Herby Olschewski

Been there, done that… doing it all over again!

I have never believed that life happens in one straight line. Mine certainly did not.

I have spent much of my life following curiosity across countries, industries and technologies. I have built businesses, written software, flown aeroplanes, travelled widely, worked in nature conservation and started again when a previous chapter no longer fitted.

Some decisions worked. Others were expensive lessons. None erased what came before.

That experience is at the heart of The Art of Living Freely! — Don’t Wait To Be Chosen.

It is not a memoir, although my life provided much of the material. It is a practical book about recognising what you already carry, adapting when circumstances change and building more choices for whatever comes next.

A fascination with technology — since 1977

I grew up in South Africa with a fascination for computers and a curiosity about the world beyond the horizon.

I built my first computer in 1977 and have been coding ever since. By 1982, I was already online, long before most people had heard of the Internet.

Over the following decades, I worked through successive generations of technology: mainframes, personal computers, networks, the early commercial Internet, cloud computing and now artificial intelligence.

Almost everything changed. The tools, platforms and ways of working changed repeatedly. Skills that once seemed cutting-edge became ordinary or obsolete.

The lesson was not that everything I had learned was suddenly worthless.

The ability to learn, adapt and apply experience remained valuable, even when the technology changed.

That distinction matters enormously today, when so many people are wondering what AI means for their jobs and livelihoods.

The first backpack: 1986

At twenty-three, I left South Africa with a backpack and went to see the world.

What began as travel became eighteen years of living, working and learning across fourteen countries.

I did not have every step planned. When money ran short, the computer skills I carried with me helped me find work. One opportunity led to another. I became involved in consulting, business and the early Internet.

My interests also took me into aviation. I bought an aeroplane and flew more than a thousand people on pleasure flights around Europe.

Living in different countries and working with people from different backgrounds taught me something that has stayed with me: opportunity rarely arrives in the precise form you expected.

Often, it begins with a conversation, an introduction, a useful skill or a willingness to try something unfamiliar.

The person who can recognise and act on those possibilities has more than one road available.

Business, burnout and a different kind of work

In 2003, I returned to South Africa intending to settle down. I built a Managed Services Provider business and spent years working in technology and computer support.

By 2012, I was ready for a different chapter.

I closed the company and moved into the northern bush, where I spent three years involved in nature conservation and anti-poaching work.

My days included walking anti-poaching patrols. At night, I continued coding websites.

It was a dramatic change of surroundings, but it was not a complete departure from everything I had been before. Technology remained part of my life. So did problem-solving, practical work and a willingness to learn.

That period also strengthened my interest in the world beyond business: wildlife, conservation, community and the responsibility we have towards the places and living things around us.

Financial independence matters. But what is the point of creating more freedom if we have no time, energy or inclination to care about anything beyond ourselves?

The second backpack: 2016

Thirty years after my first departure, I decided to travel again.

In 2016, at fifty-three, I left South Africa with one backpack and about US$1,000 in my pocket.

In one sense, I was starting over. I had left behind a familiar environment, an established business chapter and much of the structure of my previous life.

But I was not the same person who had set off at twenty-three.

I had thirty more years of knowledge, experience, mistakes, judgement, relationships and practical capability.

The backpack may have looked familiar. What I carried inside me was entirely different.

That is the meaning behind my personal motto:

Been there, done that… doing it all over again!

Of course, you never really do it all over again. Every new beginning includes the experience of everything that came before it.

And that is why one of the central messages of this book matters so much to me:

There is no square one.

A lost job does not erase your capabilities. A closed business does not erase what you learned while building it. A change of country, industry or personal circumstances does not cancel your previous experience.

You may need a different map.

You do not need to pretend you have never travelled.

Why I wrote this book now

Something important is happening in the world of work.

Artificial intelligence is changing tasks, occupations and business models. People who followed the traditional route of education, employment and career progression are discovering that the route no longer provides all the certainty they expected.

Experienced professionals can find themselves overlooked. Young people struggle to obtain their first opportunity. People with jobs may still be financially vulnerable because their entire livelihood depends on one employer or income source.

I recognise the uncertainty. I have experienced major changes of direction myself.

But I also see extraordinary opportunities in the technology now available to ordinary individuals.

