When getting into something new, whether it be a sport, a job, or a whole career, I always use a rule of thumb I call the elder heuristic. I identify the elders, the senior people who have been doing this thing for a long time. They have achieved mastery within their sport/career/job. When I trained karate in high school, the elders were the black belts – the ones who had been training with the club for the longest. When I joined my first corporate job at IBM, the elders were the most senior managers that I came in contact with. When getting into entrepreneurship and building companies, the elders were the most accomplished entrepreneurs around. Look to the elders, because they represent exactly what you will become if you go all the way – if you succeed within this sport, career or organization. If they seem grumpy or unhappy, or just despicable as human beings, beware. If they seem happy, but you could never imagine yourself as happy living the kind of life they live, beware.
You might defend yourself with "But I will not become like that guy, I will do things my way." Unfortunately that kind of thinking is flawed. Every organization, club, company, religion, whatever, has its own culture. The culture is the values that you will need to not only follow, but internalize and make your own core values, in order to advance within the organization. Since the most senior members have the most power over who advances or not, the apprentices with the values most similar to theirs are the ones who will become the new elders a few years later. Sure, you might have differing values, and might choose to do things your way. But that would mean being in a place with a culture opposed to your own values, which isn’t much fun anyway.
The required values aren’t even necessarily dictated by the elders: In order to succeed within certain pursuits, you objectively need to have certain values. For example, I find this very true for entrepreneurship. If you haven’t internalized the values of work ethic and commitment, you will never succeed. These values are not dictated by a culture – they are just necessary to become a successful entrepreneur. You will find this kind of values in the elders as well.
Take a good hard look at the elders, and ask yourself if you would be happy to become like them. If the answer is “yes,” then you have come to the right place — you will probably like it here. If you cannot stand the thought of becoming like them, you should look elsewhere.
I have always used the elder heuristic to quickly gauge whether this new thing I joined is for me or not. In the case of karate classes and the corporate job at IBM, they were not for me. When I looked at the elders in these places, and imagined myself in their place in the future, I didn't like the feeling of it. In the case of entrepreneurship, I liked what I saw when I looked at the elders. So I pursued entrepreneurship for many years and it fulfilled me. This is also the case right now, when I look at the elders within the occupation of writing. I talk to them, listen to interviews of what their lives are like, I read their autobiographies. And my gut feeling is a good one.
This is a simple rule of thumb to use whenever you are about to enter a new pursuit. Look at the elders, who have gone all the way, and then turn to your gut feeling to decide if it is worth it.