When I was trying to pivot my career, I worked with a career coach who provided support and accountability.
After my program ended, I feared I would go off track. None of my friends were choosing a non-traditional career path. I had to build my own network of people who could relate.
While it takes perseverance and getting over some nerves (reaching out to strangers can be scary!), meeting new people who’ve done what you want to do is one of the best ways to prove to yourself that you can do it too.
Ways to find people to reach out to
This is probably the lowest lift way. You already know how to do this, so I won’t spend much time here. Search by job title or company and don’t be afraid to stalk them 👀. Notice when curiosity appears (like, I wonder how she made that pivot?) and make a note to reach out.
Join a community
There are tons of communities out there. Here are a few where I’ve heard great things:
Old Girls Club for women and non-binary professionals with 5+ years of work experience (I’m also in this one)
Dreamers & Doers for women entrepreneurs and leaders
Fabrik for community-builders
Shanti House for conscious-living + wellness-focused innovators
The Agave Haus for Asian Women in Tech
Women Building with AI for women who want to create, experiment, and use AI to transform work
Attend IRL events
Luma: You can subscribe to the event calendar in your city. Some of these tend to be more tech-focused, but there are a lot of different types, esp. in bigger cities. I just went to an event I found on Luma in London!
Women in Innovation: This nonprofit I’m part of puts on in-person events and meetups in SF, NYC, and London. You can subscribe to the newsletter to see when the next one is!
Crafting your outreach message
When you reach out to someone, your messages should be short, personalized, and have a clear ask at the end.
Point out what you love
Take a look at their profile, specifically their recent posts section, to see what they’ve posted about lately to tie it into your outreach.
Highlight mutual connections
If you have mutual connects, you can highlight them but only if you actually know them (i.e. don’t highlight them for the sake of the name drop). You can just mention it more broadly (i.e. “…saw we have a ton of mutual connections…”).
Express your enthusiasm for meeting them!
Even though it’s a simple message, I can feel when someone is genuinely excited to chat with me vs just quickly sending it off. Channel your enthusiasm with every message.
A few examples:

Connecting for a casual coffee chat - it’s fine to abbreviate to fit into the character count, makes it more human!

Connecting to a recruiter for a job. Make sure to highlight your experience and make an ask in the form of a question.
During the conversation
Be prepared but don’t feel the need to overly prepare.
You can create a list of questions if it’s helpful for you but know you don’t have to have it all figured out, and you can let the conversation naturally flow based on your curiosity.
At the end of the convo, make sure to ask them if they have someone else to connect you with in their network.
Creating a system of record
When I first started, I had a Google Doc with people’s names. Earlier this year, I transferred it to Notion, where I built out more of a CRM and classify each meeting to make it easier to find later.
After lots of conversations, no matter how good your memory, you’ll forget details about what you talked about, so it’s super helpful to go back to when you reach out to check in.

Being OK with the outcome
It can be scary to reach out to someone, esp. if you don’t have any connections or not too much in common. A few things to remember:
You’re not bothering them by reaching out.
People are used to being reached out to on LinkedIn. They have a choice to accept, deny, or not respond to the conversation. If they don’t respond, likely they’re busy and you can send a polite follow-up. Beyond that, continuing to engage with the content is helpful to stay top of mind for when the “right time” pops up again.
You’re just asking for direction.
Just like if you were asking a stranger for directions on the street, you’re asking for directions with your next career step.
What if they actually wanted to talk to you?
Just because your’e the one who asked, doesn’t mean you’re not providing value. They could be getting something out of it, too—whether it’s mentorship, a sale for a program you’re the perfect fit for, or even just time to talk about themselves (people LOVE talking about themselves!), it’s not always one-sided.
🧠 Final thoughts
Change can be hard, especially if you’re doing it in a vacuum. Making tiny investments now is the only way to see the fruit of your labor down the road! So, send that LinkedIn request, go to that event, try a new community. You never know where it’ll take you.
💬 Your turn
When it comes to building your support system, what’s holding you back?
✨ Weekly Feels
My first week in London has been incredible.
Highlights have been: Joining Loom Club, a coworking/events/fitness studio. Attending a meetup event where we walked, meditated, and hung out at a coffee shop/wine bar. Played beach volleyball. Attended a Brazillian BBQ (with another DJ).
I was nervous that I would be lonely, but it’s been the opposite. It’s a good reminder that you can create community where ever you go as long as you put yourself out there.
📖 Keep Reading
💼 Ways to Work With Me
Unblock Strategy Session: Get 60 minutes of strategic support on Zoom + 2 weeks of async support on whatever you’re working on to help unblock your goals and come up with a concrete action plan.
Just Start 6-Week Cohort: A 6-week cohort for the curious soul who wants to make a career pivot, without walking away from the stability they’ve worked so hard to build. You’ll launch a mini career experiment alongside others exploring their next step.
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