The Freelance Life
Security is mostly a superstition. It does not exist in nature, nor do the children of men as a whole experience it. Avoiding danger is no safer in the long run than outright exposure. Life is either a daring adventure, or nothing.” – Helen Keller
I’m a 58-year-old freelancer, and I think Helen Keller is right. I suppose I could start by calling myself something more responsible like, “consultant,” but the pirate in me prefers “freelancer.” “Freelancer” has more of a spirit of adventure, doesn’t it? Yes, I’m part of the 1099 Workforce and I’m proud of it.
Combine this strange new world of work with the fact that my generation is hated by the other generations – particularly Millenials. Check out stories like, “Baby Boomers Are What’s Wrong With America’s Economy.” We also don’t do ourselves any favors with hashtag wars like “How To Confuse A Millenial.” It’s not easy for us more mature folks.
That hasn’t seemed to matter lately.
I’ve got approximately 126 cover letters and resumes that I’ve sent out that were either ignored, opened with, “Dear Applicant, while your credentials are impressive, they didn’t match with, blah, blah, blah,” or some form of “Dear Hans, you’ve been out of the game too long.”
I’ve done the startup thing before. I am almost officially unemployable through temperament and circumstance, so I’m doing it again.
My 10-year old was surprised that I actually do more than make dinner, meditate, and workout. That stung. It’s not too early for her to learn that there’s such a thing as “freelancing,” but there are a lot of cultural myths and head-buried ostriches in her world to make this lesson an easy one.
I intend to slip this Fast Company article under her pillow.
When she’s older, I’ll tell her about being “antifragile.” This is where stressors, randomness, and disorder make you stronger and more resilient. As a freelancer, you will need to be/become antifragile or you will fail. Nothing in your formal education prepares you for this.
I started a school in 1993. Its presence disrupted the drug trade on the block, so a contract was taken out on my life. The NYPD facilitated my getting a carry permit, and a Lieutenant suggested the type of bulletproof vest I should wear. The threats weren’t idle. There were over 2,000 homicides that year.
I was afraid. I had a few friends help me get through like NYPD Sergeant (ret.) Anthony Acosta. I stayed in an almost constant state of fear. I learned hypnosis and NeuroLinguistic Programming to help manage my emotional states. Needless to say, things worked out. Those years taught me about a certain kind of fear. I wonder if they somehow prepared me for the fears and pitfalls I’ve had to confront as a middle-aged freelancer:
- fear of failure
- fear of success
- the comfort of mediocrity
- fear of rejection
- the Impostor’s Syndrome
There is pain and struggle on the road to becoming antifragile, but the benefits are worth it. Read the news. Is there a better time to learn how to benefit from disorder?
Self-awareness and self-acceptance play a more important role in my life than my self-esteem. As I mentioned above, I learned hypnosis. I did it out of curiosity and to improve my performance. During my training, I learned that we are all in a trance. My goal was to make it a trance of my own choosing.
Part of my early trance was that I would become a lawyer to solve the world’s problems and gain some social status at the same time. Plus, I had convinced myself that I wasn’t any good at math, which knocked out medical school.
Is freelancing the right path for you? Do you live by your values or by what you’ve been told you should do? My top 3 values are Freedom, Creativity, and Service (not necessarily in that order). Freelancing holds the possibility of me being able to live by my values. “I do it for the possibility and not for the promise.” This path is not for everyone. I respect that.
The World of Work Is Changing Fast
I get it. Some people just want to turn the lights on and have someone tell them what to do. I hope that doesn’t come across as insulting. In fact, my wife fits into this category. She is uniquely talented for going out on her own and impacting a great number of people, but she has those fears.
People I haven’t seen in a while excitedly ask me what I’m doing now. They remember the award-winning school I founded and the national press that came with it, the $14 million nonprofit where I led 350 employees or the consulting I did for a major police department. When I explain that I am helping socially responsible businesses with their online marketing, they cast their eyes down and try to change the subject.
In addition to the embarrassed silence from old friends, there are a couple of other downsides. One is that it’s a lonely existence. I have really learned to like myself!
Researchers and a few legislators are beginning to study the new world of work. They are asking questions about the “gig economy” as a bridge to more traditional employment, and as a path to creativity and freedom. The lack of labor protections and the level of financial insecurity are also part of the package that comes with this new territory.
