Labor Day for the self-employed

Image: Wilstar

I’m working today. A lot of you have today off. But I’d never trade my independent life for a job again.

Here’s what it means to be an independent freelancer.

It means I get to savor the joy of concentrating on work for a whole day today while the rest of you are at the beach or having a cookout or doing back-to-school shopping or dreading going back to work on Tuesday.

It means I can knock off at four if I feel like it and nobody will be looking over my shoulder. Or I could take a long lunch with my wife. Or I could go out biking for an hour and half in the middle of the day.

It means I get to pick what I work on today. In this case, it’s editing two books, preparing for two speeches, and picking next year’s health insurance plan. (Guess which of those is the only part I don’t want to do.)

It means I can blog about whatever I want and not give a fig about whom I might offend. (Not that today’s post is particularly offensive.)

It means if I want to take a Tuesday off next week, to go to a museum, or take a long bike ride, or binge Netflix, or take care of a sick kid, I can do that, and you and my clients will never know the difference.

It means I can embrace projects I love, even if they don’t pay as much, or reject projects and people I don’t like, even if they really want to work with me.

It means Facebook, LinkedIn, Twitter, and this blog are my marketing channels.

It means I can hire designers, graphic artists, copy editors, accountants, Web developers, furniture makers, and PR folks to do what I need them to do, pick only the contractors I like, pay them what they deserve, and write off the expense.

It means my professional friends are my network, and as a result, I like all of the people I work with. If they need help, I’m going to help them. And I know they’ll be there for me when I need help.

It means my hourly compensation is the highest it’s ever been — but my clients, by virtue of not having to go through an employer marking up my rate for “overhead,” are getting my work more cheaply than ever before.

It means I can fly any airline I want (or avoid any airline I want), even go first class or stay in an Airbnb on the road, and still write off the expenses.

It means I get to keep a lot more of every dollar I make because of the tax advantages.

The gig economy works for me because I like the gigs I’m getting.

This situation is ideal for certain kinds of people: people splitting time between work and family; people with a financial cushion from liquidity events, inheritance, or hard work; people who have lucrative part-time careers and time-consuming hobbies; people who’ve developed a reputation and want to benefit from it.

Frankly there is only one drawback.

The health insurance is wicked expensive, complicated to figure out, and keeps going up. The only reason I can make that work at all is that, after 30+ years, I’m at the high end of my profession and benefiting from all those freelancer tax breaks.

A nation with more freelancers, and less people chained to corporatons, would be far better able to flex as the economy and the job market shifted. But to do that, we would have to fix the health care world.

The Affordable Care Act (aka Obamacare) is becoming less and less workable. Undermining it by removing the individual mandate will make it worse. Repealing it altogether would put me out of business. It’s time to fix it.

That’s going to take both parties working together. And you can raise my taxes to pay for it — I’ll keep doing just fine.

Please don’t make me go back to the corporate world, or force me into early retirement, or make me divorce my dear wife, who is an artist, and marry some working stiff.

On behalf of all the freelancers and independents in the world, we’re counting on you.

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  1. You hit the nail on the head regarding health insurance. It’s one reason I’ll stay in academia for a couple more years even at lower pay until my wife and I hit 65 and Medicare kicks in.

  2. I appreciate your labors, Josh. As a professor of mine at Cornell once wrote, “small is beautiful”. We’re blessed to labor as small business-persons and I’m pleased to guide my clients towards financial independence.

    Healthcare must be resolved and moral capitalists (Buffett, Dimon, Bezos) led by Atul Gawande may chart a path forward.

  3. Universal taxpayer paid medical care would free thousands, if not millions, of people from jobs they hate. Or enable thousands, of not millions, of people to go to part time work, or retire-opening up positions for younger people. Or allow people to become freelancers, or open their own small businesses, or work for small businesses. And it would allow corporations and governments and other employers to pay more and provide more kinds of other benefits, like family leave, vacation, etc. the lack of universal health care is stifling creativity!

  4. Yes, I write this as I wrap up my Labor Day workday. Yes I am also planning to play midweek as I often do. I choose to work weekends for this reason. Grocery stores, ferries and doctor’s offices are either (a) closed or (b) busy nights and weekends. Mid-day during the week I can shop or schedule appointments so much more easily. I agree an academic calendar is wonderful. Less the many members of the woodwork who really need to retire because we are all really tired of them. Financial cushion (aka FU money) or “a purse” for women of a certain age, is also necessary to avoid being a slave to “the man”. Now as an MBA on Steroids (working on my DBA) I can say that my one and only mission in life is to serve those who serve with as little of the corporate wonk routine as possible. Wish me luck. I will need it. LOL