I Didn’t Become an Investment Banker and Apparently Entrepreneurship Kills my Joy: Reflections at 30

According to the life plan I carefully crafted as a keen elementary schooler, I am way behind. Here's how it looked:

  • Age 25: get married

  • Age 27: child #1

  • Age 30 (my age today): child #2

  • Age 33: child #3

(Perfectly timed three years apart to allow “sufficient bonding time” with each child before their prized position as baby was stolen out from under their tiny toes with absolutely no say in the matter.)

And all this was going to take place while I was working as an investment banker—living in a fabulous penthouse in Manhattan.


I spent hours pouring fantasies about this posh life into my Trolls journal, including specifics that are now hilarious because they reflect values very different from those I hold today. I was so busy and so wealthy I didn’t have time or desire to bake my child’s birthday cake. Instead I bought her customized extravagant cake from the finest bakery in the city.

Well here I am, 30 whole years old. Unmarried, childless, haven’t had a steady income in four months, and living in Guanajuato, Mexico, with my boyfriend Chad and his (now “our”) dog Wayne in an old apartment outfitted with plastic utensils.

And I love it.

I don’t know what I imagined my 30th birthday would be like. Likely surrounded by heaps of friends and family at some big bash, feeling beautiful in a new dress. Instead, last week, it was Chad, Wayne, and me. They sweetly gifted me flowers, green juice, and cookies (#balance) in bed. I did put on mascara, but wore the same black down vest I've worn every day for a month since arriving at this colder region of Mexico. After a delicious brunch of chilaquiles or “breakfast nachos” as I call them (tortilla chips topped with salsa verde, easy-over eggs, and cheese), Chad told me to pack a bag for a night away. Wheee!

Soon after we hopped in a taxi, wound our way through an elaborate underground network of tunnels, and ended up outside town at a gorgeous Mexican villa turned B&B. We were the only guests. We spent a perfectly peaceful afternoon on the rooftop trying some of our new skills learned in a recent travel drawing class. We drank wine. We were quiet. We admired the stunning wash of colourful Guanajuato buildings in the distance and cotton candy clouds appearing in the sky as the day wore on.

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At some point Chad lifted his head from his paper and declared, “Life is good”—almost like he had forgotten I was there. 

I had to agree.

With no real restaurants in town we had planned on making quesadillas for dinner. However, we quickly discovered that because of the local gas shortage the stove didn’t work. I adapted and used the toaster oven. Chad used a waffle maker. We laughed about how unglamorous it all was. And how perfect it all was.

We finished the day watching the far-off sparkling lights of the city as we sipped homemade sangria in our private hot tub. What a wonderful birthday. Although home couldn’t have felt farther away, thanks to technology I received endless love from people all around the world. I was truly content.

My life hasn’t gone according to the neat plan I typed and stashed in the time capsule I made at age 11 to commemorate the year 2000. Therefore, it should not be a surprise that this trip is no exception …

I set out on this adventure in October 2018 with the romantic idea that I’d be earning income from my growing intuitive healing business. My commitment to this vision before we departed had been strong. And genuine. But, it wasn't long before I had to question whether I was as cut out for online self-employment as I believed was necessary for a happy existence. Yes, I wanted the freedom it promised, but the self-promotion, constant pressure to be posting inspirational content on social media, working solo, and effectively hustling as an entrepreneur…not so much. I constantly felt resistant and stuck.


Right now (in the eyes of millennials at least), working remotely is the holy grail of employment. FREEDOM. It’s everything to us. Self-employment, on top of that, is regarded as some noble ideal to work toward. Every day on Facebook I’m bombarded by ads for online courses promising they’ll allow you to “ditch your 9-5 once and for all,” live in Bali, and work in your bikini on the beach. It sounds sexy, it’s trendy, and as much as my ego was stoked because I was actually living this enviable “dream,” I’ve realized that such a dream may not be for everyone.

The reality was that I had gone from a highly structured, team-based work environment, and even LIVED at my work place (a boarding school) where many week nights and weekends were often scheduled to working alone, remotely, and self-employed in a foreign country. I could not have picked a more drastic jump. No wonder I felt lost. The pressure to build a business by myself was casting a shadow of stress over the many beautiful things around me in Sayulita and was preventing me from truly enjoying myself on this once-in-a-lifetime adventure. I had never felt so vulnerable or afraid because of financial insecurity. I could also envision what the next six months would look like if I continued down the road I was on, and I did not like what I saw.

