# 21: Taking the Leap

Silke Schmidt
9 min readOct 23, 2020

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Branson, Richard (2008). Screw It, Let’s Do It: 14 Lessons on Making It to the Top while Having Fun and Growing Greener, 60.

Story behind the Passage

Today, I had so many awesome conversations that I can hardly remember all of them in detail. I know, this blog is now turning into something like a diary. This was not the plan when I started almost three weeks ago. But who cares? Especially the last conversation I had tonight inspired me to choose Branson’s book today. No, this is not going to be some “motivational” firework today. Or maybe it will, let’s see.

This last conversation tonight was with an entrepreneur who has successfully founded three companies in his life. All of them are still running, even though he founded the first one at the age of 22 (he is in his 40s now). The amazing thing for me now is that I really feel I have made quite a lot of progress in these past two years of being an entrepreneur. Well, when looking at people like him with almost two decades of experience, you can tell that I am still at the beginning of the journey. Still, every baby step counts.

So, I have the feeling right now that I have really progressed because I know that these kinds of conversations would not have been possible a year ago or so. I cannot even tell what exactly the difference is. I would summarize it by saying: completely myself, no bullshit talk. And this is what you immediately sense of your respective counterpart when having these conversations. You use every second for the real stuff that matters. No small talk, no ego games, just pure conversation and a depth that feels like jumping into the ocean, diving, and then opening your eyes to see amazing creatures of the sea and fascinating corals. A conversation like this is going in smooth waves of talking, listening, sharing immediate feedback about what is being said.

One thing that stuck with me — among the many things that did — was the issue of “taking the leap.” What M. told me about the mission of his company was exactly what I do with my books. We both try to make people do something that is not outrageously dangerous or somehow crazy. Still, there are things that take people a lot of effort before finally trying. In his case, this field is going abroad. In my case, it is founding a company. Both of us, however, are connected by the same experience, i.e., that excessive learning happens when you put yourself into positions that are unusual and outside your normal comfort zone. And this kind of learning triggers a transformation that is irreversible. But this only happens if you are ready to jump — to take the leap from one shore to the other. This is not easy but entrepreneurship is a great tool to achieve it.

My Learnings

“Don’t have regrets when you lose.” Richard Branson is a very special entrepreneur among all entrepreneurs that are all special in their own way. The founder of Virgin Records and Virgin Airline (among many other companies) really counts as a relentless founder — relentless especially when it comes to his own goals and the energy he puts into everything he does. But I remember that this was something that my students struggled with very much when I read this book in class with them. They liked the motivational part of his personality but they could not really relate to him because the stuff he did was just too far away from any ‘normal’ life (like the trips he did in a hot air balloon that almost cost him his life). Many criticized the lack of responsibility for his wife and children when risking his life with these adventures.

This sentence about not regretting anything if you lose reflects this mindset. In the extreme scenario — when taking too many risks — you might not even be able to regret anything because you simply end up dead. But in most other cases, if things go wrong, most of us tend to become mad at ourselves and we “regret” doing something that was actually not enough or not the right thing to do for getting us closer to our goal. For me, when I started my business, this was especially the case whenever I met with people who were generally interested in writing a book with me but then ended up not doing it. To me, this felt like losing.

Today, I know that this idea is completely stupid. For one thing, how can you lose something you did not even have in the first place? A deal that you wanted to win has never been a deal. It only existed in your mind by means of wishful thinking. And secondly, I have learned that there is no real loss — maybe not even in life in general but if that sounds too scary for you know, let us just say that there is no loss in business. I am saying that because, from my perspective now, there really is not. Every loss in the sense of some mistake leads to important learning and only this learning allows you to move ahead.

This sounds really cheesy now?

I do not give a shit. This is how I think about it.

And one more word about “losing” a contract. If there is one thing I know for sure: There are people who will be customers and there are people who will never be customers. That is it. You will never change that — why even try? Some might start as customers but never return (in my case, this is usually the case over a long period because nobody writes a book every year or so!). And then there are people who simply live on a different wavelength. You do not click. And if you still try to forcefully make it click — which is possible with some good sales skills — my experience is that it will really end up in a mess. For a while, you will be successful in tricking your own brain and your heart by telling yourself that everything is fine. Pretty soon, however, things will start getting complicated and even nasty (I once had a client who threatened to sue me simply because I had written a book about her from my honest perspective).

