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Overcome 3 Obstacles to Start a Business After 50

Advice to get over your fears and get going on your launch

By Linda Singer

More and more Americans age 50+ are turning their hobbies, experiences, skills and special interests into small businesses. In fact, people 55 to 64 represented almost one quarter of all entrepreneurs in 2012, according to the Kauffman Foundation. And that number has grown by 63 percent since 1996.

But some midlifers are fearful of becoming entrepreneurs because of what they perceive as three obstacles: Their need for flexiblility, their fear of touching their nest egg and their feeling that they’re out of touch with technology.

Overcoming these hurdles, however, can be fairly easy. Here’s how:

Obstacle 1: The Need for Flexibility

In your 50s and 60s, you may start imagining a more flexible lifestyle that allows for some time to yourself. So you may be worried that starting a business will be a 24/7 job.

While those hours can be true for many businesses, they’re not true for all.

If a flexible lifestyle is important to you, consider one of the following four possibilities where you can set your hours to achieve balance: consulting, freelancing, home-based and online ecommerce businesses.

(MORE: Starting a Side Gig After 50)

Obstacle 2: The Fear of Touching Your Nest Egg

Touching your savings later in life can be pretty scary and you need to be protective over what you have. The way to overcome the fear of breaking into your nest egg is by committing yourself not to invest more than you are willing to lose.

Borrowing from your 401(k) is a possible source of funds for your venture, but shouldn’t be your first option. If you do decide to borrow this way, plan to pay back the money within a year or two. And seek advice from an accountant or tax attorney.

Ideally, you’ll want to put as little of your own money into your business as possible. So check out these options:

Government grants Their guidelines are stringent and usually require recipients to match the funds. The federal government’s BusinessUSA site can help you explore government grants.

Friends and family Getting money from relatives or chums can be a fairly ready source of potential cash, without the red tape. But these are the last people on earth you want to have a falling out with. The best way to approach this alternative is to present your opportunity to them as a gambling option.  Ask your family or friends to give you only as much as they are willing to lose.  Hopefully, you’ll ultimately return the money plus a generous return.

Venture capital This kind of financing is typically restricted to high-potential, high-growth startups in exchange for equity. Only 0.06 percent of businesses get funded this way.

(MORE: Pitfalls of Launching a Business in Retirement)

Angel investor This is an affluent person (or a group of affluent people) who provides capital in exchange for equity or convertible debt. Unlike venture capitalists who invest because they hope to strike it rich, angels can be satisfied with healthy returns. But angels are generally only interested in local opportunities where they can participate to some degree. Typically, you need to be referred to an angel investor. So immerse yourself in the local business community by getting your name and face out at social functions, talking to area accountants and financial advisers and checking out angel investor network websites for chapters near you.

Crowdfunding This is a fairly new online option where a project or idea gets proposed on a crowdfunding site (such as Kickstarter or Indiegogo), visitors to the site learn about it and then decide whether to make small contributions to help the founder reach a funding goal.

You could also start a business that requires little capital investment, such as a consulting firm, an e-commerce site or a home-based business. You might be able to launch one with as little as $1000, hiring freelancers for the necessary work that’ss out of your expertise. To find local experts that can get your jobs done, put up free postings on online marketplaces. (Full disclosure: Workhoppers, the site I co-founded, is one.)


Obstacle 3: Feeling Out of Touch with Technology

Technology is changing so quickly that it can sometimes feel overwhelming to keep up with it all. But you’ll be less fearful if you get a grasp on the two kinds of tools you’ll need to start your business: operational and marketing.

Operational tools are for managing your day-to-day operations. There are many easy-to-use web-based tools to help. You just need to take some time to familiarize yourself with them.

(MORE: Secrets of Successful Entrepreneurs)

For instance, a web-based phone system (no hardware necessary) will provide the services of an automated receptionist at as little as $15 a month. It can forward your calls to your cell phone so you can control your office hours and look professional. Try out different systems for free and find the one you are most comfortable with.

A Customer Relationship Management (CRM) cloud system can help you easily organize and keep track of your conversations and emails to customers and leads. At my company, we use whose fee starts at $5 per month.

Bookkeeping is now easier than ever with cloud accounting systems. When you’re starting out, the Freshbooks free package will do the job. You don’t need a background in accounting or computers, though once your business grows, you’ll want to upgrade your package.

Other options: the online version of Quickbooks (starting at $9.95 per month with a free 30-day trial) or a one-time purchase of the Quickbooks Pro Software (starting at $224.95).

Marketing tools will help promote your business or skills. You’ll need to create a website for your venture. Check out online site builders where you can easily customize your website without any programming knowledge. Search “website builder reviews 2014” to find a reputable one. Some help you build your site for free. If building a site is not your cup of tea, hire a freelance expert.

To promote your brand or services through social media, familiarize yourself with Facebook, Twitter, Linkedin and Google+. Play around with each and watching a few online tutorials. Look into social media management systems, too, so you can more effectively manage your accounts, schedule postings and keep track of customers or prospects.

Finally, investigate email marketing software to make your email campaigns more sophisticated. Prices start at $9.95 per month.

Webinars To Help You Get Started

An easy way to learn more about starting a business is to take part in online webinars. They let you learn at home at your own pace. Two great free options are: The AARP /U.S. Small Business Administration’s Encore Entrepreneurship Webinar Series and the how-to startup webinars at

Linda Singer Based in Montreal, Canada, Linda Singer is the co-founder of, a website where talented people find flexible work and companies get local help on demand. She writes frequently on topics related to the contingent workforce. Read More
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