Three Pieces of Sustainable Job Search Advice

Chris Lueb
4 min readJun 11, 2020

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“What’s wrong?”
“Are you okay?”
my roommate yelled across the hall.

“No.”
“I mean yes.”
“Yes I’m okay!”
I yelled back.

“Then why were you screaming?” she yelled again.

If I had a list of exciting Monday mornings. That morning would be on there. Since I had just received an offer letter from IDEO San Francisco. Which meant I was actually going to work at The Pier. But also because I was done job searching. No more networking events to go to. No more cover letters to write. And no more interviews to prepare for.

How wrong I was. Having moved back to the Netherlands. And having to job search again. This time around though, I was going to do it my way. As in I was going to do it in a way that worked for me. That gave me energy. And that would be sustainable. Because finding work that I care about is an ongoing practice. Like doing yoga.

Advice #1. Reframe networking.

To start off, I didn’t want to have to go networking events again. With too many people. And too much talking. Without actually connecting. The only thing that used to keep me going was the wine. Which isn’t very sustainable. How might I connect with people while actually gaining energy? Well, I like talking to people one on one. And I love coffee.

So I pulled up my notes from a Designing Your Life workshop I had attended a few years ago. At the time, it felt like “just another workshop.” But I now realized that buying someone a coffee could really work for me. Here’s the template from my notes that I’ve iterated on since then.

Hi [Someone Else’s Name],

My name is [your name] and I’m currently working on [something you’re passionate about]. I saw you’re working on [something they seem passionate about] which I’d love to hear more about. Could I maybe buy you a cup of coffee sometime this week?

Cheers,

[Your Name]

The “somethings” should be overlapping. But more on that later. The more important things to take away here are that the message is short and sweet. And that it’s about them. I mean who doesn’t like to talk about themselves? Especially to someone who’s asking for it. Literally.

Advice #2. Rethink cover letters.

So about the “somethings.” You want your job to be “a good match” right? In terms of culture. But also in terms of passion. Try not to take passion too literally here by the way. Think of it as something you care about. So what do you care about? And what does the company you want to work for care about?

Not only does this push you to articulate what you care about. But it also pushes you to do your homework about the company. And to think critically about whether the two of you really could be a good match. If so, it’s time to start writing your cover letter. Here’s another template I’ve iterated on over the past few months.

Dear [Someone Else’s Name],

[Paragraph to grab the reader’s attention. This could be a personal anecdote. A controversials statistic. A provocative question. As long as it relates to the rest of your letter.]

[Paragraph about you. What are you passionate about? Which project illustrates this? Add a link to your portfolio.]

[Paragraph about them. What are they passionate about? Which project illustrates this? Bonus points for explaining why.]

[Paragraph about you and them. How might you pursue your passions together? Explicitly mention relevant skills. And refer to your resume.]

[Paragraph about next steps. You want to find out if you really are a good match right? Suggest swinging by their office. Is there a day and time that works better for them?]

Cheers,

[Your Name]

Writing cover letters like this really worked for me. One, because it’s energizing to write about things that I’m passionate about. And two, because I get even more into the company. Or not, in which case I know the company probably isn’t a good match.

Advice #3. Rework interview questions.

Now that you’ve had a coffee chat. And written a cover letter. It’s time to prepare for your interview. Be ready to talk (even) more about things that you’re both passionate about. But also make sure to prepare some pointed questions for each of the categories below. Adapted from Gayle Laakmann and McDowell’s book “Cracking the Tech Career.”

Category #1. Insightful

Something that relates to the mission or vision of the company. Like what are your ambitions for the new year? Or how have you managed to deal with [something newsworthy]?

Category #2. Curious

Something shows your eagerness to learn. Like what does mentorship look like? Or, I’d really like to learn more about [something you’re curious about], how would you support that?

Category #3. Personal

Something you’re personally curious about. Like what would my day look like? Or who would I be working with and how?

Start off with brainstorming a bunch of questions for each category. Then, create a shortlist of your favorite ones. Having this list not only helped me feel more prepared. But it also helped me feel genuinely excited.

TLDR; what do you and your “dream” company both care about? And how might you figure that out in a way that works for you? From reframing networking to reworking interview questions. Finding work that we care about is an ongoing practice. So let’s make sure it’s sustainable.

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