2019 in Review

In 2018, I recapped my year with a blog post full of memories.

This year, I’m recapping my year with a more tangible exploration of growth: the things I accomplished, the ways I changed, the lessons I learned, my favorite memories, and the biggest things I’m carrying with me into 2020.

The Things I Accomplished:

Curriculum building: 2018 was the year I learned how to coach, and 2019 was the year I learned how to build curricula. When I came on full-time with Praxis in December of 2017, I was the team’s first-ever full-time bootcamp advisor. I spent most of my days on coaching calls and in contact with our participants. It was mentally exhausting, but I got countless reps in with coaching. This year, I dug deep into translating the things I’d learned coaching into a revitalized version of our curriculum — some areas two or three times over.
In February, I rebuilt our placement module, which at the time felt like a huge project to tackle in one month. My muscles have grown since then– in December I rebuilt our entire bootcamp.
I’ve fallen completely in love with the curriculum building process, and I’ve also learned a lot about content curation, the information simplifying process, and what students best engage with — all topics I’ll be writing about in the coming months.
Coaching coaches: we made a number of coaching hires in 2019 — which means I went from coaching participants to coaching our own advising team. When I was first getting started, I spent a morning mapping out our entire coaching process onto a whiteboard. Writing everything down was exciting as hell and I learned a that I knew a lot about coaching I’d never articulated for. It made me a better coach and a better leader and much better at articulating things I’d never forced myself to explain before.
Switched from location-dependent back to remote: this one wasn’t my doing — it was a change embraced by the whole Praxis team. But it’s a shift allows me to take action on the dream I’ve always had for my 20s — traveling widely, and living wide and deep not just in one place, but many. I don’t know exactly where this change will take me, but my plan is to drift for a while until I find a place I feel compelled to spend more time. I always wanted to live in the south and live by the ocean, and I got to do both of these things in 2019. I left Charleston to spend five weeks in Traverse City, Michigan this fall, where I got to run the dune trails and swim in Lake Michigan and watch the northern woods turn to fall and see the start of the November gales blow in off the lake. I’ve spent November and December back in Pennsylvania, enjoying quality time with family and getting laser-focused with work and study and growth.
Doubled my efficiency and output: this is an approximation, not a direct measure. I got very focused early this year on leveling up the way I work — offloading everything I could, streamlining what I couldn’t, and trying not to get too far in the weeds on anything — and it paid dividends. I haven’t sat down and measured exactly how much more I’m able to do than I was before, but I do know that the little things don’t distract me as much as they used to, the big things don’t take as much time, and the amount of weight I carry in the work that I do has increased dramatically from where it was at the start of the year. As someone who wants to push the boundaries of productivity as far as they’ll go without breaking the energy bank, this was a big win for the year.

The things I learned and the ways I changed:

Online content creation: Content creation is always something I’ve been semi-consistent with, but I got much more intentional in 2019. I re-did the 30-day blogging challenge in May to reset my focus, and this fall I signed up for David Perell’s Write of Passage course. I’ve been a big fan of David’s writing process for some time, and learning the ins and outs helped me sharpen the way I create my own content. I’m much sharper and faster at synthesizing ideas than I was at the start of 2019, and that’s exciting to me. I feel like I’ve built a framework that will dramatically improve the amount of weight I’m able to carry in 2020.
Turning 23: this sounds like a strange thing to put on the list, but it really does feel like a milestone. Growing up, people always ask you if your new age feels different from your old one, and I always thought that was a strange question — but 23 actually feels different from 22. Part of it is coincidental — smaller changes I’d been accumulating over time finally catalyzed into a larger metamorphic shift — but part of it comes with the age, too. At 22 you’re still college-aged, still at the point in life where not going to college and working instead makes you distinct. At 23 you’re past that “young and earning your stripes” phase — the tone with which you interact with the world is different.
The personal stuff: I lost both of my grandmothers in quick succession this fall — their funerals were two months and a day apart. One was an expected death; the other wasn’t. It was a strange experience, and it changed me. Being close to death and the end of life sharpens how you look at the rest of the world. The other stuff stops mattering as much. Losing the eldest generation makes everyone else in the generational cycle take a step forward, and it changes your sense of place in the world. When all the times you’ll spend with a person are finally over, you start reflecting on all the memories you’ve made, and your knowledge of the person, and categorize it. You look back on all of it, and try to articulate how it defined you. It changes the way you interact with the world — or at least, it did with me. Blood and family is strong. It’s a pivotal part of how you interact with the world. And going through shifts and reflections on that front sharpens you. You become aware of all the little connections — living next to the harbor in Charleston this summer, just like my grandmother lived right by the harbor in Long Island years ago. I went to Sarasota this spring, the place my grandparents met in the 1950. I learned to sail a sunfish, just like my grandma used to do. One made me kind, the other made me bold.

