Counterintuitive Career Advice for 20-somethings

The vast majority of career advice simply sucks. Most advisors write empty platitudes such as “follow your passion” without daring to make any specific claims, and their advice ends up helping no one or actually being counterproductive. So here are some observations on what I’ve seen work, at least for 20-somethings:

  1. Don’t work in a job or industry that people describe as “prestigious.” If a profession has reached the point where it has prestige, it has built up walls that make it harder for newcomers to ascend. So work in a job that has been respected for fewer than 10 years. Better yet, work in a role that didn’t even exist 10 years ago.
  2. Don’t be a specialist or generalist, be a multi-specialist. It’s generally easier and more (financially) rewarding to become good at 2-3 things as opposed to becoming excellent at one thing. So if you’re an okay marketer and good programmer, work in marketing. Being “the marketer who can code” gives you a rare and valuable niche, and will put you in a position where you can learn a lot very quickly. This applies to almost any combination of roles.
  3. Some people will say that you should listen a lot and not talk very much when you’re learning. This is terrible advice. You should listen and speak as much as you can. This way you’ll say a lot of stupid stuff, people will tell you that you’re wrong, and you’ll learn. Sure you’ll look like an idiot sometimes, but it’s better to look stupid and get smart than to look smart while remaining ignorant.
  4. Organization skills tend to be overrated. Especially in the United States, we tend to fetishize systems like Getting Things Done, rely on 5-year forecasts, and insist everyone keep a clean desk. That’s not to say organization isn’t important at all, but don’t let it keep you from getting real work done.
  5. Understanding what other people really want is the most valuable business skill. It’s also really hard. I saw one company develop a plan for a $3MM, 2-year project to build a business reporting tool just because they had the idea that executives needed to see a variety of reports. After going through and getting more detail on what information everyone actually wanted, my team was able to solve the problem in a few weeks for <$50k. This happens with all sorts of questions-for example, most questions on stackoverflow tend to be far too specific. Somebody tries to solve a problem, comes up with a partial solution that fails on one detail, and only asks questions about that detail. If they asked about the whole problem, they would find that there’s a much easier way to solve that problem to begin with. By learning to ask people about their problems directly and prototype on potential solutions you’ll be able to contribute significantly more value for the same amount of work.
  6. When looking for a new job, pick a specific job title (or 3) that you are interested in. The best way to find job opportunities is to have people refer you. If you tell them “I’m interested in analytics”, they’ll say “Oh, that’s nice” and forget you ever existed. If you tell them “I’m looking for an Analytics Engineering position at a funded startup with fewer than 50 people”, they’ll let you know as soon as those opportunities come up.

Categories: Career, Happiness, Productivity

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