Pam Yang has worked in marketing for 16 years since she graduated from college. But her pathway has not been a typical one. Every time she has left a job, she has taken a career break to travel before beginning the next one.
Over the years, Pam has interspersed dream jobs at the likes of the NBA, Eleven Madison Park and Nike with solo road trips, ski seasons and backpacking adventures. Along the way she has also founded her own consulting business.
Pam’s travel breaks have ranged from a month to two years, each time a new adventure. She has never left a job with a new one lined up; instead, she has utilised travel to clear her head and figure out her next steps.
In this interview, Pam discusses what inspired her lifestyle, how she prepares for career breaks, what the time off has taught her over the years, and the challenges of readjusting to new environments.
What inspired the decision the first time you quit a job to travel?
I had been at my dream company (the National Basketball Association) for two years – a place I’d wanted to work since age 10 – and was miserable. Every choice I made in my career up to that point was to get me into that company, and I felt like I had no idea who I was if it wasn’t to work my way up to being NBA Commissioner.
I was so unhappy and didn’t see a way out of it except to leave. I had wanted to drive cross-country and visit a bunch of national parks, so I figured that would be something I could do while I figured out what was next.
What were the biggest lessons you learned on that first long travel career break?
How little I really need in order to live and be fulfilled. How I wear the same things over and over on road trips. How much I loved sleeping outside, and how important being in remote, natural places meant to me.
That finding myself isn’t something that happens just because I go travel for an extended period of time. What calculated risks mean to me, specifically. And how to test my fear boundaries in a way that works for me.
How do you prepare for your travel career breaks? Have you developed a formula for planning?
Aside from the trip-planning and packing aspects I always do these two things: the most important is to clarify why I’m taking the time out, and what I hope to get out of it. This is critical to understand and it helps to determine so many other aspects of the trip.
Then I determine financial runway: how much time can I take, and what budget I need to hold myself to. And I address all financial responsibilities, for example putting bills on autopay, and getting out of current housing or sublet.
What do your friends and family think of your travel/work lifestyle – has it affected your relationships over the years?
My relationship with my mother has always been tumultuous, so the travel component is just another area she’s expressed disappointment and frustration in. It doesn’t fit a template that people are used to seeing, especially if it happens multiple times over, so many people just simply don’t know how to make sense of it since it doesn’t fit the mould they’ve been shown.
Now that I’m 37, it happens far less and people are used to it, but I got all sorts of comments from family and dear friends like… “Get a real job.” “Grow up.” “When are you going to stop skipping out on life?” “How do you keep doing this?”
People will put their own insecurities, jealousies, and fears on you in the form of critiques of your decisions, so being confident and steady in why you’re doing what you’re doing is a good foundation from which to deal with the negativity that will come your way.
More often than not, my loved ones have wished they could do what I’ve done, and the honest ones will simply say so. The others find less compassionate and kind ways of communicating.
“I was fortunate to realise at a young age that enjoyment was a very critical ingredient of anything I did in life.”
What have been your most memorable travel experiences over the years?
Living in Sifnos, Greece, solo for a month. A three-week solo camping road trip through the south-west. Travelling through Costa Rica for seven weeks. And two months living out of a car and driving all around the country.
Have any of your jobs ever felt permanent, like you wouldn’t leave again for a travel break? Or is travel always part of the plan?
It’s more that I’ve never looked at any job as permanent. I’ve never been anywhere longer than three years, and generally change things up every 1.5–3 years or so. Travel is just one way to transition, just like switching a job is a way to switch things up. But travel is a vehicle for so many things that are important to me (exploration, learning, exposure, beauty, newness) and makes me better at day-to-day, non-travel living, so it’s an ideal activity when I’m not tied to a job.
I was fortunate to realise at a young age that enjoyment was a very critical ingredient of anything I did in life. I watched my single mom work extensive hours in a field that she told me was one of the few successful paths I could pursue (finance), and by experiencing her day-in, day-out existence (and exhaustion, irritability, impatience and lack of joy), by extension it showed me two critical things. One, maybe my mom was wrong about success. And two, happiness was my priority (or rather not being miserable in my career, like my mom was).
