What I’ve Learned About Retirement as a 20-Something

Written by Holly Whitman

I’ve learned a lot in my 20s. Some of the lessons were important, some weren’t, and some were simply designed to make sure I didn’t make the same mistake twice. Throughout all of it, I’ve had one person whose advice was constant, even if it wasn’t always heeded: my mom. She taught me tons of things I never knew I needed, like how to cook a full meal with what seems like an empty fridge, how to change a flat tire without flagging down a cop and, of course, how to retire.

My mother has lived a very different life from me. She grew up with a classic ‘50s mom, a dad that led her to the state championship for rifle hunting and a single-income household. I, on the other hand, had two parents that worked, didn’t shoot a gun until I was 19 and had a mother who provided a strong leadership model.

She never settled for anything, never took the backseat to anyone for her own work and made sure her kids knew how to do the same.

Getting to Work

My mom was always a teacher. You probably know that teaching isn’t the most lucrative business to be in, but it was important for my mom to do. Honestly, the first lesson I had about retirement was that you shouldn’t base your life’s work on getting to an end destination. My mom would take me to Goodwill every year and buy shoes, socks, mittens and coats for kids at the inner city school where she taught.

Every year, she’d give them out to the ones who walked in with no coat in 20-degree weather. I got lucky with my mom. She knew the value of money, without overvaluing it. Come college, that was something that was always on my mind.

I also know that Mom and Dad created a plan early on. Once they were able to stop living paycheck to paycheck, they sat down and made decisions about how they would spend their money. They made a plan for retirement, and actually stuck to it. There was no winging it or floundering about — they set goals well in advance and they evaluated how they would reach them.

My mom still does that, asking me about setting retirement savings goals. She wants me to start saving earlier than she and my dad did, which makes sense. The earlier you can start saving, the easier it is, and the less you have to save each year. We do have some savings that are accruing interest for us, but we’re not looking at early retirement yet!


Keep What Matters

My grandparents both survived the Great Depression. As a result, my mom knew how to keep things running, long past their expected death dates. So, when she bought a car in the ‘60s, she was able to keep it running, and running and running.

It’s a 1966 Chevrolet Camaro, which she could now sell for about $40,000 if she ever needed to. For a long time, especially when my siblings and I were teens, the car went to live with my grandparents, specifically to keep it safe. It’s the one thing my mom has allowed herself to have, no matter how poor they were, and she has become extremely protective of it.

She could sell it, of course, but it’s a throwback to her wild, pre-motherhood days. I think the memories in it are more important than the car itself. Now she has the time to enjoy it again and I love nothing more than seeing her pull into the driveway in the summer, with all the windows down and a huge smile on her face.

Trouble Comes Along

I’ve talked with my parents a lot. I know that, being the youngest, I pretty much got the best of what they had to offer, monetarily speaking. When my oldest brother was born, my mom was working part-time as a substitute teacher and my dad was working at a grocery store and finishing college at night. It took them another decade to establish themselves and get the ground solidly under their feet.

Neither of my parents saw the bubble of 2008 coming. When it did come, they used a large portion of their savings to pay off the rest of their house in under a year. My mom told me “We don’t know how far this will fall, but they won’t be able to take our home.” She had a plan in case things went wrong. They were caught off-guard, but not unprepared. Their rainy day savings were a lifeline in a very scary time.

That lesson was to plan for the unexpected. You never know when you’ll need it.

Save Room for Joy

My mom had a serious job that often involved confrontations with parents, children, the police and Child Protective Services. With all that going on, she sometimes needed to let off a little steam. So, she decided on another savings goal, in addition to retirement: a dream home. For that, she had to get a little creative. Literally. My mom sold paintings to help pay for her retirement dream home.

That was an easy lesson. If you want something, sometimes you have to have more than one job. My mom painted because that’s what she loved. She taught because that’s what she loved. She did things for joy, and found ways to make money while doing it. It was hard work, it was sometimes dirty and sad and scary, but it was important to her. And in the end, she said it was all worth it.

My mom hasn’t made my life a satin-smooth ride, but she did give me the life skills I needed to be successful. She taught me joy, gratefulness, gratitude and tenacity. She taught me about retirement, yes, but more than that, she taught me to live without waiting. Retirement will come, and I need to be ready, but not at the expense of now.

Sometimes Living a Fulfilling Retirement is Not Just About Keeping Busy

If you hope to make the most of your second act you need to know what you are in for. Even with enough saved and invested to subsidize the lifestyle you envision there is no guarantee things will turn out as expected. And how can you really know what to expect when you have never been retired? Stories from those who have gone before you may have no relevance to the retirement that awaits you. Unfortunately if you are unable to predict to at least some degree what the coming decades hold you could be in for uneasy times. You need to know what you are going to do to find entertainment, satisfaction, meaning and excitement or what’s the point?

