Wanderlust Wendy

Career Tip: Trust the Dots Will Connect

Recently, I’ve received requests for informational calls to discuss my “career path”. I’ve happily obliged to pay it forward, since I myself had requested many of these calls while in grad school. A pattern soon emerged. Gleaming from my resumé, people apparently think I had some master plan to weave together my experiences in finance, international development, and tech. But truly, there was no master plan. Instead, it was a lot of impulsive decisions, and mostly, hard work and dumb luck

From Big Money to Peace Corps

In college, my part-time job was an intern at a boutique investment management firm in St. Louis, preparing portfolio review documents for some of the wealthiest people in town. My manager once asked me to stop wearing skirts because the big boss didn’t like the fact I didn’t wear pantyhose with them. Yeah, it was THAT kind of a place. But besides that incident, they treated me well, and let me hopped in and out of this job as I experimented different career options in college. Though I didn’t know it at the time, I never worked at another place that requires pantyhose. 

The summer before senior year was THE key summer internship. This was 2007, and banking was HOT. There were 3 coveted positions at Lehman Brothers in New York for students at SLU. I interviewed, but ultimately didn’t get it. I was gutted, and instead of taking another internship that’d likely guarantee jobs after graduation. I applied for the BUNAC visa and spent a summer in London (okay yes, I was there to hang out with my boyfriend at the time). From visa, to housing, to opening bank account, to finding a job (or jobs) – it was my first taste of what hustling means. 

The summer opened my eyes to a possibility of a truly global life. When classmates were applying for grown-up jobs, I googled, “international careers” and every other related terms imaginable. Peace Corps came up repeatedly. I was a Service Leader at SLU, and I loved using my skills to volunteer with local NGOs. That after-school activity and the taste of living abroad led me to apply for the Peace Corps. I didn’t apply to a single “real” job in my Senior year. I went with that gut feeling. 

From Peace Corps to Ivy League

Want to know how I convinced my tiger parents that me going to some random African village is a good idea? I said the experience would boost my application to a fancy school. I didn’t intend to realise that argument. Then I arrived in Cameroon, and Lehman collapsed (thank goodness I didn’t get that dot). In 2009, seems most of my friends were either unemployed or living in fear of getting sacked. I decided to apply to those fancy schools, and if I get in, I would go.

Meanwhile, I enjoyed my service immensely. I had been connected to a Chinese family in my provisional capital from the very beginning. They basically adopted me, and I was at their house for weekly meals. Delicious food aside, it was my first exposure to China. Non-stop CCTV (Chinese state television) piqued my interest at the country’s rapid growth. A seed planted for leveraging my bilingual, and cross-culture skills one day. 

From promoting the Books for Cameroon project, I was introduced to the world of social media. I blogged about my experiences, and people apparently liked it. I learned that “location independent” life is a thing, and around the world, people are finding unique ways to make a living, including running a money-making blog. What a dream, I told myself! 

From Ivy League to China

I had been in debt from the first day of college, before I turned 18. But when I received the acceptance letters from these fancy schools, I knew I was going to be in SERIOUS debt. I was already worrying about how I would pay off debt before I even stepped foot on campus. 

The debt repayment anxiety was a constant dark cloud that impacted decisions. I leveraged the skills that make money – finance. I pivoted myself toward social or impact investment. My summer internship was devoted to Big Issue Invest (for free). I spent another summer after graduation for pitiful pay at a bank in New York. When none of these experiences leveraged into a full-time job, I made the decision to move to DC, where jobs are plentiful for people like me. 

Jobs are plentiful but pay was for the most part, pitiful, for entry-level work. And on that fateful bus ride from New York to DC, my dots connected, and I decided moving to Shanghai to hustle it out would be a better choice. 

 From Hustling to the Big Apple

I moved to Shanghai with a contact to a family whom I never met before. They housed me for a month before I got my own place. Leverage connections is important; people are always surprisingly generous. I hit the ground running with my hustles, lining up English tutoring gigs within two weeks of arrival. 

My MacBook charger broke during that first month, and I went to the Apple Store to get a new one. The guy helping me chatted me up, and I mentioned I had just moved to Shanghai and job-hunting. “Oh, you should apply to Apple, we are hiring a lot!”. Back then, I was still naive and wanted to do something “social” and “impactful”, so I politely said “sure”, and ignored his tip. 

