20 Things I Would Tell my 25-Year-Old Self

As I settle into my early 40’s I am constantly startled by a singular thought:

“Holy shit!!! I’m in my early 40’s!”

Mentally, I still feel as if I’m in my early 20’s but my receding hairline, love handles and gimpy knees tend to give me away. But what my body is giving away in comfort, my mind is making up for in knowledge and life experience. I guess you could call it wisdom. And I’ve been pondering the wisdom I might drop on my 25-year-old self if he and I could have a conversation.

1). Have kids sooner. You weren’t expecting (pun intended) this one, I bet. Sure, you feel like a kid yourself. And in may ways, you are. You’re not ready to be a father but you will be. And you will enjoy your children and your family more than anything in the world.

2). Visit your grandparents often. One of your favorite places on the planet is your grandparents home. It is full of warmth, love and the best childhood memories that you can conjure. They love you completely, wholeheartedly and eagerly. Take the time to sit with them and listen to their stories, share their memories and give them the time they richly deserve. They won’t be around forever.

3). Indulge your hobbies. Wanna golf? Ski? Learn to play the drums? Don’t keep putting it off. Sure, it’s expensive. Sure, you might fall and get hurt. Sure, you might make a huge fool of yourself. Who cares? Do it.

4). Worry less about money. This will be written on your tombstone. Money is fleeting. Life is not. Start taking some (calculated) risks. And pick a charity and start donating to it, even if it’s a small amount. You will feel like you’re making a difference.

5). Think about retirement. Yeah, retirement is about 40-45 years away. And you might not even live that long (Look out for that bus, while you’re staring at your phone and reading this blog!) But as soon as you get a steady job you should begin contributing something — even if it’s just 2-3 percent of your income — to your retirement plan. This is when time works for your money.

6). Ask more questions. There’s a lot of knowledge floating around in that head of yours. You’ve attended some great schools, learned from talented teachers and read more than most people your age. But you still get bogged down in the details. Step back. Think. Ask questions about what you don’t know. Start trying to connect the dots.

7). Travel. One day you’ll have a passport. You’ll want to fill it with really cool stamps from countries you’ve visited. But you will have neither the time or money. You have the time now and soon you’ll have a bit more money. Go for it.

8). Stretch more. Bodies are like cars — they break down when you least expect it. In fact, you are about to undergo major surgery on a part of your body that most people don’t struggle with until they’re in their 60’s. Start signing up for yoga classes, pal.

9). Prepare for a changing job market. You’ve spent years — and tens of thousands of dollars — preparing for a particular career. I hate to break this to you but your career will change drastically just as you are beginning to get comfortable in it. Prepare your mind for changes to come and always — ALWAYS — have a backup plan or three.

10). Learn about different religions. After growing up in your Catholic cocoon, take a few weeks or months and start reading the Torah or the Koran. The world outside your borders is defined by religion and it would be helpful in your personal and professional lives if you learned about it.

11). Buy power tools. Sure, you didn’t touch a drill until you started working in the theater building sets in college. And you barely know a chainsaw from a chainlink fence but, buddy, you will one day own a home and you will need all sorts of tools that you didn’t know existed.

12). Treat yourself more often. Money is tight. It is for most people your age. But every once in a while whip out the credit card and buy yourself a kick-ass pair of sneakers or a sharp suit. Or treat your girlfriend to a fancy dinner at a restaurant that you cannot afford. Enjoying the finer things — occasionally — is an important part of life.

13). It’s about quality not quantity. This refers to many aspects of my life. What it means is that quality matters. Quality lasts. Quality is what counts. It may cost more. It may be more of a commitment but in the end, items of quality produce fewer problems over the long haul. That is worthwhile.

14). Don’t be so regimented. You live your life by a code — work first, then play. Sometimes, it’s important to play first, then work. It’s ok. No one will think less of you.

15). Make time for spontaneity. See #14.

16). You are a good guy. You spend a lot of time wondering how the world perceives you. That’s a normal for a kid going through a quarter life crisis (Thanks, John Mayer.) But, dude, chill. You’re a good guy. Chicks see that. Your boss sees that. Your friends see that. And contrary to that famous saying, good guys don’t always finish last.

17). Everything will work out. There is a career that you are aching for. You can see it, smell it, feel it but you can’t touch it yet. It will work out for you — in more and better ways than you can imagine. Relax. The journey is just as important as the destination. The work you are putting in will help you in incalculable ways.

18). Keep writing. When your dad forced you to write and rewrite those book reports in 3rd and 4th grades he wasn’t being a jerk. He was creating a foundation for your future. Limber up your fingers, kid. You’re going to be typing A LOT.

19). Get used to negotiating. In order to get what you want you need to ask for it. And you need to ask for it in a way that increases your chances of getting it. Start small — negotiate the price of something you want — and soon the art of negotiating won’t seem so daunting. It will serve you well one day.

20). It’s not all about you. You’re 25. The sun, moon and stars rise and fall on your hopes and dreams. NOT! There are millions of other people who want what you want. And they will work hard to get what they want. Realize that while you are special there are tons of special people out there and you need to work to find how your uniqueness will set you apart.

I’m hoping that my 62-year-old self will drop some knowledge on me one of these days. I’m sure a lot of the advice will remain the same — especially #’s 5, 8 & 14.

How about you? What advice would you give to your former self?

Photo credit: Leo Reynolds / Foter / CC BY-NC-SA


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About Happiest Daddy

Two boys, one wife and a ton of material. I live for family and I'm one of the most blessed people you will ever meet.

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