Biggest Lessons:

The way things evolve over time is hard to predict. People I never thought I’d be cool enough to be friends with have become close friends over the past year. People I grew distant from are now people I get to work with on a regular basis. Things aren’t nearly as black and white as they first seem. I’ve gotten much better this year at trusting the process and letting things evolve.
Changes at startups are like the weather in Kansas, where they say “if you don’t like the weather, wait five minutes and you’ll get something else.” Things change fast. Don’t be married to how things look in the present — keep focused on the end goal.
The subconsious creative process is much easier to dictate than I originally thought. I had an epiphany about this in June: I was hosting a Praxis workshop, and had put off pulling together a topic because I was distracted by other projects. I went to sleep one night thinking about it, and woke up the next morning with the topic on my lips: documentation. The concept was clear, and it took me a minute to realize what I was thinking about. I went into the office and wrote that down on my whiteboard and left it, then came back in the next day and dumped an entire framework onto the whiteboard — which became both one of my favorite workshops I ran in 2019 and one of my favorite frameworks for talking about documentation. In the months since, I’ve gotten much better at consciously prompting the subconscious, percolating elements of the creative process — and letting it be something that runs quitely in the background of everything else I’m doing, as opposed to something I have to carve large blocks of time for.
As a subset of the above point: I learned that the content I’m consuming synthesizes much better than I realize. This epiphany came to me in two parts: the first, in a live writing workshop hosted by David Perell and Will Mannon. Our prompt was to write an essay in about an hour using materials stored in our digital notes. I went out on a limb and compiled a bunch of notes I hadn’t thought critically about before, and wound up writing one of my favorite essays of this year, which you can find here. A few weeks later, my friend Nick told me one of the biggest ways I’ve changed this year is that I’ve gotten much better at synthesizing ideas — which reaffirmed that this ability has changed in a visible way, too. I just hadn’t yet become aware of it. This makes me incredibly excited for 2020 and beyond — now that I’ve learned how to consciously explore this process, I’m very excited to see what ideas I’m able to synthesize.
A lot of the limits you think you’re running into in life are limits you’re placing on yourself. I spent a large portion of 2019 feeling like I was running into the same brick walls, only to realize (in a rather anticlimactic epiphany) that really the brick walls were of my own devising. Don’t rule out the possibility that you’re running into walls because you’re placing artificial limits on how fast you can grow.
The things that make you cry are the best things in life. Heartaches, jokes, the times so good you don’t know what else to do, the projects you take on that are so hard they reduce you to tears. I’ve gotten much better this year at embracing the hard stuff — which has in turn accelerated my own growth.

