My Journey So Far

As is the case for many, the start of my career has been a bit of a maze. I took some time to connect with what I care about and what I might be good at doing. I think about work along three dimensions: (a) the work itself; what it is that we are creating and what role or function I play in that effort, (b) the people; whether I enjoy spending time with my colleagues and how they help me grow, and (c) the lifestyle; do I have the time and energy to invest in out-of-office interests and relationships?

I completed my bachelors in mechanical engineering at Northeastern University, where the co-op program offers a great opportunity to explore different paths. I did co-ops in aerospace manufacturing, medical device design, and nanotechnology R&D. This seemed like a broad swath of experimentation at the time, but narrow in hindsight. Discouraged by the pace of hardware development and struggling with big company processes, I broadened my search.

In my final semester at Northeastern, I came upon two opportunities that would shape my next several years. Harvard Business School accepted my application to pursue an MBA, through their 2+2 early admission program. This program required that I defer my enrollment for two years to gain some work experience, with the option to defer up to four years. For better or worse (a privileged, mixed perspective many 2+2 admits have), having HBS on the horizon gave me a license to continue to experiment for a few years.

At the same time, I was offered an associate position with the winter Techstars Boston class. The three-month program allowed me to meet several early-stage founders, which eventually led to me joining the team at Change Collective. I was the third employee and hired to be a generalist on the team. In my first six months, I took on projects within operations, sales, marketing, and product — it was a perfect opportunity to explore new avenues. We were building a personal growth education platform (i.e. courses in diet, fitness, mindfulness, etc., bundled in an mobile app). Inline with our mission, we built a company culture that encouraged each other to pursue personal experiments that would help us grow as individuals. I ran my first marathon, tried a full-day meditation retreat, and — after a long hiatus through engineering school — started creating art again.

I spent the better part of two years at Change Collective. In that time, I settled into a product management position (though my day-to-day activities still commonly spanned finance, marketing, and operations) and helped the company work through a few significant pivots as we brought our platform to market and struggled to find revenue. One of these pivots led to a re-brand to Ten Percent Happier; a rebrand that narrowed the scope of the platform to meditation courses, but also marked the start of my departure.

Just a few months after our rebrand, I left the company to start one of my own. In a weekend, I prototyped a conversational service modeled after the IRL “adventurous friend” that some of us are fortunate to have. The product was nothing more than a phone number that you could text, with the promise of helping you expand your comfort zone and discover more of what your city has to offer. I built a rough prototype that found some promising traction and was off on the journey to shape that initial ore-strike into true product/market fit. Six months into that process though, I realized that any meaningful company takes years to build and this wasn’t a company that I wanted to spend years of my life building.

My two product experiences at Change Collective and Ferris (the name I gave to the adventurous friend) had naturally given me some exposure to UX design. One of my mentors had recently joined a growth-stage startup called Catalant and asked that I join his team as a designer. I only spent a year in that role, but in that year I learned a lot about working with a larger product/engineering team and the role of leadership in building a cohesive and happy team.

I was entering my fourth and final year of deferring my enrollment to HBS when I left Catalant. I took another entrepreneurial risk and ramped up my contracting side-hustle into a full-time gig. I offered a mix of UX design, front-end development, and product strategy services to early-stage companies. I enjoyed meeting new companies in the area, so sales never felt like sales. A few clients (thank you again to ezCater and Own Up) were open to me working remotely, which led to a four month backpacking trip through Southeast Asia.

I’m writing this over the summer between my first and second years at HBS (Summer ’19) and still reflecting on my first year of business school. I owe it to myself to write a longer reflection of that year, but I’ll take a quick stab here. HBS has nudged me to once again open up the aperture of experimentation in my journey. The program exposed me to a diverse set of perspectives, experiences, and ways of working. The first year of the MBA was a wild experience and one that stripped down my confidence, connected me to my authentic self, and rebuilt my confidence in the face of total uncertainty (read: I still don’t know what I’m doing with my life).

I grew up on a small New York apple and berry farm that has been in my family since 1942. Many of my childhood summer days were spent sitting on a tractor until I blew dirt from my nose (thinking about this helps me complain less about sitting in front of a computer all day). When I left the farm to start at Northeastern, I thought I would never return to agriculture. It’s a complicated business and my family had been through enough hardship to encourage me to do anything else.

Sitting in the epicenter of elitist capitalism (HBS) has somehow pointed me back towards agriculture. It’s imperative that we (all of us on this little tiny rock we call Earth) build a future that works in partnership with our environment. Agriculture and the food supply chain are some of the biggest pieces of this puzzle. I may take over the family farm someday, but HBS brainwashes us to believe we are “leaders who make a difference in the world” and, for the time being, I have ambitions to make a broader impact (setting aside my belief in the power of local communities).

In the past, I thought about my three dimensions of work as a necessary tradeoff. I can’t have all three, so I’ll pursue whatever matches my current priority. A few years of experience has opened doors and has spoiled me into believing that finding all three is possible. I’m committed to building a more sustainable food system and I want to work with people who are smarter, more creative, and more empathetic than I am and who will push me to be better. But I also have a chocolate lab who needs to chase a stick and I enjoy hiking, traveling, running, and turning off my phone on Sundays.

I’m drawn to entrepreneurship to make this idyllic dream a reality, but I’m open to hearing about new opportunities. If you’d like to have a conversation, send me an email at robinsongreig[at]

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Robinson Greig

Independent Product Consultant in Cambridge, MA

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