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life at 40, Traverse City, Turning 40, Life Lessons, Self Improvement, 10 things I wish I knew, how to be happy at 40

10 Things I Would Tell 25 Year Old Me

I turned 40 about six months ago. I remember when I was 25, fresh out of law school and ready to take on the world, and 40 seemed geriatric. Then 15 years went by in a flash. In some ways everything has changed and in others nothing has changed at all.

That’s one of the things that has struck me most as I’ve reflected on this halfway point in life – with age comes wisdom, but life is just as perplexing, confounding, and full of possibility as ever. Life is different at 40, but it’s no less exciting.

My life at 40 looks nothing like I envisioned it at 25. And for that, I am eternally grateful. If all had gone according to plan, I would be a partner at one of the largest law firms in the world, living in Chicago, making lots of money…and absolutely miserable.

That’s not how I saw things at the time. I envisioned the sports car, the big house, the tailored suits and the country club. What I overlooked, and what I now see clearly, are all the tradeoffs. The stress, the strain, the missed family events and singular focus on career that would have resulted from that path.

If you had told 25-year-old-me that instead of being a high flying lawyer in a big city, at 40 I’d be living in a small town in Northern Michigan with three young girls and running a marketing agency from home with my wife I would have laughed and gone back to reading my Blackberry (if you’re under 25 you may need to Google that reference – I’m not talking about fruit). Life has not turned out as planned, which is awesome.

I’ve been asked – jokingly, sort of – if I’m having a midlife crisis. After all, this is the age of angst, and we’ve certainly done some drastic things in the last 12 months. My answer: Not sure, but if so it feels pretty good. It’s certainly not a crisis of the typical variety involving fast boats and hair plugs. For the first time in a long time I feel like I’m undoubtedly on the right track.

There are times when I wish I could go back and slap a little sense into 25-year-old-me. But, just like in Back to the Future, I realize that would disrupt the space-time continuum. In other words, if I knew more then, I may not be where I am now. And what a shame that would be.

The other problem is logistic – I don’t have a DeLorean time machine. So I’m going to have to settle for a two way/one person dialogue on this blog. Heather accuses me of having these types of conversations with her all the time – me asking her questions, then answering them myself – so this isn’t that much of a stretch.

Here are 10 things my 40-year-old-(reasonably)-mature-self would like to say to my 25-year-old-(largely)-clueless-self:

1. Don’t get married.

Kidding! Life is hard, so never lose your sense of humor. Definitely stop taking yourself so seriously. And, while I was trying to be funny at first, let’s have a serious word about marriage. You’re about to embark on a wonderful journey with an amazing person. Heather and I are going to be celebrating our 15 year anniversary this May. Of course marriage is hard at times, but it’s worth it. Don’t screw up, and never take her for granted.

2. Life will not go according to plan, and that’s okay.

You have a plan for your life. That’s great. It’s good to have goals and objectives. But your plans will go awry. New people will come into your life. You’ll be exposed to new experiences. You’ve been in school your entire life – you don’t even know what the business world looks like. Through your work as a lawyer, you’ll meet and be inspired by some amazing entrepreneurs doing things you didn’t even know were possible.

Many of your friends, some of whom did not do particularly well in school, will soon be starting businesses that have now, 15 years later, become incredibly successful. That’s the beauty of life. There’s no linear path to follow. You need to keep yourself open to the possibilities that the world presents.

3. Be yourself, and live for yourself.

It’s time to start accepting a few things about yourself. You’re introverted – always have been, always will be. You’ll never be the glad handing, back slapping life-of-the-party-guy. You’re also never going to be the smartest, or most successful guy in the room. And that’s okay.

What’s not okay is trying to be something you’re not. That’s because a great life is not determined by how popular you are, or how successful other people perceive you to be, or how much money you have. It’s determined by the relationships you form, the experiences you have, the impact you make, and the joy you derive from pursuing a life that you design for yourself and on your own terms. Plus, all those people that seem to have life all figured out – they’re all in the same boat as you, with the same fears and anxieties. So just do your thing.

4. Always be there for those you love and who love you.

You’ll have to learn this lesson the hard way. There will come a time when you aren’t there like you needed to be for someone you care about. And you’ll regret that, and have to live with it, but you’ll learn from it.

