Eight years after meeting one of my best friends, I found out he was a classically trained pianist whose first love is music. His passion runs so deep that he swore off picking up the keys until he retires, because it’s so consuming.

I didn’t even learn this trivia directly—he shared it with the friend of a mutual friend when we were all hanging out one evening in Portugal. I looked at him like he had grown horns, but I shouldn’t have been surprised.

New connections create the space for us to show up in ways that break us out of our typical scripts and patterns. The people I speak with most frequently are familiar with the things I care about, but not the person I made small talk with on an elevator yesterday or the barista who asks me how my day is going.

When we spend time with people whose lives and careers differ from our own, we discover the familiar and the foreign. The familiarity can be affirming when we feel like someone we’ve never met sees the world similarly. And the foreignness of their approach to problem-solving or to asking us about ourselves can yield insights and reflections that stay with us for years.

I look forward to amplifying this magic in Next Year Starts Now 🚀. The people who have signed up don’t know each other, and they’re all extremely accomplished in their respective fields. And even if I don’t have the pleasure of seeing you in the program, I hope you’ll share and learn something new this week.

Next Year Starts Now 🚀

Do you trust yourself? A lot of people don’t.

One of the reasons for the self-doubt people feel when trying to change a behavior or start a new habit is that sustained change is hard. Did you know that nearly 80% of New Year’s resolutions are abandoned by the second week of February?

One challenge is that we approach change from a behavioral perspective without addressing the identity gap. If your goal of working out four times a week started strong but fell off after a long weekend or a friend visiting town, it’s not just because you aren’t committed. It’s because the new identity hasn’t been fully internalized.

If you instead started with doing five air squats while waiting for your kettle to heat up in the morning—a durable habit less susceptible to interruption given the context—you can much more easily build upon this habit with more activities that eventually spill over into the gym or onto the running trail.

And after twenty or thirty days of this, the habit starts becoming automatic. After months of this, it’s hard not to see yourself as a person who prioritizes fitness because the evidence is clear.

(Put another way, caffeine addicts coffee drinkers don’t have to summon the willpower to swing by their favorite coffee shop once they’ve found it, much less do they need to put time on their calendar to remember. It’s who they are.)

This applies to aspiring writers, programmers, or mindfulness practitioners. You might not have time to publish a thousand words, code an error-handling module, or sit on a cushion for 30 minutes every morning. But I don’t know anyone who doesn’t have time to pen one sentence, write a single line, or breathe for 30 seconds.

After a while, the identity of who you’re becoming gets assimilated. You move from “how could I possibly make time?” to the day not feeling right if you haven’t done the thing to which you’ve committed.

In Next Year Starts Now 🚀, we close the gap between the person we’re becoming and the person we are today. We have a bias for action, we start before we’re ready, and we’re doing the work.

Next Year Starts Now 🚀

In 2015, I moved to NYC, founded a media company, and became Seth Godin’s in-house CTO. But my hesitation almost prevented it from happening.

At the time, I was Director of Web Optimization for a firm that made software used by more than a million websites. I was running professional services and learning a lot, but something felt off. I couldn’t shake the feeling that it was time for a new adventure.

I emailed Seth, who had previously hired me for his book publishing startup called The Domino Project, and told him I was thinking about my next moves. He responded 19 minutes later, asking me to call him. We talked about what I wanted to do next, what it would look like, what he was preparing to launch, and the role I could play.

I was living in Florida at the time, and he suggested that we continue the conversation in person, in New York. I hemmed and hawed about the next time I’d be in New York, to which he replied, “I’m not waiting.”

I booked my flight that day and moved to Harlem a few weeks later.

Things moved quickly. I secured sponsors. Helped launch altMBA. Cultivated contributors. Hired an Editor-in-Chief. Published articles. Grew the newsletter. Produced a launch event. Made a name for myself.

