People today are dealing with tough questions as they reach retirement.

After being a business owner, CEO, or any kind of corporate executive, how do you reinvent yourself? When you’ve followed a script your whole life, what do you do when you don’t know the next chapter? More importantly, how do you create a new life story for yourself?

I’m sure I’m not surprising anyone when I say there aren’t any easy answers. But I can tell you that it’s possible to create a new life story. Your life – your Life 2.0 – can be just as big, exciting, and rewarding as anything that came before.

It doesn’t matter what age you are retiring. It doesn’t matter if you’re dealing with big changes in your work or if you’re burned out. It doesn’t matter what your title is, what you are worth, or what you know. All that really matters is that you’re ready to try something different. You are ready to take a risk. More importantly, you’re ready to surprise yourself.

In order to start the conversation, I asked a wide array of business leaders to take a short quiz to assess their readiness for Life 2.0. Not surprisingly, you will see that most people were tired of working around the clock. Interestingly we have thought about a transition strategy. However, we have thought very little about our own individual plans.

Here are the results of the quiz:

Life 2.0 Readiness

Then I asked the same people who responded to the Life 2.0 Readiness Quiz to think of the “persona” they wanted to be like going forward. You will see that there is an interesting range of responses. What is important to recognize are the values of the business leader you want to be.

Life 2.0 Quiz

Finding out what’s next means doing some thinking about what your values are. If you’ve had a successful career, or had the same career for decades, this may seem like a strange question.

It’s important to remember that things other than your own passions and strengths often motivated Life 1.0. For many people, careers were driven by money, family needs, or a certain career choice. For some, in large part, there was a lot of passion tied up in what they did. That’s why they were successful at it. And that’s why it can be hard to leave it behind.

Getting on to Life 2.0 means allowing different motivations to come into play. Finding out what those drivers are can start with just one simple question… are you ready for it?


If money, energy, and time were no object – no limits at all – what would you do?


Once you have your ideas, think about testing them out on a small scale, rather than thinking you must have it all figured out. For a lot of people, this can be a big challenge. When writing a new story for yourself, part of the fun is being flexible about what that will look like for you.

One woman I talked with did a great job of testing out her Life 2.0 plan. She wanted to do a thirty-day walk across Spain. She was excited and ambitious. Then she realized that maybe it might be a better idea to first do a one-week walk somewhere closer to home before committing to a four week walk across an entire country.

Find ways to break your new plans into bite-sized pieces. Try it out for a day, a week, or a month. Talk to people who are doing what you think you’d like to do. If it doesn’t feel right, there’s nothing wrong with walking away. It’s OK to try something and not like it. It’s also OK to try something once and completely fall in love with it.

What’s important is adopting a little of that entrepreneurial spark. Just do something, because that’s the only way it’s going to happen. Getting your Life 2.0 started means taking the time to find the pieces, put together solutions, and try it out.

I certainly can’t tell you what will happen. But I can tell you that figuring it out is just a matter of experimenting and testing it out. You may or may not be surprised with what you find out – but figuring it out is more rewarding than you can imagine. If you want to begin building your own Life 2.0 persona, click here to take my Life 2.0 Persona Development Quiz.

What are the values that are important to you as you embark on creating your Life 2.0? If money, energy, and time were no object, what would you do with your life in retirement? What limitations are holding you back from reinventing yourself? Please join the conversation.

Let's Have a Conversation!