The 7 Deadly Sins of Tech Job-Hunting

I remember using Google for the first time in my dorm room. It was 1999. And I had never connected to the Internet without a dial-up modem before.

Google Search - Circa 2000

Search after search came back with pure gold.
 
"This. Is. Frickin. Magic."
 
And then, when I caught sight of the "Jobs@Google" link, my destiny was suddenly clear: I've got to work in tech.
 
So why was it 12 years before I finally broke into tech???
 
The answer lies in seven boneheaded (but common) mistakes I made along the way:

 

 

1. I thought I didn't belong
 
Despite being the world's biggest nerd, I thought my lack of a CS degree precluded me from working in the land of the nerds.

My secret shame

My secret shame

And yet, it turns out that for every tech job that requires a CS degree, there are at least three others that don’t:

Source: LinkedIn, US Internet workers

Source: LinkedIn, US Internet workers

After all, every time an engineer designs a hot new app, she needs someone to design the logo, patent the technology, market it on the App Store, manage its books, and so on.

The bottom line: Tech jobs are open to you, even if you weren’t a CS major. So don’t give up before you start!

 

2. I tried to be someone I wasn't

Thinking that my initial career in education would be a major turn-off to tech employers, I tried to make it disappear by writing the most conservative, boring applications possible.

Trust me: This never happened (especially the tie!)

Trust me: This never happened (especially the tie!)

But what I discovered when I got into the tech world many years later is that it’s actually a really nonconformist place, founded by college dropouts and run by folks in hoodies. And so a conservative cover letter or interview outfit just signals that you don’t belong.

And, in fact, I only got my foot in the door when I began to embrace my non-traditional background:

My revised cover letter to Apple

My revised cover letter to Apple

The bottom line: Tech is weird. Let your freak flag fly!

 

3. I got stuck in a scarcity mindset
 
I only applied to the one, coolest company over-and-over again. So only got one rejection letter - over-and-over again.

We have to stop meeting like this...

We have to stop meeting like this...

Only later did I come to appreciate that there are so many more awesome fish in the tech job sea. So many, in fact, that tech talent—not jobs—is the real scarce resource. 

When even a hot company like Yelp loses billions of dollars in value in a single day because they can’t hire people fast enough, finding a great job is just about broadening your horizons and putting yourself out there. Like this email to a newly-funded entrepreneur that netted me a coffee meeting that week:

Don’t hold back - tech needs you!

Don’t hold back - tech needs you!

The bottom line: Tech jobs aren’t the prize. You are!

 

4. I made myself a commodity
 
In an effort to fit in, I used the exact same cover letter and resume template that everyone else used.

It worked for MadLibs, right?

It worked for MadLibs, right?

While that approach might feel comforting (safety in numbers, right?), every successful business in history would beg to disagree. I mean, if Starbucks had taken that same generic approach, they’d still be selling coffee out of cups that say “We Are Happy to Serve You” from their single store in Seattle. And Gucci would be hawking plain black bags out of a van on the side of the road.

Starbucks as a commodity

Starbucks as a commodity

That’s because every successful business manages to differentiate itself from the competition; to prove that a cup of coffee is really worth $4.95, not what the guy at the bodega sells it for. So why would you take your own most precious asset—your talent—and turn it into a commodity?

The bottom line: Don’t be a commodity. Differentiate yourself.

 

5. I confused "research" with progress
 
In order to make myself feel like I was getting somewhere, I'd put at least 10 hours into reading tech blogs every week.

A few more articles and I'll be sitting pretty in the Googleplex...

A few more articles and I'll be sitting pretty in the Googleplex...

The problem was that, even after becoming a tech “expert,” I had nothing to show for it. Until one day, while watching a soccer match, I realized the cardinal truth of both sports and job-seeking: You only score when you shoot. No amount of fancy dribbling—or reading TechCrunch—will get you into the back of the net.

Thus, it was only when I started setting daily goals for job applications (my version of taking a shot!)—and holding myself accountable for those goals—that I started making any real progress.

My nerdy Google Doc for tracking daily job applications

My nerdy Google Doc for tracking daily job applications

The bottom line: Prioritize your time on what matters - not just what feels good.

 

6. My only metric was applications
 
I could crank out a dozen on a good day. And then I would relax, confident in the notion that I was tracking my way to success.

Just 11 more to go...

Just 11 more to go...

Well, guess what? My focus on taking shots had been a little short-sighted. It turns out that random shots into the darkness don’t score that often either. Instead, only shots on goal have a real chance of going in.

In the tech world, this means submitting a great application AND getting a referral. That’s because recruiters are overwhelmed with me-too applications. When I led hiring for a VC-backed startup, this is what I’d see on Indeed’s backend:

Ugh…

Ugh…

If I was going to put my reputation on the line and send a candidate to the CEO, I wanted to have total confidence that they’d be a rockstar. And so, it was only when my teammates started making referrals that it became obvious whom to pick. After all, why go with an unproven stranger when you’ve got a highly-touted candidate from someone you trust?

So if you really want to nail your application, find an alum on LinkedIn who can vouch for you and you’ll be interviewing before you know it.

The bottom line: An application is a shot. But a referral is a shot on goal.

 

7. I prioritized prestige over fit
 
When I finally made it to one of the sexiest companies in the world, everyone else told me I was awesome. So why was I so miserable?

The Promised Land - so many fancy logos!

The Promised Land - so many fancy logos!

In my haste to break into the tech world, I got caught up in what I call “logo fever” - wanting to associate myself with a hot brand to feel like I’d really arrived. But in doing so, I had neglected this simple calculation:

Hours Spent Bragging about Your Cool Job < Hours Spent Working in that Job

And as a result, I hadn’t thought through what it would really be like to work at that hot company. Because if I had, I would have realized that the culture of a different kind of organization would have been a much better fit.

So before you come down with a case of logo fever, spend some time on Glassdoor, getting to know what your dream company is really like:

The good, the bad, and the ugly

The good, the bad, and the ugly

The bottom line: Choose your job wisely. Optimize for happiness over sexiness.

 

Post-Script
In the end, I did wind up at a couple of awesome tech companies. And I had a blast - exactly as I had hoped, staring at that Google screen a millennium ago.
 
But I'd love for you not to wander in the desert for the next dozen years like I did. So, with that in mind, here's my complete guide to The 7 Essential Secrets of Tech Recruiting (100% Free - just sign-up for my newsletter below).
 
In it, I cover everything I learned from the mistakes I made above. That way, you don't have to make them too!

 
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