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updated: 8/4/2014 5:33 AM

How many bird houses can a retiree make?

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With retirement scheduled for year-end 2015 and son-in-law Colin Murphy apparently in good position to take over management of Simmons Engineering Corp., a Wheeling manufacturer of cutting blades, a smooth transition to retirement seems a sure thing for Bruce Gillilan.

Except ...

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"I've assumed that I'll set up a small woodworking shop in my new Door County home and start doing things with wood," Gillilan says. "My Dad was quite a woodworker, and I have a long list of projects.

"Now, though, I'm starting to appreciate that there might be a limited number of bird houses that I'll want and can give away. The point," Gillilan continues, "is that I don't have a plan. I should have been working on this earlier. I've not really looked down the barrels of this topic."

Nonetheless, Gillilan's big picture seems OK:

• The Wisconsin home was built with retirement in mind.

• Gillilan and Murphy seem compatible. "I'll be as available as he's comfortable with," Gillilan says, recalling that "my father-in-law wouldn't go away."

• Gillilan has given thought to "what 40 years of work might do -- maybe programs to help veterans."

Still, many entrepreneurs have a bird house issue, which led me to conversations with two thoughtful transition pros: Joel Goldberg and Harry McCabe.

Goldberg is principal of G2G Strategies, Northbrook, and half of Goldberg-Heinze Business Advisors, a duo that helps business owners with transition. McCabe is ownership transference adviser, Harry McCabe Advisors, Westmont.

"People end up in this predicament because they don't think about what they're going to do next," says Goldberg, who suggests planning for the post-working life should begin five years before it arrives. Among Goldberg's considerations:

• Your spouse. "You're meeting on a different level," Goldberg says. "Thirty years have passed, and you're different people. Try date nights. Know that it's OK some days for you to go one way and your spouse another."

• Inventory your interests. "Look at the things you've always been interested in but didn't have the opportunity to pursue."

• Develop conversations with people in your age group. "The whole group has issues," Goldberg says. "Join a men's (or women's) group. Play cards at the park district. Put together a group that gets together for lunch."

McCabe suggests a more structured "re-engagement plan -- an outline, written in pencil so it is easy to change -- that crafts the next chapter."

One suggestion: Use business skills to build onto a hobby. Bird houses, for example, might morph into bird baths and feeders -- perhaps "donated to a cause you really believe in" that can use the proceeds from selling the products.

Another McCabe idea: "Help someone. Give time, not just money. Pack school lunches" for needy kids.

There's more to discuss, of course, because McCabe, Goldberg and their emphasis on transition planning make sense -- especially if, like me, you're all thumbs in the wood shop.

• Follow Jim Kendall on LinkedIn, Twitter and at Kendall Communications on Facebook. Write him at Jim@kendallcom.com.

2014 Kendall Communications Inc.

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