While I garnered plenty of gigs to support myself in Shanghai and was able to make loan repayment, the speed was too slow. I needed something bigger. A friend who had been sent to Shanghai temporarily from that fruit company accepted an offer to stay indefinitely. “We are hiring right now, you should consider.” This time, I gave in. 7 rounds of interviews and 6 months later, I began the corporate grind. Luckily, no pantyhose required. 

From Corporate Grind to Nomad Life 

While I was fairly good at my job, I had zero desire to climb the corporate ladder. I was there for a very explicit reason – to pay off my debt. When asked, “why do you want this job” during my many rounds of interviews, I gave the standard answer, but ended with, “and honestly, I need to pay off my student loans”. Most Americans can connect with that pain. 

I was always ideating what life would look like when I would be debt-free. As I made more progress in debt repayment, I went through years where every six month, I would look for interesting jobs in the social impact space, go through the interviews, receive an offer, but eventually turned down the job because pay was too low. Being debt-free was more important to me than a purposeful career. 

Once my networth turned positive, we had another plan to reach financial freedom. But I quickly realised what a rabbit hole that is. One can easily get into the “one more year” syndrome to acquire more wealth. When will it be enough? I unchained myself last year, and we bid farewell to Shanghai last summer for a dream I’ve had – to travel full-time.

Next Dot in Life

After 9 months of travel, we are taking a break. I recently declared the goal to turn this writing hobby into some sort of a career. Contacts began to reach out. It’s unclear what the next phase will look like, but I feel the dots connecting again. My experiences have taught me that big leaps are always worth it, and anxiety over the future is useless

I hope my story inspires you to make seemingly scary life decisions, and trust that your own dots will somehow connect. It takes lots of hard work and a little dumb luck, but no upfront master plan required.

20 thoughts on “Career Tip: Trust the Dots Will Connect”

  1. Great perspective.

    I have walked a winding road and even the unexpected stops all seem to make sense now. I think one of the keys is to make those friends along the way and throw yourself into each opportunity along the way.

    • Thanks, Robert. You are so right, making friends and seizing connections are absolutely key to an interesting journey. I try to keep this on the top of mind along every step.

  2. Hey Wendy, thanks a lot for the article. Both of our career paths have been somewhat linear, but not trouble-free and with the occasional forks in the road. But in comparing our lives to yours, I think the common thread is if you’ve got goals in mind (in our mutual case, financial freedom), then you can achieve it in various ways wherever life takes you – which is a great message for people starting out!

    Alex and Ellie

    • So true that an overall vision of an ideal life is the motivating factor. Let that be the North Star, and life will fall into place with hard work and a little luck! 🙂

  3. YAS! I love this! I can totally connect with following the dots that life throws out to you. I went from majoring in anthropology, going to law school, working in the legal career for 2 years, backpacking for 9 months, and now starting a digital nomad life. I love your story and it is definitely an inspiration.

  4. Like others – I love this post. Definitely one of my favorite blogs posts from all blogs I read. I have circled back and read it a few times now and enjoy it every time. Completely agree with the assessment.

  5. Great post! I love the idea of connecting dots (abstract creative thought is one of my favorite topics). You have connected seemingly random pursuits into a cohesive and beautifully lived life. Best wishes on the next stop! Writing is certainly up your alley.

    “I can resonate with this: “Once my net worth turned positive, we had another plan to reach financial freedom. But I quickly realized what a rabbit hole that is. One can easily get into the “one more year” syndrome to acquire more wealth. When will it be enough?”

    I wouldn’t let myself put money into some of my passions until I had “enough.” Soon, I realized I would never hit that number. So I’m off to renew my domain name and hosting now. Here’s to another year of writing and paying for it!

    I connect my writing to my music and my teaching to try to make it all fit together. It’s kind of a forced fit right now, but I’m trying to connect the dots!

    • Individuals with diverse interests are what makes the world so fascinating. I love reading your work precisely for its unique perspective!

      Our passion projects require investment and nurturing in the same fashion as other aspects of our lives. So glad you are prioritizing it to let your creativity flourish!

  6. As someone who’s been unemployed for a little bit here and is struggling to find the next dot, I really appreciated this. Thank you for reminding me there’s something coming next for me. Your story is quite cool!

  7. Such a great perspective, Wendy! So often we don’t see the value of the things we’re doing at any given moment. It’s only in hindsight that we recognize why the heck we were ever doing that weird thing that everyone was making fun of us for.

    It takes courage to be the outsider, or do things for different reasons than what everyone else expects. You’ve got courage in spades! Keep up the adventures and wonderful writing. Looking forward to so much more.


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