Well, I did it again. I reached out to one person every day for 100 days.

My response rate, counting rejections, was 67%.

I got a positive response 52 times, I got rejected 15 times, and I got ignored 33 times and I tracked it all in TETHER, the tool I built to keep me accountable.

When I set out on this challenge I was certain that my life was not going to change, and yet, despite my best efforts, I feel like a different person.

Reaching out is not actually about making connections, it is about the attempt to make a connection. The beautiful, embarrassing, earnest effort of putting yourself out there, again and again, without knowing what will happen.

In this attempt, there are only four things that can happen:

01. External outcome

Something tangible happens that wouldn’t have happened before. From this single action, a seed is planted, a door is opened, a collaboration begins. Something changes for you and, often, for the other person.

02. Internal shift

Something intangible shifts… Maybe nothing “happens,” but something said in conversation lingers in your mind. Something written back to you challenges your beliefs or changes the way you think. These things are underrated and can fundamentally alter the way you make decisions or show up in the future.

03. Rejection

You get a no. The thing you hoped for takes a turn in a wrong direction. And even though the fear of it is usually bigger than the experience of it, it can still be the reason you don’t ever want to reach out.

04. Ghosted

You get ignored. Your email or dm floats out there in the ether somewhere. Did they ever see it? You won’t know. Is it worth following up? Who can say.

I set out on this challenge with three goals: two professional and one personal.

These goals in mind, here is a breakdown of my outcomes, in all four categories, over the course of this 100 day challenge:

01. External outcomes: 35/100

• Found three dream clients.

• Ten sponsors for my son’s formula 1 themed birthday party.

• Made some incredible and surprising friendships.

• My work was featured in CNBC, Forbes, and Ness Labs.

• I spoke at Harvard and Boston College.

• I spoke on 9 podcasts.

• Interviewed four idols.

• Hosted two, large scale events in NYC and Miami. In the midst of planning Denver and London now.

• Found an amazing home in Spain for the fall.

• Hosted four workshops with creative communities for over 3,000 entrepreneurs.

• Booked two corporate workshops for companies with over 10K employees.

• Collaborated with two of my favorite brands.

In the moment, it felt scary to ask for pretty much all of these opportunities. But reading this list back, I can see what genuine value I was able to bring.

Lots of people don’t reach out because they want to avoid feeling transactional, or more often, be viewed as being transactional. But, what most people miss is that reaching out is an opportunity to bring genuine, relevant value to people. When you ask for an opportunity, and it’s relevant for the person you’re asking, it actually becomes more like a collaboration than anything else.

02. Internal shifts: 17/100

• I gleaned lots of wisdom.

• Decided to move to Spain for three months.

• Started feeling like everything was possible again.

• In some cases, I became really comfortable asking for what I wanted.

• In some cases, I became really comfortable not knowing what I wanted.

• Built the muscle of showing up when I really did not want to.

• Fundamentally changed the way I end all professional conversations.

  

  Carly Valancy

  Mar 9

  i’ve always struggled to end great conversations, unTILL NOW.

  for a long time I’d ask some variation the question, “how can I support you?” I’d watch the person look up to the ceiling and take a huge deep breath, trying to figure out how to answer.

  this question, though well intentioned, actually really sucks because you’re asking someone to do the work of naming what they need support with, without knowing what kind of support you’re able to offer…

  and then, a few weeks ago, i met Liz Friedland and at the end…

  216

  15

  23

• I closed a couple of loops by following up with people that had been on my mind but I had been too embarrassed or something to reconnect with. Few feelings beat this feeling.

• With less capacity, I realized how powerful it can be to purposely reach out to people who feel out of your league, planting a seed for your future self to come back to. Over this time, I planted a couple of seeds that I have high confidence will bloom over the next year or three.

There is something very interesting about the beauty in nothing happening, while everything is happening. Through the practice of consistently reaching out, I started to surprise myself with who I was becoming. In this liminal space, you can become a very lucky person.

I’m more and more convinced that this category alone makes the challenge worth doing, because it fundamentally shifts the way you show up in the world, for yourself and for others. These are the outcomes that prove you wrong, shake you loose from your habits, and place you in the current of serendipity.

03. Rejections: 15/100

• I got a few “nos” that felt strongly like “not a fit now or ever, what were you thinking idiot.” These did carry the sting of disappointment, some for a few moments, some for a few days. But do I still think about them? Occasionally.

• I got a few “nos” that feel strongly like “not now, but the door is cracked open for future-you to walk into.” These kinds of rejections were actually exciting. In some, important way, responses like this put you on the hook to keep showing up and keep coming back until the stars align.

Rejection is almost always accompanied by a heaviness in your belly and a thickness in your throat. Not fun. But what I have learned is that over time, rejection costs you a little, but gives you a lot.

From my conversation with Cate Hall: We’re all laboring under a “distorting mental field” that tells us things are unreasonable when they’re not. The place where most people draw the line for what’s too much to ask is usually nowhere near the actual line. The only way to find out where the real line is, is to go looking for it.

As I started courting more rejection, it became more like a game that taught me things about myself and how I was approaching people. I became more self aware and slightly desensitized to the rubber band sting on my skin because it was outweighed by the curiosity of the experiment and the pride of putting myself out there.

04. Ghosts: 33/100

• I never heard back from a few people I thought I would, which was weird and made me question myself / feel insecure.

• I never heard back from a few people I thought I wouldn’t. I like to call these moonshots. These are the messages you never think are worth sending because the probability that someone will respond or something will happen is so so small. But small is not zero.

I’m gonna be honest this one sucks no matter how you slice it. This is the category that made me want to stop reaching out the most. When you have no time, it can be hard to justify taking the time to write something thoughtful only to have it remain in purgatory forever.

But like most things, the only way out is through. When this happens I like to think about the fact that I am refining and honing my technique. With every message, I am getting better at the skill of writing and communication all together. Everything compounds. Without these 33 missed connections sprinkled in, I may not have gotten the idea or had the language to write one of the reach outs that actually led to something.

Share

Leave a comment

The first time I finished this challenge I was in my early 20s. To celebrate, I threw myself a 100th Reach Out Party at the acting studio I took classes at. JWS. I showed everyone how I did this, what happened, and how they could do it too. For the first time in my life, I was an expert. And like most 24 year olds, I’d learned everything there was to ever learn!

I never thought I’d do this sprint again. After all, networking, I believed, was really built for those in the early, hungry, scrappy days of building their life. Once I had a great career and lots of experience, I wouldn’t need this skill like I needed it then.

Yet here I am. This time around I’m finishing this challenge in my early 30s, knowing less than I did when I started, walking away a bolder, more curious, version of myself.

I’ve gotten to see what has been underneath the tip of the iceberg all along, and have realized that this is just beginning. I celebrated again with a Reach Out Party, only this time in its most fully realized iteration, and wrote my future-self an email to be delivered in 2031.

This challenge has given me the gift of true momentum and the belief that the world is much more malleable than I’d assumed. Through it, I got to honor the younger version of me, who got me to the place I happen to be, while showing up for the older version of me, who will have access to life-changing opportunities because of the seeds I planted during this time. I cannot think of another activity that allows you to do this.

I’m not sure when I’ll do the 100 days again, but in between now and then, I’m looking forward to finding more consistency and more depth, developing a true creative practice, while helping others do it too.

If life really is about who you know, finding and keeping the connections that make us come alive is a very worthwhile pursuit.