Most career problems stem from the fac that we are terrible at picking jobs. We think we are picking a good job and then it turns out to be a bad job. It's almost impossible to pick a good job on the first try, actually. So don't think you'll be the exception.

Economist Neil Howe says that only 5% of people pick the right job on the first try. He calls those people "fast starters" and in general, they are less creative, less adventurous, and less innovative, which makes a conventional, common path work well for them. So it's questionable whether you should even aspire to be one of those people who picks right the first try. But, that said, we all still want to be good at choosing paths for ourselves. So, here are some guidelines to think about—whether it's our first career or our fifth career.

Don't Believe the Hype

We have a grass-is-greener approach to professions that are not our own. For example, this award-winnng video from Chipotle about farmers becoming more animal-friendly pretends that it's just a mental and emotional evolution for farmers to realize that going back to nature, and being good to animals, is what feels best, so they should do it. It's so easy, for example, to take the pigs out of an assembly line.

The Chipotle video is total crap, to be honest. It's not that farmers don't know that pigs on pasture is nicer. It's that there is no market for pigs on pasture because consumers won't pay enough to eat humane meat (without farrowing crates, for example, pork prices would quadruple). So the idea that being a farmer is so beautiful and back-to-the land is just absurd. Being a farmer is actually really complicated, hard entrepreneurial work with very low wages.

Another example of a hyped up job is a lawyer. You see their exciting life on TV: a gloriously safe path from college to law school to a high paying job. But behind the scenes, each year the American Bar Association conducts a survey to ask if lawyers would recommend their profession to other people, and the vast majority of lawyers say no.34
Pick a Lifestyle, Not a Job Title

Look at the lives you see people having, and ask yourself whose life you would want. That's easy, right? But now look deeper. You can't just have the life they have now. You have to have the life they lead to get there. So, Taylor Swift has had great success, and now she gets to pretty much do whatever she wants. But could you do what she did to get there? She had her whole family relocate so she could pursue her dreams in Nashville. Do you want a life of such high-stakes, singular commitment?

Look at the successful writers you read. Most of them wrote for years in obscurity, risking long-term financial doom in order to keep writing. Do you really want that path for yourself?Marylou Kelly Streznewski, author of Gifted Grownups, finds that most people who are exceptionally creative have to give up almost everything else in order to pursue "creativity with a big C." For most people, that path is not appealing.

The same is true for startup founders. It's a terrible life, to be honest. Your finances will be ruined, you won't have time for anything else in your life, and your company will probably fail. So when you decide you want to do a startup, look at the life the person had before their company got stable. Most people would want to run their own, well-funded company and control their own hours. Very few people would want the life you have to live to get to that point.

Don't Overcommit

Testing out lots of different jobs is a great idea. Job hopping is the sign of someone who is genuinely trying to figure out where they fit. Quitting when you know you're in the wrong spot is a natural way to find the right spot. A resume with lots of wrong turns is not cataclysmic. You can hire a good resume writer to fix the resume so it looks like you actually had focus and purpose. (Really, I rewrite peoples' resumes all the time. It's about telling a storyand everyone has a way to tell a good story about their career no matter how many times they've changed jobs.)

The important thing is to not overcommit to one path. Graduate school, for example, is overcommiting because if you don't end up liking that field, you will have spent four years gaining entrance into the field. Taking on college debt is overcommitting because you are, effectively, saying you will ony take jobs that are relatively high paying in order to service the debt.

Buying a big house has that same effect: you overcommit to a high-earning field. Very few people want to have the same career throughout their life. Leave yourself wiggle room to switch because there is little reason to believe you'll be able to predict what you will like in the future.

Daniel Gilbert, head of the happiness lab at Harvard, has shown that evolution has ensured that we are terrible at guessing what we will like. We guess that we will like stuff that is possible for us—that looks attainable—which is what makes us keep going in life. We are generally optimistic that things will get better. This is not rational because, for the most part, things stay the same in terms of how happy we are.

Gilbert explains in his book, Stumbling on Happiness, that we have a happiness set point, and that's pretty much how happy we are today and it's how happy we will be tomorrow. But evolution has made us certain that something will make us happier tomorrow. Which means we are generally poor at predicting what will make us happy since that was not a necessary trait in preserving humanity.
Gilbert says you need to try stuff to see what will make you happy. Do that. It's scary, because it's hard to find out that what you thought would make you happy will not make you happy. But then, it's true that being a realist is not particularly useful to human evolution either.
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Penelope Trunk

Penelope Trunk is a serial entrepreneur and author of the best-selling career guide, Brazen Careerist: The New Rules for Success. Read her blog here.
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