10 questions you should ask when considering retirement

If you're one of the many IT pros who is wondering whether it's time to retire, these insights from Alan Norton will give you an idea of what to expect and what to consider as you make your decision.

The PC generation is nearing retirement. Some of us have already left the workforce by choice or otherwise. Before you retire, you should understand that you will still have needs in your life of leisure. How you meet those needs will in large part determine how successful your retirement will be.

We ask children what they want to be when they grow up. How many times have you been asked what you want to be when you retire?

As you can read in my bio, I know a bit about retirement and what can go wrong. My current job status is, as I like to call it, semi-retired. I didn't plan the end-game this way -- I just found myself here. And that, my patient reader, is not how you want to enter what is supposed to be your golden years. So, in the time-honored tradition of making lemonade from lemons, let me share with you what I have learned from my unplanned journey into semi-retirement.

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1: Do you have the income stream to support the lifestyle you want?

Determine your projected income stream and your estimated expenses for your retirement years. Compare the two. If the difference is large, you have to determine whether that is the kind of lifestyle you want to live. About.com and The Motley Fool have some basics about this process that you might want to review.

Planning for financial security in retirement is far too complex to discuss in detail here. You might want to look at Web sites like AARP or MarketWatch or search for similar sites. Consider hiring a certified financial planner.

This is one item you should plan from day one. Having your financial needs already satisfied can be a huge step in your journey to a healthy, happy, and prosperous life after work.

2: Are all of your social connections at work?

Don't overlook the interactions you have with your peers. Many of your friends may be at your place of work. Sure, you can still have picnics and social outings with your closest co-workers, but many of these connections will be severed after you leave. If you don't have many social connections outside work, there will be a large hole in your social life. If you fall into this category, it can be all too easy to withdraw and live the life of a hermit. Humans are social creatures. A life without social interactions can be unhealthy. Look for ways to interact with others by joining groups or volunteering your time.

3: Will you be physically active?

You may not consider work as meeting your need for exercise, but count the number of miles you walk in an average day and it may surprise you how much exercise you are actually getting. If your life of leisure becomes too much leisure and not enough life, your working days may indeed provide a healthier lifestyle than retirement.

After years of sedentary living in my post-work days, I now find plenty of exercise doing household maintenance and repair. I particularly enjoy landscaping and working in the yard. I half jokingly tell my neighbors that if it weren't for weeds, I wouldn't get any exercise at all. There is something very healthy about digging in the dirt for the mind, body, and soul.

Being physically active in retirement may require discipline. Have you considered how you will burn calories when you retire?

4: Will your mind be challenged?

"My mind," he said, "rebels at stagnation. Give me problems, give me work, give me the most abstruse cryptogram, or the most intricate analysis, and I am in my own proper atmosphere. I can dispense then with artificial stimulants. But I abhor the dull routine of existence. I crave for mental exaltation."

So said Sherlock Holmes, as told by his friend Dr. Watson in The Sign of Four by Sir Arthur Conan Doyle. And though Dr. Watson and Mr. Holmes are fictional characters, it is entirely plausible for such an intelligent man with an active mind to turn to artificial stimulants when his mind is not challenged. Boredom in retirement can lead to alcohol or drug abuse to fill the void.

It is generally accepted that mental acumen, if not properly exercised, will slowly atrophy. It is unrealistic to expect light reading or crossword puzzles to fully challenge minds once tasked with complex systems development or sophisticated design and coding. I didn't find peace in semi-retirement until I found other outlets for my creative nature, my need to learn and explore, and the need to be productive. I found those needs at least partially satisfied by writing here at TechRepublic. Complex home projects turned out to be a good substitute for the development projects I loved to do while working.

IT professionals need daily challenges. How you satisfy that need will have a large impact on whether you will enjoy your post-work life.

5: How will you meet your higher needs?

Learning, creativity, a feeling of self-worth, problem solving, and a sense of accomplishment are all higher level needs. IT jobs are ideal for meeting these needs, but how will you fill the void when you leave a challenging IT position?

