We’ve all played this game before. We relive our past decisions and behaviors. We wish we had a time machine to “fix” the mistakes from our younger selves.

This exercise rarely makes you feel any better. I don’t recommend that you spend much time regretting mistakes you’ve made or things you took for granted (I often look at my college ID and long for the days where I could run my hands through a full head of glorious hair).

While there’s little value in this painful trip down memory lane, it can be extremely useful to the young person about to make the same mistakes.

As a public service to all young people, here’s a list of the character traits I wished I’d developed before turning 30.

  1. Be Courageous – I was, and unfortunately still am, a little bit of a chicken shit. If I knew then what I know now, I would take more risks, both personally and professionally. Unless the risk you’re considering is robbing a bank, there’s just about nothing you can’t bounce back from before you turn 30. Take that backpacking trip around the world. Ask out the best-looking girl in your building. In other words – live life to the fullest.


  1. Be Persistent – As I mentioned in a previous post, I spent the first 30 years of my life quitting anything difficult. If I knew then what I know now, I wouldn’t have switched majors, quit playing basketball or settled for the easy jobs (However, I would have quit law school – the last thing the world needs is another lawyer who hates the profession).
  1. Be Mindful – Up until I read The Power of Now by Eckhart Tolle, I was certain I needed to spend every moment of my life preparing for the next in order to reach my goals. Knowing what I know now, I would have spent more time living in the moment. Obsessing over the future is never worth the cost of missing out on the enjoyment of your present circumstances. Stop worrying so much about your next promotion and take Friday afternoons off to have fun with your friends.
  1. Be Relaxed – I spent the majority of my youth chasing success. From an outside perspective, it worked. I now have a jam-packed resume. However, I spent the majority of these years worrying if it was ever enough. If I knew then what I know now, I would have taken everything a whole lot less seriously. Trust me, your big meeting this Friday with your boss isn’t going to mean squat this time next year. Do you very best and learn to be OK with the results. Relax, life works itself out.

As Dr. Angela Duckworth points out in her book Grit, perseverance has more to do with your success than talent or luck.

  1. Be Decisive – As a young person, I remember several occasions where I allowed myself to drown in an internal pro/con debate over trivial decisions. If I knew then what I know now, I would pull the trigger faster on just about every decision (unless again, you’re considering robbing a bank). Not sure whether you should buy or lease a new car, go to Cancun or even Vegas for a spring vacation? Who cares? Stop over-analyzing. Make a decision!
  1. Be Healthier – I, like most single people in their 20’s ate like crap (lots and lots of carbohydrates – the bagel industry was built on my eating habits) and drank entirely too much beer. While it was a lot of fun, it made me fat and killed my energy at work each day. If I knew then what I know now, I would have eaten more vegetables, fruits, protein and limited my drinking to the weekends. As Tony Robbins pointed out many years ago, “Nothing tastes as good as healthy feels.”
  1. Be More Giving – My 20’s were focused on one thing – me. This led to an unhealthy obsession with how much I was achieving, earning and acquiring. If I knew then what I know now, I would have volunteered more. Perspective is the most important variable you can control in your quest to enjoy life. Helping those who are less fortunate is for more beneficial to you than it is to them.
  1. Be Patient – A younger version of me expected immediate results in just about everything I tried. If I wasn’t getting promoted fast enough I quit my job. If I didn’t win an award the first year I applied, I assumed they system was rigged. If I knew then what I know now, I would have been more aware that life is a marathon and not a sprint. Keep that in mind the next time you’re tempted to compare your achievements to your peers – we all finish up in the same place at the end.
  1. Be Forgiving – I saved this one for last, because even though I now know I made a lot of mistakes my 20’s, I forgive myself for each one. But, I wasn’t always that way. It wasn’t unusual for me to agonize over a small mistake for weeks. If I knew then, what I know now, I would learn my lesson and quickly move on. There’s absolutely zero value in beating yourself up over spilled milk.

Keep these in mind as you enjoy your journey.