The Risk Mindset — 3 Fundamental Risks Every Creator Must Take

We don’t like to talk about it, but big and scary risks are at the heart of a truly creative, innovative, and meaningful life.

Sam Wren-Lewis
Jun 10 · 7 min read
Photo by Sammie Chaffin on Unsplash

Every successful entrepreneur will tell you that, if you really want to make it, you’ve got to take big risks.

After Elon Musk made $180 dollars from PayPal, he invested $100 million into SpaceX, $70 million into Tesla, and $10 million into SolarCity. He supposedly spent most of the early 2000s living month-to-month and even borrowing money to pay rent. And now he’s, well, Elon Musk.

Personally, I find this kind of advice both annoying and unhelpful. Of course the people who gambled everything for the sake of an idea or their company, and then ended up being hugely successful, will say the risks were worth it. What about all those whose business gambles didn’t pay off? What do they think? Well, we don’t know because no one really cares about them.

Bold financial risks aside, there are genuinely big and scary risks that every creator or entrepreneur must take if they want to turn their ideas into reality. Simply putting in the hard work isn’t enough. Neither is having a kick-ass morning routine. Creativity and innovation require trust. Which is why three fundamental risks lie at the heart of the creative process:

  1. You’ve got to risk your entire life and invest it in something bigger — and longer — than you. Trust in being part of something truly meaningful, and that, by positively contributing to it, your work will last forever.
  2. You’ve got to risk constant failure and take things one day, week, month, and year at a time. Creativity is an inherently uncertain process. You can never know what works and what doesn’t. Trust in taking the next step.
  3. You’ve got to risk crushing disappointment and depend on the complex living systems you’re a part of. You can’t create or innovate alone. Trust in the generosity of others, unexpected opportunities, and lucky breaks.

Creativity and innovation require trust. And trust is always risky. Every creator or entrepreneur must practice letting go of control and cultivating a risk mindset. Forget about risking a few million dollars. That’s nothing. Try risking your time, your effort, your dreams. That’s the difference between truly successful creators and everyone else.

1. Risk your entire life — and invest it in something bigger

Entrepreneurs and leaders typically encourage their fellow humans to “dream big”. Steve Jobs dreamt of making a computer so small you could put it in your pocket. Martin Luther King dreamt of his four little children living in a nation where they would not be judged by the color of their skin. In their extremely different ways, they both had deeply successful and meaningful lives.

But dreaming big is only half the picture. Both Jobs and King also dreamt long. King famously said that “the arc of the moral universe is long, but it bends towards justice.” He trusted in the slow-yet-unstoppable march of progress.

King saw the “promised land” and gave himself to that vision, knowing he might never get there himself — something that sadly proved to be true. But, without investing his entire life in his ambitious and impossible dream, he would never have achieved the things he did in his lifetime.

My point is not that entrepreneurs and leaders are super ambitious — that’s only necessary if you want to go down in the history books. My point is that creators find something worth caring about —something worth risking their entire life on. Something that will endure.

When you invest in something bigger — and much longer-lasting — than you, the rules of the game change. Success does not rest on achieving an end goal, on reaching a final destination. Instead, ultimate success lies a long way in the future, and you’re probably not going to be around to see it.

If you’re not going to experience tangible success in the next 5, 10 or 20 years, what then does success look like? The answer is that success is making a positive contribution to the larger process you’re a part of. King didn’t achieve racial equality, but he certainly played his part. When you really care about something, that’s the best you can do with your one wild and precious life.

2. Risk constant failure — and take things one step at a time

When you find something you really care about, it’s so tempting to try and work out exactly how you can make a difference, a positive contribution. Unfortunately, life is far more complicated than that. You often don’t know what to do or what works exactly. You have to try, and fail, and try again.

It took Steve Jobs a lot of time and effort — and constant failures — to make that computer in your pocket. If he had set himself a 5-year goal to produce a smartphone, and given up if he hadn’t been successful after those 5 years, we would never have seen the iPhone. Instead, Jobs did what every other successful creator and innovator has done: try, fail, repeat. In a word: iterate.

