Wanderlust Wendy

Should I Have Stayed in the Corporate Grind?

January 1, 2020. This date is fast approaching. In fact, only 55 days remain according to my countdown app. Oh, how I used to obsessively check this countdown clock to our original “Freedom Day.” 

If all went according to plan, on this date, our investments, applying the 4% withdrawal rate, would have yielded enough income to cover our basic living expenses. Not all, but enough to not need full-time work. We were on this path for financial independence, and then we jumped off the train. 

I thought I could do it – working in an uninspiring job, living an extremely comfortable life, surrounded by great friends. My life was so easy. I practiced gratitude. How fortunate was I to complain about a lack of meaning. Just get on autopilot and enjoy the heck out of it. So many would do so much to be in my shoes. 

Comfort is Not Progress

Yet it is precisely because I have such good fortune that I could not waste it on living an uninspiring life. I had told myself that moving to China was to pay off debt. I had done that and stayed on a few more years to build a nest egg. The one-more-year syndrome was too easy to repeat. I desperately needed to be challenged, to feel uncomfortable. 

So, we jumped. It’s now been 20 months since I left the corporate grind, and 16 months since we left China. Last week, I returned to Shanghai for a visit. I was hit with a hurricane of nostalgia. My life was so comfortable. Settling into Saigon hasn’t been the easiest. Faced with this wave of comfort, I found myself thinking, “Should I have stayed? After all, the corporate grind wasn’t that bad, and this life was so cushy.”

Revisit the Corporate Grind

That is, until I revisited ground zero – my office. I am friends with my colleagues. In fact, I stayed with one during my visit. I wanted to see my team and see how everyone is doing. These delightful colleagues were the only reason I stayed in the grind for as long as I did. In some ways, nothing has changed. Within minutes, I was being brought to full-speed on the latest office drama. And boy were there many! 

Walking the halls of this office, and even sitting in the conference room (the team went the extra mile and video-conferenced in a colleague in Singapore), gave me flashbacks. The frustration I felt sitting in long and often pointless meetings. The never-ending emails. The corporate politics. Office drama is a lot more entertaining when I’m on the outside. 

I am eternally grateful for all the opportunities that this office had provided, most of all, the reliable paychecks that granted me financial freedom. But, that chapter has fully closed. Revisiting it served as a closure that I didn’t know I needed. Colleagues dripping with envy at my current lifestyle didn’t hurt, either. 

But It Was Only Two More Years! Worth It to Leave? 

To answer this question would depend on what I did with those two years, and how I value these experiences. In the time since I left, I had done many of the things I daydreamed about while sitting in boring meetings. I had learned to code, traveled full-time, lived on a farm, moved to yet another country. I’m also learning another language, and finally taking this blog seriously and calling myself a writer. 

I’ve learned to prioritize sleep, to live slowly, and to devote quality time to friends and family. The most fortunate of it all is we’ve been able to do it all without money worries. Even now, in Saigon, because we’ve chosen a location with a relatively low cost of living, we survive plenty fine on one income. Instead, I find myself wanting a job because I was struggling to own the writer title. What a privilege to want a job not for money, but for vanity. [Insert eye-roll emoji.]

Remember the old Mastercard commercial that would end with “priceless” to describe an experience? That’s how these past two years feel. It’s impossible to attach a monetary value to personal growth. But for every year that I would’ve stayed in the corporate grind, it would become increasingly difficult to leave. The one-more-year syndrome is so easy to repeat, because monetary reward increases nearly exponentially. I was afraid to get trapped. I wanted time before potentially having kids to try out a different life, and I am glad I did. 

Next Phase of Lifestyle Design

So, are we back on the train toward never working again? Not exactly. Primarily because we likely will always do some sort of work. Our year-long travel taught us that we don’t actually enjoy living nomadically full-time. This learning makes me extremely glad to not have stayed 24 extra months in a miserable job, only to discover this later. 

