📈 maximize slope

Or: when faced with big fork-in-road life decisions, how to decide which to take

“How do I choose?”

This is probably the number one question I get asked - whether it's undergrads considering first jobs or MBAs looking for internships; people weighing how to leave a job and others figuring out how to take a big leap on a new endeavour. All looking for data, a sign, tidy wayfinders pointing them to the “right” decision.

Well, after 20 years of navigating increasingly complex decisions with bigger and bigger stakes, I’ve realized two things.

1. That data that makes the uncertainty bearable doesn’t exist. Not in the way that would actually lessen the uncertainty.

2. In the face of needing to embrace that uncertainty, I have one guide:

Maximize slope.

Meaning: which option is going to give me the most learning and growth?

I think it's really hard to predict if you're going to like something or if you'll be successful at it. But it's usually pretty clear which option you'll end up learning the most in.

When plotting options on a graph like this, it’s easy to see how the more known option (the dotted blue line) could feel better because today, I know a lot more about it or it sticks to areas of my past expertise.

The other option (the green line) likely feels really scary because I know so little about it and in the beginning it might even feel like I’m going backwards. But the slope of the learning of the latter is clearly much steeper than the former.

😎 You don’t have to love it for it to be the right choice.

When I was 21, I had to choose between doing another internship in Vancouver at a lab I had been at the summer before, or doing a Pharma Sales internship at P&G in Toronto. I had no idea what Pharma Sales even was (or really what P&G was 😵), and I’d never even been to Toronto, so I definitely didn’t know I was getting myself into (and I'm glad I didn’t because honestly, 21 year old me likely would have chickened out) but I knew that one way or another I would learn a lot, even if I didn't love it.

Nearly 10 years later when J and I were presented with the option of moving to Shanghai and needing to decide over a long weekend - we decided that the experience we would get with a couple years in China would beat another couple in the US. From learning Mandarin to really understanding what it’s like to not live in a democracy but a Communist state to learning how to manage businesses where a 40% yoy growth rate is tame.

And that experience provided a great foundation when I decided to step off the corporate ladder and start a company - where the only thing I felt confident in was my belief that even if it didn't work, I would have learned more in that year than staying in my corporate job.

⤴Learn your way through the uncertainty to the frontier of your life.

Over time though, it's become second nature to optimize for my rate of learning over anything else - it's also what's allowed me - a non technical solo founder - to build multiple tech startups.

Because the superpower I’ve honed in my life has been to be great at learning. From the sciences to CPG to startups to AI. The what and the where and the how has shifted dramatically and often.

So that by the time I was building tech startups and even though it was daunting, I was able to become technical enough to learn what I needed about software and now AI.

Maximizing slope at every point also has the added bonus that you’ll be able to get yourself to the unique space where you and you alone occupy in the world. Where your unique set of talents exist to do something that no one (I’d argue even AI) is able to.

🙅🏽‍♀️ There are no absolutes of experience.

It’s probably no surprise that I get frustrated by people who offer definitives - ‘big companies are where talent goes to wither away” or that “every young person should start a startup”.

I think that misses the bigger picture - there are ways to learn in big companies - just ask me. And there are ways to stagnate at startups - again, just ask me.

In the absence of a crystal ball, it's really hard to know what choice is right for you. Though even if I had that crystal ball, I'm not sure I'd want to use it - because I'd have seen how hard I found cold-calling doctors for that first internship and I'd have fixated on how miserable I was in Shanghai 3 months in - and given that “data” I very well might not have taken either leap.

Worse, I'd have missed the point. That for me, the "right" decision was or is less about some objective marker of success, but an internal one of growth and resilience.

😰 Get comfortable with being uncomfortable.

A warning though: maximizing slope also means maximizing discomfort. Because it will often mean changing many things at the same time or jumping into a completely unknown areas.

In these times, I think of the 6 month rule one of my earliest mentors - Jeff Davis - taught me when he promoted me and encouraged me to move from Toronto to Cincinnati.

He said: the first 6 months of anything hard is going to suck and feel terrible. It’s when you’re having to deal with the sheer volume of new things. You're not allowed to reconsider this decision for 6 months. Instead, your job is to embrace and fully experience it. Then, at the 6 month mark, if you're still miserable, I'll bring you back myself.

What a gift - to be encouraged to do something that certainly maximized slope for me, but in a way that I felt supported. And yes, that happened in one of the biggest, most corporate companies in the world. The place where I learned how to be not just a great business manager but a great people one too.

Of course at 4 months I was looking forward to taking him up on the offer, but by 6 I couldn’t imagine what I had been so worried about.

So take a look at that decision staring you in the face. Pick a timeframe - a year or two is usually great. I truly believe there will rarely be a time you regret choosing the thing where you learned and grew and stretched yourself.

🤓 Learning is growth, not hustle or achievement.

There will be times though that you need to juggle where the learning is happening. When we had young kids and we each were getting a company off the ground, we moved back to Vancouver where we could have stability, while the learning came from building a family and a company at the same time.

There will be chapters when the slope you're maximizing isn't at work but in your relationship or on a project. And learning doesn’t have to be about “achieving” endless milestones. Learning is simply growth. In our emotional or spiritual or physical selves.

But I believe now more than ever it's important to exercise our instincts to maximize learning. To teach our kids to orient towards that and to be okay with the inevitable natural discomfort. Because increasingly, success isn’t going to look like a collection of “right jobs” but of occupying unique spaces that only I can.

🌱 Start small.

This, like anything, is a practice. Of tuning into that feeling of discomfort and making friends with it. Of acknowledging as it grows each time you do something even more bold but not letting it overwhelm so that it starts making the calls. Because to really maximize slope you have to work with that feeling and keeping it on the right side of productive for you.

But start today. With big things or little - even choosing to walk home a different way or to bike when you usually drive is learning in a small way.

All of it practice for when the biggie decisions show up at your door. So that when that question inevitably comes - “how do I decide?”

You’ll know which way to turn.