What I Wish I Had Known Before Quitting My Job To Follow My Dream

Leaving from Newark Airport in September of last year

Last fall, to everyone’s shock, I handed my boss my two week’s notice. I was embarking on a journey, backpacking through Asia, road tripping through the United States, before attempting to do a complete 180 career change. Leaving a well-paid, stable career at an oil company seemed insane, possibly reckless. But solo backpacking through Asia had always been a dream of mine, and although I was successful in my career, it wasn’t what I wanted to accomplish with my life. It was certainly risky, but I made the decision through months of planning and preparation. There was no problem I had not anxiously mulled over, no potential consequence that had not caused me a sleepless night. However, now that I reflect back on the last year, I realise that despite all the planning, preparation and anxiety, I really had no idea what I was getting into. Although I have no regrets, this is what I wish I had understood about my decision.

There’s no right time. They say this about life in general. No right time to get married, have children, quit your job, follow your dreams. There is never going to be a right time to do something scary with potential negative consequences. For me there were constant questions: Should I save just a little bit more money? Should I wait for my next promotion? Should I wait for grad school interviews to be over? What if I didn’t even get an interview — then would I have wasted my precious time for no reason? Would my partner and I make it through such a long time apart? Something will always come up to throw a wrench in your plans. Change is inevitable. It can happen even when you aren’t doing something risky. You could get sick, you could lose your job. Then you’re forced to adapt, and you do, you persevere. There will never be a right time, there will be problems and hiccups and you will deal with it and be stronger for it. During my yoga teacher training in Manila, I had to fly to Hong Kong for the day to interview for graduate school. I had to make up that day in yoga training, and the whole thing cost me quite a lot of money. But I made it work, because that’s what we do.

Travelling just emphasizes that life isn’t like Instagram. All of us know that life is not like social media, even if every so often we are taken under its spell. You can take a look at my Instagram for the last 9 months and it’s unbelievable. But behind every photo of me sitting somewhere beautiful, there are days spent in crowded buses, or even days spent sitting in the hostel on my computer (the true secret life of a backpacker). I spent three days on Gili Air off the coast of Lombok in Indonesia, and it was peaceful and serene. Every morning, I would go to the beach and practice yoga and meditate, the photos of this are beautiful and amazing. And it was beautiful and amazing. But what isn’t pictured is that for those three days, I did not talk to one person. I was lonely and bored. At the same time, I was envying the Instagrams of my friends back in America! Who were going to brunch and hanging out with each other.

Continuing with this theme: There are a lot of unglamorous parts. Sharing a room with 12 people for 5 months, shockingly, gets old. There were nights we were all chatting and giggling in our bunks like we were in summer camp, but there were also times I was kept up all night by roommates coming home late, keeping all the lights on and rustling around noisily, when all I wanted to do was get a good night’s sleep. Then there’s all your typical backpacking grungy, grimy stuff: Lengths of time without a shower, no waxes, food poisoning, cramped overnight buses, the list goes on. Developing countries are not all yoga on the beach all the time.

You will feel very alone. Travelling alone is incredibly lonely. As an introvert, it’s true that I spent a lot of my time happily wandering the streets by myself. I met some wonderful people and had some good times travelling with them, but when I look back romantically reminiscing, it’s always moments alone somewhere incredible, that float through my mind. You meet people for very short spaces of time, apart from completing my yoga teacher training, the longest I was in one destination was 4 days. Even if you make new friends, you aren’t going to be opening up to them and talking to them in the way you crave, or at least I didn’t.

People said to me that I would be fine travelling alone because I’m OK spending time by myself. But what I realised is that- it’s the people who aren’t OK spending time by themselves who are probably the happiest solo travellers. They find friends quickly and spend a lot of time with them. I never travelled with other people over long distances. I didn’t want to, but it meant that I spent a lot of time alone. Because of this, I really wanted to lean on the friends I did have, back home. But I found it was hard to keep up with my friends in America. I felt so far away from them, geographically of course, but also mentally. I didn’t feel like I could talk about the difficulties of my life because it seemed so awesome and unbelievable to everyone else. Because of this, I leaned heavily on my boyfriend. I felt that he was the only one who I could express my fears, anxieties, and concerns to; I offloaded the entire weight of my emotional burden on him. It made things hard for us at times. I blamed myself because I understood what I was doing, but I needed him and I am incredibly grateful that he stuck through it.

Things don’t turn out like you imagined. When you first start planning your journey, you have all these grandiose ideas about what you can accomplish and where you’ll go, all the amazing experiences you will have and all the wonderful things you will learn. I wanted to go travel for longer, 6 months or a year! I wanted to live and work in one location and really get to know a town, country and culture. I wanted to go to every country in Asia. But all of this wasn’t practical. I had my boyfriend back in the US, I had financial limitations, and things I wanted to see and do back home. So I couldn’t go for longer than the time I went, and that meant to go to all the destinations I wanted, I couldn’t live and work somewhere for two months. Money and time meant that it wasn’t worth it for me to fly to South Korea for just a few days. Although things didn’t work out like I had first imagined, they worked out exactly as they should have. By the end of five months, I was ready to come home and be reunited with my boyfriend. I never lived and worked somewhere, but I spent a month in Manila training to become a yoga teacher. I met the most amazing people and got to understand more about Manila and the Philippines as a whole. One day, I’ll go back to the places that I didn’t get to explore as much. I think this is just the nature of life. We don’t end up where we thought we would, but we end up exactly where we should.

That’s my gist about travelling, but what about when you return? How do you integrate back into society? No job. Unexplainable gap in your resume. These are things I stressed over a lot. When you’re as lucky and privileged as I am, there’s a lot that you take for granted, a lot you don’t ever have to worry about. There are some shocks to the system when you leave your cushy six figure job.

