Note to self: it’s okay to be awkward

Stephanie Wasylyk
5 min readMar 1, 2022


I know I’m not the only one who struggles with outreach — this is a common theme in coaching calls with my clients. My response used to be “just pretend they’re human and say what you would want to say to another human”, but now I know better. Now I know that it’s precisely because they’re human that makes outreach so hard.

To me, doing outreach and making connections in my business is like the party you dread, but have a blast once you’re there. It’s like the feeling of jumping into a freezing cold lake, but then the delight once you’re in and warmed up. I know that I’m going to love it when I do it, so I do it, but I also dread it.


Because it’s awkward.

And, upon deeper reflection with my self-doubt coaching peers, it turns out I don’t like feeling awkward. The story I tell myself without knowing it is that the situation is awkward, because I am awkward, so people will think I’m weird, and therefor reject me.

A little extreme for a simple email, right?

But these are the tricks our mind plays on us. Our inner Protector is trying to keep us safe from risk, and the ultimate risk is to be rejected and left all alone.

No wonder I dread outreach! It’s one of the most vulnerable things a person can do.

And yet, I truly believe outreach is one of the most powerful things you can do as an entrepreneur, and as a human.

Making connections and reaching out to people:

· Helps me see things differently because I learn about other people and new perspectives. Empathy is arguably the most important skill a person can have, and connecting with others meaningfully is a great way to develop it.

· Shows me the long-term impact of my work. When I reconnect with past clients and colleagues I get to see how the work we did together shaped how they are now. By hearing about who they hired after me, I can see what gaps there were in our work. By seeing the results they’ve had, for better or for worse, I can learn to do better.

· Educates me on industry trends. When I connect with colleagues, or people in complementary industries, I learn what’s going on outside of my bubble. I hear about resources I may not have known about otherwise (which is how I learned of Trudi Lebron and her amazing work bringing equity to the coaching industry).

· Fosters community. It helps me feel less alone in my business, and it’s a gift to the other person as well to be cared about and thought of. It makes it feel less like a solo journey and more like one that can be done with others helping lift each other up. Sometimes it’s as simple as meeting a new friend!

· Sometimes leads to new business, of course. It can be direct, but usually it’s indirectly because of everything I mentioned above. When this is the primary goal of outreach, though, it will likely backfire.

So why am I telling you all of this?

Last week I did an outreach challenge with a group of other entrepreneurs. Connect with 50 people in 7 days. Not for sales, not even directly for business, just to be in a spirit of connection. I do well with challenges, so I jumped right in. It felt hard, like usual, and the quantity was more than my typical 5-a-week routine, but I didn’t question it. I was the good student and just got the job done.

Then one of my colleagues admitted they were finding it challenging, especially managing all the replies. They thought it was because they tended towards introvertedness. So they were just going to take it slow.

Their admission was exactly the pattern interrupt I needed to set me into a self-doubt spiral. I had never even considered my resistance to this exercise. I ignored all of my pent-up fear. I criticized myself for putting off reading replies from people. I told myself that as a business coach, I’m supposed to be naturally good at this kind of thing, so I toughed it out.

When I spoke to my coach friends it all came crashing down on me. They helped me realize just how vulnerable this challenge actually was — which is what made it so genius! They helped me uncover all the stories I was telling myself about reaching out to people. They helped me see that my feelings were all totally valid and completely normal given my susceptibility to the risk of rejection. My Protector was doing its best to keep me safe.

So would I do it again?

Heck yeah!

Here’s what I’ll try differently next time:

· Only reach out to people I feel aligned with. I don’t mean only reach out to people like me or who agree with me, but rather people who energize me. People who are putting out great things in the world that interest me.

· Trust my intuition on who to reach out to. I’d like to start using a Body Compass exercise when deciding who to connect with. To do this you get still and learn the signs your body tells you when it means “yes” and when it means “no”. When you get to know these, then you can ask your body questions and it can respond accordingly. It will take some practice, and it does sound a little woo woo, but for me what this really means is slowing down the pace of connecting with people to make it less about checking boxes and more about the connection itself (to the other person and to myself!)

· Take care of myself before, during, and after. To me this means acknowledging the feelings I have about it, maybe do some journaling, and certainly not over-schedule myself during that time so I can give my full attention to the replies and the calls that result from the outreach.

· Cultivate self-acceptance. We all have a healthy part of us that guides our self-acceptance, and I’d like to pay attention to that part especially when doing outreach. It’s a time to remind myself that I’m allowed to be who I am, and the right people will connect with that.

Now that all the initial messages have been sent, I get to enjoy my swim in the beautiful lake. I have lots of calls scheduled with really interesting people, I’ve been able to make referrals and connect people to resources they needed, and I’ve gotten updates from people I used to work with. I will probably continue to be awkward, but I’ll keep reminding myself that it’s okay.



Stephanie Wasylyk

Business coaching and thought partnership for established business owners who want more profit and efficiency with integrity.