#1: Giving advice, breaking up, and quitting your job

Hi friends! 

Since I’ve been moving around the country, and since the feasibility of in-person events is still up in the air, I’ve decided to rebrand my newsletter.

Instead of events, I’ll be trying something new—advice. Each week, I will answer two or three questions about… basically anything.  Want your question answered?

All you have to do is send a short note to defaultefriend@gmail.com.

Breaking up is hard to do

How do you break up with someone when it’s not a completely awful relationship but you care about them? I don’t even know how to end Zoom calls.

— Breaking up is hard to do 

I’ve got to be honest, I hate breaking up with people too. We hear a lot about break ups of necessity (they were mean, they were dirty, whatever)—but not a lot about break ups because things just… fizzle. Or aren’t working for reasons that don’t feel like good reasons. It’s a lot harder to stand your ground in those cases, but ultimately… you just have to tear the bandaid off.

Here are two things I think you need to do:

  1. Work through your own feelings first. Nothing is worse than a wishy washy break up. The, “Well, actually, maybe if…” The person who changes their mind midway through their break up speech. If you want to break up, go into it with a plan to break up. If you have a problem with your partner that you think is fixable, go into the conversation with a plan to find a resolution and the strength to walk away if you can’t. Mixed signals make people mad because it gives them hope. And people can stay hopeful for a long, long time.

  2. A period of no contact is really important, but be emotionally prepared for them to not to want to stay friends. If you love someone—if you even just like someone, or have some kind of attachment to them—it can be hard to see them in a different role. Sometimes you just can’t, no matter how far away you move from the situation. One piece of advice I’ve never forgotten: just because something’s been historically good, doesn’t mean it can or should last forever.

Quitting my dream project


I'm <30 in tech, and I am having a quarter-life crisis. My job involves leading a team of ~30 people in a project that aligns perfectly with my interests, passions, and politics. It's everything I could ever want from a job, but it may severely limit my future prospects. 

I am a TVC, which immediately brings to mind all the people answering calls for when your Google Home accidentally shows your kids rap for the first time. While this is a very technical project that often takes orders from a massively-important VP of the company we're a vendor of, I worry that staying will mean I am forever locked out of the upper echelon of companies.

Do I quit before it's too late, or do I stay to lead a growing team I put together myself? I don't want to be stuck in the suckerfish economy when I'm 40.


Underappreciated in Austin

Hey Under Appreciated in Austin,

So—for those of you reading who don’t know what a “TVC” is, it’s “temporary, vendor, or contractor.” 

Working as a contractor in tech is a funny thing, that I think gets different reactions depending on who you’re speaking to. 

Here are a few that come to mind: 

  • Most saliently, when applying for a job, I think it depends on how you spin it. My instinct is if that if you have the right references and list your accomplishments, you’ll be okay. Check to see what your contracting agency’s reputation is using websites like Quora, Glassdoor or TeamBlind. They won’t give you a perfect answer, but you’ll be able to suss it out with a little bit of legwork. If you’re self-incorporated, there’s no shame in saying “self-employed” and then listing the vendor as your client.

  • Socially, people either get it or they don’t. Sometimes, it’s easy to use shorthand and say you just work for the vendor, if they’re your only client. Other times, people may assume your job is somehow fake or less important, because they don’t understand how the process works. It may even be the same when applying to some jobs, but my guess is those aren’t jobs you need or want anyway. 

There are, of course, always going to be people who judge you for not being a full-time employee, professionally and socially, but it’s mostly an ignorance thing.  

If you’re authentically doing high level work, I don’t think it’s going to negatively impact your future. Don’t jump ship if you’re doing what you really want to do.

 I would especially caution you to be deliberate about career moves in this particular moment in history, too, given the way the economy’s been behaving lately. Let’s put things into perspective: you’re lucky to be employed right now! Anyone who has work is—even in tech.

When the world calms down if your role as a contractor is causing you to view yourself negatively, however, leverage the good stuff you’ve been doing and either try to get converted or find a full time position at a smaller company. I know from a close friend (who inspired most of this answer!) that if you’re at Google, it’s not uncommon for high performing vendors and contractors to be converted when it’s a role that’s not always a contract position.