This question crops up from time to time, and my response rarely varies. If I could, I would command my 20-year-old self to be confident. The insecurities of youth are soul-destroying, and with the advent of social media and peer pressure for “likes”, young people are constantly under pressure to be better—the assumption being that they are never good enough. They have to keep striving to be one of the cool ones, the beautiful ones, the leaders, and influencers.

Baby boomers also faced peer pressure, but it was far more innocuous, especially if you grew up in a small town as I did, where you didn’t have access to all the latest fashions, fads, and fantasies. Bullying wasn’t nearly as pervasive as it is today. Ironically, bullies are usually the truly insecure ones who need and seek validation by insulting and hurting others who are most likely above them in the social network. Our parents were working-class, and today’s status symbols like iPhones, celebrity-endorsed sneakers, and big-ticket fashions would never have been an issue, but more of a never-going-to-happen. Most of our things were ordered through Simpson’s and Eaton’s catalogue order offices.

I remember skipping down Ranney Street in front of my house as an eight-year-old thinking, “I’m so smart; I’m so pretty, I’m so kind, and people like me.” I had complete and utter confidence in myself. That self-confidence begins to erode around the age of twelve as we enter puberty and our developing hormones kick in. The confidence that was so irrepressible as an eight-year-old vapourizes as we become teenagers.  We find ourselves primping for boys, while trying to be as cool and accepted as the popular girls in our class. Our insecurities take root and grow.

It takes decades for us to regain the confidence we lost as young girls. Through dating, careers, marriage, divorce, and aging, we face a constant barrage of “You’re not quite good enough” from peers, employers, partners, and the media. The truth is, we are absolutely good enough, but it may not be until post-menopause or retirement that we realize we wasted decades reaching for an unattainable standard defined by people who have no right or qualifications to judge us. Each one of us is an amazing individual, and this should be celebrated from an early age, not waiting until we’re in the third or fourth quarter of our lives.

This is another one of those times I’m glad I’m old. I would not want to be trying to function as a young person in today’s world of extreme competitiveness, peer pressure, bullying, and social media. If I could give only one word of advice to a young person (who probably won’t pay attention), it would be “Be Confident”. You are an amazing creation with skills, aptitudes, and gifts no one else possesses, so ignore any suggestion that you are otherwise. And, be kind. There’s merit in taking care of yourself first, in both your personal and business life.

While I’m at it, I’d also advise saving in RRSPs as much and as soon as possible. That’s because when you reach menopause, you might want to take a lifestyle pause, and if you have a nest egg, you will have options. Those expensive purses and shoes all those years ago will be forgotten, and remembered as a waste of money. Oh! And, I’d also advise myself to, “Buy stock in Apple, Microsoft, and Amazon”.

What I wouldn’t give today to have the body, the hair, and the energy I had when I was in my twenties. If only I also had the smarts, the wisdom, and the self-confidence that I have today. Each stage of life has its challenges and rewards. I wish I had a better appreciation back then for the gifts I had been given at a young age, but, as they say, we have to make our own mistakes. That’s how we learn and grow. And, I’m mighty grateful for the gifts I have today.

What advice would you offer to your 20-year-old self? Share your thoughts in the comments below.