I learned more in those first two weeks than I would have in two years of puttering along in Florida. It had nothing to do with where I lived and everything to do with how I chose to spend my time. I left the safety of the familiar and stepped into the unknown. It was thrilling.

And none of it would’ve happened if I had dragged my feet.

The problem with waiting is that there’s never an ideal or convenient time to do the work we’re called to do. There will always be great reasons to postpone, delay, and spend another six months “researching.”

That’s why I’m launching Next Year Starts Now 🚀.

It’s an invitation, a permission slip, and a mirror for you to hold yourself accountable. There’s still time to close the year out strong.

Next Year Starts Now 🚀

You don’t have to wait for the New Year to get started on your resolutions. In fact, I’d argue that waiting for January 1st is the worst way to make a change.

Did you know that of the 41% of Americans who make New Year’s resolutions, only 9% are successful in keeping them?

We can do better than that.

You don’t have to be great to start, but you do have to start to be great. — Zig Ziglar

As the end of the year comes into focus and the holiday season approaches, a growing list of our nice-to-have priorities will be punted to the “next year” pile. And when the fog of the new year clears and the urgency of those punted priorities comes into focus, abandoning our goals and resolutions is the easiest way to make time.

But your dreams deserve better.

The truth is that right now is always the best time to make a change, but right now is never convenient. In fact, the inconvenience of deciding, committing, and taking immediate action is what’s transformative. I know this because taking immediate action—the core of my Next Year Starts Now ethos—changed my life.

Right now prevents us from hiding, demonstrates (most importantly, to ourselves) how serious we are, and interrupts the time-honored tradition of getting ready to get ready, a pattern that kept me stuck and living below my potential for years.

So in that spirit, I hope you’ll consider joining me for an intentionally inconvenient end-of-year sprint. Registration will be open for two weeks starting today, and I hope to see you inside. Email me with any questions.

LFG 🚀

I frequently walk through an intersection in Brooklyn where cars are occasionally stopped in the middle of the pedestrian walkway. It’s a minor inconvenience to walk around the bad drivers who misjudge the intersection, but it’s still difficult not to feel a twinge of annoyance.

But when I was returning a rental car a few months ago, I found myself traveling through this same area in a vehicle for the first time. The light was yellow and there were lots of pedestrians, so I decided to stop instead of trying to make the light.

I had to smile as a couple walked a few paces out of their way to accommodate the bad driver—yours truly—whose turn it was to inconvenience pedestrians.

The funny thing about extending grace is that it flows in both directions. You might not need it today, but life is long and filled with surprises.

I love tools that make the internet a more private and secure place, and here are a few products and services that I use. Many of them will be overkill for the average consumer, but you might not be the average consumer.

• NextDNS: Cloud-based DNS service that lets you control and monitor DNS resolution on your devices with a focus on privacy, security, and content filtering. Blocks ads, trackers, and prevents your ISP from snooping on your DNS traffic.
• 1.1.1.1: CloudFlare’s super-fast, privacy-respecting DNS resolver that doesn’t log or track your browsing activity. There’s also a companion mobile app that works like a VPN and securely connects to the Cloudflare network.
• Flashrouters: Wi-Fi routers that come with open-source and highly customizable software installed, allowing you to enjoy an expanded feature set, better security, and improved performance. I run an Asus mesh network at home.
• Tailscale: A secure networking tool that creates a private, encrypted network between your devices. Works like a VPN, and uses the Wireguard protocol.
• Proton: Suite of high-quality, privacy-focused tools created by former CERN scientists. Their mail, VPN, password manager, and secure notes app are top-notch.
• Brave: Free, privacy-focused web browser based on Chromium (which powers Google Chrome) that blocks ads by default.
• Ente Photos: End-to-end encrypted, open-source, cross-platform photo backups.
• Signal: Secure, end-to-end encrypted messaging. SMS is not secure.
• Advanced Data Protection for iCloud: An optional security feature from Apple that gives you end-to-end encryption for your iCloud data.

