepest, raw and unfiltered thoughts about becoming an entrepreneur.  And because I Get It!

I get how emotionally turbulent the entrepreneurial journey is.  I get how lonely it feels.  I get how overwhelming, confusing and lost you can feel followed by moments of extreme happiness, joy and determination.  And I have had enough people confide in me about how surprised and limited they were by the emotional roller coaster of being an entrepreneur that I decided it is time to lift the veil.

Being an entrepreneur is an emotional journey…of mastery!

As part of reconciling with my own vulnerability for writing this book I drew some boundaries.  I gave myself permission to skip parts of my journaling that remains a source of personal pain.  And I would include all excerpts that were about my entrepreneurial journey and only about that.  Not only were those two boundaries very complimentary, they have also been liberating as I embarked on this project, which is but a step in my own journey of mastery.

Empathizing with Others

McLaren writes, “empathy makes us aware of and available to the emotions, circumstances, and needs of others so that we can interact with them skillfully.” Learning to understand and work with your own emotions will help you better empathize with your customers, and your team. This is a huge skill to develop.

Empathizing with your clients allows you to understand their perspective and their feelings so that you may genuinely connect with them. There’s a pervasive myth that humans are logical beings and we make decisions using reason…the truth is we are emotional beings and our feelings guide our actions and our decisions.

Customers will not buy your product because it has cool features or benefits. They buy because you made an evocative connection with a need, a pain that they are moved to do something about. The only way you can do that is by cultivating your empathic skills.

One of the ways I empathize in conversation is by listening to signals from my body. When I experience goose bumps I know that means something. Usually it happens when someone is being vulnerable with me and I think, “this is genuine, there is a connection here and I need to honor that.”

I see a lot of entrepreneurs struggle with empathy and this makes it hard for them to find the give and take that cultivates the heart of their business. Lack of empathy negatively impacts their relationships with both employees and customers because there is an absence of genuine connection. Luckily, all of us have the ability to cultivate our empathic skills because emotions are inherent to our humanity.

Digging Deeper

daring greatly

The Art of Empathy: A Complete Guide to Life’s Most Essential Skill by Karla McLaren Karla McLaren offers an in-depth look at how to cultivate one’s empathic skills based on years of research. In this ground breaking book, she shares the six essentials of empathy: 1) Emotional Contagion, 2) Empathic Accuracy, 3) Emotion Regulation, 4) Perspective Taking, 5) Concern for Others, and 6) Perceptive Engagement. She then provides practical advice on how to cultivate, nurture and utilize your empathic skills at home, work and beyond. The first step is in better understanding your own emotions.


You have made it this far, now take your efforts a step further by reflecting on the concepts here and how you will apply them to your own endeavors!

  1. What is your relationship with your emotions like?

  2. In what ways could you show more authenticity with your entrepreneurial endeavors?

  3. How well do you currently empathize with others?

  4. In what ways could you improve your emotional wellbeing so that you may rebound effectively from adversity?

Next, I will share Chapter 2…Change for a Change!

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