What I Do When My Founders Cry: How to Deal with the Personal Side of Business

Business is personal. I think anyone saying otherwise is just hiding from the true realities of what it means to run a company. I don’t care if your business is worth $10k and exists as a side hustle to fund your family’s grocery bill, you’re raising a Pre-Seed or Series A to keep your dream alive, or if you are a $25M company trying to scale internationally.

  • Rejection of your product or service feels personal
  • No response to all of the content you create feels personal
  • Spending your hard earned money on the needs for your business feels personal
  • Looking at your quickbooks and seeing your P&L feels personal
  • Doing the audit for your taxes feels personal
  • Deciding if, and how much, to pay yourself feels personal
  • Figuring out who to hire feels personal
  • Deciding what the people you hire should be paid feels personal
  • Making payroll each month feels personal
  • Being in charge of the livelihood of other human beings feels personal
  • Getting your clients and customers success feels personal
  • Managing your people feels really personal

So “business isn’t personal”, just doesn’t work for me.

It just doesn’t sit right, especially when I see and feel the emotional rollercoaster of entrepreneurship and watch my clients arms up, earnestly bracing for whatever impact may come as they navigate the ups and downs of the ride.

When we pretend business isn’t personal we gaslight ourselves. We tell ourselves a story of how we should just all get armored up, walk into this extremely vulnerable and unpredictable environment and, handle it.

Handle it? What does that even mean?

I have tried for years to bottle my approach to business coaching into some marketing tagline that tells the whole story of what I do. But, as I scale and grow, it actually becomes harder to put what I do into a sweet little catchphrase like Phil Knight’s, Just Do It.

How do I explain what it is like to hold a founder’s hand as they navigate lawyer’s recommendations and performance review data as they prepare to fire someone for the first time?

How do I describe what it is like to sit with them in the ups and downs of their cash flow and hold space for their stress while encouraging them to keep trying?

Or when their personal life is struggling because they are so enmeshed in the company, stakes feel very high, and their conditioning tells them they can’t step away from the business to take personal time and I walk with them as they try to make changes?

How do I indicate in two to three distinct words what it means to my clients when they have had the hardest week of their life, tears are billowing out of their eyes as they say, “I am sorry this is just so emotional” and I validate their experience?

Not to mention the dance I do with all of their “life stuff” that they carry into their business and that I help them confront so they can get out of their own way.

I may just be writing this to validate that whatever you are feeling as a business owner is true and real and sometimes really hard and very personal.

Perhaps those who coined that phrase just mean, don’t let it become personal. When you make hard decisions, look at the information analytically.

Ok, yes.

Yes, we can step back and see the whole board and think from a very high level place that takes ourselves out of the equation. But if you don’t think getting ourselves to that place is emotional and personal, you’ve never made a hard business decision in your life.

I think we have seen the true and damaging effects of “business isn’t personal”. Think Uber, think WeWork, think Theranos.

How do you accept that entrepreneurship feels really personal, requires a lot of vulnerability, and still withstand the pressure and make sound decisions?

Space. Taking space when you feel like you have none. Taking a beat when you feel things are urgent. Understanding the inner workings of your nervous system and having tools to get yourself to internal balance before acting. Realizing you’re human. Putting systems in place to give your humanity some room to make mistakes that won’t take your company down.

Working with your head chatter so you don’t get stuck in rumination and self-destruction. (I have a tool for this, if you’d like it reply to this email and we can chat.)

Speaking of space.

Last night I went for a walk with my dog Billy to watch the sunset. In 2021 I had an incredible Ayurveda healer guide me to wake with the sun and walk east and end my day with the sun walking west. I was struggling energetically, navigating a real growth spurt and fortunately for me, my spiritual and emotional growth spurts come with their unique set of emotional and physical experiences.

So, I have kept the ritual because when I committed to it and had the energy to drag my very comfortable and warm body out of bed to greet the sun in the cold darkness of the morning, it actually worked. I did feel significantly better as I followed the protocol each day.

And last night was no different. I felt all twitchy, carrying the stress of many of my clients, the noise of the world, the pressure of my own business, and of course all that good juicy family stuff that shows up each Holiday. I put on my walking shoes, grabbed my trusty walking partner Billy, and I set out to chase the sun.

I was utilizing the head chatter coping tool I referred to earlier and I stumbled upon a version of me from middle school. She was frail and thin, sitting alone in her childhood kitchen with her head real close to one of those mini televisions.

