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What Type of Business Should You Start in Rewirement?

Guest Post by Mike Lieberman

Mike-headshot OnYourOwnThe retirement landscape is rapidly changing.

It’s very different now than it was 10 years ago.

One of the main contributors to the change is our life expectancies.

You see your parents and grandparents typically lived 10-15 years after they retired.

Now you might live another 20-30 years. Big difference.

My guess is this might be why you’re looking to rewire instead of retire.

You’re looking to ignite the spark in this next stage of your life.

Did you know that according to the U.S. Bureau of Labor Statistics report, Self-Employment in the U.S., "the self-employment rate among workers 65 and older (who don’t incorporate) is the highest of any age group in America: 15.5%.”

Interested in starting your own online business?

I mean, why not?

Starting an online business in your rewirement can:

  • Ease your transition from your traditional career into rewirement
  • Give you some extra cash to pad your existing savings or fund some of your passions and hobbies.
  • Enable you to donate to your favorite charitable cause
  • Give you structure in your life
  • Help to keep you engaged mentally to stay sharp

The benefits are more than just financial.

Here’s the deal though:

We live in a time where the barrier to entry in starting your own online business has never been lower.

There are many different types of online businesses you can start and choosing can be overwhelming.

You need to create the right mindset and understand which one makes sense for you.

How do you know?

Glad you asked.

It starts with a question.

To save you time Googling the options I spoke to Kevin Lyles, who specializes in assisting Professionals and Executives as they make retirement transitions with the life side of retirement planning.

I asked Kevin, “What’s the first thing you’d ask someone that was thinking of starting a business in retirement?”

He responded with, “What do they want to get out of the business? That will lead to how I could counsel them because there are many possible answers.”

Before we get into the answers, I’d like to discuss why this is a critical question to consider.

You with me?

Why this is a critical question.

Step back for a second and think about your past 20-40 years of your career.

It’s been there out of necessity and it has accounted for a huge chunk of your time.

Now that you’re moving into rewirement, work takes on a new part in your life.

What this means is whatever business you choose must align with how you want to spend your time.

In your first half of life, your career dictated how you spent your time. Now how you spend your time is in your control.

This is why it’s critical to get clear what it is you want to get out of your business and make sure it supports your vision.

Make sense?

How the question can be answered.

Kevin and I discussed five common answers to “What do you want to get out of your business?”

Here they are:

1. The income is needed to survive

If you’ve entered this stage in your life and you need the income from your business to survive, think about continuing with your current job or seeking new employment.

As mentioned earlier, starting a business isn’t going to be smooth sailing and will take time to produce enough income to live off of.

With that being said, if you’re approaching rewirement, it might be a good time to start and build traction to help ease the transition.

2. Extra cash in the wallet

Ideally, you’re set with your retirement financial plan.

If so, your business might put some extra cash in your wallet that affords you the ability to go on that lavish vacation, buy yourself a new toy or whatever it is you want.

When you have the extra cash, you can do so without worry.

3. Building a legacy

Legacy can mean a variety of things such as:

  • Passing the business on to your kids
  • Handing wealth down to future generations
  • Being the example for your kids and grandkids that anything is possible

Leaving such a legacy could be what you want to get out of your business.

4. Solving problems for others

This is one of the common reasons for people to start their own business.

They’re good at doing something and can get paid to help others doing it.

5. Purpose and meaning

With your traditional career behind you, you now have a lot of time to fill everyday.

This is one of the big challenges people are having, Kevin shared with me.

 “If they’ve been working 10-12 hour days for 30-40 years, now they wake up and don’t know what to do with themselves. Having a business can really fill that void and give them some purpose and reason to get up in the morning.”

When you get clear what it is you want to get out of your business it helps to narrow down the choices for you.

It allows you to shift focus to the structure and opportunities that support your vision.

Sound off

Let me know your answer to “What do you want to get out of your business?” and why.

Mike Lieberman is the founder of Retirement Redefinition. He created the site to help you define your retirement lifestyle and start an online business that fits it. is a Top 75 Baby Boomer Blog.


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