Consequently, having regrets is completely unnecessary. And as soon as you have truly understood this, you will not even start having them. It is a waste of time and energy. This is simply the loop of constant learning and if you have gone through this again and again, you will not be tempted anymore. Even the slowest and most resistant brain will get this at some point. And this is when you are really ready to face the next level of entrepreneurship, i.e., focusing on priorities and going for them, no matter what comes in the way and no matter what other people tell you.

“But whatever your dream is, go for it.” This is the sentence that is most appealing to me when it comes to the issue of ‘taking the leap’ which we ended up discussing today. Yes, I know, this sentence really epitomizes the spirit of the American Dream and might therefore sound strange in the ears of people from other cultures. Still, no matter how corny it may sound, it is true — as true as anything can feel from a single perspective.

What is bothering me so much is the fact that so many people have great dreams and they even have the capacity to transform these dreams into reality. “If you can dream it, you can do it,” is what Walt Disney once stated. Yes, but the sad part is: just a tiny fraction of these people actually use and maximize this potential by becoming entrepreneurs. Sure, not everyone wants to do so. But I still know that many dream about making this step. Still, they just cannot take the leap — no matter what.

What we both found out in our conversation tonight is that it usually takes some major incident in life that makes you sit down and simply be at the lowest level of your existence — my famous “Point 0.” You know that nothing can happen that would make things worst — because things already are at their worst. And at least in my life, these were the most liberating situations because they made me feel so light. All baggage gets lifted off your shoulders — the baggage that you yourself put on them. And this is also where you realize how easy it will be to turn your dreams into reality: you simply need to act by taking the first step. That is it.

The only tiny problem that remains is the dreaming itself. Most grownups, at least from my perspective, have unlearned to dream. And I mean: really dream. That refers to all those things which are far away from what most people consider ‘normal.’ And the difficulty is that you cannot access these dreams simply by means of rational thinking. Yes, you had them at some point in your life and then you pushed them away — locked them up in some secret chamber. And the only way that you will rediscover them is by finding the connection between head and heart again.

This head/heart, i.e., rational and emotional, division is also something that kept coming up today. Someone else told me today that he liked my company brand because it exactly reflects this dualism which really is a coherent whole. But I told him that this is simply me. And M. tonight confirmed just this. The interesting thing to me is that many entrepreneurs start their journey on the rational side and then slowly discover that close to 50% percent of their identity continue being repressed if they only focus on facts and figures. Gaining access to the heart, due to some disturbing life incident, makes this connection visible or rather perceptible again. The rest, i.e,. the “going for it” then happens almost naturally. Without the heart as the origin of the dream, however, the implementation part can be more difficult but still possible.

“… if you opt for a safe life, you will never know what it’s like to win.” I know, all this talk about ‘winning’ might be counterproductive in a post like this one. And, of course, there is nothing wrong with a ‘safe life.” Anybody who would claim this would be suicidal. Still, what Branson might mean is simply the opposite of entrepreneurship with the latter being based on overcoming the ideal of a safe life (which does not exist anyways because it would mean that you have full control over your life which is not possible). And this is why the ‘winning’ has a special meaning to me in this sentence.

For entrepreneurs, learning in and of itself usually plays a key role in their lives. They are often autodidacts who have taught themselves everything they know about a piece of software or some other product or idea. And this learning feels like a treasure box that never ever gets filled up. And whenever you add something to it — no matter how small or large — it will definitely feel like winning. At least in my reading, this is part of what Branson teaches his readers.

I totally agree that this kind of ‘winning’ is much more fulfilling than winning a game or winning some big chunk of money at once. Permanently negotiating the fine line between risk-taking and insanity is much more rewarding to keep your brains busy than being stuck in erroneous safety. As always, nobody can guarantee anything in life. And this is the beauty of life itself. What safety is or is not depends on your definition, i.e., the stories you tell yourself about life — your own life. Whether you are ready to take the leap or not, life will tell you soon enough. Until then, I am so happy that people like M. are there to help you on your journey.

Reflection Questions

1) Would you describe yourself as a gambler? Why (not)?

2) Do you have childhood dreams that keep coming up? What does it take to make them come true?

3) What is your biggest win so far? Who helped you get there?

Learn more about Silke’s 365 Days Blogging Challenge

https://medium.com/@silkeschmidt_32637/prologue-startup-story-learning-dda4ba9d3bd9

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