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8 Great Reasons to Be Your Own Boss After 50

Why this small biz guru is big on second-act entrepreneurship

By Jeff Williams

Due to massive downsizing, forced early retirements and job burnout, more and more people 50+ are looking for an alternative to a corporate job for the next stage of their lives.

As a coach to startups run by people over 50, let me give you eight reasons why becoming an entrepreneur can let you combine passion and profit and enrich your personal and professional life:

1. Your age doesn’t matter when you run your own business.

Whether your new company is selling products to large corporations or services to consumers, your customers don’t care how old you are. They only care that you deliver what you promised when you promised it.

In fact, in some businesses like corporate consulting, a bit of gray hair can strongly communicate experience and wisdom and give you the edge on winning contracts.

2. You can combine working for mission and for money.

Often while you are climbing the corporate ladder, there’s no time to volunteer or do charity work. When you become your own boss, however, you can combine giving back to your community with making a nice living.

In many communities, local small business owners provide much of the volunteer work and charitable investments because they often have more flexible schedules than their corporate brethren.

3. You can work from almost anywhere.

If you work with your customers at a distance, deliver consulting advice at your client’s location or sell a product through an online store, the physical location of your headquarters doesn’t really matter much for your success.

Using a tablet or smartphone, you can stay in touch with your customers from almost anywhere. This means you may be able to live in more than one location during the year (a warm-weather place in the fall and winter, a cool-weather place in the spring and summer) to better enjoy your desired lifestyle.

4. You can avoid getting a pink slip ever again.

In the corporate world, one person can get you fired. But when you run your own business, your ability to survive and thrive comes from finding a group of customers who want what you are selling. Keep them happy, and many will not only buy repeatedly from you, they’ll also tell their friends.

5. You can pick the people you want to work with and the ones you don’t.

It is uncommon in a corporate career to be able to choose your boss. But, when you are an independent business owner, you can often choose which clients to pursue and which vendors to buy from.

One exception: when you sell your product through an online store, where essentially anyone with a credit card could be your customer.


6. You can have multiple sources of income.

Serial entrepreneurs have launched two or more businesses, but there’s an even larger group of small business owners: “sequential entrepreneurs.” They extend the financial foundation of their original business into three, four or more ways to make money.

For example, a career coach might build her business around one-on-one telecoaching and then add a self-published book for sale, a fee-based live workshop and paid speaking gigs to institutional and corporate audiences, talking about job-search techniques.

Having multiple sources of income gives you much more security as the economy flexes up and down.

7. You can enjoy shorter, more flexible work hours.

Corporate employees often work punishing hours, partly due to endless meetings and starts and stops on projects. When you run your own business, you’ll be plenty busy, but you can try to streamline your work process to get the job done in under 40 hours a week. Plus, if you work from a home office, you eliminate commuting time.

The hours you free up can then be used for family-oriented activities, such as visiting your grandkids, or just for more me time.

8. You determine your financial progress.

Corporate salaries have been pretty flat for a while and substantial bonuses are pretty rare for most employees. However, entrepreneurial business owners can enjoy a very different financial reality. When you’re your own boss, you can set a personal compensation goal at the beginning of the year and then roll out a sales and marketing plan to help you achieve the goal.

Your earning ability as a business owner is limited only by your hustle and determination.

Jeff Williams runs, where he leads a team of expert business startup coaches guiding people age 50 to 65 through the business planning process. offers a one-on-one coaching program, Virtual Incubator. Read More
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