I follow a blogger named Bob Ramsey and truly enjoy reading his thoughtful Saturday dispatches. In April 2020, he was the one who wrote, “Don’t let the quarantine slip through your fingers”. The next day I started writing my book.

In October, he challenged his readers to a writing contest asking us to write in 100 words or less a letter of advice to our 25-year-old self. I entered the contest and the results were shared a month later. I loved reading the winning pieces of advice and while I did not win, I was delighted to have an honourable mention (in bold below). 

Here is some fun food for thought that may get you thinking about what advice you would give to your much younger self or to the 20-somethings in your life. Maybe a great question for around the table at the next family gathering? 

Advice to Your 25-Year-Old Self by Bob Ramsay

Ask anyone to write a letter to their 25-year-old self and they won’t be kind.

Indeed, given the responses to our writing contest last month – we asked you to write a 100-word letter to your 25-year-old self — being 25 is one of the most arrogant, unknowing, unseeing and cringeworthy times of our lives. Did I really spend all that money on a watch? Hook up with a known psychopath? Treat my best friend like dirt? And don’t even talk to me about drinking and drugging. We’re lucky to be alive.

I remember back in the 80s my film festival friend, Helga Stephenson, asked if I would help her ‘chaperone’ a party for TIFF’s young financial supporters. They were all under 30. They were smart, attractive, fit and cocksure. They beamed with certainty. Helga said as we left: “Life hasn’t happened to them yet.”

True that.

Clearly, the older you drift from 25, the younger 25 looks. By the time you’re twice that age, life is often a muddle, or a slow-motion leap off the cliff. Get to threescore years and ten, and it can be a tragedy in the making. Get to 80, and more tires are coming off the car than staying on.

Growing old may not be for sissies, but it does give you wisdom about things you used to be foolish about. Not that you’ll have a chance to make those things right. But at least you can offer painful advice like what our readers did.

“Leave. Take the kids with you. Live your life. Your authentic life. It will be ok. The kids will be ok. Do it.”

Or this… “You were searching for love. Made the wrong choices. Some disastrous. Launched a business. Hit hard times. Bought a house. Divorced. Lost a house. Family declined to help. Cold mother. Absent father. You pushed yourself so hard and fast to get nowhere. Now you’re contemplating suicide as a salvation. You can’t be sure it won’t just be a return to a circle of hell. Take a breath. Hang in there and know it will all work out well. Very well.”

Or this… “You don’t know me, but I’m here to tell you not to relax. Time travels fast…”

There were also lots of upbeat entries….

“All these years later and all of the degrees and fancy jobs, and a pretty good book and articles written, you spend some of your days playing and being silly with your grandchildren. You are still a kid. That is why I am proud of you.”

“Travel the world. Don’t wait. Those daily walks with your dog? That’s your cure for almost everything.”

Some were softly regretful:

“Care a little less about what others think, and a little more about what you think. Sleep on it.”

But a surprising number viewed life as a forced walk in a bad neighbourhood. Like…

“Your horrific past is now in the rearview mirror, and you’ve got the education, family, and professional standing to make you a somebody. Sadly, along the way as you were giving the audience what they wanted – you died inside – and never realized it. Accept that you know a lot about survival and nothing about yourself. When you realize that, don’t fall for the charlatans offering quick fixes.”

Or this…

“Be kind to everyone, trust no one, and forgive all.”

Or this…

“There are vultures in human form out there…Be alert in assessing people.

Learn to discern people’s intentions, protect yourself from toxic influences.”

But the best, most realistic advice of all?

“I know you well enough to know you won’t listen to anything I say, so no advice from your older self.”

Here are the three winning entries:

Bronze: John Dale

“I am not giving directional advice for your future life because, like a Monkey’s Paw, it’s a useless and potentially dangerous practice.

You will be more things than you can imagine. Everything will change. Nothing will change. There will be heartbreak. There will be joy. There will be success. There will be failure. There will be lots of time. There will be no time. Nothing will be in equal measure.

Love when you can. Help where you can. Treat yourself with respect.

Live it all and drink in the marvellous, messy mashup that is a life worth celebrating.”

Silver: John MacMillan

“You’re perfect. You’re doing everything just fine. Luck determines the outcome of most decisions, anyway. You’re reading just enough to be curious and dating sufficiently dangerously to be wise. Your gym membership will always be underused, so don’t change how often you go.

And money: you’re making enough to afford nothing too stupid. Yeah, you could call your parents more, but that’ll just make them wary. So, just do your thing. Besides, by the time you’re as old as I am, you’ll have forgotten most of the details and much of the shame. Happy Quarter-century, kid!”

Gold: Carol Banducci

“If I could whisper to my 25-year-old self, I’d say: you made it. All the long hours, the pressure, the sacrifices—they brought success. But you didn’t need to push so hard. Titles and achievements matter far less than the laughter you skipped, the dinners you rushed through, the still moments you let slip away.

I wish you’d paused more often, traveled more, hugged without hesitation, and loved without checking the clock. You already had enough. Life doesn’t wait for “the right time.” So, breathe, look up and be present. The view is beautiful when you finally stop to see it.”

So, congratulations to everyone who entered and for putting yourself (past and present) out there, and special congratulations to John Dale, John MacMillan, and Carol Banducci.

As we said: “Prizes include the quiet pride in a job well done. But as has been true for centuries and for billions of people around the world, your real reward will be in…heaven.”

Here is my entry:

Advice to My 25-Year-Old Self by Lianne Hill

You’ve got this. Be your authentic self. Grit and that competitive fire? Those are your superpowers. Trust your gut—it never lies. That guy- he’s the one. Hold on tight. When life knocks you down, dig deep. Those childhood wounds will heal. Give them time. Most people in the world are good- stop being so afraid. Motherhood will be the best thing you ever do. Your family will be your masterpiece. Travel the world. Don’t wait. Those daily walks with your dog? That’s your cure for almost everything. You’re going to be just fine. Better than fine.