Anybody else feeling the only way to have any measure of freedom in your life these days is to run your own business? I would rather be a the whim of customers than some manager.
You'd rather give up the clarity that comes from working for a single person who you can ask exactly what they want, get near-instant feedback on whether it makes them happy, so that you can work for some fickle, amorphous, faceless people who you have little control over whether or not they keep paying you in the future, forcing you to constantly hunt for more, even paying large sums of money (i.e. marketing) to find them?
There's lots of great reasons to run your own business, but if your frame of mind is that you're working "for" your customers, that's definitely not one of them. Successful founders fall in love with solving a problem that many potential customers have, not with working for their customers. It's not the same thing.
Obsession with solving some problem experienced by many is a very specific mindset that sets tech startups on the direction of hockey stick growth.
The pizzeria focuses on the taste of the pizza, the decor, and politely refuses people who ask for canned tuna to be put on the toppings menu. The barbershop focuses on ambiance, banter, hot-towel service, and politely shows the door to people who insist on taking phone calls while they get their hair cut. The real estate agent makes sure the house is well-photographed, well-staged, has warm cookies in the kitchen (well known trick that helps people think of the house as home), takes appointments, and refuses to accept appointments at weird hours.
Even the businesses that you'd think are customer-obsessed are usually really product-obsessed. Even Eleven Madison Park, which Will Guidara wrote about in "Unreasonable Hospitality" as being focused on going to outlandish, hyper-personalized extremes for every customer they had at the restaurant, succeeded ultimately because Guidara succeeded at turning empathy itself into a product, from standard perks like putting more quarters into people's parking meters so they wouldn't have to worry about that in the middle of service, to hyper-personalized ones which were still due to standardizing a process of listening and creativity. But their process never allowed customers to dictate to them exactly what they would be served or exactly which favors they would receive.
I’ve done some contract work in the past and I think the trick is getting the right customers. I was hired by mine specifically for my expertise. They didn’t micromanage me or make me subject to my whims, they had a problem and recognised that I had the skills they needed to solve the problem.
Of course they are. After all, great businesses adapt quickly to changing market conditions, and that is reflected in changing priorities, requirements, and expectations. But reasonable managers will not hold the lack of stability against you, understanding that the work you did was, after all, what they had asked for. They will be happy with your output even if it's ultimately not useful to the business.
If your manager is fickle and they hold it against you, well, life is too short to work for bad management. It's usually much easier to find a new manager (i.e. a new job) than it is to find enough customers that pay enough money for you to not only offset your expenses but to afford a decent living.
Working for somebody is by definition a tradeoff of freedom of making decisions for stability and not having to worry about attracting capital, labor and customers, which is very hard and often under-appreciated by folks who haven't tried themselves.
It does surprise me there’s no political will to change things. Having to provide healthcare is a burden to employers, it prevents workers from pursuing their entrepreneurial dreams… you’d think both sides of the aisle would want change. But alas.
Then I branched off into https://www.moonlightwork.com which also worked quite well until I found a contract there that essentially became a full time position.
I am still contracting but serve now as CTO for this company.