My last post discussed how having written down selection criteria makes it easier to pick a job you’ll both enjoy and excel at. However, a few folks pointed out that coming up with these criteria is a non-trivial exercise, especially if you’re a new grad and don’t have much experience. This post aims to provide a few easy ways to discover what you prefer in a job (or in a life partner, place to live, etc.).

Expand the set of possible choices

The biggest predictor of where you’ll end up is the set of possible choices available (for example, in dating, it’s posited that who you end up with ~98% based on availability and 2% on stated preference). Since you don’t know what you don’t know, you’ll want to spend some time looking at opportunities you never considered and using tools that search broadly so you can expand the set of possible choices and find a more global optimum.

For example, don’t just look at companies that attend a university career fair. Use online aggregators (e.g. AngelList Talent, YCList, or Crunchbase for startups; LinkedIn or Indeed for larger companies) to get exposure to what other people are building and what roles are in demand in your chosen field, or discover paths adjacent to what you initially aimed for. I also subscribe to The Term Sheet, a daily digest of what deals are going down, so I can get a sense of what ideas/industries are getting funded, acquired, or IPO-ing.

Bonus: get people to come to you

One of the easiest ways to find new opportunities is to get others to recommend options. There are several software tools that can help with this, but you’ll also want to rely on good old fashioned networking.

I have been impressed with AngelList’s AList (my referral link), which gets startups to reach out to you based on your stated preferences. YC’s Work at a Startup is likely a similar, though they didn’t support PM roles at the time so I haven’t used it.

Your network is your biggest asset here. If you’re in college, professors will have industry connections and classmates who have graduated ahead of you will have initial feedback. Your alumni network is also very helpful, as those people are already biased towards helping you and believe you’ve already met some quality bar.

If you’re already out in the world, colleagues, folks you’ve met at conferences or meetups, friendly VCs (particularly if you’re at a startup and have done well), etc. can help provide feedback on next moves.

As a side note on reaching out to your network: people love to give advice based on their life experience (blog post to prove it ;), so reaching out and asking for advice is going to be far more effective than directly asking for a job. The adage, “if you ask for money, you’ll get advice; if you ask for advice, you’ll get money” is directionally appropriate here.

Place many “cheap” bets

After you have a broad pool of options, you’ll need to a way to test them out at low cost. Since you can’t get a true feel for all options, you’ll need to develop inexpensive proxies that track what you care about most.

When searching for a job, internships play a critical role in this process. If you’re in college, I recommend picking internships with maximal variance, so as to get exposure to lots of different roles, locations, team dynamics, etc. I worked in hardware, embedded software, and mobile develpment at a three person company, a ~30 person company, and a 30k person company in three different states, with different commutes (walking, public transit, driving).

While it can be difficult to extract a causal relationship between any single variable, over time you will build a gut feeling for what works and what doesn’t (ideally you have enough opportunities to test every variable in isolation, but practically that just doesn’t happen). Often, you’ll find that you react violently to certain things (e.g. “I need a small team”, “this commute doesn’t work for me”, or “I don’t feel like I can grow in this role”), and that’s a good enough place to start.

If you’re not in a position to intern, short term contracts (or gigs) can be useful, though they often are focused purely on role rather than location, work style, commute, etc.

Seek expert advice

Lastly, regardless of how confident you are in your correctness based on testing, I always recommend getting the advice of a few trusted sources in your life. Ideally, one or more of these people are in your field, and one or more of these people are outside it (thus can advise on “quality of life” issues).

More often than not, they’ll provide fedeback through a different lens, and help you identify what really matters. Blunt feedback around discrepancies between stated preferences and performed actions often come from these people (cognitive dissonance affects us all), and will move you closer to what will actually make you happy and productive.

As always, while I may not be an expert, I’m always happy to provide advice!

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