Goals for 2020:

Publicly announcing goals has never been a comfortable thing to me. I think of myself as ambitious and intuitive, not goal-oriented — I have a plan for where I’m going, but something better might come along two months from now that makes me scrap the whole thing and start over.
But I also like the public accountability of goal-setting, and the collective nature of communicating your goals to the people interesting enough to want to follow you.
So in that spirit, my biggest goals for 2020:
Get better at seeing places to improve: I’ve gotten much better at synthesizing observations into plans for improvement. The professionals I respect most are very good at this, and I want to do better at consistently streamlining. I love the metaphor of aerodynamic when thinking about how I work, and I want to systematize and habituate that process — reach a level of unconscious competence with it.
Get better at synthesizing ideas: two meanings for this: 1, combining the ideas I’m collecting and micro-epiphanies I’m having into more tangible, substantial things (blog posts, curriculum content, etc.), and 2, getting better at seeing what isn’t yet, but could be.
Increase my own equity: over the past few years, my focus has been primarily directed towards building things in conjunction with other people. This is a strategic decision — your impact and your learning are both accelerated and amplified by the reach of working with other people — and when thinking about growth, I’ve always been biased towards leverage. But this limits your personal worth. Your reach is tied to things that belong to someone else, not your own. In 2020 I want to be intentional about building my own equity. The specifics of what this will look like are undetermined (and I like it that way — I don’t want to be so set on an arbitrary goal that I limit myself to possibilities) — but having more equity as an independent entity is very important to me.
Curate a world-class education experience: If I doubled my output in 2019 (a trend I fully expect to see continue), I want to focus this year on improving the quality and richness of the work I’m producing. I’ve always been fascinated by alternative education, and have become more and more convinced that the path to success in our digital world is being completely re-defined. How we educate ourselves — not only how we access information, but how we think about problems and solutions and questions in the first place — will make a huge difference in our ability to capitalize on the opportunities suddenly available to us. Right now, this gets me fired up more than just about anything else. What we’re doing at Praxis is a big piece of this puzzle, and I’m excited to
Build some killer side projects: I was one of 6 Write of Passage alums invited to work closely with both David Perell and Tiago Forte in 2020 to work on a project build of my choosing. I’m still defining the details of what this will look like — I’ll share more in the coming months. But I want to use this energy I’ve built to intentionally build some really killer projects — most likely around some ideas I’ve been chewing on for a while. More on this coming 😉
Deepen my friendships: Christopher Lochhead summed this up well in the Praxis workshop he led in November — he talked about how the personal stuff in life is really what makes it worth living. I have friends scattered all across the country, and part of the incentive for traveling more often is to get to see them, spend time with them, have real and deep conversations with them. Friendships in life are strengthened by the time you spend together and the growth you get to experience alongside each other, and I intend to intentionally cultivate both.
And lastly, embody my favorite quote from Joan Didion, “to remember what it was to be me; that is the point.” 
Meaning: document the hell out of everything.

List of Favorites:

The highlight reel from 2019.
Favorite weekends:
  1. Hanging out with friends in St. Petersburg, Florida. Best part of the weekend: getting a behind-the-scenes tour of the Tampa Bay Rays training camp and Tropicana Field.
  2. Spending a weekend at my friend’s farm on the Kiawah River, where I learned to sail a sunfish, watched the sun set on the river, and watched a meteor shower on the back porch late at night talking philosophy and life.
  3. Canoeing on a still, secluded lake in Michigan while the leaves were turning colors — so much blue on the water and the orange on the trees — and having a campfire on the beach lake that night (and reading Hemingway’s Up in Michigan late at night)
  4. Spending my birthday weekend in Pittsburgh catching up with lots of old friends
  5. Spending a weekend going to the mountains and the ocean all in the same day, just because I could
Speaking at FEEcon: I got to speak at a couple conferences last year (including on a panel with Ryan Craig, author of A New U), but my favorite was FEEcon. I’ve always been a big fan of the work FEE does, and it was pretty cool to get to be on their speaker lineup.
Travels: this one’s a tough tie between Florida (which fascinated me — I expected boring commercialized retirement communities, but northern Florida has a wild feel akin to the west, but mixed with the tropics and the jungle, with a Spanish flair. Fascinating), and Traverse City Michigan.
Outdoors activity: sunset beach runs in Charleston and trail runs at the Sleeping Bear Dunes
Favorite books read:
  • A Farewell to Arms by Ernest Hemingway
  • The Inner Game of Tennis by Timothy Gallwey
  • The Hard Thing About Hard Things
  • The Act of Creation by Arthur Koestler

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