Responsive Conference is my friend Robin Zander’s two-day annual summit in Oakland, California, for founders, entrepreneurs, and executives that want to make things better at work and beyond. 

It’s a conference, yes, but in practice, it’s more of an immersive love letter to collaborative problem-solving. Everyone I know who attends Responsive Conference raves about the experience, and there’s still time to snag general admission tickets.

An unconventional and delightful preamble to the Conference is—brace yourself for some serious meta—The Conference for Conferences by the incomparable Jenny Sauer-Klein. 

The Conference for Conferences disrupts the tired conference paradigm that leaves attendees overwhelmed, overstimulated, and over-programmed. Expect an intimate, high-impact gathering for people who convene people, focusing on the kind of participatory connection that stays with you long after the Conference concludes.

Both conferences will be held at the stunning Oakland Museum of California on consecutive days in September, and I hope you can attend.

I was at a birthday party 15 years ago, and an unassuming guy that I didn’t know walked over and introduced himself. His name was Michael.

He shared how he knew our mutual friend whose birthday it was, and asked me what I was working on. We chatted for a few minutes and exchanged information before mingling with others and enjoying the festivities.

The next day, I received a follow-up email from Michael with a bullet list of five people he was happy to connect me with, along with links to their LinkedIn profiles. They were all interesting, successful NYC-based entrepreneurs that I was interested in meeting and highly relevant to the work I was doing.

Michael is a superconnector.

The introductions beget other introductions, with each new connection radiating with positive energy and goodwill from the last. It’s an infectious energy and activity, so I started being intentional about making introductions in my life as well. This has in turn added a lot of value to my friends’ lives.

You probably know dozens or even hundreds of people whose lives would be made better by knowing other people in your network. It’s easy to complicate the process, and I’ve certainly made some glowing, multi-paragraph introductions, but it’s also fine to just say, “Hey, I think you two will enjoy knowing each other.

My first sales role was as a founder, which was like learning how to swim by jumping into a river wearing winter clothes.

I was running a mission-driven media company that produced long-form content, and I sold sponsorships to fund it. Launching and running that publication changed my life, due in no small part to the lessons it taught me on cultivating a healthy relationship with sales.

I secured six sponsors for the magazine’s launch, and the fanfare around our splashy entrance generated significant sponsorship interest that sustained us for a while. But once the momentum slowed and things were humming along, sales became something I dreaded (and dutifully avoided).

The challenge was that I felt personally identified with the sponsorship I was selling, and every time someone declined to purchase a sponsorship, I felt personally rejected. I asserted that the world needed what we were producing, and I went to the market to validate that assertion.

Another challenge is that I took myself and my work Very Seriously, which left little room for creativity and fun. Work felt like work.

Things changed when I shifted from being consumed with my feelings of worthiness to inhabiting a place of generosity. When I treated money like it was scarce and unavailable to me, it was elusive. When I treated it like an abundant resource to attract, sales became more of a game with a scoreboard than a quest for survival.

This shift in perspective helped me get clear on what I was selling, which was the opportunity to be a part of something meaningful and worthwhile. When I exuded the confidence and power of the mission, my value proposition shifted from focusing on metrics and subscriber growth to the story my buyer would share with their spouse over dinner.

Being in alignment with the power of my mission also led to some weirdly awesome things happening: when I spoke with a prospect about sponsorship, he was excited and assumed the pricing I sent was per month (it wasn’t monthly pricing), and said he’d like to start with three months (as it turns out, it was monthly pricing). That was a fun email to forward to my advisor.

Ultimately, I parlayed my insights into a mission-driven career at the intersection of my passions: facilitation and public speaking, empowering people to more deeply inhabit their humanity in relationship with others, and serving as a coin-operated spokesmodel for the cause (sales).

The result was millions of dollars in sales activity that I mastered, looked forward to, and helped others unlock their brilliance around.

The shift in perspective changed everything.