As I navigate this year of my life as a 30 year old digital nomad, I’m writing advice to my 20 year old self on a few important topics. So far I’ve handled Money and Happiness, and this third in the series is on Work.

There is a question that haunts many of us, and there doesn’t seem to be anything like a public consensus on what the answer is. The internet is full of advice and there seem to be waves of opinion that periodically slosh in favour of one direction or the other. The question is something like, should you make a career out of your passion?

There are some lucky people whose path to happiness involves work or a career that falls nicely in line with the existing social paradigm and allows them to easily and happily make a career from their passion without compromising themselves more than they would like to. I’m thinking teachers and nurses who love their work despite the hardships and hours, academics who enjoy their research and giving lectures, sociopaths who love gaining and exercising power at the expense of others.

I was never one of these people. At twenty I wanted – above everything – to be free to travel, explore, and make useful, creative contributions to the things I cared about. And there are many who share my affliction. In fact this subject, work, is quintessential to the intentional living, alternative lifestyle design theme of this blog. Hence the question, and its popularity on blogs of a similar distraction.

I’ve been acutely aware of that question since my mid-teens, but I always had to revise it slightly for my own needs. The reason is that, then and now, I could never point at any one thing and say with the confidence that this question seems to require: “that is my passion”.

So my question was always something like:

“Is it better to work a job you don’t really love in order to earn enough money to do the things you love, or should you just work hard at making a career out of the things you really enjoy or are passionate about?”

At twenty I was sure I knew at least one half of the answer: working in an unfulfilling job and trying to live out your dreams in your free time is, for the vast majority of people, a fools errand.


First of all, the standard deal on offer is just terrible. Free lunchtimes, bank holidays, weekends and a few weeks off a year in exchange for 40 hours a week (plus your commute time so let’s average 45 hours in total) doing something that you don’t really care about. If you’re getting a good 8 hours sleep a night that is almost half of your waking life spent doing something that does not fulfil you. And on top of that, it’s a really inconvenient half that makes it very difficult to develop any meaningful activities in your spare time because it is so broken up and fractured. Even worse, for almost everyone this is a deal for life, until retirement essentially: 9-5 until your 65 (or 75 more likely by the time I retire).

“Perversely, there seems to be an inverse correlation between the enjoyment of the job and the need to keep doing it”

Even if you are satisfied with that deal, the likelihood is that evenings, weekends and holidays become rest and recuperation periods, giving you just enough spare time to keep you productive and motivated at work. I admire people who have the energy to make the most of their free time, but I always feared not having that energy and, even if I could find it, wouldn’t I just be desperately trying to taste freedom instead of living a free life? It always looked like, and still looks like, a terrible deal.

There is the allure of money, of course, and with what I know now about the potential for early retirement through hard work and smart investment, I might have thought a little harder about that deal. 9-5 until your 35 doesn’t sound so bad, but I was also scared to death of having the zest for life sucked out of me. Plus, you get good at what you do, so all those years spent doing something to earn money could perhaps have been spent, at least in part, getting better at something I really wanted to be good at.

I also feared the danger of being subsumed into a life of status and comfort, and that does seem to happen to a lot of people. If you’ve been lucky enough to be successful, then once you have a £30k+ salary in a job that you know how to do, where you have a reputation and a network and a secure future with a growing salary and a good pension scheme, throwing all of that away and starting again from scratch is surely terrifying.

From this wealthy position, just downgrading your salary can become impossible because, since people tend to increase their spending with their incomes, the chances are you now have an expensive lifestyle that might include payments on a mortgage that you won’t be able to afford if you start earning  less, let alone minimum wage or no wage at all. The chances of having a family by this stage are also pretty high, which of course makes everything all the more complicated.

Martin Holland Borneo Explorer and Conservationist

Expedition recce into primary rainforest in North Kalimantan

Even if you’ve been frugal and saved and your family are not daunted by the lifestyle changes, the idea of walking away from something that you have put so much time and energy into, and sacrificed so much for, for so long, is just too much for most people. How many times have you thought or heard something like, “I have come too far/worked too hard to just throw it all away and start again”.

It doesn’t seem to matter that what you are talking about throwing away is actually just shit. Perversely, there seems to be an inverse correlation between the enjoyment of the job and the need to keep doing it, as if the more difficult it has been to endure, the more determined we become to extract some benefit that is equal to our years of suffering. The harder it’s been to gather up all that shit, the more we want to hang on to it.

No. Unless you’re one of the lucky few who find their careers so fulfilling that the deal is acceptable, living to work is not the way to go.


The biggest challenge I think most people face with regard to this question is the one I identified at the beginning of the post: what if you don’t know what it is that you want to do yet? Or what if you have too many passions to choose from? Figuring this bit out is really, really hard, and there is a whole sub-culture of the modern economy dedicated to helping people through this maze.

“It is a disturbingly little known fact that any binary style lifestyle advice is almost certainly bullshit. Life does not exist in black and white.”

To illustrate, it’s nowhere near enough to say that what you really want to do is work in conservation. There are a thousand and one jobs within that sector, ranging from negotiating policy at global climate summits, to fundraising for small NGOs, to conducting field research. The day to day and lifestyle realities of those jobs are wildly different. Some people may truly just want to work in conservation and as long as they feel they are contributing they will be happy, but I think they are rare. The rest of us need to test a few different waters before we can begin narrowing down what we are really passionate about.

But let’s say you’ve figured out what it is you want to be or do. Now you face the question of how you are going to get paid for it, and this can be a real minefield. One danger is that of falling into a role that is connected to your passion but that is actually nothing like what you really want to be doing.

