Why I Left Corporate at Age 25 (& Will Never Return)

Chicago skyline from Shed Aquarium

Ahh, the American Dream. Such a famous phrase, but what does it really mean?

For me, it was very specific. Go to a good college so I can get a good job and have a good life. I was never one of those “do what you love” people. This was partly because I couldn’t think of anything I “loved” that translated to a job come time for college applications. But it was also because I didn’t really mind the idea of not doing something I “loved.” I would never do anything I HATED, but I didn’t have to find something I LOVED either. I mean, 9 to 5 didn’t sound that bad – it’s just 40 hours a week out of 168 hours, so 24%. I was fine doing something I was OK with that paid well for 24% of my life, and then using that money to enjoy the remaining 76% of my life. It sounded better than searching for “something I loved,” which I wasn’t even sure existed, and having to live a life worrying about money. So, my goal in high school became: Go to a good college so I can get a good job and have a good life.

And that’s pretty much what I did. I got into a top-20 university. Once I got there, I applied and was accepted into their number-2-in-the-nation undergraduate business school. Then I added a simultaneous degree from their top-5-in-the-nation undergraduate economics department. The summer after sophomore year, I interned at a highly competitive, big-name firm and they offered me another internship for the following summer, which I accepted. I was entering my junior year of college with acceptance into two competitive degree programs at my university, a great GPA, and an internship for next summer that I knew would result in a full-time job offer. I was set! I got into a good college, I secured a good job, all that was left was to have a good life.

After having worked so hard in high school and through college, I wanted to do something enjoyable for my senior year. So I decided to study abroad in London. I learned from my two internships that 9 to 5 wasn’t really 8 hours a day, but more like 10 at best before even accounting for commute time. So I wanted to do something fun while I still could, before committing myself to living working in an office building for the next 40 – 50 years of my life. It was a decision I made very last minute and more so because British people have cool accents I was not the biggest fan of my home university anyways. It turned out to be one of the best decisions of my life.

Thames River and London Eye during sunset

I had travelled outside the US plenty before, but studying abroad was different. I loved living in London and getting to know it slowly, rather than just seeing it in a few days. I loved how so many countries were just an hour’s flight away, and how much cheaper traveling was than I expected. But most of all, I loved the feeling of freedom I had during those six months. The rigor of my London university was a joke much less than at my home university, and I already had a job lined up for after graduation. So I basically did whatever I felt like doing each day, without much stress or worry or answering to anyone or anything.

After returning home from London, rested and re-energized, I moved halfway across the country to start my new job. I was ready to work hard, move up, and have that good life, the final step in my goal of the American dream. And for a while, I really felt like I had it. Work was going well and wasn’t as monotonous as my internships had me worried it would be. My bosses were all nice, their bosses were all nice, and I made close friends with several of my co-workers. I was still getting to travel and even worked for six months in Germany within my first year.

Prague, Czech Republic city streets

While in Germany, I had the chance to travel around Europe again, and while researching for a trip to Italy, I came across something that would later change my life. I was scrolling through Pinterest and an article caught my eye. I clicked on it and skimmed the article. As I scrolled back up through the article before hitting the “x” button on the tab, I noticed a little blurb about the author. She was a twenty-something year old from California who quit her finance job to travel the world. I sent a Snapchat of that little blurb to my friends, chuckling at how much like me that sounded, and proceed to “x” out of the tab.

Quickly I began getting responses to my snap. Most were just LOLs but a few were along the lines of “How the heck can she afford to just travel? She probably has rich parents who are paying for it.” I didn’t get that vibe while skimming her article for a few minutes, but I admittedly had no idea how she was paying for her travels… So I went back through my browser history to find that page and get my friends (and myself now) some answers. I ended up stalking her travel blog and sending snaps around to my friends for probably an hour, in shock at her story. From her page, I found a few other travel blogs, and they were all pretty much the same combination of stories: Americans who left their “good jobs” to travel on some savings for a bit and ended up never returning to their old lives. Some had skills like coding or photography that they turned into freelancing work, some taught English in other countries, some made money through their blogs, and most did a combination of many things.

I wasn’t jealous – I was very content with my job, lifestyle, and future – but I was in awe of how these people all left lives of financial certainty to basically hustle for money instead, and that it had paid off. It was like a totally new option to me. Option one was get a good job and have an easier life. Option two was get a job you love and have a harder life. And now option three was, don’t even focus on a job, just make enough money somehow to fund what you want to do in that moment. Again, I didn’t want in on this life, I was perfectly content being in option one, but this was the moment I first realized there was more than just options one and two.

Fast-forward six months later, I’ve moved back stateside and am living in the true Midwest (like not Chicago Midwest, but the real-deal Midwest). Things were slower here, and work was slower too. I left early a lot and was never too busy at work, which was fine by me since my foot was healing from a nasty moped accident in the South of France and I had to lie in bed elevating it on pillows. I had cable TV in my room for the first time ever, and had never watched so much Keeping Up With the Kardashians, Bachelor in Paradise, or History Channel in my life. I watched everything on Netflix from How to Get Away with Murder to WWII documentaries, and even kept up with the 2016 presidential debacle debates.

In short: I had A LOT of free time. And with a lot of free time, comes a lot of time to think. I started asking myself questions like did I want to move back home to California and buy a house, or did I want to try to do some more stunts abroad first. I did miss that lovely, warm, not-at-all-humid-like-the-Midwest weather my friends and family, but what would my life back in California look like? Would I move back home to Silicon Valley? I tried thinking about what I wanted for ~the future~ and tried making my plans around that.

