Considering Self-Employment in Semi-Retirement

Without a doubt, if you are considering a semi-retired life with income above a pension, social security, or IRAs, you have probably wondered about starting your own business versus working for someone else.

The challenge is creating a business that you can walk away from for two to four months at a time.

Take opening a retail establishment for example. Many businesses are just going through the motions by staying open in January and February. It’s not at all uncommon for restaurants in tourist areas to simply close down in the off season. This would be hard to pull-off, however, if your customers are quilters or scrapbookers who want product year round. You have to consider your fixed costs, maintenance, and lost market “presence” in deciding if this will work for you.

Another option would be something like a lawn service or snow blowing.   Work long hard hours during the appropriate months, and close it down during the off months.   The trick here is to maintain a relationship with your clients during the off-season so you can sign them up again the next year. Some ways to do this would be to provide helpful suggestions via a monthly newsletter, or offering them early-bird or returning customer sign up specials.

Another option many people consider is some type of Direct Selling, such as nutritional products, or retail-oriented such as clothing or jewelry.   This option is a bit different because most companies require you to produce a minimum level of sales every month in order to qualify for commissions, bonuses, and team overrides.   And if you simply disappear for several months, so will your team and your income.     Thoroughly understanding your compensation plan is critical.

So, if self-employment is an avenue that you would like to consider in semi-retirement, ask yourself these questions:

  • What kind of business? Retail, Direct Sales, Coaching, Other Services?  Then:
  •                 Where and who are your customers?
  •                 How do they get your product or service?
  •                 When or how often do they purchase/use/need it?
  •                 How are you going to acquire them?
  •                 How are you going to retain them?
  •                 What happens to them while you are off gallivanting?
  • Do you want two to four months completely AWAY from it? Or are you just looking for something portable that you can do from anywhere. (The latter is a completely different discussion and would not be considered semi-retired!)
  • Are you the product, or providing a service as a result of your individual skills?  If so, is your physical presence required to do the work?

After you have played with these questions for a bit, what jumps out at you as a possibility that might work for you?


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Recovering MBA. Writer. Photographer. Scanner. Learning Addict. Airplane Geek. Teacher. Certification Collector. Serenity Seeker. Semi-retiree in training.

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