The Why

Olga Skipper
4 min readOct 19, 2021


Photo by Josh Calabrese on Unsplash

In 2017, at one of the last sessions I had with my first coach, we were working on helping me to find my purpose, to find my path. He proposed I write the text for my “future TED talk”, to find something that was my Why, something that I was passionate about.

I went away and wrote a 300-word piece on how I viewed the startup ecosystem, venture investment, and the mental and emotional health of founders, and went on to describe how I wanted to contribute to healing those and, as a result, minimize what I called “startup waste” and maximize the innovation impact that startup ecosystem has on this world. (It was a pretty ambitious 300 words.)

These three hundred words rushed through my blood, touching every part of me and igniting a light that I had never felt before when I talked about my profession or my ‘occupation.’

It felt as if I finally knew the Why.

As soon as the text was finished, I sent it to my coach to “make the words real.” To bring them and the concepts they represented into the world, have them appear in the room and not run away from me anymore.

You know that feeling when you are the only one to believe in something, and everyone else around you seems to think precisely the opposite? In those moments, you need a witness of your opinion and a supporter of your dreams. Someone to confirm that what you see is real, that what you feel and observe makes total sense.

When no one around you believes or can hold the space for your vision to manifest, a coach becomes such a witness. They become your secret accomplice, the place from which the vision can really begin to grow. My coach became my witness and, in the same way, I became a witness to many of the Whys of my clients.

A couple of months later, I dared to show this text to my bodywork therapist; she had something to add from her perspective and a question for me to chew on. So chew I did.

A couple of months after that, I had a coffee with a venture investor that I trusted, and he and I started to talk about his vision and mine. Surprisingly close, surprisingly straightforward. It allowed me to become even braver and reach out to another VC that I admire. He held the space for my vision as well, carefully accepting its creation. Yet he also left me with another question to digest — if this is your Why, then what is the How?

It took me some time to answer this question, and the answer — The How — surprised me. I became a coach.

I had to try multiple theories and directions and, ultimately, change what I do and who I am to follow my Why, answer The How, and land in the space where I am finally answering my What.

It may seem counter-intuitive to start with the Why, then the How, and finish with the What. How can you do something if you don’t know What it is you are doing? But we always begin with an impetus, a catalyst, some realisation or belief which spurs you to take action. The Why tends to come before the What.

I don’t think I have fully formulated my What; even after more than three years of being a coach myself, I am still answering this particular question. It is not good, not bad; this is just how it works.

When you start a new journey, step on a path that you have never walked before, you will be able to predict neither where you end up nor how long it will take you to get where you intend to be.

The reason I am sharing this story with you is to give you some perspective on the timeline of your vision growing from its infancy into something solid, on the importance of the first witness and of those who can hold the space for you, however crazy your idea sounds.

I also want to make sure that you understand that even you, at some point, will doubt. It is essential to have anchors that remind you that at some point in time you didn’t: written notes, like my TED talk; people around you that trust you; visual representations of your vision that anchor you to the feelings you had that day, the day you told yourself that you are not delusional and that your Why is possible.

As you might notice, I am not sharing that note from 2017 here with you. I don’t want this piece to become a discussion of whether my vision is correct. I don’t want to derail you from the primary purpose of this text, which is to give you hope and support in creating your vision, your own Why.



Olga Skipper

Executive coach and Advisor for Tech Founders and Entrepreneurs. Asking uncomfortable questions.