Two Career Tools: The 45/55 Decision and Preparing Harder
Most weeks I find myself talking to someone about their career. It's hard to put myself exactly in their shoes — I won't understand their ambitions, skills, or risk appetite in a half hour chat — but I can share these two tools that have served me well:
- The 45/55 decision — a framing for close call decisions
- Prepare Harder — the tactical steps to fluency in a niche
Most career questions are simple, but open ended: Should I pick this career? Should I join this startup? Should I start this startup? How can I make the most of business school? Should I leave my job?
These questions all share the same root problem: wanting a plan when one doesn't exist, struggling to evaluate the tradeoffs between divergent paths, and not knowing the questions to ask to learn more.
The 45/55 decision
Early in my career I agonized between staying at Microsoft to work on the Fluid Framework or joining Limebike. Limebike was a hot company and I would have been an early hire with a lot of upside, but it would have involved leaving Seattle for San Francisco and a tough choice with my then girlfriend (now wife). Microsoft gave me the opportunity to join Steve Lucco and Kurt Berglund, a skunk works team of technical talent solving genuinely hard distributed systems and user experience problems.
I stayed, but did a terrible job making the decision. I drew it out, overthought it, and ruminated uncomfortably.
I'm smart enough. I sought expert counsel: many mentors, close friends, and thoughtful people gave me advice. I broke it down 20 different ways. I could not figure out the path forward.
There wasn't an answer. I couldn't predict the future, but both jobs would have worked out okay.
If you're smart, sought help, thought hard, and still couldn't decide, then it's at worst a 45/55 choice.
For a 45/55 choice, the error bars are large, luck and hard work are big factors, and the cost of rumination and delay is high. Just pick. Then make it work.
Prepare harder
In business school, I realized that average effort would lead to average results — not quite what I wanted. My wife, always the comedic relief, has called this advice "fairly intense", but it's worked for me, at MIT and before, to get up to speed on voice-to-text, stablecoins, CRDTs, and venture capital.
I developed a system of preparation, my own "there's no speed limit" approach to preparing harder.
And I think this system is basically always useful, if over the top for some goals. Just yesterday, a family friend asked me how to move from consulting to finance within their industry. I said, get valuable, get knowledgeable, get prepared. Here's what I would do:
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Map the field: Work with ChatGPT, Google, and friends to make a list of the ~30 most important, interesting, and unique companies in a space
Not healthcare, but the narrower "provider-payer negotiations"
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Profile each company/product: For each company, write down the leadership, key metrics, business model, home base, and key features. Include two bullets on what you like and don't.
In 2022, I did this for voice-to-text. I logged founder, location, $/hour, realtime support, self-host options, and a developer experience review.
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Look around: Google the founders and companies. Find recent news. See which investors write about them. Note the investors and firms.
Find and evaluate the industry newsletters. Find and follow the key product person or analyst who secretly has the deepest perspective.
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Reach out: Email the CEOs, thought leaders, and investors. Don't be afraid to buy them a beer or a coffee. Try to be helpful and informed. Tell them you're studying the industry closely.
Read their recent writing. Share a product insight. Tell them why their company/product/insights are differentiated or impactful. Ask a well-researched question that an expert would find interesting.
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Build the network: End with "who are you most impressed by in the field?" or "is there anyone local that might make sense for me to talk to?" Make sure you ask how you can help.
Offer (and send!) competitive tear downs, warm intros (when requested), or articles relevant to your discussion.
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Stay up to date: Occasionally do an evening of work on a small project (build an app, write a brief, compare functionality across products). Share this work with your network and ask them for feedback. Incorporate and thank.
Build an app, write a comparative product review, use all the products, model the business economics.
Congratulations, you're now in the top 5% in general knowledge of your niche. If you want to break into VC, you can cover that niche. If you want to start a company, you know the landscape. If you want an engineering job, you know the product, toolkit, or domain.
In my experience, steps 1 through 3 take about one full weekend. Steps 4 through 6 take about a quarter of 3x weekly work until you feel the compounding effects.
Conclusion
Pick when the choice is 45/55 and get to work. Take the obvious tactical steps and do them very well. Be useful and give energy freely. Help people.
The good news is none of this requires much special talent, just consistent effort and the nerve to commit to a direction.