5 Questions to Ask Yourself After You Retire

Retirement is a destination, for sure, one that we have been working toward for decades. But retirement is also a journey. It begins when we leave work, and can easily last for 20 or 30 years. As with any journey, it sometimes makes sense to stop and review where we’ve been and where we’re going.

Here are five questions I can think of that are important to ask ourselves, when we first retire, then again on a regular basis throughout the rest of our lives. Maybe you have other questions that you think are important. But the point is, just because we're retired doesn't mean that life is over. It means we're living for ourselves rather than someone else, and we should examine our situation every once in a while . . . so we stay true to ourselves.

1. Am I on track? You probably had a vision -- or at least some dreams – of what retirement would look like long before you accepted your Apple watch. You might even have had some concrete plans – and maybe even a budget by the time you actually left work. Now we should ask ourselves:: How am I doing?

Think about your lifestyle. Are you retired to Arizona, like you planned? Or are you still living in your family home, cutting the grass, shoveling snow, and storing old textbooks for your kids? If you haven’t launched your retirement life, what’s stopping you? Is it an emotional issue, or a financial problem? If you haven’t made a plan, or have deferred a lot of decisions, now is the time to take control and get on with your life. 

2. What has changed? Retirement involves a transition from working and saving to relaxing and spending, from answering to others to answering to ourselves. But the way we begin our retirement may not involve the same lifestyle that we settle into a few years down the line.

In my own case, the early retirement years looked similar to my working years, since my partner hadn't yet retired and we were living in the same house, with the same friends. Now we've relocated to Pennsylvania. We're finding new activities, new friends, and trying to figure out how to spend the winter in a warmer clime. Eventually we'll settle down – and we can then re-evaluate our expectations after we’ve tried out our new lifestyle for a while and have a better sense of what the future holds.

3. What do we want to change? We might get a few surprises when we compare the vision we had for retirement with the reality of our current life. So is there anything about your new lifestyle that hasn’t measured up to expectations? Maybe you’ve checked off a few items on your bucket list, and now you’re ready for more. Or maybe some of your original items no longer seem interesting.

Change doesn’t stop just because we’re retired. Some people relocate to Florida only to find they can’t stand the heat, and they move back home – or halfway back to the Carolinas. However far you’ve come in your retirement voyage, stop and consider if you still want to continue in the same direction, or if it’s time for a course correction. 

Don't let the retirement train leave without you

4. Are any surprises in store? When you set your retirement budget, you presumably projected the everyday expenses that will likely not vary much from month to month or even year to year. Then you took into account some discretionary items – a new car or a trip to Hawaii -- and developed a plan to balance your financial resources with your spending expectations.

But sometimes we get a surprise. If you’ve received an inheritance, you might make more ambitious plans. If you faced an unexpected medical bill  or major home project, you might have to make some cuts in your discretionary expenses. The recent surprise in my life? My daughter got married. Yeah, I know, I should have figured she would get married eventually. But who knew they would be sending me the bills . . . and that it would cost so much?!? Anyway, if you haven’t yet been hit with one of life’s surprises, look ahead to see if any unexpected events could be on the horizon.

5. We should have a plan … and be willing to change. It’s prudent to plan ahead. But it’s also important to remain flexible, especially from a financial point of view. We make a plan based on everything we know, plus some reasonable projections. But every once in a while we have to stick our heads out the window to see if the weather is changing – and make adjustments as needed. If you’re overspending, for example, you might consider cutting back on discretionary items or taking a part-time job to fill the gap.

          More importantly, if you realize that you're not doing what you want to do in retirement, that your retirement has gone off the rails, there's no reason in the world why you can't get back on track Sometimes retirement doesn’t play out exactly the way we envisioned when we were younger. There may be periods of uncertainty. But if we’re flexible, and periodically review our situation, then we will most likely find a clear road ahead.