Middle school me was in the thick of her mother’s battle with terminal cancer. She felt ugly and worthless, afraid, and very alone. She used diet as control and was starving for nutrients she never learned to give herself because her parents were preoccupied with the reality of their lives.

I realized that this is where I go now when I am feeling afraid. I return to that little TV in that dark kitchen, everyone else in the house asleep at 7pm with no dinner on the table because, cancer, and me feeling overwhelmed and helpless. The kitchen is now my cozy bedroom, the mini TV is now my laptop and my food of choice is still vanilla bean ice cream with chocolate chips.

I saw it so clearly, as if I was standing in that kitchen watching myself navigate 1997. I had so much compassion for her. My body still recalls the feelings of loneliness, deep belly pains, just like I get now when the stress is compounding.

As I sat staring at the sun slowly setting into the distance, I worked hard to keep myself separated from her experience. This is key to keeping a safe emotional distance from the pains of our past, we must remember that we are witnessing not experiencing those feelings.

I saw her there in that kitchen, I felt enormous love for her. I wondered how she may have fared had someone like me been there to love her through that. What might my life have been like if someone was there to make me dinner? How may I be different if I felt I had someone who understood the depths of what I was experiencing as I watched my mother die?

I realized these were her questions she was pondering. Where are my parents? Why doesn’t anyone understand me? What is so wrong with me that I am alone?


I wanted to hug her so badly, scoop her up from that lonely kitchen table and take her to a place much better and brighter than she had ever known.

And so I did. I invited middle school me to join me and my happy dog on our walk to chase the sun. I told her how sorry I was that things were hard and that she felt alone. I told her that I have her back, that life is different now, and that even though mom isn’t here, I’m here, I’m always here. I will nourish her, and love her, and help her make her body strong, and that we would create as much joy as we can, together.

I came home, made a delicious pot of white bean chili and put on a playlist instead of a mind numbing television show. I kept my promises to her. I will feed you delicious food, I will help you get strong, I will bring you joy.

This is the stuff. This is the stuff that shows up when we go to make hard decisions. Old coping mechanisms appear as we navigate through new challenges but can’t tap into a new approach, so we reach for what we know.

What happens when what we learned to do then doesn’t work for where we are now?

What do we do when numbing out and feeling abandoned and helpless is interfering with our ability to feel like an empowered leader who is confident to create?

We can’t lead our people from that place. We can’t make hard decisions about budgets from that place. We certainly can’t serve our clients from that place.

This is the work. This is the hardest work in our lives but especially in our business. This is why we slow down. This is why we check in. This is why we carve out space, even when there is no business rationale behind it.

We are humans. We are complex. We are emotional. This is the work my clients face and do with me. This is where we go when the tears appear on our calls and we can’t move them forward without going deeper.

If you’re crying over business decisions, or you’re feeling intense emotions, good. It means you are in the arena, striving for greatness. It means you are tapped into the energy of your people, working hard to create a great place for them to create and strive for greatness. Or as that solo-entrepreneur, you are tapped into creating an incredible experience for your clients and customers.

You can’t pour your heart into something and expect not to feel anything.

This stuff, it’s hard. It’s also rewarding and at times, immensely impactful.

“Middle school me” matters, it matters that I have the space to see her, to be with her, to understand her. My company exists because of her. That little me, she wanted more from life than sadness and cancer. She wanted the joy of being a part of something beautiful and meaningful, and she grew up to build it for herself.

Without her, I don’t have a business. Without her, I don’t have vulnerability. Without her I am not able to access the deep parts of me that must show up to hold space for my clients.

And without knowing her in this way, she carries on, afraid, alone, worried. If I leave her there, back there in that kitchen to ruminate alone, then that’s how she shows up in my business; afraid, alone, worried. And that is not a place I care to lead myself or anyone from.

So I do the work. I carve the space. I take the walk. I chase the sun. And each year my business grows, our clients expand, our work becomes more impactful.

That’s what it’s like to be a founder of a company; messy, creative, emotional, rewarding, scary, unpredictable, and on many days, a lot of fun.

So if you made it here, congratulations. I am so proud of you. I am proud of you for continuing to do the work, for continuing to believe in your ideas, for putting your heart on the line. I stand with you as you face the hard past to build a brighter future. You are a beautiful, courageous human.

If you need someone to walk with you along your path, always remember we have an incredible community waiting for you to bring us your full and vulnerable self so you can grow your business without feeling alone and navigate these emotional growth spurts with strategy and kindness.

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