TG: Thank you so much for doing this with us!  What are your “4 rules for finding your dream job” and why? Please share a story or example for each.

Sure! Thanks so much for having me. The biggest challenge people under the age of 30 face is optionality. This is realized usually in terms of career choice. Studies show that the more options you give somebody the greater regret they have even if they picked the same choice in each situation. Take that and combine it with lower switching cost for choices and you’ll be left with the cohort of people that regret everything and never stick with something long enough to become great at it.

I’ve thought a lot about how to decide what career to pick. Sometimes I’ve chosen correctly, other times I’ve been wrong. I’ve developed a few rules for how I decide what to do to maximize the chances of getting what I want.

You’ve got to like whatever it is you want to do.

The first rule is that you’ve got to like whatever it is you want to do. If you don’t like investment banking, don’t go work at Goldman. If you don’t like software engineering, don’t try to do that at Google. I know this will sound simple but it’s really hard for people to understand, especially if they’re talented people that have a natural gift for that kind of work. You must have the courage and self-awareness, however, to be honest with yourself about if you’re happy doing whatever it is you sign up for. If you don’t like it, you’re not going to be able to physically put in the amount of hours required to become really good at it. And if you can’t become really good at it, you’re probably never going to reach the level of success you’d like.

You’ve got to have either talent or taste in what you want to do.

That brings me to my second rule which is you’ve got to be somewhat naturally talented at whatever it is you choose to do. Love and passion will sustain you in the early days if you’re not talented in the beginning, but if you ever really want to be world-class it’s something you’ve got to have some natural talent. I love playing basketball as much as anyone, but the truth is I’m really not that good. If I simply did whatever my passion told me to do, I surely would face tremendous hardship and disappointment pursuing my NBA dream.

There should be a market need for your work.

The third rule is the world needs do you have some need for whatever it is you want to do. The level of that need is going to be up to how ambitious you as a person are. If you really love painting toy soldiers and you’re really quite good at it, you can maybe make a living doing that but because so few people are interested in it your level of impact is going to be limited. On the other hand, If you’re really into psychology in relationships and you’re decent at engineering, you can have a massive impact on the world by building a dating app because the need is so severe and so widespread.

You should be strategic about launching your dream career.

The last rule is something that people forget about but for me has been really important – and that’s that whatever you want to do should derive from your strategic position right now. If you’re making sandwiches at Subway and you like math and you’re pretty good at it so you’re thinking about becoming an engineer, you shouldn’t immediately quit your job and apply for a job at Google. Instead you should be strategic and buy an online course on engineer in interviews or enroll in a boot camp were you can be smart about getting to that next step. If you’re working a job in IT and you’d really rather be doing music instead and people say you’re quite talented, don’t immediately quit your job and make music all day. Instead, on nights, weekends, and early mornings, try to record songs and put them in an album and sell that album so that it’s making enough money that you can live on. This last step is often forgotten but is a sure fire way to hedge most of the risk in doing something you love.