For me a fulfilling retirement is pretty straightforward. I don’t feel the need to necessarily find deep meaning in every moment spent during each day. I don’t want to look back and feel like I wasted my time but there is a lot of leeway when it comes to what I actually do. Each day, I keep busy spreading my efforts across multiple activities and interests until at least until five o’clock, otherwise known as happy hour. As shared in previous blogs I have concocted a mix of exercise, hiking, playing the piano, gardening, travel, reading, and on line courses that keep me feeling engaged and content. My blogging keeps me involved just enough with the business world so those skills do not entirely waste away. The truth is I can’t sit still for long – I get restless. So it is also important to stay open to new avenues to explore. And if that is not enough we just added a Boston terrier to our family so who has time to be bored!

But what if you are not happy just keeping busy? What if retirement takes you away from a working world that you do not hate, maybe even enjoy? Not everyone is okay with doing a little this a little that until the day is done. I may be happy with my retirement agenda but someone else may find such a life incredibly boring and unfulfilling.

A reader of LoveBeingRetired.com recently shared a challenging situation. After a successful and meaningful career in a high level position he gave retirement a try. Within a year he was back at another job, not nearly so satisfying or engaging. During that brief interlude he discovered work was his passion, what defined him and made him feel good. Retirement was not what he hoped for – “I am not a hobby or volunteer guy”.

When your work defines who you are – when what you value most about who you are is intimately tied to what you do for a living – the transition into retirement can be that much more difficult. Not only are you challenged at cocktail parties with providing a pithy answer to “what do you do?” but you must also find an answer to your own dilemma: since I am no longer working how am I contributing? What is it I do that matters?

If I was not happy or satisfied in my retirement just keeping busy, what could I do?

First I would try to identify what is it that gives me the most satisfaction in life, a true feeling of fulfillment. Is it doing good for others? Might it be achieving a challenging goal? Do I feel best when I attempt to improve the person I am? Can I be fulfilled simply spending time appreciating all the little things that feel good  to do? Each of us is driven by a different spark, something that more than any other makes us feel good, happy, and complete. If that spark can be identified maybe we can better focus our efforts in a direction that offers the most bang for the buck. Pursuing what you are passionate about is a lot more fun than just killing time. But it is not always easy to identify such a source of bliss in retired life.

I would ask myself if I can do whatever I want how would that look? The freedom to choose how you spend days is a wonderful part of retirement – if you can fill in the blanks. What do I like to do? What would I prefer to avoid? What gives me pride in accomplishment? What is it that lights the fire to get me out of bed each morning raring to go? It is likely a variety of activities and experiences combine to make your ideal day. And that is perfect – variety keeps things fresh. A balance between activity and leisure works best for many. Another plus for retirement is you can always change your mind. If something does not work out as you hoped, move on. Maybe you spend half the day “being productive” and the other is free time. I always like to do something productive first so I feel I have “earned” the right to relax.

If it is not about the money is there a post-career-career that may be interesting? Many enjoy the comradery and challenge and meaning being part of a business concern. I believe if you enjoy working there is no reason not to include it as part of your retirement. The retirement just right for you comes down to doing what you want – you make the rules. Perhaps part-time at a local start up where you can utilize all your skills wearing many different hats. Maybe the thought of building your own business sound intriguing. Without the stress of having to make a lot of money you can experiment a bit. There is a lot to be said about being your own boss.

My wife retired just over a year ago. She was initially somewhat afraid, unsure if she could find enough to keep her engaged for the next twenty plus years. Having worked in numerous start-up environments she loved the regular interaction with bright minds, the excitement of growing a company and the satisfaction of actively being a part of its success. Over recent months she has begun to fill her dance card with a combination of jigsaw puzzles (nothing less than 2000 pieces), artistic quilting (not like what your grandma used to make), and experimenting with a variety of recipes (win-win with that one). But something is still missing. So she keeps her eyes on employment boards for just the right job that might fill in the blanks to create the perfect retirement for her. The combination of a part-time job with her other hobbies should be just the right mix.

How much of your time do you need to spend in meaningful pursuits versus relaxing or just going with the flow? I am relatively happy with the retirement I have. But there are times when I get a bit restless, feeling I could or should be doing more. Occasionally I feel guilty when someone asks what I have been up to the past weeks and I cannot quickly come up with a list of significant achievements. If you need to feel you are spending your time in worthwhile pursuits maybe you make a list of goals. Having something to focus on each day adds a bit of purpose to your endeavors. And achievement of goals that are important to you personally may give you that feeling of satisfaction you desire.

Do you prefer doing your own thing or interacting with others? My wife and I differ in the amount of socialization we desire. She loves people time and I am very comfortable with me time. Knowing where you stand in this regard can help you channel efforts toward the best end.

Who ever said retirement is easy? You would think with the freedom to do whatever you want it would be no problem to enjoy every day. But there is something to be said about living meaningful moments. What makes us happy, satisfied and glad to be alive differs for each of us. The trick is to figure out what it is that makes the retired you tick. And then by all means do it.