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From Self-Employment to Retirement

From Self-Employment to Retirement – Making the Move After Working for Yourself

Did you know, the older you are, the more likely you are to be self-employed? One-fourth of those 65+ call themselves ‘boss’. But where does that leave you when it comes to retirement?

For the self-employed, retirement looks different than for everyone else. If you are your own boss, you need to plan your own exit strategy. After all, you do this to fulfill your own dream, not an employer’s, right?

You need a plan for our long-term needs and lifestyle goals, especially since we’re living longer. According to the SSA, married couples at age 65 today have at least a 50/50 chance that one of them will live to at least age 90.  Need help getting going? Here is where to start:


SELF EMPLOYMENTOf course, the ability to retire starts here. A first step is to create a spreadsheet with investments, savings, etc, and their current value.  You can insert projections about what you’ll save until the day we stop saving and start taking money out. Will you have some continued income from your business? This will affect your rate of saving and what you will need to withdraw.

Take stock of your social security benefit, as well.  The SSA has excellent resources to help decide when to start receiving benefits, strategies to help maximize those benefits and getting started with Medicare as you approach age 65. See:


Evaluate any plan that you have…do you still need it? Is it possible that additional payments are unnecessary? Whether your employer offers benefits into retirement or not, it is worth taking note of individual plans you might need, even if they are just supplemental. For example, our eye health is even more critical as we age. VSP Individual Vision Plans save you money on essential eye care needs, materials and more. Think you don’t have a vision need? Well, comprehensive eye exams are about more than just correcting blurry vision. They provide clues to your overall health than you might think, like offering a clear view of blood vessels and cranial nerves.

Your Home:

SELF EMPLOYMENTA big piece of the retirement puzzle is figuring out how and where you want to live. Options around house and home are many, so just take it back to your personal situation and goals. Do you own your home and is it paid off? Do you want to be closer to the grandchildren or move to where it’s always warm? Do you want to stay put, but access your home equity? These are all things to consider when entering retirement.

Comprehensive eye exams provide many clues to our overall health.self employment




Being self-employed is about building the life you want, whether you want to retire at 65 or give up working altogether.  Think about how you may eventually feel. Even if you can afford a life of leisure, will you miss working? So much activity has moved online that you might be able to work on the side from anywhere for a long time to come.

There is much more!  Learn more by downloading the resource guide: Self-Employment to Retirement – Making the Move After Working for Yourself, brought to you by VSP Individual Vision Plans.


Finally, let’s look at the big balance. In a large corporation, the workers work to fulfill someone else’s vision, dreams and goals. But in a small business, you work to fulfill your dreams and goals.

Being self-employed is all about building the life you want. So your retirement needs to look exactly the way you want it to look. This is your retirement! You don’t have to do it at age 65. You don’t have to sit on your porch. You don’t have to give up working altogether. You can literally do anything you want. Just make a plan.

About VSP:  self employment

VSP is America’s leader in eye care benefits and offers affordable individual vision insurance to people who don’t have employer-provided vision care.  Serving 72 million, VSP helps one in five Americans with their eye care needs.  Visit VSPDIRECT.COM for details or to enroll in a VSP Individual Vision Plan today.

Christine Crosby

About the author

Christine is the co-founder and editorial director for GRAND Magazine. She is the grandmother of five and great-grandmom (aka Grandmere) to one. She makes her home in St. Petersburg, Florida.

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