Help for the Emotional Entrepreneur

This journey does not look like a journey you or anyone you know has taken. Even if they are entrepreneurs themselves, they did not walk this path with your unique professional heritage.

Almost every person who comes to my office for brand strategy services cries. Sometimes it is a small welling up of tears out a relief that they can share their fears about their business with someone who can help them solve their problems.

More often than not, it is a big, half of a box of tissues cry. Because the fears around entrepreneurship are real and they go beyond concerns about making enough money. They go deep into our internal dialogue and they love to engage with our insecurities.

And we are grateful to these fears! Yes! Because without them, we would have no indication of the life altering changes that take place on our entrepreneurial journey. More importantly, we would not be empowered to do the necessary and serious reflection we need to do in order to be successful.

Like everything else in life, when you move through challenges — rather than avoid them — you are rewarded with confidence, which comes from learning lessons the hard way.

While I truly believe that detachment is the key to success, I also know that there is a long road of emotional turmoil to travel before we reach a positive detached mindset.

Let’s look at that phrase again: a Positive Detached Mindset. Meaning, a detached mindset that works for you, not against you. Detachment here does not mean uncaring, flippant, or selfish. Detachment here means to remove judgement from yourself so that you can keep moving forward.

We all get emotionally invested in our businesses. We put our heart and soul into them. Many brands are built around a personal passion or an expression of art and creativity. It is natural that our emotions get wrapped up in the end product. But these emotions can be detrimental to success when we get stuck in them.

So how do entrepreneurs learn to cope with this new and unexpected set of emotions?

Spend time with people doing better than you

Mindsets are contagious. When we spend time with people who have overcome the hurdles we are facing, those hurdles diminish in their capacity to block our path. When we hang around with trail blazers, our trails are ignited. When we surround ourselves with great minds, positive thinking, and great senses of humor, our world opens up in ways we could not have imagined.

The problem is, these people are rarely found in our immediate crowd. We have to put ourselves out in the world and make intentional efforts to connect with the strangers who will become integral parts of our journey.

Don’t worry, this the kind of necessary, challenging growth that comes with great rewards.

And I hear all you introverts moaning! But have you heard that introverts are often the most valuable people in the room? Introverts are observers, so they often have powerful insight into what is going on around them. They also tend to seek intentional, quality connections. So yes, introverted entrepreneurs, there is a place for your wisdom at the table. I challenge you to find a comfortable space for your voice — and then use it!


Spend time looking inward at what motivates you to be an entrepreneur. Why do you crave independent success? And what are the internal resources that you possess that will fuel your journey? Attach to those thoughts, because you will have plenty of thoughts that will work really hard to diminish your strengths. You will need to call on lots of positivity in order to navigate this road.

We each possess unique skill sets coupled with unique paths of experience. Get comfortable with what makes you special, celebrate what makes you stand out. Get proud of your past experience, even if — and especially if — it wasn’t ideal. Forgive yourself for past (perceived) failures and surrender to going way outside of your emotional comfort zone.


Let go of your professional traumas. We all have them. We have all been fired, let go, laid off. We have all had bosses who passed their professional traumas onto us. We have all been miserable at work, not wanting to get out of bed or, worse, have had panic attacks at the thought of walking through those office doors again.

Let it all go. That mentality is dated, old, out of fashion and does not fit into your entrepreneurial life. Maybe you write them down and (safely) burn the page. Maybe you scream it out into the universe and release your pain. Maybe you meditate on it and come to peace with your life’s journey. Maybe you need a therapist or a coach to help you sort through it.

It doesn’t matter how you get there, as long as you ground yourself in a renewed mindset once you arrive.

Then, once you get there, Don’t Look Back!

Get a mentor

Every single person, no matter where they are in their journey, needs a good leader to learn from. You cannot do this on your own. Solopreneuership is bullshit. Get out and meet people, connect with the world around you. Isn’t that what you are trying to do with your business anyway?

How, you ask? Volunteer your time and talents at an organization that needs them. There are a million ways to give back to the world. These organizations are led by well connected people in your community who will notice your talents and spread the word about you.

I promise you there are organizations and resources in your city that are waiting to connect you with the people who will light your path and make you a stronger leader in the process.


Celebrate every step of the way. Sent out a proposal and didn’t get a reply?Didn’t get a gig you really wanted? Celebrate the fact that you took another step on your journey. Because this journey does not look like a journey you or anyone you know has taken. Even if they are entrepreneurs themselves, they did not walk this path with your unique professional heritage. This journey is personal in a professional context.

That’s what motivational speakers mean when they tell you to show up as your best self! And every time you celebrate your successes and your failures, you are one step closer to embracing the authentic best you that you need to be in order to enjoy success.

Don’t worry, you can still come to my office and cry. I get it. I cry plenty. But I wouldn’t change one moment of my journey. The lessons learned on the entrepreneurial journey will shape your entire life. Enjoy them all.

One more note about that Positive Detached Mindset. When you start to practice it and you remove judgment from yourself, you will find yourself a lot less judgmental of the world around you. In doing so, you will grow your business while you help to make the world a better place.



Brand Strategist and Creative Non-Fiction Writer Developing Intelligent Creative Content

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Susie Ippolito

Brand Strategist and Creative Non-Fiction Writer Developing Intelligent Creative Content