Hi Kalejaiye,

Thoughtful question.

I would tell him money only has one purpose in life: it gives you freedom to live life on your own terms. Many people 27 tell me money isn't important, it is something from another generation. Then you get into your late 30s, have kids, parents get sick, and money is important. Make money because you can take care of yourself, never be held hostage by anyone who wants to dictate your life, and you can help others when they need it.

I would tell a guy this young to date, experience the world, try on other people, but do not consider marriage until your late 30s. Live, experience travel and dream at 27, but stay free until you are mature enough to understand love. At the worst, live with someone, but hold off on marriage until you both get near 40.

I would tell him to sit and figure out what he really wants in life? Few people at 27 know, or will admit, what they want from their own life. Try a few different things now, but you do not have to commit to a career until you are older, Experience the world, but give yourself room to experiment.

I would also tell him to start with lifestyle. I knew early, after working in a large company, I hated it. I figured out how I wanted to live, where, and what I needed to achieve that life, then built a career around my life. I figured out a way to make money, yet still give me freedom to take big chunks of time off, live where I wanted to live, and travel. Lifestyle first, then figure out a way to pay for it. Remember, money is freedom. Make a lot of it. You can always use it to help others if you make too much.

I would tell him we all make mistakes. We drink too much, chase drugs, get addicted to crazy partners, but if you think and understand yourself, you can move past all of that. I would tell him we all make a mess of our life, and that is what creates us. I don't regret a thing, as stupid as I was, it has been a great adventure.

Finally, I would tell him to believe in himself. Good days, bad days, stupid days. I always knew it was my fault, but I never stopped learning and trying to get better. You can't carry the world if you can't carry your own ass first. Have faith, we all fail, but I always knew messing up just meant go again. I never lost faith in me.

Thomas