Sometimes it will seem like you have a very wide network of people you know – and that’s true – but the circle of people who really matter is rather small. Others will come and go throughout your life, but never lose your grip on the close friends and family in your life. You will at times, but the nice thing about old friends and family is that it takes a lot to truly break those bonds. In other words, you’ll have second chances, but don’t ask for a third.

5. Learn to wake up early and work out.

You’re not going to like hearing this, but you’re soft. Yes, soft, literally and figuratively. I can kick your ass. Seriously, I’m 40, and I’m in much better shape than you. It’s pathetic. It’s not even close. (Note to readers lest Heather is compelled to comment: I’m nothing special now, I just was pretty bad 15 years ago).

Why, you ask? It’s called consistency, slacker. You work out for a week, then you’re off for two. What kind of a program is that? But what do you expect, you are all over the place. Sometimes you hit the gym in the morning, other times in the evening. That’s no way to form a habit. Too many things get in the way. You know what you need to do?: Get up early and get it done first thing. That’s right, set your alarm for 5 a.m. and get to it. You’ll feel good all day for having accomplished something before sunrise.

Exercise will become an increasingly important part of your life as you get older. It’s a luxury to be squeezed in now, but it will become a priority. It’s a mental stress reliever and it’s important to be able to keep up with the three precocious girls in your future. You won’t have kids until you are in your mid-30’s, which means you’ll be in your mid-50’s when the twins finish high school. Better stay in shape.

6. The people that are hardest on you are those who make the biggest impact.

You have a bad habit of complaining about certain people. Your college baseball coach, and that tax professor from law school come to mind. In about six months when you start at your law firm you’ll be complaining about a certain partner you work for, too.

Do you know what all of these men have in common?: They were (or will be) tough on you. They saw through your bullshit. They expected nothing less than excellence from you. They didn’t mince words. You didn’t like it at the time, but guess what?: You’re so much better for the experience. You need to surround yourself with coaches, bosses and mentors who will give it to you straight. These are the people who see your potential, and care enough not to let you throw it away.

You’ll find this hard to believe, but you’ll still be having dreams about your baseball coach all these years later. He’s still going to be yelling at you, pushing you, willing you to be better as you sleep. And you’ll wake up as a 40 year old man with a little smile on your face knowing that the coach who still haunts your dreams still has your back all these years later.

7. Two drinks are usually enough.

You’re 25. You just got done with school. You still think it’s normal to have drink after drink at the bar until 2 a.m. You’ll learn.

Getting drunk will become less fun as you get older. You’ll start to regret the consequences of saying and doing dumb shit more. You’ll wish that you had a crisper recollection of conversations with friends, and date nights with Heather. And the hangovers – let’s just say that your ability to bounce back will greatly diminish.

So stick to two drinks in most situations. If it’s a work function, make two drinks a hard stopping point. If it’s social in nature, use it as a rule of thumb. I’m not expecting any miracles here. You’ll still have your moments 15 years from now. Just shoot for moderation as much as possible.

8. Time first, money second.

You can always make more money, but time is finite. You can’t get it back. You’re too focused on work and on making money. And for God sakes, stop obsessing over the possibility of a secure retirement 40 years from now. Yes, I’d be remiss to tell you that saving is not important, but you could get hit by the proverbial bus any day. So don’t just focus on saving at the expense of experiences. Have some balance and take that epic vacation once in awhile. But don’t be stupid. It’s not the accumulation of stuff that will make you happy. Stuff will just make you trapped.

Finally, remember that one of the reasons people focus so intently on retirement is that they hate what they do. You’re about to learn that you don’t like being a lawyer, so start evaluating your options for a career pivot to something that inspires you. If you love what you do then saving for retirement will become less of a concern because you’ll be able to work – and derive satisfaction from it – as long you’re physically and mentally able to. After all, you’ll come to realize that the prospect of days of endless freedom in retirement may not seem as satisfying as you think now.

9. Focus on your strengths, not your weaknesses.

You’ve been told your whole life to focus on your weaknesses, whether they be dribbling with your left hand or doing long division. Like a lot of conventional wisdom, “focus on your weakness” is folly. Life’s too short to focus on weaknesses.

