Whatever you call it -- leaving, retiring, or moving on -- it’s a really hard thing to leave your organization, especially if you love your job! It can be scary to step from the familiar and comfortable into the uncertain and unknown and this stress can make departing your job a difficult and emotional transition. In fact, it can be a significant factor in why you (or your boss) hold back from making changes.

Life transitions such as retirement are usually far harder than we imagine. It’s easy to talk about letting go, but when the time comes, it’s hard to do. The emotional aspect of departing is difficult to fathom, but at a recent meeting I attended, a health care system CEO put the dilemma in succinct terms to a group of us.

She said, “I finally realized that my job had become my best friend. It’s very hard to leave your best friend,” I watched the expressive face of this fantastic leader as she shared her personal feelings about leaving her job and her organization. The other people in the room hung on her every word. “It seemed like I was getting promoted every few years. I loved the company, my co-workers, and our customers. Going to work was a joy for me,” she said, sighing. “The time just flew by and then one day, it was time to leave. It hurt,” she said.

Preparing for Departure

One way to make this big step more manageable is to prepare, though most of us, even the most successful, don’t do this well. One of my executive friends knows that he is going to have to retire in about a year. He has done nothing to prepare for it! I asked him, “If you knew that your business was going to radically change in one year, would you plan for this eventuality?” He laughed and replied, “Of course!” I went on, “Your life is more important than your business. Maybe you should start planning the rest of your life.”

No matter where you are in your career, it is good to think about how leaving is going to feel and what you might want to do if you did leave. Time passes very quickly. Every executive I have ever met is amazed at how fast the years fly by.

Today people live a lot longer than they used to, and they are a lot healthier at 65. And, if you have the drive and energy to become a successful leader, it is unlikely that these traits will immediately stop when you leave your company, so you better plan for an active retirement!

The happiest “transitioned” executives I have met are still making a contribution to the world, they are finding meaning and contentment in what they do today—not just reflecting on the past.

Think about “life after work.” How can you make a contribution? How can you find meaning? What will make you happy? You might have 20 or more years to live after your primary work is finished. How can you make this time count for yourself and the people around you?

Now is a good time to start planning.