It’s okay to stay (until it’s time to go)
I’ve had the idea for this blog post floating around in my head for a while now. Ever since I hit around the 2 year mark of my career at Aviary, I’ve been getting increasing pressure from the people around me to go do something else. “Wow, 2 years - that’s a crazy long time in the startup world.” “Don’t you want to try something else?” “You’re wasting your time; no one learns anything after 2 years at one company.”
And I kept wishing that someone, somewhere, would tell me that it was okay to stay. Because for me, staying felt right.
I knew I wasn’t ready to leave when talking to any other company just made me appreciate Aviary more.
I knew I wasn’t ready to leave when I noticed I was learning something new every single day.
I knew I wasn’t ready to leave when I was balancing 4 jobs and lots of customers and partners very literally depended on me.
I knew I wasn’t ready to leave when I laughed my ass off for an hour straight at lunch with my best friends.
But then? One day, I was. I woke up and I realized that it now suddenly felt okay to go. Aviary is doing great and getting better every day. The team is stronger than ever, and has perfected a bunch of smart processes to automate various things and make sure nothing goes wrong. And - while I still felt like I was contributing - I no longer felt like I was the only person in the world who could do my job. For the first time, I felt like I could leave and both I and Aviary would be okay.
So: I just wanted to put the word out there that it is okay to stay. Stay as long as you’re happy. Stay as long as you’re learning. Stay as long as your company needs you and you need them. And the moment will come when you know in your heart that it’s time to do something new (and that your company will still be able to thrive without you).
On that note: while I’m very sad to be leaving the incredible team at Aviary, I’m thrilled to say that I’ll be starting at Betaworks on Monday. I truly believe in their mission, have an insane amount of respect for everyone working there, and can’t wait to help them change the world.
How to land your dream startup job!
To a lot of people, working at a startup is an unattainable pipe dream. I know it seemed like one to me. I’ve already covered why I think you can still kick ass without a technical degree, but here’s some tips on exactly how you can get started.
(FYI: I’ve been desperately unemployed, so I’ve made a lot of these mistakes myself. And now I’m one of the people responsible for hiring at Aviary, so I see a lot of these mistakes every day.)
Startups are certainly becoming more common - especially in Silicon Valley, Silicon Alley, Silicon Prairie (I didn’t make that one up), and Silicon… Swamp (oh my god I made that one up but it’s real) - but that doesn’t mean they’ve lost what made them so magical in the first place. These companies have a ton of flexibility, and that changes the rules.
These companies don’t have an HR department, so there’s not a person in a suit reading your resume. Most of them probably don’t even have a dedicated hiring manager, so it’s likely that the person reading your resume isn’t looking for the traditional things you’ve been taught to say. And almost definitely, everyone in the company is (happily!) exhausted, swamped with terrible job applications, and looking for someone who stands out. That’s where you come in!
Step one: searching for the right job
I may not know you, but if you’re anything like every single one of my friends who have been looking for a job for the last 10 years, you are probably doing the following:
- Searching job boards like Monster and Indeed (I hope you are not still attempting to use Craigslist) for general titles like “project manager” or “junior developer.”
- Sending out a resume you haven’t really looked at in a year.
- Sending out a cover letter which, the first time you wrote it, was really really genuine and passionate! But now is… not so much.
- Feeling really bored and sorry for yourself, and complaining to everyone around you that the economy sucks and there are no jobs.
First of all, let’s get that last one out of the way - the economy definitely sucks, and there are definitely not *enough* jobs, but we can find a good one for you. Because you’re good enough, you’re smart enough, and doggone it, people like you!
Feeling better? Cool. So here’s what you should be doing. First, please never search a generic job aggregation website ever again. You might get lucky enough to find some legit corporate job on there, but startups just don’t use them.
So if you can’t use those garbage websites, what option does that leave you? Well, the hard one. The one where you need to sit the hell down, with no distractions, and think about what you want to do. Wanting to work at a startup isn’t enough (and is too general to help point you in any one direction). Assume a startup’s a given. What problem do you want to solve? Which companies do you really respect? Which industry do you want to be in, long term?
Hopefully you can answer one or more of these questions and that’ll get you on the right track. If not, a website like Made in NYC (or your town’s equivalent) is a great place to get some inspiration. If that’s not an option - if you’re not lucky enough to live in Silicon Swamp - try thinking about which products you use on a daily basis that you love. And think about moving.