Generally speaking, accept them and move on. Live the 80/20 principle – 20 percent of your effort will result in 80 percent of benefits. Excel at what you’re good at, and what comes naturally to you. Don’t be a jack-of-all-trades and master of none. {tweet that}

10. Enjoy that nice full head of hair now.

It doesn’t get any better with time. But no hair plugs  – everyone will think you’re having a midlife crisis.

Good talk. I think that’s enough for now. You have a lot to think about and process. Keep in mind that I barely even mentioned kids. I’ll save that for another conversation, maybe when you’re 30. We can discuss that topic over a beer, or three.

Readers: Is there anything you’d like to say to your younger self? Go ahead and leave a comment below – it’s cathartic, and you may even help someone who could benefit from a little wisdom that comes with age and experience.


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  • Gene

    Another great one Jay. I’m sharing it with my 2 boys in college and my daughter in high school. I also thought of a couple others “It’s a marathon and not a sprint” – time will move fast enough for you so you don’t have to help it along” and of course the postings on social media that may seem funny at 25 that will likely haunt you later in life.

  • Jason Blumer

    So glad you mentioned #8. Saving for retirement is a huge scare tactic retirement companies are pulling on people lately, and it’s just not that necessary. Like you said, saving IS important, but there is a huge amount of fear in this area and I think it’s unnecessary.

    Let’s love our work, and work until we are 95. I will not watch the Price is Right from ages 65 to 95.

  • Steve

    40 year old Jay may kick the crap out of 25 year old Jay, but it would be one of those slap filled, hair pulling duels we see between middle school girls.

    All joking aside, I’d go back and tell 25 year old Steve to pay more attention to his health. Exercise sure; but also visiting the doctor once a year, learning about healthy food options, etc. Those types of habits are easier to create, and maintain, at 25 than at 40.

  • Brittany

    Yes! I second waking up early, travel as much as possible and don’t spend on “stuff!” Luckily, as early as 18 I knew my priorities and have never ended a year at a job with a lick of vacation time left and have never regretted a dollar spent or long day of flights to reach a destination.

    #6 is really interesting to think about. I’m hardest on myself. I never responded well to coaches, bosses, or instructors that were yellers or even slightly stern, in fact, I think those people taught me how I didn’t want to be perceived. I guess that’s my INFJ personality coming through!

  • Rita

    Whether you find this encouraging or depressing……… At age 70 (almost), “life is just as perplexing, confounding, and full of possibilities as ever”! Keep up the great posts.

  • Brian

    Not sure how I originally stumbled upon your blog Jay, but I’m glad I did. Thanks for sharing your thoughts & story. It hits very close to home for me and my little family.

    I was late(r) to the party on #9, but I’m doing better with it now.

    I would tell my 25-year-old self all of that time you spend questioning why those typical 25-year-old things don’t interest you will pay off big-time when you’re 35.

  • Sheila

    Life and Whim,
    What a GREAT read.I resonate with so MANY of your points. At my recent milestone 50,.. I will take your advice & put pen to paper.
    I truly enjoyed meeting you and look forward to meeting Heather. I’m enjoying leaning into your blog/ insights. Well done and bravo for choosing life- Northern Michigan style! We are blessed to have you and your family in our great community!

  • John Wise

    Spot on Jay. Life is a Journey, so take the trip.

  • Judy

    Loved your article.

    Thinking back when I was forty, my children were teens. Worked full time job,life was very fast.
    I just don’t know where the time went. The children are adults now and I’m grandma.

    I have learned to take time to smell the roses.cherish your friends like they are gold. Never expect anything and you will never be disappointed. Family is everything


  • Robyn

    Love this post! It just might be my favorite. Maybe because I can relate to all of these, minus #10, thankfully😁

  • Stevie Renee Wells

    As a 25-year-old college student, I needed to hear these things. I went to college right after high-school with high expectations, and failed. In the last 7 years I have enjoyed a variety of vocations, but I couldn’t tie down my passion. Almost by accident, I figured out what I wanted to do someday “when I grow up”… theoretical physics. So, I’ve started an endless journey of education and grad school a little later than most, but I am so priviledged to have a supportive husband (who is also in college) and life which allows me to do so. Your advice will not fall of deaf ears!