Some Thought on Career Building in the Age of Freelancing

Or as a friend called it on facebook, “career” “building” in an age of freelancing.

This post is inspired Professor Hanley’s post on the Minimum Wage and various conversations I’ve had here and with other people over the past few years.

I’ve mentioned it before but law was not my first career choice. I originally wanted to be a theatre director but switched to law because I was starting to realize how next to impossible to have a career as an artist. My general thought is that there are three kinds of people who can work in the arts: The independently wealthy (because it places you out of the realm of normal economics), people who were raised poor and think destitution is the norm, and/or people who are absolutely incapable of any kind of office work/corporate structure (aka true bohemians.) I know people in all three categories. Many people are like me and try to do art in their 20s but eventually switch to law or some other profession because the hand in mouth existence thing sucks. Interestingly, true bohemians might be the least common group.

The problem is that I choose to go to law school at the worst possible time and graduated during the height of the law school crisis/scam. Since then I have been in a kind of middle ground. On the plus side, I have been working on a full-time basis as a lawyer for the past few years and making contacts and impressing people. I have many friends who never worked as lawyers and potentially never will. On the other hand, I have been freelancing for the past few years and have not received an associate offer yet and I know many people who have received associate positions and are advancing in a much more traditional sort of way. Right now I often feel like I am treading water. Sometimes I am treading water in a gentle pool. Other times I feel like I am treading water in the middle of Pacific Ocean during a raging storm. With that overly long introduction, here are my thoughts:

1. The American Media has a way of focusing too much on the rare few that get the lucrative jobs that pay high salaries right away. These are the people who become junior bankers on Wall Street at 22-23, or they work for the big tech companies like Google/Apple/Intel/etc. In the case of law, the people who end up working in BigLaw.

2. Despite their largeness, these brass ring companies do not employ the majority of Americans. Most lawyers in the United States do not work for big, prestigious and multi-national law firms. I never wanted to do BigLaw so it was never the brass ring for me.

3. I think the media focuses on these brass rings because in an age when many people have huge student loans, these jobs can help someone pay off their student loans very quickly. They are also easy and concrete. It is entirely possible to be a well-compensated professional or have a good career without the brass ring jobs but they sure give you a head start. However, it is very hard for the media to focus on people who might start off earnign 30-50K and work up to a very respectable and profitable salary when they are in their 40s and 50s. That story is kind of dusty but common. It is much sexier to focus on 22 year olds with poor impulse control and large salaries because those 22 year olds will do outrageous things with their new money often enough.

4. A person can realize that careers take decades to build on an intellectual level but still have a hard time dealing with it on an emotional and day to day level because it is hard to watch everyone seemingly pull ahead of you. A friend who was in a similar place as me until recently compared it to being picked last for the kickball team in elementary school. I think my other friend called “career” “building” in the age of freelancing because once you are on a non-standard path, you are sort of locked there for the long run and whether things work out or not. The treading water in the middle of the Pacific Ocean feeling is when I think things will not work out for the long run.

5. Long-term freelancing/temping is also a drain because you are usually surrounded by people who have benefits like PTO and Health Insurance. I’ve been paying for my own health insurance for the past few years and have yet to have a job that offered PTO. This means that if I want to take a vacation I have to do a lot of double planning. This is not just economic planning but also a calculus of will I have a job to return to when I get back. So for the past few years, I have taken mini-vacations only of four days maximum and usually less than that and I always come in on the weekend to make up missed work so I don’t miss the income. So it is sort of vexing to see my friends talk about their two to three week vacations in Europe or Asia or whereever. I often feel like Tantalus when I think about things like PTO and company healthcare, they just feel a bit out of reach.

6. Luckily I am pretty healthy but the same calculus exists for being sick, I don’t have sick days and need to think about whether to go in or not if I were to come down with the flu. Likely if I were to miss three days of work from illness, I would probably end up trying to make up the time.

7. There are all sorts of other minor psychic injuries about long-term freelancing. Many law firms will pay for the annual bar dues and continuing legal education expenses of their associates and partners but they will not pay for these expenses for their freelance/contract lawyers. There are also many times when I wonder what is up with me that I can’t seemingly land a permanent position yet. I’m a rather quirky person and often an acquired taste. I’ve been told by many people that they thought I was kind of odd and awkward at first but they really started liking me after getting used to or knowing me. So maybe I have to get a job through less than traditional means but non-standard processes can drag down. Again this feels like the myth of Tantalus, you see your friends advancing in traditionally recognized ways and you feel left behind. I realize on an intellectual level that I should not confuse today for tomorrow and it is also entirely possible that I will be a late bloomer and more successful than the rest of them. My dad took a year to find is first law job and that job paid a third less than his teaching salary. He is now one of the most successful lawyers I know but it took him a long time. This could be me as well but being a late bloomer can also be a very emotionally frustrating experience in the immediate and there is a feeling of possibly never blooming at all.

8. Will Truman frequently notes that people who are not making it in big cities like NYC or SF can always move to places like South Dakota or Montana but I don’t think that is as much of an option for many people except the truly bold. People are social creatures and most people like living near their families and this limits geographic moving rates. Skype doesn’t cut it for people and I don’t blame them for it. There is also the issue that if someone is a member of a minority that makes you want to stay close to fellow tribe members. I’m Jewish and have spent most of my life in very culturally Jewish areas except for a year in Tokyo. I feel very strongly about living in an area with a lot of Jews and/or an area so liberal that most people would consider anti-Semitic comments to be a serious faux paus. I have friends who grew up in areas with very small Jewish population and it does not sound very fun based on their stories. At best you are an exotic curiosity. At worst, you are the victim of real anti-Semitism and bigotry. It doesn’t even have to be a majority of people who commit anti-Semitic or other bigoted attacks. Bigotry follows power laws and all it takes is a handful of committed bigots to make someone feel unsafe and unwelcome. I think this concept is very hard for people to understand unless they are in a minority.