Introducing: Hard Mode First

Have you ever graduated from college in the midst of a recession? Had a baby at the onset of a pandemic? Taken a job you’re wholly unqualified for? Cooked dinner from an Airbnb in a foreign country while alone with a newborn baby and a screaming two-year-old? 

Welcome to Hard Mode First, a publication dedicated to the things we learn when we put ourselves through the ringer. Stick around if you’re at all curious about what it’s like to work fractionally at the precarious intersection of emerging technology and IRL community-building.

If you’re reading this today, it’s either because you’ve signed up for one of my many, diffuse content streams over the past decade (ie: Medium, my personal website, my short-lived podcast, Mirror) or have attended one or more events from my community event series. 

With 250-odd blog posts now aggregated onto this new platform (ie: Paragraph.xyz), I thought I’d use an anchoring post to jumpstart a new writing era. Future posts will cover thoughts and observations on a more singular topic or theme (including: community-building, how we learn, working in tech, career paths, and a little anthropology around emerging tech trends). 

No hard feelings if you opt out from here. 

For everyone else – welcome. Let me catch you up a bit.

I left the concept of a single, full-time job back in 2021 and have been working fractionally ever since. This means that I pick up contract-based projects that interest me, carry them as far as I can, then pass the baton onto someone else to bring them across the finish line. Typically I work on 3-5 projects at a time – a blend of some deep embed work, some advisory / board work, and short-term contract assignments. So far, I’ve helped kickstart a web3 builder network, a micro-internship program for high school students, a crypto grants program, a burgeoning revenue model for an open source engineering team, and now, a “clinic” for non-profits to level up their AI capacity.

Sometimes these initiatives work out great. Sometimes, it’s a little harder to clock the win. I’m learning to be okay with that.

You might think fractional work is just code for “fear of commitment.” You might be right. But by now, I’ve seen enough twists and turns to know that most playbooks get tossed into the trash before you finish writing them. Maybe we’re all living in an era where a full-time commitment to any plan is an impossible standard. Maybe instead of moving quickly to get a plan in place, we might try moving quickly to simply get that first rep in, even while the piercing cries of your tiny children bounce against the walls of an empty Airbnb like rebel space lasers cutting into your brain.

Not that I’d know anything about that.

I eventually caught on that I might be more of a practical applications learner vs. a theoretical learner. In math class, this meant word problems, not formulas. In domains like history, I needed stories and lessons, not rote memorization. To compensate for the lack of creativity in classic study tactics, I’d construct deep embedded scenarios to help me learn. It’s thanks to a particularly rousing game of stuffed animal Jeopardy! hosted by my dad that I managed to ace that 7th grade history test simply naming every country and capital in Africa.

That particular exam, by the way, generated so much fury among peer students and parents alike that the teached copped out and converted it to an “open book” test at the eleventh hour. Still energized by the success of my late-night study tactics, I insisted on taking the test memorized anyway, filling in on the back side of the page the accurate name and capital of every (other) country in Africa that he’d failed to include on the simplified quiz. 

You might say my priorities were out of whack.

That we’ve been conditioned to believe perfect information recall is the definition of success is problematic in a world where digital tools have all but removed the requirement to truly know anything. Perhaps that’s why I first gravitated toward a degree in journalism, a perfect-on-paper blend of these two learning methods: theoretical writing principles fused together with practical applications of the craft. 

While I do still carry quite a bit of resentment for the dozens of hours I wasted memorizing entire segments of writing style guide books, I treasure the way I learned how to work on a deadline. In 3-hour “lab practical” classes, we’d conceptualize a new article, conduct the requisite research and interviews, then write and submit the final piece, all in one go. Though, back in those days, even one spelling or grammar mistake would mean failing the assignment entirely.

Hard mode first.

This is, after all, how I really learned crypto. While I’d been around crypto, I hadn’t really built anything. To fast-track my way into an industry I wanted badly to participate in, I short-circuited a version of how I’d initially learned how to work in tech. I found a so-called “sherpa” to point me in the right direction, then embarked on one mentor-heavy role as I got my sea legs, which eventually culminated in publishing an insights piece based on what I’d learned. You can still read it today – it’s called What We Can Learn from Decentralized Community Building. It took me about 100 hours to complete.

After that, it got a lot easier to get real (ie: paid) work in the crypto industry. And over the next 3 years I’ve worked across a half-dozen projects – startups and VCs alike. Each has given me a little more confidence in my own ability to call myself an operator in such a nascent slice of emerging tech. Each has offered an usually high degree of autonomy and hands-on work at the highest levels of leadership. I’ve spent the night in hacker houses all over the world, helped craft multi-million dollar budgets, and trained entire teams toward strategic pivots. 

Looking back, I’ll admit that it’s the “learning from doing” that really got me over the final hump toward feeling enough confidence to call myself an expert. Whether or not you’ve been the one frozen in place, spatula in hand, letting pasta sauce drip unceremoniously onto the floor while triaging a mild toddler head injury and a simultaneous diaper incident that can best be described as a “poop-splosion” is beside the point.

I haven’t done a great job of sharing what I’ve been learning lately (to be fair, I’ve been busy). But now I’m ready to change that.

Welcome to: Hard Mode First.