By selling your business, you'll have the money and time to do things that you've always dreamed of doing. However, the loss of purpose and social connections could leave you feeling empty. So before making such a huge decision, you need to take the time to determine what's right for you.

For some guidance on the matter, I turned to Gretchen Rubin, the author of The New York Times bestselling book The Happiness Project; Marshall Goldsmith, the author of 30 books, including his latest about getting and keeping your 'mojo"; and Chris Guillebeau, the bestselling author of The Art of Non-Conformity. Based on my conversations with Rubin, Goldsmith, and Guillebeau and my own personal experience of having recently sold a business, here are seven ways to evaluate whether selling your business will make you happy:

1. Decide what type of business owner you are

According to Goldsmith, there are two types of entrepreneurs: 'Serial entrepreneurs go in with the plan to start and sell their business. They get squirrelly if they don't sell it,' he says. 'The other type is the founder who builds something fantastic over a very long time. He or she will find it very hard to let go. The second group need to ask themselves if they want to manage a mature business. In many cases, the answer is no. What they really find exciting is the innovation and creativity of a start-up. Some can make the transition, and some cannot. The reality is it is a different job. The question is, will they find the same happiness and meaning in the new job as they found in the previous job of starting up a small business? The answer is sometimes yes, often no.'

2. Think back to when you were 10 years old

'One of the biggest reasons we become unhappy is that we fall out of sync with our deepest personal values,' says Rubin. 'A great way to get in touch with what really makes you happy is to recall what you enjoyed doing as a kid.' Rubin explains, 'Recalling your pastimes before all of the pressures of adulthood took over gives you clues as to what will make you happy now.' Rubin points to a friend who used to love playing with dollhouses as a child, and now she is incredibly happy with her career as an interior designer. Another friend of Rubin's spent his childhood rambling through the woods every chance he could and is now very happy with his life as a park ranger.

'Sticking with a business for many years can become a life-avoidance strategy,' says Guillebeau. 'Running your business becomes something you do because you don't know what else you would do. It's convenient to get up in the morning and know what you're going to do instead of thinking about what you really want to do.'

3. Read your alumni magazine

One of Rubin's suggestions for evaluating whether or not you're doing what you should be doing is to flip through your alumni magazine. 'Read the updates from your classmates and ask yourself if you feel envious of anyone else? If so, it may be a sign you would enjoy doing something else. Jealousy can be a helpful emotion if you use it to give you a new direction,' she says.

4. Imagine your post-sale life in detail           

If you still want to sell your business after reflecting on what excites you, Rubin recommends you get very specific with how you will spend your time after the sale. Do you have another business you want to start? Or would you prefer to volunteer or dedicate yourself to a hobby?

Instead of saying something vague like 'I'll do more traveling,' Rubin recommends you dig deeper: Where will you travel? Who will you go with? What will you do? How long will you stay? Do you know anyone in the place you're going? Will you learn the language? This level of detail helps you get clarity on whether or not you would enjoy post-sale life.

5. Confront your demons

Many of us use the 'if I had more time' excuse to avoid doing things we don't want to do. If you sell your business, you won't be able to use time or money as an excuse for not losing that extra weight, finishing that renovation or volunteering. Make sure you're comfortable ditching the comfortable excuses.

6. Develop a sense of purpose

'For many business owners, their business gives them a deep sense of purpose,' says Rubin. 'If you sell your company, you need to replace that with something else that makes you feel like you are contributing to the world.'

Guillebeau encourages business owners to 'think about what bothers you about the world. The answer can help you identify your deepest passions and a new direction.'

7. Think about your social network

Social ties make us happy, according to Rubin's research. If you sell your business and all of your friends are still at work during the week, you will feel lost. Cultivate a group of friends and contacts who have flexible schedules to make sure you have people to spend time with after you sell.

I can say from personal experience that Guillebeau's, Goldsmith's and Rubin's advice is sage. One of my deepest personal values is the need for challenge, so when my last business was becoming too predictable, I knew it was time for me to sell it, which I did in 2008. I stayed on for a while, but left in 2009. The first few weeks as a 'civilian' were unnerving. I didn't know what to do, and all of my friends were at work during the day.

Since then, I have started to write and get a sense of purpose from the readers I hear from. I joined a triathlon and a cycling club, so I get a lot of social interaction through sports. It took some adjustments, but I have no regrets—other than wishing I had discovered Rubin, Goldsmith and Guillebeau a year ago.

So, will selling your business make you happy?

John Warrillow is a writer, speaker, and angel investor in a number of start-up companies. He writes a blog about building a sellable company at