Taking Instagram Connections Offline: What I’ve Learned

There are few things I love more than meeting Instagrammers IRL.

A few minutes before I leave my house to meet them, I usually run around like I’m about to go on a date, making sure I don’t forget my phone and wallet.

Then I start to over-obsess about how the conversation is going to go.

Do I need more talking points? Should I have created index cards with icebreakers just in case? Wait, do I know all of the projects she’s working on?

Even though we’ve had countless conversations in our comments and DMs, it’s hard to know what to expect out of your first meet-up.

Rather than let the stress overwhelm you, you can step into your first meeting with more confidence when you keep these few things in mind.

Taking Instagram Connections Offline: What I've Learned 1

Don’t feel like a creep for reaching out first (because you aren’t!)

It’s not uncommon to feel a little odd before you press ‘send’ on a message you took a few too many minutes to write. Reaching out to someone for the very first time can be tough.

Many times, we tell ourselves that the person wouldn’t want to hear from us. Who are we to take a few seconds out of their busy day? We’ll probably just be a nuisance, tipping their annoyance scale for the day. They probably won’t even reply back… right?

Does it feel like I was just inside your head? So many of us feel this way before we reach out to someone, especially if the person is an influencer or an entrepreneur who has a larger community than we do, but they could be just as pleased to hear from you!

Instead of psyching yourself out, why not try? The worst thing that could happen is you don’t hear back from them, but that’s okay too. At least you tried! And besides, you’ll never know if they would like to have a conversation with you too unless you get on your radar.

I can’t tell you how many times I’ve sent messages to other entrepreneurs, only to hear from them weeks or months later about how excited they are to meet up. Just because you don’t get a reply back right away doesn’t mean all hope is lost.

Keep a level head about connecting with other entrepreneurs on Instagram and remember that many times, their response has nothing to do with you but rather their own bandwidth.

If they do, however, reply back and are excited to meet you too, it’s the best feeling in the world! And it happens more often than you’d think. Even if you aren’t in the same local area, you could still meet them on a Zoom, Skype, or Google Hangouts call over a virtual coffee. It’s well worth the effort to reach out!

Taking Instagram Connections Offline: What I've Learned 2

Don’t agonize about what you are going to say

Once you decide once and for all that you are going to take the leap and send a message to another entrepreneur, a whole new collection of questions starts dancing in your head. Usually, they are centered on what you are going to say.

Do you send a long, thoughtful message to get their attention, or do you send a quick message because you fear you might waste their time otherwise? Do you send it on a weekend or a weekday, in the morning or the afternoon?

There’s no real cheatsheet to help you successfully reaching out to other entrepreneurs. Every person is different, so following along with them for a few weeks before private messaging them is smart. Then you can see what they are more likely to respond to.

When in doubt, just keep it simple! Open with a friendly greeting and include their first name. People love being addressed by name, especially since so many people send templated messages that are clearly done by copy and paste.

Then you can mention a personal detail you’ve picked up after following them for a while, like how much you love the earrings they wore in their new brand photos or where they got the blanket they showed on the couch when giving an Instagram story tour of their living room.

These details may seem silly to add, but they aren’t! It really shows that you’ve been tuned into the content they’ve been producing, which helps you become more memorable. When influencers get lots of messages each day, going the extra mile with these personal details can mean a lot.

You can then ask them if they’d ever like to hop on a virtual coffee date or would like to meet up in person sometime. Depending on their location and availability, you may be able to schedule something.

Taking Instagram Connections Offline: What I've Learned 3

Try to meet face-to-face if possible

As your connection on Instagram grows into a friendship, you’ll definitely want to meet face-to-face. However, distance may come in between you and your new bestie.

If so, this might be a great opportunity to brainstorm ways that you both could meet up! Sure, you could take a dedicated vacation to visit your IG friend, but there can be other ways to get real face time together.

Maybe you both have your eyes on a mastermind retreat or conference that fits within both of your niches. Then you’d be able to meet each other while learning from experts and connecting with other entrepreneurs too.

I love being able to take Instagram connections offline when I travel. I go to a few events in the Bay Area where I’m currently located, but I’ve also been known to swing by Alt Summit and make pit stops in Chicago, Portland, and Columbus for some hybrid work and R&R time.

No matter where I travel, I always share where I’m going with my Instagram audience in case I know anyone in the area. Meeting people while I’m jet-setting gives me a whole new appreciation for entrepreneurship and travel.

You can do the same whenever you travel! Not only will you be able to meet new people from Instagram, but they will also give you some of the best local recommendations for where to stay, eat, drink, and have fun while you’re in town. It’s the best!

Taking Instagram Connections Offline: What I've Learned 4

Make a personal connection

Because we are in the business world, it can be easy to feel like you need to be all about business 24/7. On the other hand, the best way to make connections is to find something you and the other person both enjoy or have in common.

If you are both calligraphers, that’s awesome, but it’s even better if you are calligraphers who love iced coffee, spending long days at the beach, and can make Gilmore Girls references in almost any conversation.

Maybe that doesn’t resonate you, but it will for someone. You may have another set of quirks, traits, and qualities, but there are bound to be other Instagrammers that share the same ones. This will bond you much quicker than doing the same thing for a living.

Always remember to be yourself! You don’t need to wear a mask, pretend you like something you don’t, or do what everyone else is doing to fit in. Be your own person! That’s who people will connect with.

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