10 Questions to ask yourself before you quit your job and travel the world

By Eric Koelma | Dare List Dad

In September 2016, I had a significant choice to make:

Finally make a decision to stop the pain, quit my job, take a leap and travel with my little family.


Stay put for another 3 months, 6 months, 2 years..?

We'd been considering the decision for 6 months, and the past 2 were downright painful. But let me clarify. I was fortunate enough to be working full time, with a great bunch of people I'd become close with. The problem for me was the time spent away from my wife and (then) 1-year-old son. I spent day after day travelling 2 hours each way (that's a lot of time commuting to consider your life...), getting home with either 20 minutes to spare to see my son or just missing out if I got delayed by one train or connection. It was no way to be a father. I wasn't authentically living. And to me, enough was enough.

I spent a lot of my time in commercial kitchens taking photos of food. Not the worst job in the world...

Sometimes I even went on site to the food manufacturing plant and got to dress like an absolute muppet

I decided that to take the leap, I would need to answer ten questions of myself. Here they are, and I hope they help you if you're in a similar predicament:

1. Do I actually like my job? Does this authentically fit with my life purpose? If I had the option, would I be doing what I'm currently doing Monday to Friday?

For me, the answer, deep down, was no. And it's hard when you're in the routine of seeing people every day. You feel loyal to them. Dedicated. But I guess the thing about working for an employer is that you don't owe anyone anything.

I mean you're paid for the work you do, sure. But if you decide to stop doing that, then they stop paying you. That's the realistic transaction at play (as base as that may seem). The people you work with are there consequentially; you didn't choose them. They, like you, also do a particular task and are paid for that. So they face the same transactional reality. You are there to help each other, but you don't owe those people or that company anything further (outside of giving notice appropriately and leaving professionally - no middle fingers on the way out of the office!).

And even in a 'stable' job, you and those other people can realistically be 'restructured' anytime and be out of work tomorrow if the company execs decide.

What I chose to do in 2017 instead

2. What would it look like to do the opposite of what I’m doing now?

This helps to compartmentalise and rationalise the things you are doing in your life and see what you couldn't live without. The 'opposite' is a bit vague, so I broke it down into five categories: friends, family, work, social, my time.

It's easy to pick out the things that currently suck in those categories that 'doing the opposite' would fix, but make sure you also look at the great stuff, that you would miss if you flipped everything on its head.

3. What are the areas of my life currently committed to ‘dead time’ (commutes, meetings you don’t need to be in, water cooler conversations)? Am I okay with that?

Perhaps this was more prominent for me than it is for you.

I was commuting 20 hours a week. 

That's 20 hours of dead time.

Sometimes I wouldn't have enough work to do, or I'd spend an entire morning clearing out an email inbox. This also felt a total waste of time. What significance does clearing those 50 emails have now? ZEEEEERO.

Next, take those dead hours per week and times them by 52 for weeks of the year.

I won't even bother with the laundry list of menial/meaningless tasks in the office. Let's just look at that commute.

20 x 52 = 1040

I wasted more than a thousand hours each year commuting.

Shiiiiiiiiiiiit, right?

That's like 43 days and nights on a train, without getting off.

It's wasted time, but it's also a massive amount of inactive time just sitting on a train. A metal can full of people. And not even happy people. Just people, like me, seemingly similarly resigned to an average existence - spending their time asleep, or on their phones.

When I looked at people 10-15 years ahead of me, was I inspired?

Heck no!

Speaking of dead time, I took this photo on one of my last days on a commuter train. Note the amount of devices in hands on the platform.

4. Are we running from something if we pack up and go? Do I have personal issues to work through first?

In some respects, I think we'd all like to run away from something. No one is 100% happy with everything. Content perhaps. But it's only natural to have those aspirations or regrets.
In my circumstances, there were things that I loved about the life we had. But we can also have those things in the future.

The list of what we wanted to change was much longer. Was it running away, or was it merely a desire to find space? I came to two conclusions:

1) You can't change from within the environment you want to change away from.
To put that another way... How can you change the way you're living, when you're in the middle of it? Space allows clarity to breathe. That's what our family needed, and I could feel it. 2017 was a year of intense personal growth for Grace and I, beyond just the experience of travel, so the initial feeling was accurate.

2) You're not ONLY running away. You're running towards something too.

The great thing about the darkness of something unknown is that it is excitingly adventurous AND scary at the same time. In reality, the things we fear are rarely as bad as we catastrophise them to be in our heads. And often step one is the biggest and scariest.

5. What will I do to earn an income for the first month? 3-months? A year? Long-term?

I didn't know, but I couldn't keep living inauthentically, pretending to get excited over products I didn't believe in.

I decided that I needed to jump off the cliff and build the plane on the way down.

Fortunately, we crammed in with our parents, who very graciously took us in for four months of transition, creating a type of mini-buffer to find our feet and make it work.

It was scary and unknown and liberating.

7 steps to becoming a digital nomad

Working from a co-working space in a resort in Thailand. Not bad, eh?

6. Can we afford to earn less in the short term to fund the long term?

Again, crashing with the parents helped. And we're forever grateful. I think the mix of us being allowed a room or two as a trade-off for more grandparent time before we set off for an extended period of world travel was a good exchange. 🙂

When it comes to expenses, living a domestic middle-class life in Australia is expensive. Here was our regular monthly expenditure:

Rent/mortgage: $460/wk (yeah Australia is expensive): $1840 per month

Electricity: $360/qtr: $120 per month

Water: $330/qtr: $110 per month

Phone plans: $19.99 and $17.99: $38 per month

High-speed Internet: $60 per month

Petrol and owning two cars: Estimation tank and a half per week ($80): $320 per month

Car operating costs including servicing, insurance, registration etc would be (conservative estimate) $3000 per year: $250 per month

Health insurance: $50 per month

Home insurance: $50 per month

Okay, they are the more major and most consistent things...

