Would you like career advice?
Before you ask someone “if they’ve heard of something” for you… try these questions on for size.
I’m flattered to be asked, though time is short — so these days I’m only able to connect directly with people who already matter to me, or matter deeply to someone who matters to me (plus I’m more open to talking with folks from underrepresented backgrounds or when, to be honest, I’m just intrigued!).
This post originally started as a private post I’d share with people who reached out to me for advice. Some of the questions might be useful to others, even if you’re in a different stage in your career than the questions below contemplate.
I try to avoid telling anyone (particularly people I’m just meeting) what they should do, because I find most advice autobiographical: the advice-giver either justifies their own choices (usually from another, obsolete, era) or, worse, lives vicariously through the advice-getter and tries to get them to experiment with paths the giver was unwilling to take. I’m happy to offer my perspective, and I’m public about my scar tissue and many other aspects of my professional life (at Bloomberg Beta, we aspire to be the most transparent investors).
First, a framing question: to what degree do you “know where you want to go” next in your career (at whatever timescale)? Are you just scheming on how to do it, vs. feel like you’re “still figuring out what you want.” Cf. the idea of an objective function for career: what are you solving for in the next step?
It’s hard to think straight unless you know the yardstick by which you’ll judge your options. (Many people try to reason by comparing options — “should I take this new job or stay at my current one” — and that’s as limited a way of thinking as negotiating by positions instead of interests.) To be clear, I avoid asking the tired “where do you want to be in 5 years” question. Sometimes we need to explore and discover before we can generate those specific plans.
A few specific questions that help me orient:
> Do you know what you want to get out of the next chapter, professionally, in terms of its benefits to you? For example: do you want to be able to experience something for the first time, or demonstrate you have a skill so you can do something else in the future, or discover whether some career is right for you? If you know, is there a single dimension that you want to maximize in your next chapter (e.g., you want to solve for maximizing your pace of learning, ability to create wealth, caliber of people, etc.)?
> What are your “side constraints” — Do you need to live in a certain place, make a certain amount of money, etc.? Care for a sick relative? Work in a workplace that has a particular kind of culture? Any other special considerations for you? Constraints help — they focus creativity. The indelicate question I almost always ask: how much money do you need to make to make your life work. Things work better if we try to be open about money.
> How much risk are you willing to take, and which kinds of risk? (Some people want to work for a known brand. Some people are worried about working for a startup that may go out of business. Some people need to hit a financial nut to make their life work.)
> What homework have you done to generate ideas for what you might do next? Unlike years ago, these days the truth is out there. You can use tools like LinkedIn and Crunchbase, et al., to draw up “a list” of companies you might want to work with, people to meet, or industries or roles you might like to have.
> Any particular waypoints to which you’re navigating one day? (You want to be the head of the Fed, or CEO of a company that does ____, or retire on a beach in Bali in three years, or… whatever you’re seeking!)
If you’re being asked yourself for career advice, my friend Merav Bloch has some thoughts for you on how to make this kind of thinking work.
As for how not to use me: I’m crap at “ideating” career moves for people (“what do you think I should do?”). Most career searchers believe others might “hear of something” for them — in my experience, that happens, but it’s only blind luck, and I myself have terrible active recall. Again, we live in a world where most of the information is out there — which firms are thriving, which are struggling, etc.
How to use me, or someone like me: to test your hypotheses (a place to work, a person to chase down) when you think I may have a useful perspective; to validate the information you’ve researched; to introduce you to people I know; to serve as a reference if I know you well enough, or backchannel with people who might hire or support you.
Occasionally I’ll offer a pattern I’ve seen too many times: like the “ex-boyfriend syndrome” (aka ex-girlfriend, ex-partner, etc.) where a person hated some one thing about their previous job, and overcorrects for it in the next one. “I hated working at a big company, so can I work at a place with 2–3 people?”
Many people also ask “what makes sense for someone with my experience to do next?” Who cares. Nobody is tracking your story but you. Deciding a next step based too much on past experiences limits you. Focus instead on what you want and what you need to do to get there.
If you’re interested in breaking into tech for the first time, I generally believe a default good move, is to go to a startup at a particular stage: post product-market fit, already scaling rapidly. This piece by Hunter lays out good reasoning for joining these “mid-stage” companies. (People often join v. early companies as employees simply because they have no other choice.)
Sometimes people ask how to generally prepare themselves for tech — how to build the “asset of you.” The obvious: get smart on tech! Read all the things. We even have a reading list. On which technologies will be important, I think the “meta-skill” — figuring out which technologies are important and master them — is more important than the skill of learning the right technologies right now. That said, a few areas where I’d go deep:
> Professional tooling. Getting expert in the obviously-great tools like ChatGPT, Airtable, Notion, Slack, CloudApp, UpWork, etc. Also experimenting with stuff that’s more at the edge.
> Building software. More important than understanding *about* AI (or any other software) is understanding the experience of making software. Take a GA course, learn on your own, build Crypto Zombies, use Repl.it (#proudinvestor), whatever.
> Statistics. AI is, sorta, just a branch of modern statistics. Automation is just one of many applications of AI. (The book Prediction Machines was useful for me in understanding this.)
> Yes, AI, crypto, etc. are all important despite being cliches.
As far as careers in early-stage venture in particular, it’s tricky because the junior roles IMHO are terrible preparation for being an investor. Recommending to others what they should do doesn’t teach you much about how to do it yourself, unless you’re working on big-analytical investing (growth-stage venture, PE, etc.). Better to angel invest, or find a firm where you can actually make your own investments, or build exceptional operating experiences from which to draw. Otherwise you have to get lucky with a firm that actually has experience getting people from the junior roles to the full partner roles — rare, like 1 in 20 rare. You want to avoid being a second-class citizen.
If you and I are corresponding, I realize it can feel a little awk to do this stuff over email, feel free to share as little or as much as you like.
Happy researching :)
If this post sparked more questions for you, try this chatbot some friends made (on my work, and Bloomberg Beta and #thisisnotadvice content).
