Becoming a retiree has been "challenging" for Barton Miller.

The 56-year-old co-ran his own business for 28 years, building it from the ground up. "I dealt with 300 people and their problems every day," he says. "The decisions I made affected the progress of my company and the lives of the people that worked there. Now the biggest decision in my day is whether to cut the grass, and whether to bag it or mulch it."

Mr. Miller says he was euphoric for the first months after selling his business in 2013. He stayed on for a brief transition period, then left to golf, travel and putter around his home and cottage – doing all the things that he never seemed to have time for when he was working full-time.

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But as time went on, the lustre wore off some of those activities. "Before, when I played golf, I was sneaking away to get it in," he says. "I always felt a little guilty – like 'If I'm not at work I should be with my family.' Now I can golf every day. But I find I don't want to."

Like many Canadians, prior to retirement Mr. Miller focused almost exclusively on the financial side of preparation – worrying more about what cash would be available than about how to fill his days without work.

"You have to get your ducks in a row when it comes to finances," says Lynn Biscott, a long-time financial planner and author, now semi-retired. "That's important. But you also have to consider what you're going to do with your time."

Here's how to find contentment in your golden years.

Ease into it.

Mr. Miller likens retiring from his fast-paced job to "being on a highway, going 60 miles an hour, and all of a sudden ending up on a country road." Some employers offer a chance to transition to retirement slowly, either through working part-time or consulting for one or more years.

"A friend of mine works for a company like that right now," Ms. Biscott says. "He's working three days a week on a kind of extended retirement plan. He can do that for up to two years and then he has to take a full retirement."

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Such a scheme can work out well, she says. You get a slower pace and more free time to do the things you enjoy, "and it gives you that adjustment period." If you're self-employed, Ms. Biscott points out, you may be able to build in your own transition period by paring back work slowly until your retirement activities fill the time you once spent on the job.

Prepare for bumps in the road.

Not everyone has the ability to stretch out the retirement process. While some will manage the transition quite nicely anyway, Ms. Biscott says, others experience feelings of loss. "That's to be expected," she says. "You're losing the social context of work and maybe the friendships that you've had. You can try to keep that up to a certain extent, but people who are working don't necessarily have time to keep in touch with you, particularly beyond the first year."

The good news: You're entering a new phase of life and there will be opportunities to connect with new friends and perhaps older friends that you've sacrificed to the daily grind of work and family.

Ms. Biscott regularly shares coffee with five women from her Pilates class and meets with a French conversation group in an attempt to improve her rusty language skills. "I'm really enjoying it," she says. "I remember trying to keep up my French years ago when I was working full-time and it was just too much of a struggle."

Find your happy place.

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Think about what you enjoy about work, Ms. Biscott suggests. Is it the social contact or being in charge of a project? What gave you pleasure? Once you've figured that out, look at ways to duplicate the best things about your job in retirement.

In Ms. Biscott's case, taking up volunteer work at a local community centre fit the bill. "I do tax preparation for low-income people under the Canada Revenue Agency program," she explains. "It keeps me in touch with the financial planning that I enjoy and I'm able to help people and get immediate feedback." Her clients are often elderly and living on OAS and GIS. "They're so grateful that there's someone there to help them out," she says.

Other options include taking on a part-time job, starting a new business, learning an instrument or a new language or serving on the board of a non-profit. "If you've been goal oriented in your work career, sometimes you need some retirement goals as well," Ms. Biscott says.

Make sure you can afford your lifestyle.

The interrelationship between what you want to do and your financial resources is a crucial element of your retirement plan, Ms. Biscott points out. If your goal is to travel the world, you'd better have the resources to fund your voyages or you're going to have to consider a "more pared down retirement lifestyle," she says. "You really have to look at the two things together."