Sponsored by
How I make career decisions
The Four Pillar Framework:
Criticism is the tax you pay for doing anything that matters.
Something I've changed my mind on recently:
When I was younger, I had this intense desire to make my name known for something, to be one of the best to ever do it.
What I've realized is I would much rather live a life I'm proud of than chase a legacy. The pursuit of public greatness, at least for me, has always come from a state of lack, a feeling of "I'm not enough."
As I've gotten older, I've felt that fuel burning out and being replaced by something cleaner. I don't actually want to go to Mars. I'm more than happy being in orbit and enjoying the view.
Call me soft, but I actually think it’s far more ambitious to define the limits of your ambition. Anyone can be reckless in their pursuit of more. It takes wisdom to realize when you’re sacrificing the war of life to win the battle of business.
If you commit to nothing you’ll be distracted by everything.
"A life without commitment is a life spent hugging the X-Axis." - David Perell
Great reminder: Activity ≠ Achievement
Philosopher Alan Watts on the trap of introspection without action:
"A person who thinks all the time has nothing to think about except thoughts. So, he loses touch with reality and lives in a world of illusions."
How I make career decisions
The Four Pillar Framework:
I weigh career opportunities across four categories: Learning, Earning, Network, & Story. I rank each one out of ten and add them up. The opportunity with the highest total wins.
I'll explain each in a second, but first, to be clear: these are the things that matter to me at this stage of my career. They're not the only four categories (and they don't have to be yours).
Maybe proximity to family matters more to you right now because you're helping take care of someone at home. Maybe values alignment is high on your list because you need to believe in the mission to do your best work. Maybe it's energy: what lights you up versus what drains you? The exact categories matter less than defining them for yourself.
They also don't all have to count equally. When you're early in your career, learning and network probably deserve more weight than earning, because the skills and relationships you build now are what drive your earning later.
The point isn't to build a fancy spreadsheet or turn this into some purely logical, no-emotions calculation. The point is to get specific about what matters to you so you can make an intentional decision instead of a reactive one.
Let me walk you through how I think about my four, and then I'll show you exactly how I used this framework when I was deciding whether to drop out of college.
1/ Learning is the skills and knowledge you'll gain.
Specifically, what are the constraints currently preventing you from getting to your North Star? Does this opportunity help you close those gaps?
When you're scoring this one out of ten, my caveat is to be honest with yourself about what you're actually going to learn. It's easy to tell your friends and your parents that you're joining a company because you're going to “learn a lot.” But what specifically are you going to learn, and is the role actually going to give you reps in the thing that's holding your career back?
For example, say you're a marketer who's great at organic and social but has never run a paid media campaign, and you know that's the gap you’re missing. If you join a company that's world-class at marketing, but you come in as a salesperson, then you're getting reps in sales every day, but zero reps in paid media. Not great.
That doesn't mean it's a bad opportunity. Maybe it's the right foot in the door, maybe the network is incredible, maybe the earning is great. But the learning score isn't an 8. It's a 3.
2/ Earning is straightforward. How much money will you make?
Note: this matters much less when you’re early in your career. Money is the byproduct of the value you create in the marketplace, and the best way to create more value is to first stack more skills and make yourself more valuable (but I’ll explain this more in a later chapter).
That said, don't sell yourself short. You still need to make enough to not be drowning. If you're stressed about rent every month, you're not going to be in a position to learn or do your best work.
3/ Network is the people you'll work with and the people you'll meet because of the opportunity.
This, other than learning, is the single greatest thing to optimize for when you're early in your career, because those people will eventually become your future investors, co-founders, employees, customers, and partners.
It’s hard to calculate the benefits of compounding relationships, but I tend to score this one generously.
4/ Story is how well you can leverage this experience to get future opportunities.
For example, working at a prestigious company or on a high-profile project creates credibility that opens doors you can't see yet.
Your personal narrative and story is one of the most undervalued assets you have because people make decisions about you before they ever meet you, and your story creates ripples in the room even when you're not there.
—
When I was deciding whether to drop out of college and join Acquisition.com or stay in school and continue running my ghostwriting agency, I sat down with a notebook and wrote out these four columns.
My current path looked like this:
Learning: 6. I was still learning how to run a business by running one, which was valuable. But I didn't know what I didn't know. My agency had capped at mid six figures, and I spent all my time trying to get better at marketing because I thought that was the constraint. It wasn't. The real constraint was that I didn't have enough hours in the day to fulfill on more clients. I needed to learn how to hire, onboard, train, and retain talent so I could scale the agency past my own time (That's something I learned at Acquisition.com).
Earning: 6. High cash flow but was constrained by my time.
Network: 3. My only real network was from social media, and the people around me in college were mostly behind me, asking me for advice. That fed my ego but didn't feed my learning.
Story: 2. Being in college didn't open many doors for me and didn't give me much credibility.
Total: 17.
Acquisition.com looked like this:
Learning was an 8. I'd be working inside one of the biggest business media teams in the world, getting exposed to paid marketing, operations, and content at a level I couldn't get anywhere else.
Earning was a 4. I took a 50% pay cut from running my own business to become an employee. It was still a six-figure salary, but it was a sizable step down.
Network was a 9. The people at that company were A players and subject matter experts in their respective fields. Some have become some of my closest friends.
Story was a 9. The name, the credibility, the doors it would open after I left.
Total: 30.
I added up the scores and compared them to my current path. Acquisition.com won.
What I liked about that process was that it was black and white. I had a lot of emotions pulling me in different directions. I looked up to the people I'd be working with and wanted to impress them. I was terrified to drop out of college and leave everyone behind (FOMO). But the framework took the emotion out of it and let me make a logical decision.
How Jennifer Aniston’s LolaVie brand grew sales 40% with CTV ads
The DTC beauty category is crowded. To break through, Jennifer Aniston’s brand LolaVie, worked with Roku Ads Manager to easily set up, test, and optimize CTV ad creatives. The campaign helped drive a big lift in sales and customer growth, helping LolaVie break through in the crowded beauty category.
What'd you think of this week's newsletter?
Forwarded this email? Sign up here
Follow me on Twitter & LinkedIn
Wear YCJDT merch
