As a college student, the question of career direction is on my mind a lot. After spending a few years bumbling around in confusion, I realized:
Based on this, I started running Life Mapping sessions at my college. I wanted to share the thinking behind this initiative. If you have any feedback on these questions and frameworks I discuss, or suggestions for frameworks that you've found useful, I'd really love to hear it – you can contact me here.
- How much value I got from good, strategic, introspective conversations
- Having these conversations was haphazard, and depended on me having friends who were good at asking strategic questions.
Based on this, I started running Life Mapping sessions at my college. I wanted to share the thinking behind this initiative. If you have any feedback on these questions and frameworks I discuss, or suggestions for frameworks that you've found useful, I'd really love to hear it – you can contact me here.
1. Motivation
The fact that my most valuable conversations were mostly just luck seemed like a huge oversight. Where and how were people finding opportunities to have such personal, reflective, and strategic conversations? The sense I got from my peers was that people weren't having conversations where they intentionally delved into their values, what they wanted in life, what resources they had, and possible career trajectories in a strategic way. Career services, which is nominally meant to provide this kind of support, focuses fairly narrowly on more tactical advice (how to get an interview, how to do On Campus Recruiting, etc). In my brief dalliance with career services, I was also astounded at how many assumptions they made about my goals and worldview. Most advice that isn't either explicitly tailored to one's circumstance, values, and general paradigm, or accompanied by an acknowledgment of the values and paradigm from which it was generated, is of limited use (in my experience).
I wanted to see if I could provide value simply by sitting down with people for an hour or two and asking them questions. The immediate response was strongly positive: most people's reactions were along the lines of: 'Ohmygosh I need this right now.' The people I worked with found the sessions useful and clarifying, so I wanted to share the prompts and frameworks I used. This is an ongoing endeavour, and I plan to continue to add to this as I discover and develop new frameworks.
2. Overarching Framework
To help them, I concretized frameworks I had been implicitly using for my own life. The overarching framework was that there are three key components of career success: Knowledge of long-term goals, alignment of short-term goals with long-term goals, and tactical success. This framework points to many of the failure modes I think people run into. For example:
- Not knowing what your long-term goals actually are (which is common because this is actually just really hard)
- Broadly knowing your long-term goals, but pursuing short-term goals that create a trajectory that is misaligned. This is really easy to do when peer effects, which I think are incredibly strong, come into play. It's easy to pursue money/power/status without endorsing whether this leads to your long-term goals.
- Knowing your long-term goals and aligned short-term goals, but not being able to execute on the tactical level (getting the interview, getting the job, etc).
A lot of emphasis in career advice is placed on the tactical level; I wanted to focus on the first two levels. The coaching took the form of asking questions, guiding the introspection, and mapping out their answers. I stressed in the sessions (and stress now as well) that I don't really know anything about career success and don't think that my frameworks are at all comprehensive. Rather than advice-giving, the sessions were about helping people think through and verbalize their beliefs and desires. If something didn't seem useful, we moved on.
Below I list some of the questions I used to prompt people.
3. Questions
3.1. Long term goal access:
- What are your values? A good way to access this is to ask yourself, what are times that you've felt really frustrated?
- When have you been happiest? When have you been least happy? What are the themes underlying them?
- What cause areas do you care about? What does frontier work in these areas look like?
- What does success look and feel like?
- When you’re 80, what do you imagine fulfilment looks and feels like?
- What does winning in the area you care about look like? What have you contributed to this so far?
- What’s your worldview? What’s your underlying life philosophy, your cornerstone? * (Questions to help you figure out your worldview below)
- What are your implicit drivers? It’s ok if you don’t fully endorse them, it's useful to be able to simply notice them
- What is your superpower? What do you do better than 95% of people?
- If you keep asking why, what do you get to?
- What’s the last belief you’d let go of?
- What activities do you find deeply meaningful?
3.2. Short-term goal access:
- What are the goals that feel instrumental to you (i.e. you're pursuing them as a means to an end)? What ends are they helping you get towards?
- Explain the path by which your next step leads you to your final goal
- What do you currently think the best way to achieve your long-term goals is?
- What are your ordered priorities? Being explicit about priorities allows you to make better trade-off decisions
- What are the three things you’re focusing on? Focusing allows you to make more progress on the things you care about – Smarter, Not Harder
- What’s feels urgent? Why?
- What validation signals do you need? How can you get those?
