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The Pros and Cons of Being Self-Employed
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How To Start A Business With Your Customer's Money

Many of us dream about quitting our jobs to work for ourselves. That is especially true around the April 15 tax deadline, because we imagine having to fork over less money to the government.
Nearly 17 years ago, I was laid-off (again) from a tech. support position at web hosting company.

You have to plan, and save aggressively, to make the most of the arrangement.

When you work for yourself, tech firms such as Dropbox and Apple become your IT department. 

Going out on my own has been worth it both personally and financially. I have to plan, and save aggressively, to make the most of the arrangement.

It is true that you can deduct business expenses from taxable income, while those who earn a salary from an employer can only deduct business expenses when they exceed 2% of adjusted gross income. If you are the type of person who spends money from your own pocket on business-related items, such as a laptop computer and work-related travel, the deduction can be a real benefit.

Yet all expenses claimed must "have a legitimate business purpose," warns Jeff Porter, a certified public accountant in Huntingdon, W.Va., and chairman of the tax executive committee of the American Institute of CPAs.

Meal and entertaining expenses are only 50% deductible, he says, and you must keep accurate records. Using one credit card only for business expenses can help.

That legendary deduction, for using part of your home as an office, is often "much ado about nothing," Mr. Porter says. To take the deduction, he notes, you have to set aside space exclusively for business use—you can't just stick a desk in the family recreation room.

The savings may not amount to very much anyway, often just a small share of items such as insurance and utilities. Renters will usually benefit more than homeowners, who already can deduct mortgage interest and property taxes from their income taxes.

The self-employed have to be disciplined and pay estimated taxes by the end of each quarter. No payroll department is withholding taxes for you. Furthermore, once you are self-employed you have to pay more in Social Security and Medicare taxes, as you are now both employer and employee. The extra taxes are themselves deductible from income tax. Depending on your income-tax bracket, this is apt to cost you in the end maybe an additional 6% on income up to the $117,000 Social Security cap, above and beyond what other workers pay, and about 1% extra above that.

On the other hand, I have saved a bundle on taxes by setting up my own 401(k) plan. A "self-employed" or "solo" 401(k) plan, offered by many brokerage and investment companies, lets you save the first $17,500 of your income tax-deferred, plus another 25% of your net income. The limit on annual contributions is $52,000, plus an additional $5,500 if you are 50 or older.

Few big 401(k) plans allow salaried workers to save anything near that much because of complex rules designed to prevent favoring highly compensated employees.

To get the full benefit, naturally, you have to save a lot. Many find it difficult to sock away the limit each year. David Kautter, managing director of the Kogod Tax Center at American University in Washington, says he often recommends using a Self-Employed IRA instead. It lets you save 25% of net income—again up to the $52,000 limit, plus $5,500 for those 50 or older—and the paperwork is lighter.

Controlling your own retirement plan also means you can choose whichever investments you like. You are no longer restricted to an employer's menu of mutual funds.

When you are self-employed you lose out on certain benefits. For example, you no longer get a company match to your 401(k) plan, and you have to pay the full cost of your health insurance yourself. But for many workers, the value of such benefits have been shrinking for years, as companies shift more costs to their employees.

Many people are worried that health insurance will cost them a fortune if they buy it themselves. Yes, it costs more. But it hasn't broken my piggy bank, and there are some offsetting benefits. You get to choose your own plan. As insurers can no longer exclude pre-existing conditions, it is easier to shop around, and that can save you a lot. Furthermore, thanks to the complexities of the tax code, choosing your own plan can sometimes allow you to make more of your health-care spending tax deductible.

Going solo brings other costs and benefits. You are your own boss, though if you want to eat, your customer is really your boss. But you have greater freedom to work for multiple customers and pursue higher value-added work.

You also are liberated from office rules, politics, meetings and the associated costs. A 2008 study by Thomas Astebro of the business school HEC Paris and Jing Chen and Peter Thompson at Florida International University in Miami, found that those most likely to gain from self-employment are "stars and misfits" who feel held back in a large organization.

When you work for yourself, you exchange your company's IT department for Google or Apple or Dropbox—for better or worse. You also are spared a daily commute, which studies show is among the least popular uses of time. Depending on what you do, you also may be able to work where and how you like. It is easier to be independent than many think.

Monty Henry, Owner

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DPL-Surveillance-Equipment.com is a world leader in providing surveillance and security products and services to Government, Law Enforcement, Private Investigators, small and large companies worldwide. We have one of the largest varieties of state-of-the-art surveillance and counter-surveillance equipment including Personal Protection and Bug Detection Products.

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