Half Moon Bay beach in Northern California Bay Area

But what did I want for the future? I already went to a good college, I currently had a good job, and so I guess I had good life. I sat there at age 23, already having accomplished everything on my three-bullet-point list, and I felt a little unfulfilled. Was that it? Now all I needed to do was move back home, get a nice house, and continue going to and from work five days a week? That used to have a much nicer ring to it back in college than it did now… Now it sounded… like hell empty and mundane and…boring. I mean, I guess somewhere in there I’m also supposed to find the ~love of my life~ and he’d make things more worthwhile or at least interesting… I guess?

My whole life, I was working towards some arbitrary ~ future~, and at age 23, I was already there. I had reached the future. So, what do I do now? I could say, OK my new goal is to become a manager. But, then when I was a manager, I would be in this same position I am now, saying, now what next? I could make another new goal to become a controller. But what about after that? CFO? And after that? I could keep tricking myself by making bigger, newer goals, but that felt silly. I didn’t want to create new goals just for the sake of keeping myself distracted and giving myself an easy answer to the question “Now what?”

I was going through the motions without a purpose, and, now that I realized it, I was suddenly no longer content with it. I didn’t mind what I was doing everyday, but not minding something isn’t really a reason to do it – at least not for me. I considered if I should change jobs – do something ~more fun~ like marketing or work for a ~cool company~ back in Silicon Valley. But that wasn’t me either. I didn’t go to work because I thought it would be fun or for the prestige. It was always just a means to provide the life I wanted.

You see, I had always intended to work to live, but slowly realized I had instead been living to work. There was no purpose in my day-to-day except work. Where I lived – depended on work. What time I left home – depended on work. Whether I could make dinner plans with friends tonight – depended on work. Whether I could take days off to fly home to family or take a vacation – depended on work. I spent all my free time daydreaming about traveling the world on a yacht how to best use my vacation days and literally had specific vacations planned out years in advance. I started reminiscing about my time studying abroad, and how much I missed life without a care in the world besides what I wanted to do that day. I missed that freedom to live for myself, and I was dissatisfied now that my eyes were open to the fact that I was living for a corporation.

I continued with the routine for some time. Then one morning, I woke up abruptly and immediately had a clear, single thought in my mind: that one girl’s travel blog. And all those other blogs too. All those people were living a life of freedom. They were slave to no routine, and though they had no certainty about their futures, that didn’t sound all too bad to me this time around. I had certainty about my own future, and I was horrified by it. My mind was spinning and spinning the whole day around how these people decided on a life they wanted first, and then decided how to afford that life second. It clicked in my head that this is what I also had to do. And once that clicked, I never could return to the old mentality.

Yes, yes, my life was OK right now, but what if it could be not just OK, but good? I’m an economics major; I don’t make decisions on absolutes, but rather on how things compare to my next best option. And once I saw that my current life was just a safe, certain, mediocrity, I couldn’t un-see it. I knew I had to try to build a life I liked more than I liked this one. I wasn’t sure how to try, or even when I would start trying. But I knew then and there that I would not be in corporate for the rest of my life.

I went to work that very next day and submitted my letter of resignation.

I stayed at my job for a couple more years, always changing my mind about how best to try and build this new life. Should I save as much as possible first? Should I move abroad? As I became better friends with more people and held more important roles in my teams, it became harder and harder to find the best answer. But eventually, a combination of over a year of 50 – 60 hour weeks, feeling like I was the only person around me who was bothered by that fact, and several mini breakdowns about how I was letting my young years and the world pass me by as I sat in a cubicle led me to finally GTFO resign. I had no plan, I just knew it had to be done now if I was ever going to try my hand at building that ~better life~.

Dubai jet skiing with buildings behind

And, honestly, several months later, I’m sailing the world on a yacht still not sure how I’m going to do that. I’m still figuring that out, and for now, I’m just freaking my family the hell out traveling around a bit while I do so. Traveling is probably the one thing that I enjoy most, and so why not use this strange break in my life to do that? While I do, I figured I would create my own travel blog to bring my story full circle. If it were not for those first travel bloggers upon which I stumbled, I might never have realized that living to work is not the only option. The travel blogger space is ridiculously oversaturated, and I do not expect to make an income off this blog. But I figure it can at least be a fun and creative outlet through which I can share some of my favorite aspects of travel, like itinerary-making, giving travel tips, and sharing photographs, as well as challenge myself through new things like writing and website design.

If you’ve made it all the way to the end of this long story, you’re probably my mother (hi mom!) thanks for sticking through! If you’d like to follow along my journey and see if I ~succeed~ or fall flat on my face and return to corporate with my tail between my legs, the best way to do that is to quit your job too so I have a travel buddy sign up for my newsletter email updates.


Are you a millennial who is also realizing the American dream of 9 – 5 might not be for you? What’s your journey in figuring that out been like? Drop a comment below or shoot me an email – I’d love to hear!


  • Amy Bishop
    August 23, 2021 at 12:45 PM

    Wish I had read this at 23!!

    • That Travelista
      August 26, 2021 at 6:22 AM

      And I wish I resigned at 23 instead of waiting two more years! All we can do is live and learn 🙂


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