The Personal Newsletter Revolution

Social media keeps everyone more connected than ever before, in theory. In practice, it’s a highlight reel. A curated feed where people reveal very little about what’s actually on their mind.

The above thoughts are cliche at this point. So what’s to be done? Delete Instagram? Sure. Delete Twitter? If you want. Delete your Facebook? Well you probably want to use groups.

I deleted a bunch of these apps a while ago, but I found it wasn’t feeling more connected to my friends and family. It made more space for human connection, but so many of my friends and family live hundreds of miles away and I still want to know what’s on their minds.

My solution was to start a newsletter. I would share my favorite podcasts and articles from the week, along with a few ideas on my mind and some life updates. I rarely posted on social media, so this was and still is the best way for my friends to stay in touch with me. I’ve sent the newsletter out every week for the past year and a half and it’s one of the best decisions I ever made. It takes a load off me to constantly be updating people about my life. The newsletter provides personal updates at scale.

One of the coolest results has been seeing friends start newsletters of their own. Nothing is more exciting than receiving a personal newsletter from a friend. I know it’s going to be genuine and interesting. I love subscribing to newsletters because the I actually get to hear what’s on someone’s mind. More so than I ever would if I followed them on Instagram, Twitter, LinkedIn, Snapchat or Facebook.

That’s the best part. A personal newsletter creates space to share genuine thoughts without the pressure of 500+ “connections.” There’s no reason to post something “just for likes.” It creates a place where you can share with your grandma, your best friends and your colleagues all at the same time.

The only problem is that I send to 100+ people and only receive from 4 of those. I would love to tip the scales the other way and get more people sending their thoughts every week. I want to hear what’s on your mind! I’m ready for a personal newsletter revolution.

The big promise

Sometimes the hard work is getting to the point where you’re able to set the right expectations.

Not everyone can say “I created an experience that will transform you.” Not every chef can say “I made a dish that will blow your mind.”

It might take an entire career just to get to the point where people will believe a bold statement like that. An entire career of making small promises and keeping them. Then making medium promises and keeping them. Slowly working your way up to the opportunity to make a big promise and keep that one too.

Monsters in the closet

“You can’t worry about the monsters in the closet when you haven’t even opened up the door to see if they’re real.”

I heard this quote today from a local entrepreneur. She was asked about the fear that business owners face when first launching a venture and I thought her analogy was profound.

So often we fear potential outcomes far into the future. Getting sued for abc, or getting bad press for xyz, yet, we’re not even close to opening those doors yet. Those monsters may not be real, and even if they are, we’re down another hallway and not near to the closet yet.

Don’t let that fear hold you back. Check to see if the monsters are real. What you’ll probably find is that you have no idea what closet they might be hiding in. Keep building and keep the lights on. Monsters aren’t real.

When to bring in the sandpaper

Polishing your project is an important decision. So when should you do it?

Say you’re carving a wooden sculpture of a person. As you carve away, the figure starts to look like a human being. You look at it, think it’s good to go and bring in the sandpaper. You spend a couple hours smoothing out the rough edges until your figure feels ready to present.

You leave the dusty studio and show it to your friend. She lifts it up, looking at the piece from all angles and makes a skeptical face. “The torso is way bigger than the legs,” she says.

You pick it up and give it a full look-over just like she did. You realize you were looking at it from the same perspective the whole time. You had never considered what it would like from below and from a side view. She’s right. The torso looks way too big.

Back to the studio you go. Whittling away at the torso and getting it down to the proper size. Once again, it’s time to bring out the sandpaper. Smoothing over the edges yet again.

It’s clear by this story that you brought in the sandpaper too early. You didn’t need to spend hours smoothing over the rough parts in order to get the feedback about the torso being out of proportion.

This doesn’t just happen in sculpture, though. It happens in any kind of creation. Writing, music, painting, entrepreneurship.

We need to spend less time sanding and more time seeking feedback. Don’t wait until it’s all polished before you get a new perspective. Hold off on the sandpaper just a little longer.

My purpose

Here’s a story about when my perspective changed:

In the winter of 2010, I was just another kid on a high school basketball team. Until I wasn’t.

In one moment, a few words from my coach changed the way I saw the world. He told me I wasn’t just a passive observer on this team. I had to be a leader. It was my responsibility to help my teammates. I suddenly had a new lens through which to view the world.

That moment set me along a path of transformation to become a leader on my sports teams. Soon, my new mentality changed the way I did everything. I was an active participant in my education, my college applications, my internships and everything else I did.  Rather than waiting for opportunities, I became a person who created them.