Imagine you want to work in the outdoors (I don’t mean just outside here, but in the mountains and places like that): when you look around at the jobs you see that the majority of them involve either being a guide or an instructor. Perhaps you love the outdoors for the space, the solitude, the personal challenge of a summit attempt. The last thing you want is to be taking a group of overweight city folks with no real love of the mountains to the top of Snowden every weekend, or rafting down the same mile of river 10 times a day.

If you love the idea of guiding, perfect, but if you hate it, you might find that it destroys the very passion you were trying to pursue.

“Remember that not all those who wander are lost”


It is a disturbingly little known fact that any binary style lifestyle advice is almost certainly bullshit. Life does not exist in black and white.

At twenty I always thought there was middle ground, and there most certainly is. It is a broad middle ground which offers many routes over the mountainous terrain of working age life.

“Ask yourself… who is the real drifter?”

One such path is to eschew the career option, but to take the pressure off your passion, by working in low skill, low income, part time or seasonal jobs that give you the freedom and flexibility to do things like quitting when you like and moving between towns and countries when you want to. There is a lot to be said for this, providing your ego can stomach it and you can create the sort of low cost lifestyle that will mean you have a bit of spare cash to put towards the development of your passion projects. Low cost lifestyles come with a slew of other benefits so these are worth pursuing for their own sake, something I touched on in Money.

Compared with the career option you are trading income and security for time and freedom. You might earn less per hour – and you might work fewer hours – meaning you are financially much poorer than a career high flyer, but you have two things that they can never buy with all that extra money – time and freedom.

Imagine working a three day week and having a four day weekend, every week. Or working three weeks a month and taking a ten day holiday every month. Or taking 6 months off every year to live in a foreign country, maybe volunteering, or studying the language, or making a documentary, or learning a new skill, or writing a book, or doing whatever it is that you really want to be doing.

Martin Holland Triund Himachal Praadesh

My back yard while living in northern India for 5 months this year

One huge advantage of this approach is that as well as having more free time in a given month or year, you also have more time to figure things out. As much as you need in fact.

You don’t need your passion to pay the bills straight away, or ever for that matter. Over time you might develop your passion into a real skill, and you might find a niche and decide that the time is right to start making money from it, but you might decide you never want to compromise your passion with the demands of earning an income from it.

You’re free to explore different interests, countries, jobs and lifestyles until you get a sense of what it is you really want to do, and how you really want to live. Doing this as a 40 year old with a mortgage and a family and a career is (I imagine) incredibly difficult, which is why there is such a market for Finding Your Purpose type blogs and seminars.

And who cares if this takes ten or twenty years? Remember that not all those wander are lost, and ask yourself, who is the real drifter: a 40 something who has explored the world, her own mind, her passions, and found her path to a fulfilling and meaningful life; or a 40 something banker who has no idea why he is there except for the money. And bear in mind that after five, ten, twenty years of searching you might find that what you’re really intent on doing is becoming a lawyer, a doctor, or an accountant. The difference between beginning this journey after a good amount of soul searching, and jumping into it as a twenty year old because it sounds like a good career, is that you will really know why you are there and what you are getting out of it.


There’s a potential downside to the Third Way which is that, even with a low cost lifestyle, these low skill jobs really do tend to be low pay which can limit your options, and they might not be the kinds of jobs that you want to be doing forever, even if they are only part time or seasonal, and even if they are giving you the freedom to pursue your passions.

“…dream like a dangerous man, a dreamer of the day”

Since my twenties I’ve been wondering: instead of low skill, low pay jobs, perhaps there are high skill, high pay jobs that offer the same freedom.

In short, what if you could earn very good money in short amounts of time in a way that, although not exactly fulfilling, was still rewarding and in line with your ethics and other lifestyle desires.

Now, with experience, I can say that these jobs do exist and are not as difficult to come by as you might think, although they might require a small initial investment of time or money.

My favourite idea was becoming a yacht delivery skipper. Get paid very good money to sail yachts across oceans to their new owners or to holiday destinations. It’s adventurous, freelance, there seems to be a lot of work available, and once you’re a skipper it is very handsomely paid. I actually trained up to Coastal Skipper a few years ago and landed a job quite quickly, and I still get offers from the agencies I signed up to, but I ended up taking a different path.

Freelance wedding photographer/videographer seemed to be another good choice. Obviously the best money from this is to be had from running your own business and working year round, employing staff to increase the amount of business you can take on. But that is a full time job (and then some probably), and you’re not trying to get the best money, just enough money, quickly.

Something I’m currently considering is facilitating personal and professional development seminars and workshops for businesses and teams. The pay is very good, it’s useful and rewarding work if done well and with integrity, and can be scheduled in to certain periods of the year around more fulfilling projects.

There are loads of similar jobs, and the point is, with a bit of creativity and lateral thinking, there are ways to earn a decent amount of money in short periods of time, freeing you up to spend your time doing things that you really love, and perhaps figuring out how to make a living from those things in a way that doesn’t compromise your enjoyment of them. I’ve been making this work for years and it means I can write, build my charity, have adventures, live wherever I want, and dream like a dangerous man, a dreamer of the day, in the full knowledge that I can make my dreams a reality.

So my advice to younger me is: pursue some of those higher paying freelancer gigs sooner, and with more vigour, with the aim of earning a years worth of cash in 3 month spurts, and then do everything else the same, just with less debt, less stress, and a bit more financial freedom.

I’d love to hear your opinions on that, or your own experiences, and definitely your ideas for high income freelancer jobs that most people could learn to do. Hit the comments!