The process of iteration is how creators and innovators make things happen in conditions of high complexity and uncertainty — i.e. life. It’s also the bit that hardly anyone else sees. Most of us just witness the finished product — the amazing work of art, the best-selling book, the beautiful iPhone. We don’t see the years of exploration and experimentation, the multiple versions and iterations that didn’t work, the mistakes and setbacks, the constant failures.

Risking constant failure isn’t easy. It requires taking things day by day, which doesn’t come with any guarantee of results. Instead of thinking about whether you’re on track to write that book, you have to narrow your focus. Think about what you can realistically write today, and commit to that. Then do the same the next day. And then the next day. And then the next.

Eventually, you’ll start to get a rhythm going — habits and routines that work on a daily basis, even if you still have no idea where they’ll take you in the long run. You can begin iterating on a larger scale, of weeks, months, and years. What days of the week do you need downtime or periods of inactivity? What can you do differently next month? What periods of the year are you most productive and when do you need to go into hibernation mode?

Hopefully, you’ll come out of this iterative, cyclical process with something brilliant — the end product that the rest of the world gets to see. But you could also not. You might end up hitting a dead end. You might go down a completely different path instead. You just can’t know in advance. That’s the risk you need to take. You need to trust in the process, wherever it goes.

3. Risk crushing disappointment — and depend on the complex living systems you’re a part of

Investing in something bigger, and taking things one step at a time, are both risky strategies because they involve letting go of control. It’s much less scary to invest in something that’ll make your life tangibly better in the near future. And it’s much less scary to pursue goals you know you’ll achieve.

Letting go of control is a terrifying thing to do. But it’s at the heart of a truly creative, innovative, and meaningful life — to trust in a larger, longer, iterative process with absolutely no guarantee of success.

The third fundamental risk is no exception. The creative process cannot be done alone. No one creates or innovates something brilliant in a vacuum. Instead, you have to depend on the complex living systems you’re a part of — your close relationships, friends and family, colleagues, wider social networks, communities, society, everyone and everything.

The 1950s Mount Everest explorer WH Murray knew this well. He said that “the moment one definitely commits oneself… all manner of unforeseen incidents, meetings and material assistance which no man could have dreamed would have come his way.” His conclusion was: “Whatever you can do or dream you can, begin it. Boldness has genius, power and magic in it.”

Trust in life and it will care for you in return. That’s the principle behind a number of related ideas, some straightforwardly scientific, some positively woo-woo: gratitude, generosity, abundance, the law of attraction, optimism, serendipity, unexpected opportunities, karma, and lucky breaks.

These phenomena can be seen as stemming from either a magical universe or the vast networks of relationships you’re embedded in. Either way, you can’t produce anything of worth without depending on them.

Depending on others and unforeseen opportunities isn’t easy. Of course, all the successful people — like privileged, White, male explorers from the 1950s— will tell you how great it is to trust in larger systems you’re a part of. But it’s still an inherently risky process. It still involves letting go of control. There’s still no guarantee of results, no matter what the lucky ones say.

Here’s the thing: despite the fears and the very-real-dangers, you must take these fundamental risks simply because that’s how brilliant new things get created in this uncertain, complex and messy world we all live in. Trust isn’t easy, and taking risks is certainly not something to brag about. But that’s part of what it means to be a creator, whether you like it or not.

It’s time we started talking about it.

If you want more thoughts like this, please sign up for my free weekly newsletter, Human Thoughts.

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Sam Wren-Lewis

Written by

Writes about happiness, social change, and the link between the two. Sign up for my free weekly newsletter, Human Thoughts, here:

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +724K followers.

Sam Wren-Lewis

Written by

Writes about happiness, social change, and the link between the two. Sign up for my free weekly newsletter, Human Thoughts, here:

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +724K followers.

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