(Note: don’t be scared to reach out to your dream job. I know it seems like they’ll just say no, but you seriously have nothing to lose. And if they DO say no, ask what you can do to get there in a year. Ask if you can take the person who rejected you out for a coffee. If they’re unresponsive, find someone else in the industry - or me! - and ask them where you went wrong. Don’t give up!)
Step two: updating your resume
Ok, so I’m going to assume at this point you’ve found something (or multiple somethings!) you think you might someday be able to be passionate about. Now you have to do some actual work, but the good news is that you can make other people do most of it for you.
That’s right: show your resume to everyone you know. Show it to your mom and your sister and your best friend and that guy you went on a date with last year. If you’re too embarrassed to show it to them, think about why. This is the trick: if you can’t show your resume to the people who care about you, don’t you dare send it to a stranger.
Send it to all these people, and really listen to their feedback. Don’t get defensive. If they say it’s boring, jazz it up. If they say it looks ugly, use a template in Word (or ask a designer friend to spruce it up for you). If they say it seems like you’ve never done anything, or that they can’t tell what you’ve done, think about why and fix it.
Step three: choosing a job
You might think you already did this in step one. But this is exactly why people often get stuck at step one and give up. You’d love to work at Barkbox, but they don’t have any non-technical positions listed? Or worse, they have non-technical positions listed, but you’re not qualified for them? This is not where you sigh and give up. THIS IS WHERE YOU REMEMBER HOW AWESOME YOU ARE.
You just spent days or weeks revamping your resume to make yourself sound as incredible as possible. Even YOU should be completely convinced at this point. Yes, it’s good to research what positions are officially available at your dream company, but honestly? Don’t even worry about it, because:
No startup will pass up someone perfect.
This should be your mantra every day while you’re applying to jobs. Get it tattooed on your hand Memento-style if you have to. If you are smart, passionate, awesome, and in love with a startup, you can convince them to hire you. They will create a position for you. That’s one of the great things about startups!
So even if they don’t have your ideal job listed, write to them and tell them what your ideal job is. Convince them (in a charming, reasonable way, of course) that they just didn’t realize they needed you. Which brings me to…
Step four: writing your cover letter
I know what you’re thinking. I know that you want to just whip up a generic cover letter so you can send it out to as many companies as possible in the least amount of time. Great idea. How are you at math, hotshot? Because I’d love for you to tell me which of these is better:
- Emailing 100 people and getting 0 jobs.
- Emailing 1 person and getting 1 job.
We good? Okay. So cover letters seem daunting, but they’re actually the easiest part, because all you have to do is be yourself. Show your personality, and your passion. Explain why THIS ONE COMPANY is the one for you (because, remember, you’ve hand-picked it and you actually want to work there). Make a joke or use a silly pun. Nerd out and tell them that you love the dinosaur on their 404 page or whatever.
The goal of your cover letter is to prove that you can fit in.
Do not, under any circumstances, do the following:
- Attach your cover letter as a document. Write it in the email like a normal person. (Similarly, send your resume as a PDF. Not a Word doc. A PDF. No exceptions.)
- Start your cover letter with something formal. If I see “Dear Sir/Madam,” “Dear Hiring Manager,” “To Whom it May Concern,” or any of their relatives, I will not read further.
- Bypass the application process outlined on the company’s website. If they tell you to email email@example.com, don’t email their CEO or designer directly. The ONLY exception to that rule is if you have a direct connection to that person. Otherwise you just look like you can’t follow directions.
- List everything on your resume in your cover letter. It’s obviously good to give a quick overview, but remember that the point is to explain (show, don’t tell!) WHY you are a good fit. (Protip: prove that you are smart and get things done.) They’ll get the details from your resume if they want them.
- Fill your cover letter with all the things you think you could do better than the company itself. It might seem like a good idea to point out flaws in the company’s website (typos, broken links, etc) but I promise you - the company knows about them. The company hates them as much as you. The company will project this hatred onto you.
TL;DR: you need to remember two things.
- You have ONE chance to impress this company. Try your hardest, and mean it, and you’ll do well.
- You are great, and you can be an important asset to their team. Convince yourself, and you’ll be able to convince them.
There’s a ton more material here, but this post is already dangerously long, so we’ll leave it at that for now. I hope this is a good start for you to help you get moving in the right direction.
And if you need a second pair of eyes on your resume or are paralyzed with fear, email me and I’ll remind you how awesome you are.