A person with a laptop can learn new skills, research unfamiliar industries, develop an idea, publish useful work, create a portfolio, test a service and communicate with people almost anywhere in the world.

AI can assist as a researcher, tutor, editor, career translator and thinking partner.

It cannot eliminate real constraints. Rent, mortgages, family responsibilities, health, debt and other circumstances do not disappear because a new technology arrives.

Nor should AI replace human judgement.

But it can help people make better use of the knowledge and experience they already possess.

After nearly five decades around computers, I still regard myself as a student whenever the technology changes.

Do not compete with AI. Put AI on your team.

That idea became an important part of the book.

How my experience became the book

Looking back, several lessons from my own life kept coming together.

Technology taught me to adapt. The tools will continue to change. Our willingness to learn and apply judgement must continue with them.

Travel taught me that skills are portable. The place, language and circumstances may change, but what you know and what you can do travel with you.

Business taught me to create genuine value. An idea becomes meaningful when it solves a problem for somebody. Revenue must be connected to something useful.

Starting again taught me that nobody returns to zero. Experience does not disappear because a particular chapter ends.

Aviation taught me the value of ambition and planning. You can aim for a distant destination while remaining responsible for the conditions, resources and decisions involved in reaching it.

Conservation and community taught me that freedom carries responsibility. Greater independence should create opportunities to care for the world and the people around us.

These ideas eventually formed the practical philosophy behind The Art of Living Freely!

The book does not ask you to copy my journey. Your circumstances, interests and definition of freedom will be different.

It asks you to look at what your own journey has given you—and what you might do with it next.

Ubuntu: I am because we are

As my work and interests expanded, so did my desire to make the next chapter about more than my own ambitions.

My mission is to help people from all walks of life gain greater financial independence while caring for the world around them.

I describe that mission in three words:

Earning. Caring. Sharing.

It is grounded in the African philosophy of Ubuntu:

I am because we are.

None of us becomes who we are entirely alone. Teachers, colleagues, customers, friends, family and sometimes complete strangers contribute to our development.

I have benefited from people who shared their knowledge, made an introduction, gave me an opportunity or helped me find a different road.

I want to help create more of those opportunities for others.

That is also the thinking behind my phrase, charity begins at the cash register. When people can support themselves, create value and participate in economic activity, they may also have greater capacity to support causes they care about.

Earning and caring need not be competing ambitions.

You do not have to become wealthy before helping somebody. Share a useful skill, make an introduction, teach someone how to use a tool or help them recognise a possibility they had overlooked.

And when you need help yourself, ask.

Ubuntu works in both directions.

Shoot for the moon

I have always said:

Shoot for the moon. If you miss, you will be amongst the stars anyway!

I still believe in thinking big.

But ambition is not an excuse to ignore reality. An aeroplane needs planning, fuel, sound judgement and a suitable place to land.

Our ambitions deserve the same practical attention.

That is why the book combines the freedom to imagine something different with small, affordable experiments, measurable progress and the willingness to change direction when evidence requires it.

You do not need to know exactly where every road will lead before taking your first step.

You do need to begin.

Why I am giving the digital book away

I wrote The Art of Living Freely! for people who may be waiting for an answer, an interview, an opportunity, a change in circumstances or simply enough confidence to begin.

Some are financially stretched. Others have experience and resources but are searching for a different purpose.

I do not want the price of the book to become another reason to wait.

That is why the complete digital edition is free.

There is no registration requirement, email gate or credit card needed to download it. You are welcome to read it, use the exercises and share the complete, unaltered PDF with somebody who may benefit.

A paperback is available for readers who prefer a physical book.

I am not promising that reading it will change your life. I cannot know that.

I can share what I have learned, provide practical tools and encourage you to test what might be possible.

The decisions and actions remain yours.

The next chapter is still being written

At sixty-three, I am still a technologist, entrepreneur, pilot and nomad.

I am still learning, building, travelling and experimenting. My interests continue to span technology, AI, business, aviation, conservation, community and practical ways to help people create greater independence.

I do not regard my life as a finished story with a lesson conveniently attached to the end.

There are more roads to explore, more things to learn and more opportunities to create.

That is what living freely means to me.

Been there, done that… doing it all over again!

And if this book helps somebody else recognise that their own next chapter has not yet been written, it will have served its purpose.

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Don’t Wait To Be Chosen. Choose yourself.