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career

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Do you start your retail career at the Gap or Abercrombie? Your marketing career in-house or a digital agency?

It doesn’t matter because you can always adjust your trajectory. 

But when you’re mid-career, finding your next tech job, each decision carries more weight. You have a finite number of career moves left. 

The hardest part of selling a home and moving a family of 5 overseas wasn’t the machinations or logistical Jenga:

  • “What about your house?” Sold it to my brother
  • “What about the kids?” Enrolled in daycare
  • “What about work? Taxes?” The work situation was negotiated at the hiring phase. Taxes were… confusing. And expensive. I bought an hour from a tax consultant, so now it’s less confusing (still expensive though)

The hardest part was answering: why move in the first place? 

Young[efn_note]Image is from Maggie (2015) a post-apocalyptic horror drama film Arnold stars in. It’s a dramatic turn for the action star. I love that he continues to push himself in his roles.[/efn_note] Arnold Schwarzenegger plastered his childhood bedroom with pictures of the greats: Steve Reeves, Bill Pearl, Jack Dellinger, Tommy Sansome, Paul Winter. All were influential in Arnold’s life, but none more so than the winner of Mr. Universe in 1974, Reg Park.[efn_note]Source for all things Arnold: Total Recall by Arnold Schwarzenegger – https://www.amazon.com/dp/B009G3MSC0/[/efn_note]

Reg Park provided Arnold with the blueprint for his own career:

  • Become a world-class bodybuilder
  • Win Mr. Universe
  • Leverage that success into Hollywood

On February 22, 2021 Reforge raised a $20 million Series A, led by Andreesen Horowitz. It was a big win. A huge milestone after 4 years.

Six weeks later on a Friday afternoon, I clicked Zoom’s “End Meeting” button and completed my last day at the startup.

I am a founding member of the team, and there hasn’t been much time to reflect on the journey until now. I wanted to share lessons learned in getting an early-stage company to its Series A, from someone who didn’t know what a Series A was when he started.

In this post I’ll explain:

  1. What is Reforge and where it fits in the online education ecosystem
  2. Why you should join an early-stage company
  3. Lessons learned over the last 4 years

What is Reforge and where does it fit in the online education ecosystem?

Reforge is an online education platform for mid-career technology professionals who want to do great work and keep leveling up their careers. We started with growth marketing and expanded from there.

We’re solving the need for career development in that gap between entry-level roles (college or boot camps) and executive roles (networking and executive coaching).

A house with “good bones” is one with the potential to go from “frumpy-to-fabulous.” She is structurally sound, regardless of the missing shingles, broken windows, and peeling paint.

She may look beat, but like Tyson Fury in the 12th round against Deontay Wilder, she’ll weather the storm.

It doesn’t require a master architect to list the ingredients of a house with good bones: a solid foundation, a strong frame, put together with thought and care.

It made me wonder: what are the common ingredients of a good life? What does a life with “good bones” look like? 

Recently, I spoke to three different students from my alma mater.

They wanted advice on getting started in filmmaking, developing online courses, and marketing.

They asked good questions, and most of it centered around a central theme: “what skills should I focus on?”

Skill development is crucial, no doubt. You must have the chops. However, looking back at my career thus far, in the 3-4 industries where I’ve done well, I focused a lot less on skills and more on habits.

I like to think this served me well, despite a scattered career trajectory, for a few reasons:

  1. Skill sets change but the ingredients to build skills — your habits — remain the same.
  2. Habits are always under your control. Control your habits, control your destiny.

My friend Michael Alexis keeps a running list of life lessons, the way others might keep a list of half-baked business ideas or ex-lovers. He started compiling this list 3 years ago.

The entire list is worth a deep read. Here’s one I’ve been thinking about a lot:

“I am constantly blown away by how little I know.

If you roll back to any ‘six months ago,’ I thought I knew a lot, but in hindsight I’m surprised I was even functional.

I expect this cycle to continue indefinitely into the future.”

I find this inextricably true in my life as well. I’m confused about how I got anything done six months ago. That’s doubly true if we rewind to a full year.

Ever think you’re not very good at your job?

You’re not bad per se. You’re not incompetent or lazy.

You put in the hours. You don’t drop the ball. You check off your to-do list.

But perhaps when you look at your peers, you notice them stacking promotion after promotion on their LinkedIn profile. Or at drinks, they casually mention receiving a second raise this year.

Maybe it’s politics or luck. Perhaps they “play the game” better than you do. Sometimes that is why people get ahead.

But what if you suspect they’re just better at their job than you?

If that’s the case, how would you uplevel your skills? What skills do you improve, and how would you do it?