Updated April 30, 2024

Where are you going? On Choosing Destinations in Travel and Career


Eri Ochiai

Japan Dev contributor

It’s Golden Week. It’s that time of the year when people in Japan take advantage of the consecutive public holidays to take trips and go on holiday. I love traveling but recently realized that I haven’t traveled much during this time of the year for the past few years. The idea of going somewhere sparked some daydreaming thoughts.

One of the exciting parts of going on a trip is deciding where to go. When was the last time you traveled? How did you choose your destination? Choosing where to go is a fun process, especially for leisure travel. “I want to go to a nice beach,” “I want to see the view from the top of Mount Fuji,” “I want to see the historical site.” Wherever it might be, whatever activity you imagine yourself doing (or not doing), choosing where to go brings a feeling of expansion. You’re expanding your worldview and/or about yourself.

Where am I going again? The Career Conundrum

I often use the metaphor of a journey to describe a person’s career. As I mentioned in a previous article every journey is unique and in many ways, is like going on a long trip. What I notice is that there is a noticeable difference in how people choose a destination for travel versus a destination in a career. 

These are some things I have heard people say to me:

  • I’m not going anywhere in my job search. Should I get certified in [Something]?

  • I feel like I don’t speak Japanese well enough at work. Is it the best idea for me to take a Japanese course?

  • I’ve taken so many courses but I don’t know where I’m going with my career. 

  • I’m completely lost on what to do next in my career. Do I need an MBA? Do I go back to school? Change Careers? Help! 

We seem to be in constant search of our next step, our next goal. We open LinkedIn and we see a friend from school who just got promoted. A former colleague getting a new certification and advancing in their career. Then there are motivational influencers who tell you how to find answers to what you should be doing next. The next thing you know, you start wondering if you should be doing something with your job or life. 

With all this information, the temptation to compare yourself with others is ever so insidious and slippery that sometimes, we don’t notice these thoughts start creeping in. I am no exception.  I remember clearly during maternity leave, scrolling through LinkedIn while I was in my pajamas, trying to put my daughter to sleep on my back, the feeling of falling behind to some race, as I read celebration after celebration of promotions, new jobs, relocations. Even today, I still feel the small voice creeping into my mind sometimes to say things like, “Shouldn’t you be getting some kind of advanced degree?” or “What you have is not enough. Look at them! You should do what they did.”

Why do we choose destinations in a career from a place of insufficiency? 

Why is it that so many of us feel we lack or that we need to ‘get somewhere’? What does that even mean? 

If you are currently feeling lost on where to go next in your career, you’re not alone. The good news is there are ways to change this. 

The Starting Point

If I don’t go to Venice and see the Gondola, I’m not enough. Said nobody.

A leisure trip is a nice-to-have for most of us. Sure, if I can budget and find time to go somewhere a few times a year that’s great! But would not going anywhere make me less of a person? No! We don’t plan to go to places because we’re worried that not going will make us feel like we’re not enough. Going somewhere is additional, not for filling in missing holes in our experiences. What if we supposed for a second that this was the same for careers?

What if our starting point was the idea that you are already enough?

Regardless of age, years of experience, job title, or financial success, that you are enough.

You are enough and are exactly where you need to be.

What kind of questions would you ask yourself to choose where to go next, if you knew you were enough?

Self-acceptance is no doubt much easier said than done, but just like the excitement that comes with thinking about the next trip, we can allow ourselves to have fun even when we think about our professional journey.

Unveiling your True Destination

Coming back to travel destinations, if you zoom in and take a look at how we choose where to go, it’s a pretty fascinating process. For example, a few years ago I went on a trip to Vietnam with my partner and we decided we wanted to do something different from our typical vacation (that is visiting his friends and family in Italy or mine in Japan). We wanted to go on an adventure and explore so after looking at some flights, pictures, and info online, we landed in Ho Chi Minh City as our first destination.