So around Christmas I shared with Chad that leaving my job and the security it offered had thrown me in ways I hadn’t anticipated. I told him that I didn’t want to be building my own business, not out of laziness, but rather from a strong feeling (almost on a cellular level) that it wasn’t right at this time. He listened to my feelings intently and lovingly, and my initial nerves quickly faded away. I told him that I’d been feeling like I needed to prove myself to him, and this was the last thing that I needed to be worrying about during this upheaval. Finally, I asked for compassion and unconditional love while I considered my next steps.

He asked innocently, “But what do I tell people? That I’m working and you’re…?”

“I couldn’t care less what you tell strangers we’re never going to see again. Tell them I’m figuring out my life.”

Our conversation ended up being one of our most constructive and honest to date, and so despite the uncertainty that still lay ahead of me, I walked away feeling much less fearful about life and significantly closer to him.

Shortly after this conversation and as the year was came to an end, it occurred to me that the solution I was looking for was a happy medium: online work but not self-employment. I think that frequent conversations about “finding your soul’s purpose” and “discovering your gifts to share with the world,” creates a set-up for people to dismiss work that does not feel like their life's mission. People repeatedly hear that they need to be doing something totally unique, something of great meaning to the world, and following their soul’s calling. I’ve definitely fallen for this, feeling the pressure.

But sometimes we just need to make money! Sometimes passion must be saved for free time; sometimes work just needs to be work.

That's the point I arrived at recently—when I discovered that what I needed more than anything else was finding the best route to ending my financial stress. So that I could fully enjoy the rest of this experience.

I’d been hearing more and more about people teaching English online as a second language, and although it was unrelated to my original vision of an alternative health career—after seeing a job posting for a company called VIPKID that didn’t require a formal TESL certificate—a spark went off inside, which nudged me to look into it.

With this company you set your own hours, can work in your pjs from anywhere in the world, don’t have to develop your own lesson plans, get paid decently to help kids learn, and have fun! It sounded perfect. So for 10 days I threw myself into learning all that I could about the company, teaching techniques, and how to pass the required class tests. I built a micro classroom in the corner of our apartment and became Teacher Sarah. I spent enjoyable hours browsing local markets for magnetic alphabet letters, puppets, toy animals, and colourful props.

And I practiced, practiced, practiced like crazy.

In order to pass two test classes, I "taught" an experienced VIPKID instructor who acted like a young Chinese student. While I was warned that some people could take up to five attempts to pass successfully, two days before my 30th birthday I passed both tests on the first go, which gave me the confidence to believe that this was the right new direction for me at this time. I will still get have the freedom of location that I’ve craved for so long, but without the 24/7 pressure of entrepreneurship. The weight that has been lifted off of me has been transformative.

Like almost everything in my life, this trip will wind up looking very different from what I thought it would or should. But maybe that’s actually for the better.

Sometimes we must release a vision we've been holding to make mental health and happiness a priority.

For me everything shifted the moment I decided that plugging away disheartened for six more months to prove I was smart or capable or had great work ethic was not worth sacrificing my well-being or the incredible experience of this trip. I believe that when we trust our intuition and honestly admit, “This is not working for me," the Universe can then point us in a direction that will be for our highest good and greatest happiness.  

So after three months on the road I’ve decided the following:

  • It’s OK to change your mind. It’s actually courageous. Even if you’ve invested serious time, energy, and money on your education, if you’ve built a nice website, or if you’ve told everyone about your plan. If you’re being true to who you are and how you feel today, consider that you’re doing great.

  • It’s OK to realize that "trendy" is not necessarily right for you.

  • It’s OK to put passion aside in order to earn money that will give you piece of mind.

  • It’s NOT OK to compare your path to anyone else’s and consequently think you're “falling behind."

  • It’s NOT OK to force yourself to do work that feels out of alignment just in order to earn the approval of others.


So I’m 30 and have not have checked off many of the classic life milestone boxes that many of my peers have. I may not for a while. I am also not a wealthy investment banker. But where my savings account lacks, my life is abundant with love and rich in experiences.

I’m proud of myself for following my intuition; for caring less each day about what people think of me; and for taking risks to walk the path less travelled. I also feel deeply grateful to have the opportunity to re-create myself and change my path if I need to. Many people never experience this sort of freedom.

La vida es buena.

With light and love, Sarah xo

PS. If anyone is curious about learning about the VIPKID hiring process, send me an email at sarah.h.nattrass@gmail.com. I have some great resources and very helpful tips that I’d be happy to share with you!