Some of the purest joy I experience is not just when helping someone but when helping them in a way that I was not helped. I think everyone with children experiences this joy: there are ways that you provide for your children that you were not provided for, and — although they are likely unaware of it — you take the greatest joy and pride in knowing that you have provided for them in that way. They will not experience what you did, and, because they don’t, they will not even know how to appreciate what you’ve done for them. Why does this type of giving give us so much joy? I think because it involves self-sacrifice, which is the highest expression of love for another person. Charity is great. But self-sacrifice is literally transcendent because it requires going beyond one’s self. And I think only such transcendent acts can give transcendent joy.
Why am I talking about this? I want your kids to have what I wish I had at their age, and I think you might find that you want this for them too.
What I wish I had was professional guidance. There were some things my parents (like all people) were less familiar with, and so they could not provide a 
broader horizon than they knew. Don’t get me wrong, I am extremely happy with where I am, but some of my most informed peers followed a roadmap that I did not know existed: start college and join the Blue Chips Club (at the University of Chicago), internships over the summer with banks or consulting firms, what classes to take (including some graduate courses at UChicago’s Booth School of Business while in undergrad), where and when to apply for full-time positions, etc. By the time I figured out what I might want to do (at the end of undergrad), my most well-informed peers were already hired.
But, more than that, I wish there had been someone besides my parents to introduce me to what I could be. If you have teenagers, most (probably 
all) of you know what this feels like: most or all of what you say is wrong. But we’ve all been there. We get it. Teenagers want to and need to find themselves and find their independence. While I was doing that (and not heeding wisdom and advice from my parents), I wish there had been someone with wisdom and advice whom I would have listened to. I wish I had someone to tell me to “fail” more. I put “fail” in quotes because it’s very rare that open-minded people every really fail. They learn, surely. But failure implies the absence of winning, and, even in “failure” you can massively win from learning from that experience. Thus, as long as a person is self-aware and open-minded, it’s overwhelmingly more accurate to say: Sometimes you win. Sometimes you learn. It is actually difficult to truly fail as long as you want to learn from your mistakes and improve yourself.
So I wish I would have challenged myself dramatically more. How so? Although I took difficult courses in college, I only took classes that I knew I could succeed at. 
So, when I had finished undergrad, I had no idea what my limits were. No idea what I could really achieve. I did not push myself to become more than I knew I could be because I was terrified of failure that would shatter my image of myself and hurt my ego and my pride. Dramatic, right? Well, at least I have learned. As long as you understand learning from life, not achieving a given goal will not crush you — it will equip you for what comes next. The sooner people learn that lesson (which some never do), I think, the happier and more successful they will be.
Maybe no one could have given me the confidence and the urging to push myself. Maybe I would not have listened to or followed a prescribed roadmap to success. But I wish I had had the option to do so. I don’t know who I would be or what I would be doing right now, but that’s the point. You can never re-write the past. You can only write the future.
We can help write the future of our children. That is why I love my job so much: I get to help empower students to write their futures, to succeed in life, and to succeed beyond what I have.
I also wrote this post with one specific person on our team in mind: Andrea Reiter, our Success Coach. I feel incredibly privileged to have her on our team and see how she helps to guide my students to a more successful future. I wish I would have had her professional guidance when I was a teenager, but I am glad that my students have the opportunity to work with her to increase their success.