We also learned the importance of having a meaningful project. After a while, travel became another routine, and we were yearning for another challenge. For now, this challenge is making Saigon our home as Shanghai had been. Learning the language and attempt to understand this intricate culture. Meanwhile, we are back to fueling the freedom fund, and also back to the drawing board to ideate the next phase of our ideal life. 

Take Some Calculated Risk and Get Uncomfortable.

So no, I would not take back these past two years of experiences for anything, not even for never needing to work another day. That’s not the point. The point is freedom. On this journey, I had learned what financial freedom means to me. It’s to be free from misery, to be challenged in a meaningful way, and to grow as an individual. 

To be challenged requires being outside of a comfort zone. For us, that meant literally leaving and be surrounded by newness. But one can seek discomfort in a myriad of ways, without uprooting life. It takes understanding our unique risk tolerance, and then push it to the edge of our limits. Calculated risks yield challenges that are uncomfortable, but not miserable. 

For us, figuring out how to fund our ever-evolving lifestyle fits the bill. No one knows what the future holds, but to live every day without regret is blissful. A meaningful life isn’t easy, and jumping off the Freedom Train two years early provides just enough discomfort to grow and, hopefully, thrive. 

10 thoughts on “Should I Have Stayed in the Corporate Grind?”

  1. Great read thanks
    I am in the comfort zone now but will keep working until FI
    Because I don’t really have something thing that my job is keep me from doing.
    I will then be free to explore ideas and if they don’t work out I will still be financially ok.
    If my job sucked or a I had a passion for something that could earn some money I would leave but until then 3.5 yrs more for me

  2. This is a great post and your conclusion is spot on Wendy!

    I would add that happiness is about living free of suffering and I know lot of people who suffer from the 9-5 life (to various degree of pain of course). Such ppl would be much happier (& safer) if they would decide to free themselves for it. By taking the time to listen to themselves to design the life they want, not only they will be in a better position to enjoy the limited time they have in this planet, they would also free themselves from living a life that other people want them to have.

    Happy to see that you’ve made this decisions while back and that you are now truly enjoying and cherishing every single day!

    • Being intentional really is the key. Certainly, there is nothing wrong with a 9-5 life if that life has been chosen intentionally! Challenges are necessary elements for growth, but not suffering.

  3. Your post is exactly what I needed right now. I resigned from the corporate life 11 months ago to pursue my passion of traveling and writing. As you know, there are highs but there are also some lows. Not a fan of ambiguity, this new lifestyle has challenged me to grow and be okay with the unknown (not there yet as it’s a struggle every day). But I have no regrets leaving and am proud of what I’ve accomplished so far.

    • Glad to hear from someone who is on a similar path! Being comfortable with being uncomfortable is certainly one of the most challenging aspects of this lifestyle.

  4. This is such an interesting read and I love that you took the plunge and went for the life you wanted. I feel a change coming to mine, not necessarily like yours, but I feel like a big step and a just-do-it kind of thinking may be just what I need! Thanks for sharing!

  5. Love this post!
    I started reading about FIRE a few years ago, right around the time the small, fun company I worked at was bought by a much bigger, much less fun one. I set a date in my head (based on some golden handcuffs) to my FIRE (light) target. I managed to stay the course, but those last 12 months were pretty crappy. Even so, I considered staying longer just to shore up my bank account. I’m soo glad I didn’t.
    Since then, I’ve travelled for 4 months, spent a couple of months with family, some more travel, and now I’m back working part time for a tiny startup and loving life. Maybe I did need the travel too, but if I had known how much better I’d enjoy working again for a different type of company, I’d never have stayed for the payout.
    I think everyone on a FIRE path should explore slower FIRE. There really is something special about part time work, that’s not steeped in bureaucracy and office politics, that gives most of the benefits of ER and adds in some more.

  6. “I thought I could do it – working in an uninspiring job, living an extremely comfortable life, surrounded by great friends.” THIS. This quote is exactly how many people get locked into jobs they don’t actually like for their entire lives. Kudos for taking this very brave leap! I’ve also written about some of the fallacies and illusions in the corporate world based on my experience:


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