Lowering one's tax burden is not the reason to pursue self-employment, but it is something worth understanding if you're exploring self-employment.

It's tax preparation time, the secular equivalent of crawling around the temple on cobblestones littered with broken glass. When our numbed minds read instructions like this--"Enter the smaller of line 10 or line 14. Also enter this amount on the applicable line of your return (see instructions)"--we wonder which is more applicable--Kafka's Castle, filled with unseen workers toiling away 24/7 getting nothing remotely useful accomplished, or Huxley's loving our servitude, or perhaps a tortuous mix of both.

The simplified form for wage earners is much easier, of course, but it offers precious little in the way of deductions or tax breaks. The tax system for wage earners without huge mortgage interest or out-of-pocket medical expenses deductions is relatively skimpy in terms of tax breaks. The complexity--and the tax breaks--apply mostly to enterprises, from sole proprietors on up.

I am not a tax professional, I am only sharing my experience as a self-employed worker. This is not tax or financial advice, it's an account of what I've learned preparing my own taxes for decades. Like most people, I rely on the tax preparation software to comply with tax codes and to do the heavy lifting of preparing the tax return.

Of my 54 years of working and paying taxes, 14 were as an employee and 40 were self-employed, so I have experience in both realms. What continues to amaze me is the number of straightforward tax breaks available to the self-employed / sole proprietor.

Let's avoid sugarcoating self-employment: it's difficult, demanding and risky. As a general rule, self-employment demands more of us than being an employee on all fronts: we own it all, victories and mistakes. Regulatory burdens and shadow work eat us alive. Much of what passes for self-employment now is low-paid gig work with little upside.

So there is a trade-off here: self-employment is difficult to build up and keep going (taking a vow of poverty is a good start), which is why so few people manage to earn a middle-class income via self-employment outside the professions (accountant, attorney, etc.)--and even those fields are not easy paths to reliable livelihoods.