If given the chance I am not sure I would want to go back almost 30 years to give pointers to my 40 year old self. The rule of unintended consequences would might make such time travel a disaster. But, for purposes of this post, let's pretend it would be a good thing.
Experience is unteachable. It can only be gained by living and learning. If you will allow me to tell you what is to come in the next few decades of your life, I may be able to spare you a lot of wasted time, effort, and heartache.
I am not going to detail what happens with your career. If I do you might be tempted to change something and therefore miss both the highs and lows you will experience. So, just trust me, you do well and you will overcome some sizable bumps in the road. And, since you are reading this letter you know you won't die young.
I won't tell you what is ahead in America or the world. Nor, will I make you a rich man by alerting you to inventions before they are reality, or tell you if the Cubs ever win the World Series. Those are mysteries that will unfold, in their proper time and sequence.
But, I will tell you four things now, that if you pay attention, will make your life fuller and more satisfying than you might imagine. They are in order or importance, so don't skip to #2 before you deal with the first one.
#1) Nothing is more important than relationships & friends.
There is nothing in life that can make you happier and more joyous, or more depressed and sad than neglecting important relationships. No amount of money, no second home, no possessions, no fame, no power, nothing can fill the void in your life if you allow meaningful relationships to die.
We are not designed to be alone. We need others to care for, and care for us, to allow us to feel alive. A strong and fulfilling marriage is not required for a satisfying life, but it can make things so much sweeter. Don't put off fixing problems or assume that things will work themselves out. Your marriage will endure (spoiler alert), but you will lose a few decades of true partnership and joy if you place your career and self above your wife's needs.
You need friends, true, deep, share-everything-type friends. Take whatever steps are necessary to keep renewing your roster of friends. It becomes much harder to develop deep relationships the longer you wait.
#2) Trust your common sense and yourself.
Experts are highly overrated in too many areas of life. A doctor, a good lawyer, a caring spiritual advisor....in these areas pick the best people you can find. But, for many of the decisions you will have to make for the rest of your life, depend on what mom and dad taught you, what you have learned so far, what trusted loved ones tell you, and your moral code.
Believe in the gifts the Creator gave you to pick the right path, or get back on track if your steps falter. Now and then, self doubt is normal. But, don't let it paralyze you. Any action is better than inaction. Doing nothing is actually a choice. Decide to take a step and see what happens.
#3) Good comes from every experience, even the ones that seem bad.
You have been raised to believe their is a superior being who has a plan for everything and everyone. Every bad experience you have has an eventual good purpose.
Whether it is to teach you a lesson about pride, or hope, or trust, or perseverance, there will be a reason everything in your life occurs.
Be open to what lies ahead. Don't hide from what life will bring to your doorstep. Trust me, the journey will change you for the better.
#4) Don't be afraid of risk-taking.
Up until this point, you have led a rather conventional life. Yes, you experienced the loss of your job 10 years ago, with two young children and a wife depending on you, but you took a big chance on yourself and it has worked out so far. Generally speaking, though you have played it safe.
I don't mean just in your career, but in how you live. You hate being a beginner so you are loath to try new things. On vacations, you pick safe places and "normal" activities. You rarely push the envelope in much of anything.
From where I sit now, I wish you (I) had been more willing to stretch myself. I wish I had tried different lifestyles, hobbies, creative outlets, and physical expressions. Over the last few years I have come to appreciate what pushing back a bit can mean to the fullness of life. Get a jump start. Take more risks now, when you are still healthy and young enough to do so.
Your older self