No choices without contexts.
How it's not the surface choices we need to be obsessed with, but rather the reasons that made them right.
“Do you wish you had started your startups earlier?”. “Would you get your MBA again?”. “Why did you do YC again?”. “Should I go work for a big company or work at a startup?”
These are the questions I often get when I do office hours or “coffee chats” with students or people in their 20s evaluating what path to take.
They’re questions that we invite as a society when we make it feel like we always have to “choose the right path”. So we become obsessed with the choice instead of the journey.
But these are all questions with no right answers. My choices aren’t and can’t be your choices. They’ve been the right choices for me because I’ve fought to make them right for me.
When people look at my choices — especially now, building venture funded tech startups — all they see is a bundle of contradictions. I have an MBA and yet I’m a start-up founder. I wasn’t technical and yet I was funded by Y Combinator twice. I chose to learn how to code even though I don’t use it day to day. I chose to work at super safe/ super traditional companies like P&G and Starbucks and BCG and yet managed not to stay there.
So I get that I’d be the target of the “would you choose that choice again” line of questioning. But what I’d say is: look beyond the choices listed on my LinkedIn and seek to understand the contexts in which they were made. That’ll tell you a lot more about the choice and if it’s the right one for you (the thing you’re really trying to figure out anyway).
Often what you’ll find is that tucked within the labels of “safe”, you’ll find the appeal of “security” — as important a reason to choose a thing as anything else, especially early on in a career.
Let me explain.
When I was 14, my family moved from Regina, Saskatchewan to Vancouver, British Columbia. My parents had run a tour and travel company for 16 years by then but it was time to make a change. That change ended up essentially starting over in a different, bigger place, with much less than we’d been used to.
We went from a 3,000 sq ft home to a 1200 sq ft 2-bdrm apartment. One brother slept in the living room, the other in my parents’ room. I started high school all too aware of our precarious finances. I worked summers in their office, helping them keep their costs down.
When it came time to apply to university a couple years later, we had improved our circumstances, but even as I dreamt of Stanford and took the SATs on a whim, I knew there was no way we could afford it.
So I never applied.
Instead, I ended up going to the very good, but very local, UBC. I chose the very best of the options that were practical and available to me.
It is shocking to me how much privilege is dripping from statements that do not acknowledge that not everyone (hell, not even a fraction) of people are able to pursue opportunities that are eminently qualified for.
Instead, I focused on what was most pressing – making choices that had the highest probability of pulling me (and my family) into different circumstances.
So when the likes of Procter and Gamble offered me the chance to make an incredible salary and move to Toronto, I didn’t see all the other things I could have done — I jumped at the chance of this sure thing.
A couple of years of hard work at that thing opened up the chance to be moved to the US and prove myself on a bigger stage. Another couple years and I had confidence (if not any belief of success) to apply to Harvard Business School.
I had zero belief that I’d actually be accepted. It’s why I also applied to U of T, Western and Yale (the only way to make sense of those choices is to understand how far from this world I grew up in and was trying to navigate essentially alone). I only applied because 8 years later, I had built up the confidence that I should at least try.
So on March 29, 2006, at 12:02pm, when I found out I was accepted, it’s not hyperbole to say my life changed.
And not for the reasons that everyone might think – yes it turned out to be an incredible experience, and network and all the things. But because it was the single biggest leap into an entirely different band of circumstance.
For 25 year old me, it was everything. Even though I had multiple managers suggest that I could stay at P&G and get an equally compelling education, I never considered not going.
Could I have had an incredible career and life experience without HBS? Undoubtedly. In fact, assuredly. My husband’s career with P&G that eventually took him (and us) around the world is evidence of that.
But you miss the point for why HBS was such a pivotal decision for a kid that scraped for every bit of opportunity.
It’s been the same for why I chose BCG after graduating – business school doesn’t come cheap. Neither does permanent citizenship. For people that have never had to give thought to quitting a job and starting something else, when you’re on visas and have debt, the idea of an incredibly well paying job while you work with THE smartest people you’ll ever work with, and they’ll sponsor your visa and greencard? Again, a no brainer.
We need to start seeing choices through the practical lenses of necessity and optionality. Which choices build your foundation, give you options and cement your position so that if you fail, you don’t tumble all the way back down the mountain you have painstakingly scraped up.
For kids like me, these pivotal choices are less about them and more about cementing a backstop for failure. So that if we try something big and bold and fail, we don’t tumble all the way down, taking our families with us, but rather slide a bit and get on to the next thing.
My story took me from P&G to HBS to BCG, adidas and Starbucks. From Canada to the US to China and back again. Were there other things I could have done had I started with a failure safety net? Assuredly.
And this wasn’t just about my 20s.
When I was eventually in a position to be able to build a tech startup, I had citizenship, we had some savings built up. But still, in tech, I was a nobody. So I got to work to find the backstop – and that, for me, was Y Combinator.
Once a YC founder, always a YC founder.
Trying to raise VC or even angel funds in 2016 as a solo, non-technical female founder, in the space of care I was more often than not dismissed by the “oh that mompreneur building a babysitter app”. I knew I had to change my context.
Being funded by YC has opened up opportunities and network and trajectory changing impact. But first and foremost, no one questions my tech CEO chops.
Again. My reasons. My context. My choices.
Instead of trying to explore other people’s choices, I would focus on other people’s contexts.
Why did they choose that path? What purpose did it serve for them? What barriers did they bust, what doors did they open?
Seeing choices through a frame of context and curiosity allows each of us to perhaps choose the same thing or not, but for our own reasons.
There is no right answer on “should I do B-school” or “should I apply to YC” or “should I learn to code”.
Just there are no choices without a context.