Travel the World as a Suitcase Entrepreneur: a Conversation with Natalie Sisson

Natalie with her suitcase and laptop, relaxing in the woods

In recent years the term ‘digital nomad’ has become a buzzword for a new way of living and working – travelling the globe with a laptop and living in a succession of exotic countries, all the while running a business from the road.

Plenty of hype and myths have grown up around the subject. One suspects there may even be a few armchair nomads. But there are people out there walking (and flying) the walk – and Natalie Sisson is one of them.

I ‘met’ Natalie online several years ago via our blogs. Whenever I hear from her it’s rarely from the same place twice: Buenos Aires, Paris, Tokyo. Even cycling across Africa. The one constant is Natalie’s enthusiasm – for travel, entrepreneurship and life.

And I’ve seen her reputation and business grow, as she inspires and helps others take to the sky through her speaking, coaching, training and products. She shares her journey, and the lessons learned along the way, in her Amazon No.1 best selling book, The Suitcase Entrepreneur.

Last week we finally met up in person, over coffee in London. I took the opportunity to ask her some questions on your behalf, about the opportunities and pitfalls of life as a Suitcase Entrepreneur.

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Video: Public Speaking for Introverted Creatives

If you want to succeed as a creative professional, sooner or later you’re going to have to stand up in front of an audience and persuade them of the value of your work.

If you’re a writer you’ll be invited to give readings and talks.

If you’re an artist you’ll be asked to talk about your work at salons and exhibitions.

If you’re an agency creative, you’ll have to pitch ideas to your colleagues and clients.

If you’re an entrepreneur you’ll need to tell investors and potential buyers about your company and products.

If you’re a consultant, you’ll need to persuade clients and conference audiences of the value of your ideas.

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Unlock Your Creativity (and Win Pitches) by Starting at the Finish Line

Start and finish line on athletics track

Image by digitalista via BigStock

When I teach my workshop on ‘Fundraising for Artists,’ we play this game: I give the class an imaginary check for $10,000 and I ask an artist to come to the front of the room and describe her project.

Participants have to decide if and when they’re willing to give the artist the check and if not, what questions they want answered. Suddenly, the attendees who walked into the room as unsure artists transform into savvy philanthropists with smart questions about the artist’s project and vision.

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How Interrupting Your Sleep Can Silence Your Doubts and Boost Your Creativity

Red alarm clockAre you the type of creative person who only generates ideas and solutions when you’ve had your full eight hours of shut-eye? Or perhaps you find your mind firing off with so many bright ideas that you sometimes find it hard to get to sleep?

Here’s how to consciously use sleeplessness to your advantage – by tapping its power to silence your inner critic and open you up to new streams of innovative thinking.

I was a student when I first came across Dorothea Brande’s book Becoming A Writer. At the time, writing loomed large in my life: I was writing essay after essay for my degree (English Literature and Language) and had also been appointed as a roving reporter for the student newspaper. Quite apart from that, writing was my first love and if I wasn’t doing it as part of the curriculum, I was doing it in my spare time.

I got Brande’s book out of the library because I was looking for a book that would help me to improve my technical writing skills. It did that to some extent, but the thing I remember most about it is an odd little exercise which seemed to be anything but practical.

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Why You Need to Ask More Creative Questions

Man looking over city with question marks raining from skyI love crime dramas, especially ones where the protagonist appears to have a psychological edge over everyone else, such as The Mentalist, Sherlock and Luther.

The way they look at the crime scene from a different perspective and as a result get new insights into the case that ultimately leads them to the villain.

The majority of times what leads the protagonist to get fresh insight is the quality of questions they ask. When I coach my clients, I do so with the understanding that the questions I ask influences the direction of their thinking.

For example, if I ask you “What will ‘X’ get you?” you will tend to think about specific things (more money, less stress, more time). However if I ask you “What will that do for you?” you are more likely to come up with more value based abstract answers (freedom, contentment, acceptance).

The brain is goal seeking

Questions can lead you to more creative insight due to directing your thinking in a way that requires an answer. Your brain is a goal seeking mechanism, so if you ask it a question you prompt it to find an answer. These questions can provide a way of looking at a problem that provides solutions you hadn’t thought about before.

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