Reflecting on my First Seven Jobs

During college and in high school, I was almost always employed part-time. I rarely worked during the summer, and I liked the challenge of juggling coursework with employment. So it’s no surprise that I was only 19 years old by the time I had worked my #FirstSevenJobs.

Here they are:

1. English as a second language tutor. 📝 Sometimes, I forget that I started my first venture in middle school. On an external hard drive of archived data, I still have the worksheets I made for my students.
2. Babysitter. 😊 What teenage girl didn’t babysit? I never babysat actual babies, just children younger than me. I’ve always loved children and I also volunteered in childcare centers and preschools.
3. Punahou School math tutor. 🔢 Yup, I’m a true nerd. For as long as I can remember, math has been easy for me. My parents signed me up for Kumon in elementary school and I started learning calculus in middle school. I was that annoying kid turning in math tests 15 minutes into the 50-minute period. Being in the honors math track in high school, I had the privilege of spending my free periods sitting in the math tutoring center waiting to help the students enrolled in less advanced math classes.
4. Punahou School Physics Honors teaching assistant. ⚛ I graded assignments and tutored students. I’m sure I had other responsibilities, but I don’t remember what they were anymore.
5. SAT-prep tutor. 📓 Yes, I’m proud to admit that I’m a nerd. Back when the SAT had only two sections and a combined score of 1600, I got a near perfect score of 790 on the verbal section and 800 on the math section (see #3 on being a math nerd). Anyway, doing well on standardized tests is a sure-fire way to get tutoring clients. This was my second freelancing gig, not including babysitting.
6. Retail sales associate at Quiksilver, Newbury Street, Boston. ☀️🏄🏽  I’m from Honolulu. Before attending college in Cambridge, I had never before been to the East Coast. And I had not seen snow fall. So on a cold winter day, when I walked down to Newbury Street from the Boston brownstone I lived in, I was over the moon to find a newly opened surf shop that reminded me of warm days on the beach. In a way, even in this job I was freelancing. I saw the store struggling to penetrate the market, so I took it upon myself to start marketing the store to other homesick students from Hawaii. It would have been a lot easier if Facebook had existed then.
7. MIT Introductory Biology tutor. I don’t recall how I got this job. 🔬 It must have had something to do with having declared a double-major in Biology and Chemical Engineering. The work was easy, helping students with homework assignments and grading homework assignments (or, problem sets, as we they were called at MIT).

And there it is.

Number 8 was being the MIT Undergraduate Association Office Manager, and number 9 was supporting women’s recruitment at MIT Admissions. And my first “real” job at the MIT Technology Licensing Office, was number 10.

This trip down memory lane has reminded me that I once wanted to be a teacher. I loved children and thought I wanted to be a preschool teacher. Given my math and science aptitude, I later thought it was my duty to become a high school teacher focusing on Advanced Placement courses. And I’ve long wanted to participate in yoga teacher training to get certified to teach yoga, which I’ve been practicing since 1996. But the memory of a Punahou teacher telling my parents that I was too smart to be a teacher is what has always held me back from pursuing that career path.

I’m reminded now that I’ve always been passionate about education, lifelong learning, and helping others. It’s why I volunteered in a childcare center for toddlers from low-income families, and volunteered in a homeless shelter for women and children, and was once a volunteer tutor for immigrants studying to pass the US Citizenship Exam. And it’s the reason I have been an Alumni Mentor for MIT’s 12.000 Solving Complex Problems for the last decade.

And I see that I’ve always been a freelancer and entrepreneur, creating my own career, searching for work-life fit, seeking new challenges and skills, and looking towards the future of work. So it’s no wonder that my path has led me to entrepreneurship and small business consulting. My specialty is creating and improving processes to maximize efficiency, reduce costs, and increase customers and revenue. But my job is really teaching and helping small business owners so they can grow their business. ​

What were your first seven jobs, and how have they shaped your career? Let me know in the comments or contact me personally!