Cass Is Practicing Retirement. Should You?

I've been giving retirement advice for 31 years, but it turns out I've learned a few things this year by practicing retirement myself.I now have four-day weekends, and I like to say I have two Saturdays and two Sundays. Every Friday morning, I wake up with a little sense of wonderment: What am I going to do with this day?

I've been painting more, playing more Mahjong, babysitting the granddaughters with Tom and taking a few day trips. We even flew to Jackson, Wyoming, to spend time with friends.

None of this is particularly dramatic, and I think that's the point. I'm learning what I enjoy doing when work isn't organizing my day for me, and it has made me think that maybe more of us should practice retirement before we actually retire.

We spend decades preparing financially for retirement. We calculate how much we'll need, when to claim Social Security, how to invest and whether our money will last.

But there is another retirement question that may be just as important: What are you actually going to do all day?

Today, retirement can be surprisingly abrupt. You work 40 or 50 hours a week and then - boom - you're retired. One day your calendar is full with deadlines, coworkers and people who need you; the next, you have an astonishing amount of free time. That can be wonderful, but it is also a major life transition.

What Are You Retiring To?

People often know exactly what they are retiring from: the commute, meetings, stress, travel, boss and schedule. But ask what they are retiring to, and the answer can be less clear.

“Travel.” “Spend more time with the grandchildren.” “Play golf.” “Relax.”

All good answers, but they may not be enough to fill 20 or 30 years of retirement.

Before you retire, imagine an ordinary Tuesday two years after you stop working. Not the Mediterranean cruise. Not Christmas with the grandchildren. Just a Tuesday.

What time do you get up? Where do you go? Who do you see? What are you looking forward to? And, because I am a financial advisor, I have to add one more question: What does that life cost?



Freedom Is Wonderful. So Is Structure.

After decades of alarm clocks and obligations, having nowhere you have to be can feel terrific. But most of us still need some structure. An exercise class, volunteer commitment, lunch with friends, church activity, art class, part-time job or standing date with the grandchildren can give shape to a week. Structure isn't the enemy of freedom. The right kind of structure helps us use our freedom well.

Don't Underestimate Your Work Friends

Work provides more than a paycheck. It gives us social interaction and a sense that we are needed. That's why I encourage people who are still working to invest in friendships outside of work. Reach out. Make the reservation. Plan the walk. Invite people over. Building social connections can be every bit as intentional as building a financial portfolio.

Start Before the Retirement Party

I've had clients tell me they can't even meet to discuss retirement because they're too busy working. “They need me at work!” I gently remind them that after the big retirement party, their coworkers really will figure out how to carry on without them. That's not always easy to hear, and I am personally feeling that now!

Much of our identity can be tied to what we do for a living. Leaving work can involve a real sense of loss, even when retirement is something we've looked forward to for years. You have spent years preparing financially for retirement. Now spend some time practicing retirement, building a life you can't wait to live.