- Importance of optionality. How much do you care about optionality? How much do you expect this to change? What’s your track record of stability of desires/how well do you have a pulse on what you want?
- High-risk vs low risk. How much do you trust yourself, versus wanting to rely on external validation signals?
- What are you uncertain about? Can you resolve these uncertainties by finding out more information?
3.3. Tactics:
(This section was much more sparse, because I think a lot of people already have a good grip on this)
- Networking – who you know matters a lot
- Going above and beyond – show you are dedicated, take initiative, etc
- Frame your narrative strongly and cohesively
- Make it easy for them
- What are your current resources?
4. Frameworks
Along with these questions, I also collected various frameworks of success that I found useful when trying to make choices. These aren't necessarily correct, but can be useful as thinking tools.
4.1. Non-prescriptive Frameworks
- Specialization vs generalization
- Where do you want to sit on this spectrum?
- The Generalized Specialist
- Paradox of success/sub-optimizing in order to optimize (Toni Oloko)
- Are you taking on too many things because you're good at them? How can you focus more?
- Because of limited resources, if we're trying to optimize everything, we aren't actually doing as well as we could at the things we care more about. Sometimes, truly optimizing means making trade-offs such that some things are sub-optimized to free up resources for other things.
- Notably, school does a bad job of training this skill. We're expected to maintain high grades in all classes, and excel at extra curricular activities, and do research, etc. We're trained to keep all the bars high, rather than investing in a few bars and letting the others drop.
- What are you uncertain about? Is it possible to find out?
- Where possible, eliminate your informational uncertainties by learning more about the world. If the uncertainties aren't informational (e.g. inherently probabalistic or in some way unpredictable), it is still good to be aware of them.
- Useful to ask the question: "Can I find out?" whenever you're unsure
- Investing in yourself vs in the system
- Investing in yourself is a bet on your capabilities – it means making choices that may not immediately offer branding or a success signal, but have fundamental value and so will eventually pay off
- Investing in the system means conforming to systemic brand signals. You don't have to constantly rely on your performance, you can rely on external signaling that you've accumulated. This is sometimes the best thing to do, and also works if you're risk averse
- Intangible vs tangible skills (Jungwon Byun)
- Tangible skills are more 'hard' skills: excel modeling, coding, running marketing campaigns, etc. These are necessary to get your foot in the door.
- Intangible skills are more 'soft' skills: leadership, reading people, negotiation, etc. Eventually, intangible skills are what will differentiate highly successful people; but you have to have the tangible skills as a foundation.
- Intentionality
- I think we often don't examine our motivations for our actions. I've found it valuable to know the motivation/principle behind choices, even (and especially) if we don't endorse them, so we know what monkeys we're fighting against inside us and what our expressed values are.
- Instrumental vs fundamental causes
- Valuable to ask whether the motivation is a fundamental motivation, or whether it's actually instrumental (and to what extent you want to pursue instrumental things)
4.2. Prescriptive Frameworks
- Take any seat on a rocket ship (look for the 10x wins)
- Leverage things that seem like weaknesses (e.g. need for validation), rather than pretending they don't exist
- Focus on what you’re fascinated by – you'll win at the thing you think about in the shower
- Attach yourself to the most epic person you know
- Develop grit as a priority – Grit
- Don't overevaluate – choose something, and stick with it until a pre-specified point in time when you can evaluate and make adjustments
- Never make career decisions instrumentally – only do what you are really interested in (Ethan Berman)
- Go somewhere where you have outsized responsibility – where people would be surprised you had that much responsibility at your age
5. Worldview Questions
I ran a separate discussion event focused on building a worldview. Below are some of the questions I asked to access people's worldview. These are similar to the 'long-term goal' questions, but extend on them.
5.1. Questions to help you build a worldview
- What does your utopia look like? Describe the physical vision.
- At the end of your life, what are you going to look back and be proud of?
- What are your values, without using any words that are one-word typical answers (e.g. describe justice without saying justice). Why are these values important to you? What is the ordered hierarchy of these values, so that you can make trade-off decisions?
- What is something you’re interested in? How would you build/describe a model of this to people?
- What is the last belief you’d let go of? Why? Or, what would you be most upset about if you found out it wasn’t true?
- "The way you do one thing is the way you do everything." How is this true and false for you right now?
- What are your principles?
- What’s a belief that you hold about the world? Why? Why is it important that this belief is true?
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