WIP: Job advice from someone who's been fired 4 times (at least) 🚧

Yes, I've been fired 4 times. Maybe even more and I don't even realize it. 🤷‍♂️

But that's not the point. The point is "how do we make you standout in a sea of other fishys?!"

The first thing you want to do is go here.

Before you jump into "working for this wonderful tech company that I am really interested in", you want to take a step back and figure out what's important to you, how you want to live your life, etc. You want to use that info and essentially create a rubric or criteria for your life (as best a vision as you know right now).

Then you can use this criteria/rubric to evaluate opportunities and decisions you have to make.

This article is for people who have already done the above. If you haven't done the above, I wouldn't even continue reading. There's no point.

Further, this is for people who want to standout. And that's not everyone, which is totally cool.

IMO, you have to do things that make you stick out from the noise of everyone else.

You should be thinking about "The Opposite Test" but from a career perspective. What is everyone else doing? And then do the opposite (or at least something different).

For example, I speak to a lot of people who do "informational interviews" OR they might actually be in the recruiting process.

After an interview, most people send a follow up email to thank the other person for their time. Think about it from the other person's perspective; they get A BAGILLION TRILLION EMAILS from people saying thank you. So if you're sending a thank you email, you probably aren't really sticking out from everyone else.

When I was getting recruited at Shopify in 2016, I knew this, so I tried to do something to make myself stick out more. After every interview, I would at the very least send a hand written card in the mail to the office of the person who interviewed me. First off, how many people get mail to their office? Second off, how many people get hand written thank you notes? Not very many.

For a few of the interviews, I took things to the next level. After having an interview with what would become my manager and knowing that Shopify had this concept called "Draw The Owl", I dediced to adopt a Snowy Owl in Shopify's behalf, which came with a cute, fluffy plush owl creature. (at the time, I was big into social enterprises so this "lagniappe" was a good blend of Shopify and me).

Then, when I got to the VP level, I found out that the VP's wife was from my hometown. So I got my mom to go buy a big jug of maple syrup from Sault Ste. Marie and send it to his office.

How do you compete with that shit??? I'm now the "owl and maple syrup guy" when everyone else is sending emails 🤣

In hindsight, the maple syrup and owl were childish tricks but there are other ways you can take it to the next level that are more professional.

For example, when I applied to Notion, I suspected most people were responding to the job posting that said, "Send a resume and cover letter to this email."

I knew that if I sent a resume and cover letter, I'd end up being just thrown into a pile with everyone else. So I wanted to do something to allow me to 'transcend' the competition.

So, instead, I decided to make a quasi-cover letter and resume INSIDE OF Notion (i.e. their own software). And I cold outreached both founders directly.


This past summer, I applied for a job (which I didn't end up getting but that's outcome bias) but I decided to do this but a bit less childishly. Instead of combinding the cover letter and resume, I was just like, "What would I be doing if I got this job?" And then I decided just to go start doing that. So I was providing value IMMEDIATELY to the organization without even getting the job.

—> Check out "The First 90 Days". It's a book about what you should be thinking about in the first 90 days. It's kind of HBS bullshit but it's still somewhat useful.

Ultimately, you kind of make it so that the employer would be dumb NOT to hire you. Become so good, they can't ignore.

Will any of this advice work? 1. I have no idea. LOL While I have gotten these jobs, I've also been fired / left. So maybe they are good for attracting but aren't great strategies in long run. 2. Paradox of Career Advice

From Thiel's Zero to One but same advice applies to careers and differentiation IMO.


Buying maple syrup for a partner at an Investment Bank who's very rational and economics focused might not be the best strategy. I'm sure it would be nice but she's probably making decisions based on what's going to make him $$$ in the long run. Instead, you have to adapt this strategy accordingly, if you so choose to adopt it at all.

This is stolen from Thiel and "Zero to One" —> he describes it in terms of businesses, but same thing could be said for people and their careers.

Most people copy others. They see lawyers, doctors, etc. being successful so they copy that. For whatever reason. However, it's not a secret that these people make money; so, as a result, people flood the market to become a lawyer, doctor, investment banker, whatever. Bc there are so many people, they actually make it so that, in the long run, there are no profits to be had by the individuals in the market. This is exact same as the theory behind perfect competition and businesses —> if there is profit, more people will go and produce whatever is profiting until eventually, the profits are wiped out.

With careers, the same thing happens. Ppl flood the market so that there are no profits. And it becomes super cut throat — you have to step on the other person's neck to get to the top. If you're not there to answer the call at 4 am, someone will willingly step into your spot.

That's why Thiel advizes to find secrets. Being a lawyer is not a secret. And when push comes to shove, take away your name, you actually are very similar to the other people you're competing with.

How to view your career:

  • Make hypotheses and create expirements to test those hypotheses. Iterate fast.
  • Read books.
    • Defining Decade
    • How to Fail at Everything and Still Win Big
    • So Good They Can't Ignore You
    • Springboard
    • Designing Your Life

Written: November 18, 2020

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