Writing a Letter to Your Loved Ones

Writing a Letter to Your Loved Ones

This site is all about living a better retirement and having a bigger impact. An idea I have heard from a few people recently is to write a letter to your loved ones – particularly those you hope to have some sort of impact on. In my case, I have two young sons. Regardless of their age, I am making a commitment to write a letter to them each year on my birthday (next week I turn 36) where I intend to share principles, values and general life advice that I hope to instill in them as they grow older.

My hope is that these annual letters become a keepsake for them as well as offer some relevant and practical life advice that (maybe, just maybe) they can refer back to through the years.

One privilege I have in working with so many retirees is the level of life wisdom I hear each day. It inspires me! I hope what follows below inspires you to put your thoughts on paper to share what you’ve learned through the years with people you care about.

You don’t need to be a “writer” and there is no “right” way to do this. Just write down your thoughts distilling life wisdom you’ve accumulated through your years. Then, give it to your chosen recipients whenever you feel appropriate. Again, there is no right way to do this.

I know if a letter was written specifically for me, it would be something I would cherish for the rest of my life and even pass on. So, in an effort of encouragement, I thought I would share my version of this exercise. These are the lessons that I want to pass on to my sons at age 36. Given that this is my first attempt, perhaps next year’s version will be shorter as I won’t have to repeat this list. I guess we’ll see.

As you read what follows, think about the lessons you hope to pass on.

A Letter To My Sons

  • Character is everything. Many people say it’s your reputation that matters, but reputation is what others see, character is what you really are. Good character ensures a good reputation.
  • Tell the truth. The truth does not change based on somebody’s ability to stomach it. If you always tell the truth, you never have to remember anything.
  • Integrity is what you do when no one else is watching. You may not always be accountable to others, but you are always accountable to yourself. 
  • Use your manners. You are never too old to show respect. Please, thank you, yes sir, yes mam, no sir, no mam, Mr., Mrs. never go out of style. 
  • Care for people around you. There are always people who need help. Look out for people around you and see what you can do to help them. Seek them out; don’t wait for them to come to you.
  • Greatness courts failure. Failure is part of the success equation. It’s during these periods of struggle you will learn humility. But the only way to know your limits is to test them. If you aren’t making mistakes, you are probably stagnant. Choosing comfort usually results in mediocrity.
  • Excellence is born in preparation. We can only excel to our level of preparation. If you choose to enter the arena unprepared, you have placed an invisible cap on your potential. On the contrary, if you physically or metaphorically sweat and bleed in preparation, what you accomplish may far exceed your wildest dreams.
  • Action defeats fear. Feeling fear is natural, but the outcomes we fear most are rarely as bad as we envision in our mind. When you feel fear, you can consciously choose to act despite your feelings. That’s called courage.
  • Never give up. Every so often, life presents a decision point – choose to go on or give up. The point when you want to give up is the exact point you should accelerate because it’s often the same point that everyone else wants to give up. This is what makes discipline, determination and grit an advantage.
  • If you find yourself on the side of the majority, ask yourself, “What if the way everyone is thinking about it is all wrong?” You may find it’s right, but asking yourself that question will at least force you to think independently.
  • Keep an open mind. I’ve changed my opinion on a lot of things through my life because I’m willing to ask questions of people I respect who believe something different. Seek those people out. You’ll either walk away with renewed confidence in your viewpoint or you may change your mind. Both outcomes are good outcomes. Learning from other people is the best way to learn. Be encouraged to hear other’s perspectives. 
  • Don’t be impressed by money, job titles, or achievements.  Be impressed by integrity, generosity, humility, and kindness.
  • Cut your own path. This was one of my favorite quotes from my grandfather that has stuck with me. Believe in yourself and bet on yourself. Betting on yourself and your potential is always a good bet if you put in the work. Take a chance on yourself. If you won’t, why should anyone else? 
  • Inner scorecards are all that matter. Ego is a desire for external validation. Never worry about what other people think about you. If you know why you’re doing what you’re doing, that’s all that matters.
  • Do not try to change people. It won’t work.
  • Do not judge people and be quick to forgive. You never know what someone else is going through; give them the benefit of the doubt. You’ll appreciate the same in return when life is being tough on you. Instead, choose kindness.
  • You are the company you keep. In lieu of trying to change people or judge people, hang around good people. Choose your friends wisely. Choose people of high character. Proverbs 13:20
  • When you make mistakes (particularly life mistakes), don’t drown yourself in sorrows and regret. Instead, reflect on the mistake and learn from it. Part of life is learning to navigate. Sometimes your boat will run aground or into rough seas; it is how we learn.
  • How you respond to those situations that will determine your future, not the seas you’re currently in. Your response is often the only thing in your control. You cannot control things happening around you, but you can control how you respond.
  • Time is a remedy. You are going to be disappointed from time to time. You are going to disappoint yourself. You are going to disappoint others. Time cures everything. Pick yourself up, dust yourself off, and get back at it. Be the best you can be today. Then do it again tomorrow. It’s the only thing you can control.
  • Be present in the moment. This day and age, distraction is everywhere. Soak in your life, not what’s on a screen. Stop and pay attention to what’s going on around you. The great pleasure of my life is watching you (Emory and Turner) grow up. Laughing, learning, and exploring. It is so easily missed as each day rolls on. Life passes quickly, so pay attention or the small joys of life will pass you by.
  • Don’t forget where you came from. More is not always better. In case you become “really successful” by worldly standards, stay humble. Otherwise, you may find yourself surrounded by people but lonelier than ever.
  • The world doesn’t owe you anything. It’s up to you to make it happen.
  • More stuff will never make you happy.
  • Follow your inner moral compass. If you have to ask if you should do something, you probably shouldn’t. Your gut is an amazingly good decision-maker. When your gut is making you question your actions, it’s probably best to avoid it.
  • Don’t ever be afraid to do something you are not qualified to do. Many times, the people who change the world are not the most qualified.
  • Treat ladies how you want your mother to be treated – with love and respect. Hold the door for them. Chivalry dies only if you let it. Don’t.
  • Lastly, always remember two things: I love you more than anything and always try your best. I am here for you through all that life will throw at you!

I hope this post inspires you to write a letter to your loved ones to share ideas, philosophies, and principles that you hold near and dear.

Special Request: If you have any life advice that you’d like to share – I would be honored if you would share it with me? If you’d be so kind, send me a note via my “Contact Ashby” page and I’ll be sure to respond! Many thanks!

Related Reading:

A Letter to Grandparents

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