Needless to say, that transformation has had an enormous impact on my life. But most people never have that moment. Not because they don’t deserve one, but because these moments happen by chance.

I’m driven to create more of these moments.

I believe transformation can be designed.

I know it can be done.

Inherent in my hypothesis is that there is an irreversibility the perspective shift described above. It only needed to happen once for me to believe it for the rest of my life. There comes a point when a person crosses a threshold and becomes someone different. Once they adopt that new lens, there’s no going back. You can’t unsee it.

With enough time, we can help more people see possibility and take action. With enough resources, we could bring transformation to everyone.

But we’re running out of time. There are millions of people out of work. Many people struggle to make ends meet. Sadly, few of them feel empowered to make the change they want to see in the world. There are brilliant ideas locked up in people who don’t have seats at the table. Somewhere out there a child has a passion that can change the world, but they don’t feel ready to share it.

I’ve seen programs change people in just four years. I’ve seen internships do it in six months. But can we do it faster? Can we do it in a month? In a week? Or just a day?

The faster we can accelerate this process, the more people we can reach.

My goal is to get students to a transformative moment and push the boundaries of how fast we can do it.

That’s a goal I can commit to. I’m happy to say I will spend a year, a decade or even a lifetime trying to test how fast we can achieve transformation. How quickly can we help someone adopt a new lens? Because once you see the world as a leader, a creator, an entrepreneur, a social innovator, there’s no going back. You can’t unsee it and you become the change the world needs.

I stopped meditating for month

I stopped meditating last month.

I won’t do it again.

Since last fall, I had a consistent meditation practice of spending 5-15 minutes every morning doing some version of mindfulness or meditation. I used apps, YouTube videos and Souncloud to play guided meditations. Some mornings I just sat and focused on my breath. Overall, I went an entire year keeping up this practice.

Around August of this summer, I started incorporating exercise into my morning routine at the expense of meditation. I thought it would accomplish the same purpose. I thought that fitness would ground me the same way focusing on my breath would. I was wrong.

While it was great to have done physical activity before 8:00am, my mental state suffered. Last month I hit some low points. I got down on myself. More so than I ever have. I wasn’t sure if these were the growing pains of adulthood. Maybe it was just the harsh reality of life after college. But as I’ve adopted my meditation practice again, I’m starting to see more light.

My month of no meditation wasn’t a deliberate experiment, but it provided as much evidence as I needed to decide I won’t stop meditating again. I make time for meditation every morning now and I won’t be changing that habit any time soon.

Describing life-changing

It seems the most meaningful things are the hardest to describe. All of the best experiences in my life have been severely undersold. Horn Entrepreneurship, University Innovation Fellows, Seth Godin’s Tribal Gathering, BIF 2017 are the ones that come to mind.

These events and experiences changed me. They connected me with like-minded individuals and gave me a tremendous sense of purpose. But the websites never seem to capture this magic. “Words can’t do it justice” is something you hear a lot, but words can do a lot of justice to a lot of things.

My new hunch is that perhaps it’s so hard to explain these experiences because we never had them growing up. Before I participated in Horn Entrepreneurship’s network of motivated creatives, I had no concept for what it felt like to be part of a professional community. Before I went to the University Innovation Fellows meet up I had no idea how powerful it would be to meet hundreds of change-makers on other campuses across country.

I knew what it felt like to go to basketball camp. It felt fun and competitive, but it didn’t leave me a deep sense of purpose or a community to help me succeed. I knew what it felt like to have a good math teacher, but there was no communal magic.

Perhaps what’s missing from school is the communal magic. The shared sense of purpose and community that is the thread running through all my most life-changing experiences, but such a nebulous idea is tough to describe. It’s especially hard to describe when nothing else in our lives has felt the same way.

Maybe I’m missing the mark. Here I go trying to describe a life-changing event and I’ve fallen short just like the websites of so many.

So what is there to do? Take the risk. Step out a limb and try something new. You never know where your next life-changing gem might be hiding.

Collective Loneliness

We are collectively living a lonely existence.

It’s cliche to say that right now is the most connected and disconnected time ever.

We don’t need more technology. We need more humanity.

Bringing the humanity back to innovation

It’s okay to cry at an innovation conference.

Saul Kaplan

And I did.

Ami, Carl, Teny, Courtlandt, Mark and more all brought me to tears sitting in the Trinity Repertory Theater in Providence, Rhode Island.

A good story can change the world

These were the words written on the website for the event Business Innovation Factory Summit 2017 (referred to affectionately as “BIF” from here on). What set BIF apart from being another player in buzzword bingo was their commitment to storytelling throughout the event.