So we're looking at $1840 + $120 + $110 + $38 + $60 + $320 + $250 + $50 + $50 = $2838 per month

And we haven't talked about food yet...

Or random purchases.

Or house repairs.

Now compare that with life on the road.

Internet, water and electricity come with wherever you stay. Can you find accom for less than $2000 a month... yeah usually very comfortably in many countries. That's $66 per night. We aim for $40 or less.

We bought health/travel insurance for $2300 for a year. So that was somewhat expensive (but SO worth it - we've already used it for some tech gear that died along the way).

With cars at $570 per month at home, can we travel between destinations for less? Yes. On average our travel expenses are far less than that.

We have one phone and buy a local SIM in whatever country we're in. To date, the most expensive has been France at 30 euros ($43 AUD). Still better!

7. What will I do with all my stuff (belongings, investments, etc.)?

Oh yes... The reality of all your stuff! Oh my gosh, we had a lot of crap.

It's funny how when you live in one place, you seem to buy the exact amount of stuff to fill it to about 150% capacity, no matter the size. We had so many trinkets, Kmart furniture everywhere and sporting equipment that hadn't seen the light of day in 3 years. Once we decided to travel full-time, we quickly (over-)filled our garage and hosted a garage sale.

After selling about 40% of our stuff on Saturday, we still had a somewhat-depleted but still full garage. So we had a choice. Bargain with people over '$2 for this' and '$1 for that' all of Sunday, or get it done.

We don't work for $2 an hour, so we jumped online Saturday night and posted on Facebook groups that we were doing a garage giveaway on Sunday. That worked a treat.
80+ people on the front step at 7:30 am on a Sunday to take our free leftover crap. The garage door rolled up at 8 am. By 8:20 - garage empty and we got on with our Sunday.

Funny side note - We ended up making over $100 in that 20 minutes as people taking more significant items (cabinets, drawers etc.) said: "I couldn't possibly just have this for free". Better than bargaining for $2 an hour...

So where are we at? We still have a bunch of stuff in our parent's garages. We recently went through it all, and it was interesting to see how unattached we feel to it all. Practically speaking, we can set up house again, but there's no emotional attachment.

8. Is this an irreparable change? If I quit this job, could I never get it again? What can I do to mitigate the risk?

I find that present-state FOMO is a significant part of decision making. "If I change now, I won't be able to be in this workplace/team/house/etc. ever again."

Once I asked whether it was irreparable, a definite shift happened, and I started seeing what we would gain instead of what I would lose. I could be in an even better team. I could start a company that does X. I could build a team.

Can I attain this exact scenario again? Probably not. Can I get a similar or even better job elsewhere, yep!

What can I do to mitigate? Networking. Don't leave your job by being an ass. Don't drop the work rate. Even on your final day. Do something epic after you give your notice. Screen-record a one hour video and produce a 78-page document of everything you do (yes, that's what I did).

Make your time after giving notice really count. Network to solidify friendships, especially if you're leaving to start your own thing. The people you meet in corporate life can be precious for future market research (chances are you won't entirely change industries/skills).

Garden outlook in Bali - What my office looks like these days...

9. What's the greater fear: The fear of making the change or the fear of the regret of not doing it when you look back 5 years from now?

As I said, fear is the primary driver behind not making a change. But at some point, a switch occurs. You start saying "every day I don't decide, I'm choosing to stay stuck in this shitty reality".

Grace and I went months back and forth (and there were many tears). But we finally decided to switch things up and work our asses off to make this work.

We have a concept in our nomadic household:

FIGHT OR FLIGHT (back to Australia)

We are dedicated to the cause and absolutely love being on the road. It might change in future, but for now, we enjoy this nomadic lifestyle.

An intimate family moment in Florence, shared with a million other tourists. Better than sitting in an office.

10. Does this benefit my partner and kids?

This one was a no brainer... Of course it benefits them! It's a chance to widen their horizon. To give them a new perspective, a new set of boundaries and a greater appreciation for how people live, gobally.

We live in the most connected world this planet has ever seen. Never has a generation of people been so accessible to each other at such short notice, without borders. And our son is going to grow up an even more interconnected world still.

Who are we to rob him of the opportunity to grow up in the world he's operating in, and to see it physically and meet those people face-to-face?

​Will he remember it? Perhaps not vividly.

But I'd like to think that this is going to shape the way he views the human condition, the way he grows in compassion for other cultures, races and societies. To see the world not as Australians, Chinese, Afghans and Russians, but as humans, humans, humans and humans.

And we're willing to give him every opportunity to achieve that.

Are we wealthy? Not overly. We work while we travel.

But are we rich? Yes, absolutely.

Rich in experience, culture, understanding, compassion, encouragement. We're able to appreciate the local store owner in rural France who doesn't speak a word of English but speaks the international language of hand gestures.

And it's beautiful and confusing and leaves you feeling way out of your depth, and it's incredibly enriching.

How could this not benefit all of us as a family?

Eric Koelma

Eric is husband to Grace and Dad to Leo, exploring the world and doing everything he can to align the travel itinerary with world sporting events (hello Tour de France!). He's all logical precision and epic decision-making. Eric's also a rare kind of super-human who works best between 9pm and 2am, and still manages to get up early and chase that wilful toddler, WITHOUT coffee (he hates the stuff!)