Self-Employment: A Life-Changing Tool for Freedom & Adventure?

I am not a rich man in the traditional sense.

(Money…? What’s that?)

But self-employment has given me enough of the modern world’s most scarce resource — time — to have spent my twenties on the kind of adventures that most cash-rich, time-poor nine-to-fivers can only dream about.

I believe that embracing self-employment (not necessarily poverty, I might add) has the potential to unlock unlimited doors to adventure for a great many people.

How Self Employment Supports Adventurous Living

By taking control of the parameters of our working lives that are usually in the hands of someone else — in particular our hours, holidays and place of work - we can actively redesign our work around planning and executing adventures.

I’d like to share a few thoughts on making the transition from employment (a.k.a. slavery) to self-employment (a.k.a. freedom), for it is no small decision. I’d also like to share some of the resources I’ve found most useful in making a living on my own terms.

But before you take any of this as gospel, it is important to ask whether or not self-employment is really going to help you.

Perhaps you’re fine in your career, and you just need to negotiate a bit of a break.

Perhaps you’re an utterly terrible boss and would run yourself into the ground the instant you became your own.

Perhaps your direction is entirely unclear at this point, and it makes more sense to save up, quit the job and hit the road with no strings attached.

But if self-employment does feel like a framework in which you might open up space to satisfy your adventurous ambitions, I would encourage you to give it some serious thought.

(Note once again that self-employment in and of itself means neither poverty nor riches; these are simply the outcomes of decisions you make when designing your a business.)

Principles of Self Employment

If it’s difficult to know where to start, try the following line of thinking out for size:

1. If you were absolutely free to choose anything in the world, what would you really love to do for a living? Anything at all.
2. Write your answer down, put it in an envelope, and put it somewhere safe. You can come back to it whenever you like.
3. Now that’s out of the way, think about the things you’re really good at. What are your strongest skills? (They may be secondary to your main profession, or derived or adapted from it.)
4. How could you use these skills to serve the needs of a significant group of people?
5. How could you package them into a product or service that has value to members of this group?
6. Where will you find the first member of that group (a.k.a. your first customer)?
7. How would you gain their trust and convince that person of the benefits of what you’re offering?
8. How could you give that person the opportunity to accept your offer, and sufficient reasons to do so immediately?

These are the foundations of business, entrepreneurship, self-employment, freelancing — whatever you want to call it — and I hope they’ll already be sparking a few ideas.

It boils down to making available something useful of sufficient value that someone else will pay for it.

In even simpler words — how can you help people?

Next Steps To Self Employment

I’m still learning myself and wouldn’t like to pretend otherwise. So if you do want to pursue the idea of self-employment further, I can highly recommend the work of Chris Guillebeau, a native of the USA’s Pacific Northwest who I’ve mentioned before on this blog.

Over the last few years he’s made a living helping people live “remarkable lives in a conventional world” — or, in plainer English, transition to one form or other of self-employment in order to satisfy broader principles and priorities such as travel and adventure.

He’s also just finished visiting every country on the planet, which is good proof of concept: it is possible to combine meaningful work with extended travel, to do it on your own terms, and to do it without sacrificing a respectable income.

What follows are the key resources that Chris has created to guide those who want to make the transition, identify the route most appropriate to them, and avoid common pitfalls in the process:

• The $100 Startup* is a book I constantly refer to, and of which I have sent unsolicited copies to a number of unsuspecting friends who were struggling to see how to strike out successfully on their own. It’s the best introduction I know of to going it alone.
• Designed To Sell* is a toolkit for creative people of all kinds. Available in 3 versions, it will guide you through the process of harnessing your creative energies and building a successful, sustainable microbusiness based around your craft.
• The Unconventional Guide to Freelance Writing* has been specifically created to help freelance wordsmiths build a dependable income from their writing. Turns out that doing so has far more to do with understanding how to market yourself as a writer than the quality of your copy.
• The Unconventional Guide to Art and Money* is an ebook and interview series dedicated to training artists (in the broad sense of the word) in the basic skills of business, connecting to and keeping customers, and turning creativity into income — in short, half the job for any artist wanting to or forced to go it alone (that’s most artists).
• The Unconventional Guide To Publishing* is specifically aimed at aspiring or established authors looking to share their work with the world, whether via self-publishing, a traditional book deal, or a mixture of the two. The core eBook is written by a veteran literary agent with more than 1,000 book deals under his belt, and the three pricing options include varying levels of interviews and additional content depending on your ambition.
• The Empire Building Kit* is the biggest investment, by far the most far-reaching, and (if followed correctly) the most powerful and sustainable for the ambitious & determined self-employment convert. Built around the concept of taking one specific piece of action per day, it aims to take the user from zero to hero in 365 steps. It also includes candid case studies of successful ‘lifestyle business’ practitioners, video interviews, product launch checklists, and more. (Quick version: Successful self-employment in a year for less than your daily latte, regardless of twee metaphors.)

For the record, I am indeed affiliated with Chris, and proudly so, having collaborated with him on a screening of Janapar in his hometown of Portland, Oregon and having learned a huge amount from his blog and guides. I can personally attribute to his guidance the fact that this blog you’re reading still exists, that Janapar exists, and that I’ve not had to make a post-travel return to my previous life as an office-bound web developer.

Not just me, but he’s helped several close friends of mine and thousands of others to actualise what we feel are important principles through our work, by evangelising and remaining true to a few very sound principles. His own blog, The Art Of Non-Conformity, is required reading for anyone wanting to learn about the many ways in which we can make a living on our own terms in today’s world.

It’s worth mentioning that transitioning to self employment does not have to be a scary, in-at-the-deep-end experience. You don’t need to fire your boss tomorrow or anything like that.

Rather, it’s something that can start with a spark, smoulder away as a side project, and only eventually replace the day-job. That way, the worst that can happen is that if the side-project fails, you simply wrap it up and start work on a new one.

Could transitioning to self employment help you achieve your own adventurous goals? What skills from your current profession could you adapt to serve the needs of others on your own terms?