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

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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?

Comments (skip to respond)

16 responses to “Self-Employment: A Life-Changing Tool for Freedom & Adventure?”

  1. Just found your Blog, Tom, and stumbled across this post. It’d be interesting to hear from folks who aren’t self employed, but are still granted substantial time off and freedom to work where ever this wish. It’s a real shame that while more Americans are learning to live better with less, that we’re still working 40hrs a week, 50 weeks a year, for 40 years. I blame it on the unwilling American corporate environment that still believes the workforce needs to work this much in order to productive, and on myself, the worker who takes the job and asks about the vacation time after. Next time I won’t be so foolish.

  2. Broadly I agree with you; my Dad made the transition from Scaffolder to Fish ‘n’ Chip kingpin and went from sleeping in his van to houses around the world so it is doable but, and it’s a big but, for 15–20 years he did not have freedom, he was grafting seven days a week 8–9 months of the year, with a lull in winter where he would ‘only’ work five days a week. Sure now he doesn’t have to work again, but he’s 59.

    On the other hand I’m a cowardly wage slave but I did get to have adventures in my 20s and I have carefully picked a job that can be done anywhere there is a phone, internet and powerful laptop. Earlier this year I spent a month in Budapest ostensibly at work. My boss has been in Mexico for the past six weeks. Again, at work.

    I hear what you’re saying though, and I’ll be definitely be going the self-employed consultant route when I’ve got the grey hairs, but for now it’s a nice compromise.

    1. It’s certainly not a one-size-fits-all formula (like travel). It helps to define what you’re aiming to end up with in terms of income, free time, commitments etc before you get stuck in so you can measure how you’re doing.

  3. SEA monster avatar
    SEA monster

    LOL. What was originally in the can (the stove is made of) on the picture? Was it Gin & Tonic?

  4. Hi Tom, I am not self employed in the progress to be at least unemployed for the coming years. I expect this will broaden my view and what my mind is interpreting. One concern i really wonder about is the sustainability and return to the community. Do you wonder about this? By the way yes Chris Guillebeau is inspiring having read the 100$ startup.

    1. I always took the view that if setting out to travel the world would teach me anything, it would be to clarify my strengths and weaknesses and show me what I really cared about. I hoped that from that would emerge a direction to go in upon returning to a more rooted life. As for sustainability, that’s a big question, but I think the answer lies in choosing to do something that has timeless value and can evolve with time (e.g. storytelling, being of service).

  5. Jennifer Hill avatar
    Jennifer Hill

    I’d love to figure out what to do when I grow up! I’m pushing 60, w a wonky heart & other illness, but my passion is theology & linguistics. So , I decided to dig in & teach myself Koine Greek, Ancient Hebrew & Ecclesiastical Latin . I’m Catholic & meet up w a Jewish friend to study Hebrew once a week. The rest is on my own. It gets crazy, but fun. Who knows where the journey is going. If widowed, in the future, I’d love to have a hermitage in a village where we could get together & garden, maybe put together a cob bread oven, have picnics?
    Talk about the Universe & God. That is what I want to do when I grow up.

    1. Who knows indeed! 🙂

    2. Ha, ha Jennifer, I like it…in the spirit of ‘Candide’, “ut operaretur eum: “And the Lord took the man, and put him into the garden of Eden, to dress it and to keep it”(Genesis 2:15). As Candide, Pangloss and Martin discover; man is not born to rest and keeping busy helps to fight off perpetual philosophising with nothing more to prove than ‘a priori’ proofs of Optimism. Still it has its place in between the fruits of seasonal labours 🙂

  6. I’ve been thinking about buying the $100 Startup for a long time and this post just made me finally do it. I’m working towards self-employment and I could use some advice. Going to grab my kindle and start reading right away!

    1. It’s a supremely useful book — I hope it’s as handy for you as it was for me…

      1. I agree that it’s a good book. The biggest lesson is that you don’t have to come up with some world-changing new idea. Just make people a good offer and some will take it. You could be selling anything from contact lenses to stories of adventure

        1. Precisely. If you think the entire world is watching you, you’re probably labouring under false pretenses. Best concentrate on those you can serve…

  7. A great subject to explore. I remember working full time as a carpenter for a building company, after 18 months I realised that I was tied in on a contract earning a meagre £7.50 an hour and my boss was driving a Jaguar. I had a lightbulb moment and realised that the reason he was driving his Jag was that I was doing the work, I was in fact the “middle man” between him and his clients, and he was getting the lion’s share of the money. In which case I decided that it would be better if I worked directly for my clients, more money, more freedom, self employment. I remember my first day working for myself, I earned half of what I used to take home in a week in just three hours, wow! What a buzz that was!
    The main fear of going self employed was the the only thing I couldn’t control, how was I going to get the work? Call it serendipity if you like, my phone didn’t stop ringing for the next ten years…
    I made it so I could spend one month of the year travelling in other countries, I enjoyed my work immensely and felt like a very lucky man. I had complete control, choices, freedom and good money.
    Since then things have evolved and I now have a business that is run in a completely hands off manor, giving me the freedom that most people dream about, my last trip was spent living and travelling in Argentina for 18 months.
    If I hadn’t changed anything, if I hadn’t stepped out, faced my fears, took risks, trusted in the unknown, I would probably still be working for that building company. Nothing changes until I change something. I spent a lot of my life in a three sided prison cell, then I found I could walk out at any time, that I was always free!

    1. The “lightbulb moment”… I remember mine well. It’s an incredibly life-affirming moment, to have proof that you don’t need the ‘safety net’ of a salary and a pension to make a living. Great story — thank you!

Something to add?