There were no speakers or keynotes — there were only storytellers. Each of the sessions featured people from education, government and social entrepreneurship. Some were professional speakers, but all were asked to throw away their canned talks and tell us a story.

Philip Sheppard finishing off his talk with a piece of music

And the storytellers didn’t just use words. They used props, music and most importantly, emotion. Former Patriots lineman Joe Andruzzi told us about a battle with cancer and how it led him to start a charitable foundation. Antoinette Carroll wasn’t afraid to share amazing ideas and how failure encouraged to keep innovating. Carl Stormer taught us how control is for beginners and that we need to accept what world gives us.

Everyone told a story. Though we stayed seated in the theater, we were transported to other places with their words.

A room full of empathy

Mark Brand is a restaurant entrepreneur who started “cool guy restaurants” before he found his purpose. Mark put his ego aside and talked to a homeless man he’d seen on the streets in his Vancouver neighborhood. He learned about the difficulties facing people without a home, the struggles they have in finding employment and living their purpose.

He didn’t step away from food, but he saw problems in the system and decided he could start to make a change.

Mark redesigned the way he hired people in his restaurants. He partnered with ethical farmers. He trained people to work in the kitchen and gave them a place to belong. He even reinvented what it means to donate to someone on the sidewalk by creating special meal tokens. The tokens can be redeemed for a free sandwich at his restaurant, encouraging mutual trust between those giving and those receiving.

Meal tokens (image from

Through initiatives like the token program and other hunger relief efforts, Mark has given over one million meals to those in need. It all started with a little empathy. He took a minute to listen.

A commitment to transformation

Mark Brand took us somewhere new by challenging our preconceptions of poverty, homelessness and hunger. Teny Gross did the same for our notions of inner city violence. Teny doesn’t study non-violence as part of a master’s thesis; he’s just committed to the multi-year process of making a change.

As part of an long-term initiative in Boston, he helped the city reduce the number of homicides in a year from 150 down to 30. Then he moved to Chicago to implement a similar anti-violence program. When he arrived in Chicago he interviewed over 500 city residents to learn about their circumstances. Initially he felt resistance — interviewees didn’t trust his intentions. They asked “Are you going to be at the University doing a two-year study and then leave?”

Teny’s commitment is on a deeper level. He’s dedicated to being a figure people can trust and providing a sustainable solution to a terrible problem.

Commitment to the long-term process of understanding people is at the heart of transformation.

Technology won’t save us

The stories from BIF suggest that technology isn’t going to save civilization. Silicon Valley can’t innovate us out of not caring about public service. A faster micro-processor won’t reduce inequality in the healthcare system. Self-driving cars won’t help increase empathy for people who don’t look like us.

Like Angela Blanchard said, “We may not be at fault, but we are all responsible.” It’s on us to start making the change we need to see in the world. At the end of the day what can save us is our humanity.

We may not be at fault, but we are all responsible.

Angela Blanchard

If we have any hope of changing the world, we need to bring humanity back to innovation. People need to be seen for who they are, not just as consumers and users. For that to happen, we need to take a risk. We need to jump into an empathetic interaction without the protection of a screen. We need to commit to a multi-year process of caring about people. When we can do that, real change starts to happen.

It happened for two days at BIF 2017, but it needs to happen every day. With the person bagging your groceries. With the neighbor you pass on the way to your car. With the people you see each and every moment.

We think of changing the world in a grandiose way. Every single action we take is changing the world — it’s up to us whether it’s for better or for worse.

Antoinette Carroll

Be ready to feel, be ready to challenge your perspectives, be ready to break down and just be.

Making small-talk less evil

People are looking for permission to get vulnerable. We go through hours of networking events and leave without any great connections. But are we opening the door for meaning? Are we putting ourselves out there in a way that encourages a genuine conversation?

Without any prompting, people paint the rosy picture: “This is what my organization does and this is what my role is.”

A conversation about a false ideal is a great way to start off, but it’s not the basis for a meaningful connection. To take the next step, you need to get vulnerable. Someone needs to talk openly about where they’re stuck.

Once stuck-ness can be expressed, people can help and you can exchange valuable assistance with each other. Without vulnerability, none of that is possible. It’s not normal to bring up your biggest business challenges over drinks, but it turns out it might be the best thing to do.

Get vulnerable. Give others the permission to do it, too. Without sharing honest struggles, you’ll never dive deeper. Small-talk isn’t evil unless you let it be. Transform the conversation into something meaningful.