In July, my calendar was empty.
I was busy. I was raising my two-year-old son and working on a startup I had launched in May. We had daily active users, and my husband, a product designer and full-stack engineer, had started helping me think through features and growth.
But I wasn’t meeting people.
As a community manager and social media marketer, I was comfortable writing posts, responding to comments, and having conversations in DMs. Then someone asked if I wanted to hop on a casual call, and I froze.
A conversation with someone I didn’t know, in real time, sounded horrific.
Somewhere underneath that reaction, a small part of me said, “Just say yes.”
So I did.
Over the next few months, I had more than 200 calls. Eventually, I started co-hosting a weekly group session, appeared on a handful of podcasts, and did my first live session on X.
Getting there involved scripts, awkward introductions, a meeting I almost fled, and a lot of practice.
If you’re staring at an invitation you want to accept but feel tempted to decline, here’s what helped me.
1. Start with one conversation that feels manageable
That first call was fine. The person was lovely, we had an interesting conversation, and we planned to talk again.
It also made something clear: growing my project into the business I wanted would involve getting comfortable talking to people.
I signed up for Boardy, which offered introductions that both people opted into. That structure gave me enough of a safety net to try. I knew the other person had agreed to be there, too.
I still panicked before my first introduction. Then the person said hello, and we started talking.
Nothing monumental happened. I had a business conversation with someone I didn’t know. At that point, that was plenty.
Try this: Choose one conversation with a clear reason for happening: a warm introduction, a shared interest, or someone you already exchange messages with. Make accepting that one invitation the next step.
2. Give yourself something to lean on
In my early calls, I had a strict script.
I would let the other person introduce themselves. When it was my turn, I would launch into the story I had rehearsed: how I started my project, why I had been offline for two and a half years, and how the product was doing.
I left very little room for questions or exploration. I was busy trying to get through the part I knew.
Looking back, I can see how much I relied on that preparation. It helped me stay in conversations long enough to get more comfortable having them.
You can prepare a few sentences without expecting yourself to become a brilliant conversationalist overnight.
Try this: Write down...
A short introduction: who you are and what you’re working on.
Two questions you’re interested in asking.
A simple way to close: “I’m glad we connected. Thanks for making the time.”
Use those notes for support. As conversations become easier, you can rely on them less.
3. Give your attention a useful job
After enough calls, I began dropping the script.
I started entering conversations with two objectives:
Be curious about the other person and what they were doing.
Look for a way I could help.
Maybe I knew someone they should meet. Maybe I had seen a tool that could be useful. Sometimes the most useful thing I could do was listen and ask another question.
Having those objectives gave me something to focus on beyond how I was coming across.
Some conversations became mutually helpful. A small handful became friendships.
Try this: Before your next call, choose one thing you want to understand about the other person. Let yourself follow the answer instead of immediately preparing your next line.
You don’t have to arrive with a solution or a valuable connection. Curiosity is a place to begin.
4. Expect a new format to take new practice
After getting more comfortable one-on-one, I tried a group session through a founder club.
The description sounded casual. I joined without looking closely at the format and discovered that everyone was giving formal introductions.
As my turn approached, I almost left the meeting and the club altogether.
Instead, I took a breath and stayed.
What came out was something like: “I get really nervous in big groups, and I have this product for indie founders to help them with distribution.”
I had spent almost two months talking about my product. I couldn’t believe that was the introduction I managed.
Then someone corrected my use of the word “indie” in that setting. I was mortified.
That meeting felt awful. It also showed me that a group introduction was a different situation from a one-on-one conversation. I hadn’t practiced it yet.
Try this: When you try a new format, give yourself permission to prepare for it separately. A short group introduction, a podcast conversation, and a casual call can each ask something different of you.
One difficult experience doesn’t undo the practice you already have.
5. Find a setting you’re willing to return to
After that introduction, I considered giving up on group meetings.
Instead, I joined another group while keeping my membership in the first. The new group felt more like friends around a campfire, sharing their wins and losses for the week.
I started attending regularly.
There were small things to learn: how to raise my hand, when to mute myself, and how people took turns speaking. Some of what had felt intimidating became familiar once I understood how the meetings worked.
The atmosphere mattered. I was much more willing to keep practicing somewhere I felt comfortable.
Try this: Pay attention to how a group treats people. Look for a place where you can ask questions, be new, and imagine showing up again.
You can stretch yourself and still choose an environment that helps you participate.
6. Take on a little more as you get comfortable
Eventually, I was asked to co-host a weekly session in that more welcoming group.
I immediately wanted details. What were my responsibilities? What should I do? How could I be useful?
I made a Google Doc with guidelines for myself and the other co-hosts. Having a reference gave me somewhere to start.
I was still using preparation to help me do something unfamiliar. The unfamiliar thing had simply gotten bigger.
Try this: When you’re ready for another step, make it specific. You might welcome attendees, bring one discussion question, or help host a session.
Identify what you need to know, prepare for that part, and give yourself room to learn the rest.
Keep track of what you can do now
If you had shown me my current calendar back in July, I would have thought you were crazy.
At the time, I was trying to get through one call. I couldn’t have pictured co-hosting sessions, appearing on podcasts, or speaking live on X.
Each experience gave me something I could use in the next one: a little familiarity, a better question, a clearer introduction, or evidence that I could survive an awkward moment and come back.
The process hasn’t always been easy, but it has been manageable.
If there’s something you want to do and fear keeps making the decision for you, start with one manageable step. Prepare what you can. Notice what you learn.
Then give yourself a chance to do it again.
