“How do I start?” – The definitive answer to our most frequently asked question


As we’ve said before, we started Making It Anywhere to make friends – so we love it when people get in touch to say hi, and we’re more than happy to help if there’s a specific question or problem we can help out with too.

But of all the emails we receive, a frustrating minority read like this:

Great blog! I’m 25 and I live in Idaho. I hate my job and I’ve always loved to travel, so I want to have a lifestyle like you guys. Any tips?

It’s frustrating because we absolutely get it – but at the same time it doesn’t feel like there’s any reply that would actually be helpful.

I suppose we could say “Just follow your passion and everything will work out”, but it probably wouldn’t be true – and besides, we prefer to deal in gritty details than motivational platitudes.

So here’s the thing: it’s totally fine to love the idea of being an Anywhereist but be stuck as to how. But if you ask for help at this point, you won’t get a good answer.

Instead, you need to do a bit of work to increase your understanding to a point where you can ask better questions. Here’s how I recommend you go about it.

There’s no great mystery to travel

Because travel is the most appealing and visible part of this lifestyle, people get too caught up on it. The actual “getting started” of travel is pretty easy: buy a plane ticket, dispose of the place you live, and go. The tricky part is sustaining yourself financially.

So the question you’re really asking at this point isn’t really “How do I have a life like you guys”, but “How do I start my own business?”

(Alternatively you could negotiate with your employer to work remotely, or find a job with a distributed company – but presumably that’s not an option or you wouldn’t be asking the question.)

So…how do you work out how to finance a life like this?

Step 1: Brutal self-honesty

Are you prepared to do the work? If you like the idea of bumming around the world having a good time and exploring your passions, that’s cool – but we’re not the people to help you. Look into volunteering or teaching, or picking up casual work as you travel.

Doing the work means having the discipline to get things done – even when more fun alternatives are on offer – and putting in a whole lot of graft without any certainty that it will work out.

Are you willing to take responsibility for your own life? Nobody will tell you what to do, which is great…but there will be times when you really, desperately want someone to tell you what to do – because it feels like nothing’s working and you don’t have a clue how to fix it.

When things are going well it’s the best feeling in the world to be totally independent…but a lot of the time, things won’t be going well.

Do you enjoy learning? You’ll need to constantly learn new skills, learn from others’ experiences, and learn from your own mistakes. The people who make this work the best are those who read a lot of books, introspect a lot, and take a real interest in other people’s businesses.

Step 2: Decide what you have to offer

Unlike when you’re a cog in a big company, there’s no place to hide: you need to have skills that are valuable to other people (so they’ll give you money in return), or skills that you can use to build a business.

So if you honestly think this life is for you, the next step is to think about what skills you have.

You might be lucky enough to have a very obvious skill, like computer programming. With a skill like that you can immediately do work for other people, or use your skill to build something of your own that will make money in another way.

Or your skills might be less clearly defined, like being good at explaining difficult concepts or managing a team. It’s not so easy to work out how those skills translate into money, but knowing what they are can be very useful in determining what your business should be.

Or, being very honest with yourself, you might not feel like you have many useful skills at all. Even that’s not a major problem – you can learn anything for free on the internet, so you just need to have the time and the willingness to develop new skills.

When we started, we had very few obvious skills. Our writing ability was probably above average, but we still practised on our own for months before we tried to sell that skill to anyone else. Everything else we know we’ve picked up – for free or very cheaply – as we’ve gone along.

The key point of this step is to realise that there’s no free ride: nobody owes you a living, so you need to have something to offer that’s valuable to other people.

Step 3: Watch and learn

There are a lot of people already doing this, all in very different ways, and you can learn a lot by watching or listening to how they do it on their blogs/podcasts. You can study their businesses for ideas you can adapt, and get a glimpse into their lifestyle to see if it’s something you’d want for yourself.

Just start by observing, then start commenting or making contact when you’re ready. If you’ve got valuable skills, you might even find that you’re able to do some work for them in exchange for an insight into their business.

If you follow these blogs and podcasts, you’ll see a a few different ways of making this work/travel thing work – from people who are legitimately doing it, not just talking about it.

Step 4: Choose a business model

There are a lot of different business models to choose from, and we rounded up some of them here.

The biggest distinction to make is between selling products and services. If you use a skill (e.g. design) to provide a custom service (e.g. building a website), you can make a good amount of money relatively quickly. But you might not have a skill you can sell in that way, and even if you do you might not like the idea of being beholden to clients and their demands.

The alternative is selling products: making or buying something once, and selling it to multiple people at a lower price than a custom service. This has many advantages in the long-term, but it can take a lot longer to reach the stage where you’re making enough money to support yourself.

(A hybrid model is the idea of getting the best of both worlds through productised services.)

Whichever business model you choose, it doesn’t have to be forever – it just needs to get you started. For example, we started out selling pure services, but we’ve moved towards productised services and added several sidelines in pure products.

Step 5: Refine your proposition

Knowing what business model you’ll pursue – services v digital products v affiliate marketing v dropshipping etc. etc. – is just the start. You then need to work out how to make your offer valuable and be found by your target audience.

Doing this involves answering three questions, which seem like they should be easy but it can take months or years to iterate towards good answers to them:

Who are you for? “Everyone” is a terrible target market, because how do you reach everyone? If you’re for “small personal injury law firms who want to become less dependent on expensive TV advertising and get leads through the internet”, it’s much easier to imagine where to direct your marketing attention.

What makes you different in a way that’s meaningful? Life is very hard when you’re indistinguishable from hundreds of other people offering the same thing. And “meaningful” is the difference between a gimmik (“We’re called ‘Ewe Choose’ and our site has lots of sheep puns”) and something customers care about (“All those other guys take a week – we do it in a day”).

How will customers find you? Getting attention is probably harder than you could possibly imagine if you’ve never done it before, and without having a steady supply of leads nothing else really matters. Whether it’s free (like blogging) or paid (like AdWords), you need to develop a repeatable, reliable way to get found.

Step 6: Ask for help

Even if you’re really struggling to come up with decisions for steps 4 and 5, you’ll now have a better understanding of the options open to you and what your sticking points are. That means you’ll be able to ask a specific question, and be far more likely to get a good answer as a result.

If you’ve got more than a quick question, we offer coaching sessions to help you figure out how to start or grow your business. We do have a package for people who feel like they don’t have a clue what they want to do, but you’ll still be able to make better use of our time together if you attempt to follow these steps first.

Now share your thoughts

If you’re going through this process, which step are you finding the hardest? Or is there something else you’re struggling with that I missed out?

Or if you’ve already made the transition to Anywhereism, what other advice would you have wanted when you were at the very start?

Let me know in the comments!