Dear Seeking Wisdom

The short essay below comes from an advice column written by a lady who goes by Dear Sugar – her real name is Cheryl Strayed.

Dear Sugar received a letter from a reader (who used the name: Seeking Wisdom) asking Dear Sugar what advice she would now give to herself if she could go back in a time machine and talk to herself when she was in her twenties, i.e., “What would you tell your twentysomething self if you could go back and talk to her?”

I found this about five years ago. Admittedly, it deviates a bit from MindSet’s usual focus on business leadership and culture. Yet it is consistent with MindSet’s focus on helping staff members to be successful in life. Cheryl’s response is also beautifully written; it’s worth reading slowly.

With just the slightest of edits, here is what Cheryl says she would like to be able to go back in time and say to her younger self…

There are some things you can’t understand yet. Your life will be a great and continuous unfolding. It’s good you’ve worked hard to resolve childhood issues while in your twenties, but understand that what you resolve will need to be resolved again. And again. You will come to know things that can only be known with the wisdom of age and the grace of years. Most of those things will have to do with forgiveness.


Don’t lament so much about how your career is going to turn out. You don’t have a career. You have a life. Do the work. Keep the faith. Be true blue. If you aspire to be a writer, keep writing and quit your bitching. Your book has a birthday. You don’t know when it is yet.


You cannot convince people to love you. This is an absolute rule. No one will ever give you love because you want him or her to give it. Real love moves freely in both directions. Don’t waste your time on anything else.


Most things will be okay eventually, but not everything will be. Sometimes you’ll put up a good fight and lose. Sometimes you’ll hold on really hard and realize there is no choice but to let go. Acceptance is a small, quiet room.


One hot afternoon during the era in which you’ve gotten yourself ridiculously tangled up with stupid things, you will be riding the bus and thinking how worthless you are when a little girl will get on the bus holding the strings of two purple balloons. She’ll offer you one of the balloons, but you won’t take it because you believe you no longer have a right to such tiny beautiful things. You’re wrong. You do.


Your assumptions about the lives of others are in direct relation to your naïve pomposity. Many people you believe to be rich are not rich. Many people you think have it easy worked hard for what they got. Many people who seem to be gliding right along have suffered and are suffering. Many people who appear to you to be old and stupidly saddled down with kids and cars and houses were once every bit as hip and pompous as you.


When you meet a man in the doorway of a Mexican restaurant who later kisses you while explaining that this kiss doesn’t “mean anything” because, much as he likes you, he is not interested in having a relationship with you or anyone right now, just laugh and kiss him back. Your daughter will have his sense of humor. Your son will have his eyes.


The useless days will add up to something. The shitty waitressing jobs. The hours writing in your journal. The long meandering walks. The hours reading poetry and story collections and novels and dead people’s diaries and wondering about sex and God and whether you should shave under your arms or not. These things are your becoming.


And one Christmas at the very beginning of your twenties when your mother gives you a warm coat that she saved for months to buy, don’t look at her skeptically after she tells you she thought the coat was perfect for you. Don’t hold it up and say it’s longer than you like your coats to be and too puffy and possibly even too warm. Your mother will be dead by spring. That coat will be the last gift she gave you. You will regret the small thing you didn’t say for the rest of your life.


Say thank you.