Being unemployed in America isn’t easy. It’s obvious I know. But no steady stream of income is extremely stressful. Suddenly every expense makes you nervous, and you feel incredibly vulnerable to sudden emergencies. Most importantly, you don’t have health insurance. Intellectually we all know that not having health insurance is bad. But until you no longer have employer subsidized health insurance, you don’t fully understand. With Obamacare subsidies, insurance plans are affordable, but going to the doctor isn’t. You find yourself questioning your own health concerns and wondering if it’s worth checking them out. It could cost thousands of dollars, and with a $6,000 deductible you may have to pay it all. It’s not fun when you’re forced to make your own health decisions because you don’t want to be slapped with a huge bill you can’t pay.

Being unemployed isn’t easy, and it turns out getting a job isn’t easy either. Especially as a career changer. Over the last few years, I’ve become increasingly passionate about a number of social justice issues, and I wanted to change my career and focus on fighting for social justice. I still haven’t figured it out, but I have been searching for internships at nonprofits and political advocacy organizations. Despite my educational and professional pedigree, no one will hire me, even for free! I have no experience in the nonprofit or political world, and people are confused about where this career change is coming from. Apparently you can’t work as an engineer and care about racial justice or women’s equality. I’ll continue to work at it, but changing careers isn’t easy, and it doesn’t help to be unemployed with a big gap in your resume while you’re trying to do it.

So despite the planning and preparation I did in the months leading up to my big life leap, I discovered there’s no amount of planning or prep you can do to avoid some of these difficulties. However, I do have some recommendations for everyone out there who wants to do something similar.

Be financially prepared. I don’t just mean save up some money for travelling or time off. You need to do that of course. But you also need to save up for the time where you are trying to reintegrate into society. Plan for a period of time that you won’t have a job, that you will be living in a major US city (i.e. paying to live there) unemployed, searching for a job. The amount you need to save depends on how little you are willing to live on.

This is pretty boring, grown up advice but get any healthcare concerns resolved now. If you plan to quit your job, definitely go to your doctor now. Follow up on anything that has been concerning you, and perhaps get your teeth cleaned.

Be prepared to live on very little, and make very little. Obviously with no income you have to live cheap. It may not be something you are used to, especially if you are used to a high paying salary. You’d be surprised how many coffees or juices you buy, how many exercise classes you go to, or how many random useless material belongings you purchase. You will likely have to give that up. I’ve cut my eating out purchases to basically nothing and avoid new possessions (thank god because our apartment is tiny). If you are looking to career change like me, you also have to be prepared to make very little income. A couple months ago, I gave up on trying to find a paid internship because very few exist in the nonprofit world. Now I am just desperately searching for unpaid work. This can be quite disheartening and insulting. Especially in our culture, one that defines your worth as a human being, by your annual income.

Finally, there are a few things to contemplate in advance: Understand what your own limitations are- what are you willing to sacrifice in luxuries, spending and time? How will you act, and what will you be willing to do when things don’t work out like you planned? If you couldn’t imagine life without your soul cycle membership, then I wouldn’t risk it. Are you willing to take a job as a barista if you need to make money? Think about what employable skills or interests you have that could get you a side hustle. I am working at a local yoga studio in exchange for free classes, and I’m making a steady income stream from private tutoring. If you couldn’t imagine hustling with the masses then you might not cut it. If you are unhappy with your current work life balance, you may find you have to work harder, for less money and less time in your new life. Which brings me to…

If you’re considering quitting your job to follow your dream, think about why? What makes you unhappy about your current situation or job? Are you actually unhappy? Or do you just want an adventure? Or a break? If you just want a short lived adventure where you travel the world and slip comfortably back into your life. This is probably something you could talk to your boss about. Take a leave of absence! Very few employers will guarantee your position when you return, but most will take you back. I know more people that are considering quitting their job than simply asking if a leave of absence is possible. Although it doesn’t seem like something you could do, it may be a far better option than quitting. You could have the wild and free adventure for 6 months, with few negative consequences. It is feasible! Putting your career on hold for half of year won’t set you back decades.

If you’re not happy with your job- why? Is it work/life balance? Then work less, or get a job in the same field that’s less committing and competitive. As I mentioned above- your new life isn’t necessarily giving you more time to do the things you love. Even if you think your new job will be doing what you love. All jobs come with downsides. Perhaps if your passion becomes your job, you will start to hate your passion. Perhaps your passion is only such, because it currently IS your leisure time, it’s your escape. Think about that.

If your career path isn’t fulfilling, consider exploring career options while in your current job. You could even try and negotiate some time off between jobs. You will have a lot more financial security, time and flexibility to really explore feasible options. You should also consider broadening your interests and experiences while you work. Is there something you can do after work or on weekends that will be useful in a career pivot? Are there some classes you can take, or volunteering opportunities that would give you this experience? You may discover something about that dream career that doesn’t actually suit your needs. In the end- do you want to sacrifice luxury, comfort, and financial security for an unknown dream?

I know I sound very negative right now, but it’s because I want people to understand the realities of a decision like this. In the end, even though I didn’t know all of this last year, and I didn’t fully follow the advice I shared, I wouldn’t have done it any other way. I fully endorse anyone’s decision to upend their life and pursue a dream, whether that’s travelling the world, living out of a truck and rock climbing every day, or changing your career. You may just learn a few things. You may discover the only material possessions you need fit into a 45L backpack, or that living in a truck with your boyfriend is quite cold and not romantic. But I guarantee you will gain unparalleled life experience, and every day will offer a new opportunity to challenge your views on other people, society and yourself.