“I want to go see the cherry blossoms”  “I want to try the local sake breweries”. Where you go is tied closely to what you do there. When you’re planning a trip with someone else that’s also what you tend to talk about. Even though you don’t say it, you want to do something when you go somewhere because you want to experience an emotion or feeling. If you break down the process of choosing where to go, the real destination isn’t where you want to go but how you want to be when you’re there.

  • You want to feel relaxed and carefree so you go to a nice hotel with a big comfy bed and lie in it, listening to the sound of the waves outside.

  • You want to feel excited and alive so you go hiking for 4 days in the Alps with a tent, a sleeping bag, and a few other essentials.

How you want to be is the unwritten expectation of the trip. The expectation is sometimes a cause for frustration and anger. A classic example is when you book a ticket to a beach resort but it rains the entire time. You’re disappointed even though you’re there because your expectation of how you want to be is different from reality.

Why does it keep raining? I should be spending my days out by the beach enjoying the sun!

It’s frustrating because your expectation of how you want to be is not met. When you’re trying to decide whether you should change your job or get an advanced degree, you can break it down to see what’s going on:

  • I want to get a new job because I want to be [Blank]

  • I want to get a degree  because I want to feel [Blank]

Now you can start to see that where you want to get to is in the latter parts. You want to be someone or something. You want to feel something. That’s why you’re looking for different options.

I want to feel more appreciated for what I do so I want to change my job.

I want to enjoy the process of learning in depth so I want to go back to my studies.

What wants do you see for the options you have in mind? Without judgment, give yourself some space to draw these connections. The more honest you can be with yourself, the clearer your true destination will be.

Redefining your Destination

When it’s pouring outside during a trip you planned months for, there are 2 things you could do:

  • Find ways to enjoy your time anyway or,

  • Complain and be miserable

It’s natural to feel disappointment in the face of unmet expectations but at some point, it’s your choice to decide what you want to do with the situation. The understanding of how you want to feel as the true endpoint can help you break the link between your satisfaction and that situation. 

Essentially, it’s about finding ways to create how you want to feel, without being dependent on the circumstance.

If you came to a beach resort because you expected to feel relaxed by lying down by the beach, you could look for other ways to feel relaxed, like getting a spa treatment or listening to music you love.

If you want to feel more appreciated for the effort you put in at work, you could look for new ways to do that today. You don’t need to limit yourself to a few options that feel daunting to decide on. You could try something outside of your job like doing something nice for a friend or helping someone out. When you can see that what you’re seeking is how you want to be, you can be more creative and lift the heaviness of decision-making in your career. 

You don’t need to plan for years ahead to get ‘there’ because you’re already here. 


The experience of deciding what to do next in a career is vastly different compared to how we plan our vacation. People talk about not having enough years of experience, knowledge in something, educational attainment, etc. These thoughts of insufficiency are exacerbated by tools that make it easy for people to measure themselves with others. Does it have to be so?

When I was about 10, I went to a museum and asked my mom to buy me a magnet with a quote on it. “You are who you are and that is enough.” - Walt Whitman. When we can see that ‘getting there’ in life is really about how we want to feel about ourselves, and we choose to be the ultimate guide and traveler of our own thoughts and emotions, we are met with a world full of opportunities.

We don’t need to choose to get an MBA just because that’s what others do. I don’t have to have a specific job title to feel like I’m important. You don’t have to take a Japanese course to feel like you are accepted for who you are. You could, but come rain or shine, you can still be at peace with yourself.

So, whether you are going on vacation this year or not, or you’re going to enroll in a new course, the destination lies within you. Happy traveling!


Eri Ochiai

Eri is an Expat Career Coach in Tokyo. With a background in HR at an IT startup and expat life in 🇮🇹, she's partnered with +300 expat job seekers in tech. Currently, she specializes in supporting expats towards fulfilling careers drawing on her unique insight and experiences. On a constant quest for good bread.