The Sharing Economy, Automation, and the End of Work
Another downside is the lack of perfect clients. Perfect clients are the ones who pay what you ask, recognize you as the expert, and who have an ego one step down from yours. I’ve found a few – mainly in Australia, strangely enough. I have lowered my rates for people who can’t afford them, and I have been burned by some of them. I’m now focused on clients who have the need, understand their need, and who have the budget to get it addressed. If I make more money, I can better support the people and organizations I care about. This has been another hard lesson. Do you also suffer from a “caretaker personality disorder?”
I have two new books on my Kindle. One talks about the *genius* of business leaders who are automating as fast as they can as they reduce their workforce. The other talks about how American workers are getting screwed because of automation, artificial intelligence, and the sharing economy.
We did the AirBnB thing when we had our Harlem brownstone and I’ve flirted with the idea of doing Uber on the side. These enterprises reward initiative and drive. They also encourage competition and redundancy.
Technology and efficiency will be pursued by businesses of all sizes, regardless of the human cost. Decreasing consumer demand and too few jobs will usher in an economic Singularity that we can choose to fear. Or not.
I don’t think enough attention is being paid to how we’ll harness AI and other technology for the benefit of the larger group vs. the benefit to the oligarchs and tech giants who create and control the machines. The social contract has been broken. Most workers are unprepared for this and the school system is definitely not providing the skills necessary for navigation in this new world.
We have national leaders arguing about the minimum wage and whether to protect jobs from “unfair” foreign competition – or not. They won’t tell you that the jobs that may or may not be up for grabs, won’t be around much longer anyway. They would do better talking about the merits of a Universal Guaranteed Income. Insitute that, and no one will question me anymore if all I do is make dinner, meditate, and workout.
Promise vs. Possibility
Most of us are looking for guarantees. As a freelancer, there are none. It helps to reframe your outlook from being anxious about the outcome to loving the process. I’ve learned to love the process. Combined with my dislike for bosses, I feel that I’m in a pretty good place, in spite of my *advanced* age. While I’m not an Ayn Rand acolyte, I dislike crony capitalism and the coercion of the State. If Soros or the Koch brothers wanted to fund me, I would have a boarding school where the students’ first job would be to learn how to be useful.
Some of this comes down to fighting against the “victim society” we’re becoming used to in favor of the dignity/honor society. Dignity and honor used to hold a special place but is now derided as primitive, hyper-masculine and tribal.
Are You Prepared?
Don’t want to make the leap to freelancing but still want to be prepared for what’s coming? I’ve got you covered:
-Start a vegetable garden.
-Develop a side hustle. Start exploring things like Upwork and LinkedIn Profinder.
-Start an exercise program that makes you stronger. Strong people are harder to kill.
-Understand that your body is not the limousine (or minivan) for your brain.
-Improve your nutrition.
-Learn how to draw.
-Instead of asking, “Why is this happening to me?” Ask, “Why is this happening for me?”
-Develop a morning routine.
-Read about Artificial Intelligence and Aeroponics.
-Join a Maker’s Space.
-Have a fixed mindset? Change it to a growth mindset. Carol Dweck writes about this.
-When something goes wrong, ask yourself, “What’s one thing I can do now to make it better.” Do that every time something goes wrong.
-Track your blood sugar levels.
-Develop your creativity/idea muscle.
-If you’re the smartest one in your group, find a new group.
-Create a meditation practice.
-Change your relationship to failure.
-Learn lifesaving skills.
-Thoroughly research the alternatives before getting that back surgery.
-Learn hypnosis. We’re all in a trance. Make it one of your own choosing.
-Don’t trust experts.
-Take a reality-based self-defense course.
-Determine your top 3 values. Mine are freedom, creativity, and service.
-Take stock every day to determine if you’ve lived by those values.
-Take an improv class.
-Whether you like it or not, you’re a sales person. Get good at it.
-Learn carpentry or how to use a chainsaw.
-Scare yourself in a survivable way at least once a year.
-Learn how to shoot. You don’t have to buy a gun but it will at least give you some common ground with the Red Staters you’ve learned to shun.
-Join a homeschooling group.
-Decide where your passions, skills, and market demand intersect.
-Do a monthly fast.
-Learn the Emotional Freedom Technique
-Take a *forest bath* as often as you can.
It’s a long list. I know. Email me at firstname.lastname@example.org and we’ll schedule a free consultation on how to put this together or talk about why you even should.