Straight Talk About Being Self-Employed

Straight Talk About Being Self-Employed

This is by Bob Bly, freelance writer extraordinaire. You can sign up for his e-newsletter here. I highly recommend it!

Don’t get me wrong.

I would much rather be self-employed than working for a company.

But I do think the idea of being your own boss and starting your own business is a bit oversold by promoters of courses on how to do those things.

Their marketing tells you the many advantages of being a freelance, solopreneur, or small business owner … and most of
what they say is true to one degree or another.

But what they do not tell you are the drawbacks of being out on your own.

So in the interest of fair play and full disclosure, here are a few of the things that are not so good about being an independent
contractor or small business:

1 — Every 3 months you have to make a large quarterly payment toward your estimated federal and state (if your state has it)
income tax — whether you have cash in the bank or not when the payment due date arrives.

2 — If you work at home, you have to empty your own waste basket. I know, that sounds like a small thing. But mine seems to be filled to overflowing every 15 minutes or so. At Westinghouse, a janitor emptied my trash every night — no cost to me. Now I even have to buy my own trash bags to line the waste can!

3 — When you work for someone else, they provide and pay for just about everything. When you are self-employed, you pay for everything from office space and furniture, to computers, printers, and printer ink cartridges (which cost a fortune today).

4 — There is a health insurance crisis in the U.S. today, and health insurance costs an arm and a leg, no pun intended. But
there are few things more dangerous to both your physical and financial health than going without health coverage. A huge

5 — Self-employed? No pension for you — and no matching contributions by an employer to your retirement plan. Today fewer
and fewer corporate people have these things — but many still do. We freelancers do not.

6 — Life has gotten more and more expensive today. Incomes to me it seems have not kept pace with inflation. When I got my BS in the late 70s at the University of Rochester, it costs me for all 4 years — tuition, room, and board — around $16,000. My son spent 4 years getting his BS at Carnegie Mellon. He graduated 2 years ago, and the total bill was around a quarter of a million dollars — more than 15X what I paid for my degree. I know the average white-collar worker today does not earn 15X what my dad did when I was in school.

7 — Freelancers do not have the luxury of getting sick because we do not get paid sick days. When an employee takes the week off with bronchitis, his corporation chugs along fine without him, with others easily taking up the slack. If I were home sick for a week, not only would my copywriting business make no money, but I would worry and fret about clients, projects, and deadlines.

8 — My friend KK has been in IT with his company for over 3 decades and at this point gets 5 full weeks of paid vacation a year. I have never taken more than a week’s vacation in a year in my life. For many years I only took long weekends, because the demands of my clients did not allow me to be gone for an entire week.

9 — Most freelancer writers work alone, sitting in a room, with no co-workers to chat with. While I am usually fine with that, you can, like Jesse the Maytag repairman, get lonely. If you are a people person, in a corporate job you spend a lot of time near and with team members and other co-workers.

10 — Many small businesses have a crisis-lull-crisis rhythm: they are either too busy and pressured to fill orders on time, or they are slow and in need of new business and cash flow. For them, it either rains or pours — and only rarely is the workload at a happy middle ground.

And believe me, this is far from a comprehensive list of the dark side of being an entrepreneur or independent contractor. I could easily double the number of items.

So to paraphrase Sylvester Stallone’s speech to his son in Rocky Balboa — the freelance life ain’t all sunshine and roses. Be

But for me and many others I know, it sure beats the alternative.


Bob Bly