If We Can Do It, So Can You with Sean from What Happened After I Left

Sometimes walking away from a good job, and the security that brings, can be one of the hardest decisions to make. I think it is one of the main things that makes taking a grown up gap year so different to taking one straight from school or college. This week’s If We Can Do It interviewee Sean knows exactly what it takes to walk away, after giving up his Wall Street job for a life on the road.

1. Why did you decide to take your grown up gap year? Was it a difficult decision to make?

I had been working on Wall Street for years, but could see that there was a shelf life to my job because technology was making humans more dispensable; we were becoming the equivalent of travel agents in a world of Orbitz and kayak.com. When the 2008 crisis happened, bankers became society’s pariahs. 2009 – 2011 were lean years for the industry and the US government was looking to regulate the industry more closely, so I can’t really say that the last few years were fun.

Leaving was an easy decision. The real catalyst for me was that I looked at my boss, who had spent two decades with the firm and was still reporting to a half dozen other bosses, who in turn reported into other faceless people further up the organizational chart. I didn’t want to work for years towards a promotion that would lead to more bureaucracy, less job satisfaction and premature ageing. Nonetheless, it took two years for me to feel ready to walk away from it all.

2. What were other people’s reactions when you told them your plans?

My colleagues were thrilled for me and most said they wished that they had had the guts to do the same. Clients congratulated me and took me out for lunch and dinner. My friends were all happy for me, although they were less enthusiastic that I was taking a year off with the possibility of not returning to New York.

3. How long will your trip take and where will you go?

I am currently two months into a seven or eight month trip through Asia. So far we have been to Thailand, China, Japan, Hong Kong and Indonesia. Plans are fairly fluid, although we will do some volunteering in Cambodia for a partner of charity: water, and I plan to meet and blog about some of the people that I have loaned money to in Asia through micro finance charity kiva.org. When we have finished travelling through East Timor, the Philippines, Laos, Vietnam and Myanmar, we will fly to South America in time for the Rio Carnival in February. As you can see, this grown up gap year gig is much better than having an office job!

4. How are you financing your grown up gap year?

The trip is being financed from savings. I was thinking of doing some consulting whilst travelling, but I am enjoying my time out from working and I don’t want to be a consultant when this gap year is over.

5. Are you travelling alone or with family/friends?

I am travelling with my girlfriend who was unemployed back when I quit my job. It was not very hard to convince her to pack up and join me.

6. What is your travel style? (Ie. Budget hostels/Mid-range hotels/Luxury travel – less is more, travelling slowly/pack in as much as possible)

I have done a lot of backpacking over the years, and have learnt that continuity is your best friend. Whilst there are a million-and-one beautiful places to visit in the SE Asia Lonely Planet guide, I would much rather limit myself to quality rather than quantity, because travelling in SE Asia can be uncomfortable, tiring and expensive.

We have been lucky to stay with friends in Bangkok, Hong Kong, Tokyo, Osaka and Beijing, which has helped to keep costs down, in particular in Japan where youth hostels can cost $70 per night for a couple. We have had a few bad experiences in standard rooms in budget hotels (rats, bad hygiene, lack of a fan or air conditioning) so in general we go for the deluxe room in a budget hotel or a standard room in a mid range hotel.

7. Do you go for tours or do it alone?

There is so much information on the web, that I don’t really see the point in using a tour, unless it works out cheaper or more convenient. Where we save on tours, we spend on a local guide, which in general still works out cheaper.

8. What is the best thing about taking a grown up gap year?

Apart from the obvious trade-off of swimming with sharks whilst your friends are sitting in the office, taking a grown up gap year gives you your freedom and puts you in control of how you spend your time. I have left the rat race. I don’t have to wake up at 6.22am any more, I don’t live under the yoke of the blinking red dot on my work BlackBerry, I don’t have to fly out to the Midwest at 6am with a hangover. I can now do the things that I’ve always wanted to do, like learn Muay Thai in Thailand or surf in Bali.

9. And are there any downsides?

If you don’t like your job or career trajectory, there is very little downside other than financial.

10. What advice would you give to anyone thinking of setting off on their own grown up gap year?

I think that the biggest hurdle to taking a year off is a financial one, both in terms of the cost of travel and the opportunity cost of not working for a year. Walking away from a job might seem silly in the short term, but what you lose in money you gain in time, which is a much more valuable commodity. Taking time off will inspire you, provide you with new people skills, teach you about other cultures and increase your global network of contacts, all of which will be huge assets when you decide to start looking for a job. Surprise yourself and make the leap, you won’t regret it.


To follow Sean’s adventures visit his blog whathappenedafterileft.tumblr.com