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8 Reasons Not to Become Your Own Boss After 50

A rebuttal to a Next Avenue piece on midlife entrepreneurship

By Jack Fehr

Last month, Next Avenue published 8 Great Reasons to Be Your Own Boss After 50 by small business adviser Jeff Williams. While Williams made valid points, I’m here to tell you that there are also equally great reasons not to pursue this option.

As a small business owner for 25 years, I know that running your own show has lots of pluses. But, in contrast to each of Williams’ 8 Great Reasons, here are eight considerations to ponder before making the jump:

1. Your age matters a lot when launching a business. While it’s true, as Williams said, that your product or service might trump everything, ageism can rear its ugly head whether you’re an employee or business owner. Even without overt ageism, people will buy from people they relate to.

Age also matters when it comes to the tons of energy and time that being your own boss will require. You may be fitter than you were 30 years ago, but there’s a good chance that you aren’t in the best shape or health of your life.

2. You can’t always combine working for a mission and for money. Williams’ article talked about how flexible schedules give entrepreneurs more time for charitable work. That’s not always going to be true. If, for example, you open a retail store or restaurant, expect to work long hours.

One way to guarantee you can do both, if you have the means, is to start, fund and run a foundation. Another way is to work part-time, maybe in retirement. Otherwise, you’ll have the same difficulty finding the time to give back whether you are an employee or a boss.

3. You can’t always work from almost anywhere. I can, most times; I’m a writer and Have Laptop Will Travel. And an Internet-fueled business might provide an opportunity for mobility. Others aren’t as fortunate, though.

If you’re the boss of a brick-and-mortar business, your physical presence is required. With this line of work, unless you own something like a summer ice cream stand or a beach business, you’ll have a hard time scheduling snowbird trips to Florida.

4. You can’t avoid getting (part of) a pink slip. No, you won’t fire yourself, but your customers might give you the heave-ho by moving their business elsewhere.

Minor issues can become major, like a customer complaint that snowballs on social media and damages your brand. Or the 800-pound gorilla — a poor economy — can squash it. Sooner or later, the economy will slow.

According to the U.S. government, about three in 10 businesses established in 2011 were history three years later. And that was during relatively good economic times.

5. You can’t always pick the people you want to work with and the ones you don’t. Ah, one of the great myths of small businesses: choice. Yes, you can choose your employees and vendors. And you can choose your desired customer market.


But you can’t always pick your customers. You have little control over who wants to buy your products and services. Moreover, you won’t want to discriminate against potential paying customers when getting a small business off the ground, even if they are difficult.

6. Yes, you can have multiple sources of income — but you can have multiple sources of expenses, too. You may become a multi-threat business owner/consultant/author by leveraging a lucrative skill (assuming you have the desire to work 24/7). But understand that owning multiple businesses often means incurring a boatload of new expenses.

Depending on your legal structure, you may now owe the half of the Social Security taxes that your ex-employer paid before you became your own boss. And you’ll now pay for things like staff, benefits, accounting and legal services.

7. Sure you can enjoy shorter, more flexible work hours — if lower income isn’t a problem. As a writer, I expect to slow down and work fewer hours at some point. But not every entrepreneur newbie will have that luxury.

And whatever business you own, you will still need to do the increasing amount of marketing via social media that is vital for success today. Sorry, but most experts don’t equate flexible and shorter hours with new business ownership.

8. Yes, you determine your financial progress, but only to a point. The economy, your health and other impediments can block your financial success.

In short, starting your own business can be a life-changer, grow your income and give you greater purpose. Or it can cause more stress than before you were the boss.

So do your research to ensure that starting your own business will really produce the changes you want.

Jack Fehr is a financial writer, blogger and content creator whose specialty is making sense of financial-speak. Read More
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