Consider creating a list of tasks and projects you want to accomplish. Set goals and reward yourself when those goals are met. By donating your time and valuable skills to your church, library, or a nonprofit organization, you can help others and meet those higher needs.

Retirement is perfect for tackling those IT projects you always wanted to do but never had the time for. You might want to build and maintain your own Web site, learn a new programming language, build the perfect PC, or install and explore Linux. Your employment status may be "inactive," but that doesn't mean you can or should stop learning.

6: What will you do on day 1,000?

A couple weeks of vacation can be enjoyable, but don't use it as a barometer of what an extended life of sequestration will be like. What is it that you really want to do on day 100 or 1,000? Will you travel? Take up a hobby? Take up golf or tennis? Move to a retirement community?

At about age 50, I began looking at my own mortality for the first time. It's not exactly a pleasant exercise, but it does help you focus on what's really important in life. What will be your legacy? Retirement is the time to do those meaningful activities you couldn't do when working.

7: Do you need a structured lifestyle?

My daily morning work routine went something like this: read my email, spend one to two hours on conference calls, listen and respond to voice mail, resolve any crises, and decide where I was going to eat lunch. Your workday may be similarly structured with routines you are comfortable with.

When you retire, you will find yourself with a lot of free time, no schedules to worry about, and little or no structure in your normal day. This can be unsettling as time goes by. Some people need structure in their life. Others thrive in an unstructured environment.

Know which type of lifestyle you are comfortable with. If you need structure, where will you find it when the familiar events of the daily grind are gone?

8: Are you a live-to-work or a work-to-live type?

When it comes to retirement, there tends to be two personality types --the type who takes the plunge and then wants out and the type who takes to life without work like a fish to water. Making the transition from 60+ hour workweeks to full retirement can be a welcome change at first. But if you are the live-to-work type, you may find yourself months later in a meaningless and unhealthy life. Determining which work type you are will help you decide if early retirement is for you or whether you should consider working longer than originally planned.

9: Do you have a fallback plan?

Realistically, what are your chances of being rehired? Assess your skill set carefully. If your skills aren't up to date, retirement may very well be a one-way trip.

Don't burn your bridges with your employer. Discuss the possibility of returning should retirement not work out for you before you leave. Assess both the job market and your network of connections for possible alternate job opportunities before you retire. What you learn may have an impact on your projected retirement date.

Should you decide that retirement isn't for you, your employment options may be limited. You can work as an independent contractor or start your own business. But don't kid yourself. It's not easy running your own business.

10. Is traditional retirement for you?

I admire and envy those who can travel, spend time with family, focus on a hobby, and enjoy their retirement. I have learned the hard way that I am not one of those people. You have to decide for yourself whether you can live the typical retirement lifestyle or you would be happier working full or part time.

Consider carefully before changing jobs as you age. A sabbatical at age 55 probably isn't a good idea unless you are willing to accept that the sabbatical may last until the day you pass from this earthly plane.

The bottom line

The IT industry is notorious for intelligent and dedicated workaholics -- the very type of person who would find a life of ease boring and unrewarding. If you are such a person, your challenge will be to find ways to be challenged.

Plan well in advance of the big day how you will meet your needs and the needs of your family. If you view retirement as an opportunity and not as the sunset of your life, you are more likely to have a full and meaningful life after work.

Just because you will no longer be working for the man doesn't mean that you retire from life. Find a way to keep living. In the final analysis, we all need a reason to get out of bed in the morning, especially in retirement.

So what do you want to be when you grow up?

Author's note

Don't put me in a box -- I won't stay there. We are all complex individuals, so I cringe more than a little when suggesting that there are types of people who crave structure and those who don't and those who live to work and those who work to live. Let me resolve this paradox by suggesting that we each may tend toward one personality type but are not governed by it.

I must ask myself: Well...how did I get here?

By Alan Norton

Alan Norton began using PCs in 1981, when they were called microcomputers. He has worked at companies like Hughes Aircraft and CSC, where he developed client/server-based applications. Alan is currently semi-retired and starting a new career as a wri...