The first thing that comes to mind in the category of “advice for my younger self that might or might not be heeded by my younger self were he available to receive the message” is the importance of seeking out mentors. Here’s what I didn’t realize twenty years ago, and still need to remind myself of regularly: mentors need mentees as much as vice versa. Older people, by and large, are positively aching to share what they know. This reservoir of knowledge, and the appetite of those who have it to share it, should be seen by younger people as a natural resource. Seek out people who have climbed, or attempted to climb, whatever mountain you have your sites on. Not all the advice will be good advice — it’s critical to correct for distortions in the lense, to ferret out the biases or non-transferrable elements of a given mentor’s experience — but the process will usually be fruitful. The conclusion may be that you are looking at the wrong mountain. In my experience, a huge preponderance of the mistakes made in business and life are made over and over again, and more lessons than we think are broadly applicable — innovative internet companies confront a lot of obstacles that also confront lampshade manufacturers.
Why are mentors so accessible? Because sadly, this post title notwithstanding, we can’t give advice to our younger selves and we want to. Sharing what we’ve learned with someone in an earlier stage of life is as close as we get. If they have the same haircut we’ve had at the time, all the better. Many people get paid to relieve this urge through professorships and book deals — a great solution. Everyone else over a certain age, who thinks he or she has learned a thing or two, tortures his or her children (whether six months old or sixty) with an overabundance of unsolicited advice, and bottles up the rest.
Much can be learned from reading the blogs and books of mentors — I am making a note to self to do more of this — but a direct relationship makes possible advice customized to your needs, and the longterm possibility of useful introductions, support for your endeavors, and maybe even lasting friendships. But it is always best to focus on the request for counsel — the “flattery-for-wisdom” exchange is the foundation of the mentor-mentee relationship, and offers the most immediate reciprocal benefit.
Speaking even more broadly, it seems to me that intergenerational relationships are good for everyone. They make younger people wiser and older people more tuned into new ideas. It feels like these days most of us have fewer intergenerational relationships than was common in past eras, when generations lived and socialized together. We should seek them out. I hope when I am 90, if I am so lucky, I will have friends in every stage of life, and the good sense to hunt down the 100 year old down the hall and figure out what she knows.