How to reach out to people when you're tired and busy and distracted

You already know a lot of people but something in you wants more

If you’re an actor in NYC, networking can feel like a vicious and performative game of social climbing. If you try to approach important people through official channels you’ll be one of the 100 singing, dancing, hot people trying to barge into the same inbox. (Turns out this is true for other industries too but with less hot people.)

But one time I met a woman on the subway and we were carrying the same book (Andrew Lloyd Webber’s memoir). She had a bright orange bob and looked like she got her glasses from the MoMA design store. When she got off the train she gave me her card and told me I had good taste in books. She was the Executive Director of Lincoln Center. She was so impressive and intimidating and I was 22 and scared.

Who am I to reach out to her?

It took me three months to finally gather the courage to email her, which felt like a stupid amount of time to wait. She probably didn’t remember me at this point. But I knew I’d always regret it if I didn’t send it.

We met for coffee and she hired me on the spot. This was the first of many times I experienced the power of reaching out. Since then, I’ve done it hundreds of times. Emails, dms, handwritten letters, I’ve tried it all. If I have one skill, this is the thing I’m best at, and yet, I don’t always do it. Why?

I know why I don’t reach out because it’s the same reason you don’t.

• It’s kind of scary and sometimes that’s just a lot.

• You’re tired and busy and distracted.

• You don’t want to be rejected or judged or desperate.

• You think that even if you somehow connect with someone cool it’s not going to lead to anything anyway.

• Most of the time, you don’t have a strong enough intention or goal that justifies spending your energy overthinking a message to someone.

• Something about a cold email or dm feels gross and you’re not gross.

These are all very real but also very convenient excuses we stay in our own way.

I know how easy it is to talk yourself out of reaching out to someone. It’s like having a great idea, always talking about it but never building it. One day you will see it out in the world and feel a pang in your stomach because you know deep down that it could’ve been you.

But connecting with strangers, asking for what you want, potentially getting rejected is the best risk return decision you can make any day. These are the ways I remind myself:

Life is about who you know and that is a fact.

Listen to me closely. Dream jobs and careers, deep romances and friendships, great ideas and stories, all started with one person bold and curious enough to reach out to another.

Who you know used to be solely based on your family or location, but now almost anyone you want to connect with is accessible.

Life is long.

I’m only 30. Sometimes it’s easy to think 30 is old. Everything I see tells me I should already be trying to look younger. I feel like I should be a real adult by now. Fully formed and assured, with all the major things figured out.

But I don’t and you don’t either. Just because you have a career and a busy life does not mean it’s time to stop reaching out. This is actually the best time to start because you’re established, but not all the way yet. This is not the time to let your network settle. Don’t discount how the seeds you plant now can open up doors and opportunities your “actually old” self will look back at and thank you for.

I need to remind myself constantly that I’m actually just at the beginning. Matt always says we’re at the part we’ll talk about years from now. Figuring out our careers, starting a family, moving around a bunch. I love this. We’re in it. And we will be for a long long time. Life is long.

Life is short.

I’m already 30. I’m already 30? How is it possible for a decade to pass so quickly? How the hell did that happen? Will I blink and be 40 where I’ll start saying stuff like, “the days are long but the years are short?”

We only have so much time on this earth to find our people. You cannot wait until they find you. You cannot wait until you’re in the mood. You cannot wait.

As Dominik Gmeiner says, “If I’m not intentional about making space now, another two years will go by. And all the conversations, friendships, and connections that could’ve happened—won’t.” Life is short.

Now that I’ve said the most obvious tropes in the world, we can go on.

Building a good network is not linear.

Reach out to people who have your dream jobs, who make your favorite recipes, who write inspiring essays you love. Reach out to people you are genuinely curious about. Reach out to people you think you’ll vibe with, even if it seems unrelated. A lot of the time, their emails are right there. Their dms are wide open. Building a good network is not linear. The best connections often come from the most random places.

One time I sent a cold reach out to a playwright I loved and we lightly kept in touch. Two years later I told him I’d been moving away from theatre and into early stage tech and he connected me with a friend who ended up giving me my first job at a startup.

Be as real as possible.

You’re a person with hopes and dreams and anxieties and fears and ADHD probably. The key to finding your people is to be as “yourself” as possible.

Lots of people think that reaching out needs to feel buttoned up, kind of like a LinkedIn post.

People write emails that are like, “hey here I am, look at how important my announcement is, how good my writing is, and how professional I am. Now can you pay attention to me or give me what I want?” Gross this sucks! Instead, be as real as possible.

I promise your best connections will come when you strip away everything performative you’ve been taught about how to build a network.

‘No’ is not always final.

Maybe it’s starting my career in theatre, or maybe not, but I’ve been rejected a lot.

I’ve been rejected chorus like style in a line of other girls who looked just liked me. I’ve been rejected from countless opportunities I was underqualified for and also overqualified for. I’ve been ghosted after great dates and meetings and interviews. This kind of rejection is a natural part of life if you’re the kind of person who puts themself out there.

There are a few devastating rejections I can remember in my life, the ones that haunt me still. This kind of rejection is the kind that feels raw the way your cuticle does after you pick at it a little too much. Like, I will never forget the feeling of making it to the final round to book Jenna in the national tour of Waitress and not booking it. Or the one time I interviewed with a VC for 6 weeks, made it to the final round and they never emailed me back… I will not name them but I want to. Rejection is the most painful when you start to picture your new life, when you want it so bad you can’t sleep.

Aside from the rare dream crushing moments, most other rejection is a natural part of life. All this to say, getting rejected over email isn’t going to ruin your life. If anything it will help you learn and refine the ways you communicate.

Also, I read this in the 13 laws of good luck and it kind of exploded my brain. Mitch says, “always remember, conditions can change and then the answer changes.”

Basically if you can be yourself and aim to make a real connection, ‘no’ might be temporary. And it might even make the eventual yes even sweeter.

Ask without shame.

Stop trying to please everyone. You think you want to send a pleasant email that doesn’t really offend anyone. But actually, just being likable does very little for you if it means you’re not actually getting the desired result. You want to be a bit polarizing, a bit risky, a bit dangerous. You want people to either be like hell no or hell yes.

>What you think you want is this

>What you actually want is this

And on that note, ask for things damn it. Ask often, ask without shame, ask for what you want most. Cate Hall says it best: “Ask for things that feel unreasonable, to make sure your intuitions about what’s reasonable are accurate (of course, try not to be a jerk in the process). If you’re only asking for things you get, you’re not aiming high enough.”

Cate has this way of writing that sits you right down in your place and reconsider your life choices.

Real, honest truth is like that. The more you ask, the more you refine and reshape what it is you actually want. With repetition, you’ll learn how to say it in a way that feels good in your mouth. You’ll get feedback on who to say it to. You will find more confidence and conviction in your own voice.

The magic is gratitude.

Gratitude. It’s wonderful to practice gratitude in your journal, but it is even more wonderful to share it. The magic of gratitude is that it improves everything it touches, especially the person who offered it in the first place.

You have to believe luck is coming for you.

If you’re going to reach out to people you have to believe that it is WORTH IT.

You have to believe that the more you try, the more luck will come for you.

So believe!! Have that little glimmer of hope. Sparkle in your eye.

Be slightly delusional and believe that maybe, MAYBE reaching out could actually change your life.

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If you want networking and making connections to become a part of your life in a more meaningful way, but you too are tired and busy and distracted, you should join the Reach Out Party. Applications open twice per year. 🫶

P.S. thank you Sasha Chapin for making this better and keeping me accountable.