Hi, new friends! 👋

So you all really like Packy McCormick, huh? Last week’s Outsider was a barnburner — 1,000+ views and two viral tweets later, I’m feeling the love and excited to introduce Silicon Valley Outsider to so many new readers!

My niche is the intersection of three topics:

1. Understanding startups and the magic of Silicon Valley

2. Becoming a badass business generalist

3. Navigating your career

This week, we’ll focus on #3. One of the most important women in my life is at an important career moment, and this is a thinly-veiled letter to her.

Careers are adventures into the dark.

You’re dropped into the middle of a foreign land after college with little to guide you. Maybe an older sibling or a parent can offer a glimpse of future possibilities, but they’re so far off (and the path to them so unsure) that you have to decide how to operate largely on your own.

I started my career in consulting and it felt like playing Minesweeper. I clicked the first cell and revealed a “6.” Great! …but out of what? 10? 100? It was hard to know if my current job was any good because I lacked any data for comparison, and I had no idea which tile to step on next.

I stayed for a second year in consulting, uncovered a new tile, and saw a “7.” Year three was an “8,” but year four plummeted to a “5.” Not great — but at least it was more data.

After four years, I had a high degree of confidence in the kind of learning and fulfillment I could expect from consulting. I also found more data by talking to my friends from undergrad, observing my clients in Fortune 500 companies, watching co-workers leave for other jobs, receiving messages from recruiters (ignoring the one from DoorDash… oops), and following news about Silicon Valley startups from afar.

That data gave me subjective ratings from folks in those roles and — just as importantly — an understanding of what those roles even were. My mental map grew larger, more accurate, and far more detailed.

I ultimately identified one role that seemed like an exciting hypothesis to test out, “startup founder,” so I moved to Silicon Valley to try it out. And the data gathering continued.

In those early days wandering around in the dark, I was anxious: I feared that I might be messing up my career (and, therefore, life). I had massive FOMO. How could I be sure the grass wasn’t greener in other careers? Even the concept “career” took on huge, mythological importance — I had previously lived in four-year cycles at school, but this new phase would last the rest of my life? I figured that I had to get started on the right foot, and fast: else I would never find my one true passion.

With every year and every data point, however, I’ve calmed down as I’ve improved my career thesis.

✨If an investment thesis is how you spend your money, a career thesis is how you spend your time.

In the early days of my career, it would have been a minor miracle if I happened on the perfect way to spend my time with that first shot in the dark. My first job at Deloitte was effectively picked out of a hat: I only received two full-time job offers after applying to many, many more companies.

As I’ve continued through my career, I’ve gained more experience trying out different kinds of roles myself, a better understanding of what else is out there, and therefore greater perspective. I know that what I have at Astranis is an amazing opportunity, and that certainty is so, so refreshing.

Here are a few tips for building your career thesis and finding a job you’ll love:

🧘‍♂️

Chill out.

You can’t expect to know how to spend your time without data. So, relax! If you’re unhappy in your first job, don’t fret — proving a hypothesis wrong is a fine use of your time. The average American has about 12 jobs throughout their career. There’s a lot of game left to play!

👨‍🔬

Be intentional in your data collection

It’s easy to be non-specific with how you feel about a job, but don’t let yourself get off too easy. You should try to be comprehensive: what sub-components of this job are good/bad/neutral?

Think about working hours, compensation, the people, communication styles, the amount of process, financial incentives, the risk/reward profile, the predictability and repetitiveness of the work… there’s a lot to consider. You’re looking for a match between your preferences and reality.

For extra credit, you can even try asking others for their take:

Sahil Bloom @SahilBloom

The data collection should be both internal (your own perspectives) and external (the perspectives of others). To collect data from those around you, ask about their experiences working with you: What are you great at? What are you bad at? When do they perceive you as in flow?

October 30th 2021

11 Retweets268 Likes

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Find people to emulate, not job titles to pursue.

It’s great to want to be a CEO someday, but that’s not as operational as saying “I want to be like Ana Fabrega.” Find people who have a job you’d might enjoy, get to know them, and ask them how they found their way into their current position.

Most folks are limited by what they have seen — so go out of your way to see as many job possibilities as you can. (Pro tip: if you still think of “business” as a meaningful category, you have a lot more work to do!)

👩‍⚖️

Learn which rules are actually rules.

Most folks assume that there is strong path-dependence in your career, meaning that the career choices you make today will limit your choices you can make in the future. But there’s no rule that says that must be the case!

Even for technical careers, you’re allowed to keep learning new skills deep into your career. Non-linear careers might not be “normal,” but who cares? I fully intend on starting to earn a technical degree later in my thirties, just because it seems fun. Many “rules” aren’t rules, they’re just social norms repackaged as impersonal laws. But if you wouldn’t jump off a bridge just because your friends are doing so…

🌒

Try “careers” outside of work.

You don’t need to go all-in to improve your career thesis. Whenever young professionals ask me how to become an entrepreneur, my advice is simple: start today. You don’t need anyone’s permission to try out a new career. And you can easily fit in experimentation after work or on the weekends.

It’s tempting to want to wait until you’re “ready.” But in today’s world, people forget about mistakes quickly — it’s hard enough to get people to pay attention to your successes! I certainly don’t think I was ready to write a good newsletter when I started Outsider, but those first (bad) editions are largely lost to the sands of time (as are Packy McCormick’s original “Per My Last Email” series).

Just get started now, be intentional, and you’ll find your path. You have a long career ahead of you, and it’s only just begun.

What’s your career thesis? If you think entrepreneurship might be in the cards for you, I think you’ll enjoy following Silicon Valley Outsider and joining 550+ other startup-interested folks

Thanks for reading Silicon Valley Outsider! I’m Christian, the Chief of Staff of Astranis, and I write this newsletter for folks who are interested in startups and live outside of the SF Bay Area. Here are a few past editions that you might like if you enjoyed this one:

• 🧠 An Outsider’s Search for Meaning

• 🕴 What startups want from business hires

• 😱 Startups aren’t as risky as you think