What have you learned while travelling over the years that has helped you in your career?
The most valuable are the critical soft skills that I leverage far more often than hard skills as I grow in my career and get more senior positions. For example, adaptability to uncertainty. Problem-solving on the fly. Practicing facing fears. How to connect with all sorts of people from all sorts of backgrounds. Having an extensive library of stories to share in various professional conversations, and having that many more touchpoints and experiences to connect with people from.
“Each time I’ve travelled, one of the goals was to further clarify what I wanted next.”
Do you have a particular strategy for finding a new job after travelling? How do you find the right role for you, and do you mention your travels in the application process?
“Right” is a slippery slope. Finding good fits for you requires doing the work to define what you want to begin with. I mention my travels if it’s part of the story I want to tell for that opportunity.
As for strategies, I didn’t know this is what I was doing at the time, but I’ve been networking since my internships years and kept my networks strong since I started working. I’ve been very fortunate to not have to do a lot of job searching when I’ve come back because my networks have been great resources to tap into.
Having a few exploratory conversations and informationals have led to opportunities that have been great next steps. But each time I’ve travelled, one of the goals was to further clarify what I wanted next, and in those networking conversations, being able to articulate what I wanted and was looking for created an extended army of other people who helped connect more dots that ultimately led to my next step.
Have your regular travel breaks ever come up in job interviews as a concern?
They’ve never come up as a concern, and nobody has asked about any break specifically. If we’ve discussed it at all, it’s come up in the context of me sharing my overall story.
I feel lucky to have never been concerned with gaps in my resume. I think it’s important to tell our story the way we want to tell it, so if you’re concerned about employers questioning your travel breaks, I would get ahead of it and share the narrative you lived before they question you about the one they perceive.
If you don’t have the opportunity, or if they probe, being honest and appealing to the human side of the interviewer is what I advise my clients to do.
Do you find it challenging getting back into a working routine after each travel break? Any tips for readjusting?
Of course. More mentally and emotionally. But completely shifting your day-to-day activities is always going to be an adjustment.
No blanket tips as it will depend on what situation each person is dealing with, but creating, as much as we’re able, an environment that fits our working style and ability to be productive. There are a few things I know I need, like structured time in my calendar, but it’ll be different for each person.
“Our lives need different things at different times, and staying attuned to our current and shifting needs is paramount to know whether it’s focus-on-career time or transition time or travel time.”
What are your plans for the future – do you intend to keep breaking up your career with travel, and how do you see the pandemic having an impact on your lifestyle?
Overall, my commitment is to keep learning and exploring the world. At times in life that’s been through a professional environment developing skills I wanted to hone, or being in a community to collaborate with. Other times it’s been through activities like travel and learning through immersion and physical place.
Our lives need different things at different times, and staying attuned to our current and shifting needs is paramount to know whether it’s focus-on-career time or transition time or travel time.
The pandemic is giving me an opportunity to see more locally and appreciate what’s right around me. I’m grateful mother nature is getting a break from all of us taking advantage of her and can rest for a stretch. I’m excited to take this time to live for short periods in different areas, maybe a month in the Rockies for ski season, and a few weeks on a warm beach for new years.
What advice would you give to other people considering taking time out of work to travel?
The most critical for me to ensure you get the most out of the time is to get clarity on why you want to take significant time to travel. And be as specific/detailed as you can. Travel is certainly great just because, but people can place undue expectations on travel being a saving grace or void filler for what they’re unhappy with or lacking in life.
If the goal is just to go and enjoy and be, then that’s a fantastic reason, as long as it’s the honest one. Hint: “finding yourself” is not a guarantee, so I’d spend some time defining what “finding yourself” means to you.
Then organise and plan your finances. Most of us don’t have endless reserves to draw from, so figure out what runway you have to travel and how much you have to spend.
There are tons of logistics to consider, but the big ones for me are: pack less than you think you’ll need, get travel insurance, and make scans and photocopies of your critical documents (passport, driver’s license, insurance cards, emergency contact numbers). Then send the scans to your email or save it in the cloud!
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