Most of my financial planning clients are business owners, older folks who want to focus on retirement planning, or sudden wealth recipients (think inheritance, lawsuit settlement, business sale, etc.). I’ve been working with clients for over 20 years, so many of my clients now have kids of their own that I also advise. These younger clients – Millennials for the most part – often have similar financial questions and concerns. They are worried about student loan debt, finding a good job, and creating financial success. I enjoy these conversations and they have caused me to think back to when I was younger.

What are a few of the things I wish I knew then? I’ve come up with a list. It’s not exhaustive, but I think it highlights many of the more important ideas that would have been critical for me to know when I was younger, and are equally as relevant today for Millennials (and really anybody who wants to improve their finances and life).

In no particular order, here are 20 things I wish I could tell my 20-year-old self…

1. Take bigger risks. You are playing it too safe. You are worried about little things and worried about failing when you shouldn’t. The time to learn to walk is when you are young and short. If you fall, you don’t fall that far. You think you have so much to lose if you fail, but you don’t when you are young. This is the time to take the big risks because you have time on your side if it doesn’t work out. Do you think when you’re older and have a mortgage, kids, bills, and a career that it will be less risky?

Think about a risk that scares you – it could be starting a business, inventing something, taking a year to join the Peace Corps, backpacking across Asia, whatever – and then think about risk versus reward. If it doesn’t go well, what could you lose? I’ve talked to many older people who have regrets. People who say, “When I was younger I wish I would have…” Guess what? You are younger. Now is the time! It will never be less risky than it is today.

2. Invest in yourself more. The single best investment you can make is in yourself. This is especially true when you are younger. Why? You get to benefit from the education longer. Think of it this way, who is going to benefit more financially, the person who becomes a lawyer at age 72 or age 22? And it’s not just formal education or degrees that I’m referring to. Invest in yourself can mean anything where you are learning and growing. It includes reading, taking online courses, getting certifications, or even things like personal development programs.

You are your best asset. The more you can invest in yourself the more valuable the asset becomes. What if you took an online course on how to become a better negotiator? You’d have 70 years where you could benefit – negotiating a better price on cars, houses, and even raises. I always suggest you learn a skill before you need the skill. This means keeping an open mind about what to learn and an open wallet. Nowadays, there are many free courses available, but don’t be afraid to spend money to grow. It’s the best investment you can make.

3. Get money smart. This is one of my favorites because it is so easy and it will pay you back year after year. One of the reasons people struggle financially is because they make uninformed decisions, but more commonly, they make no decision. Financial paralysis is real. I see it often in my practice. Nobody said investing or tax or personal finance was easy. In fact, it can be mind-numbingly complex. This causes a great deal of people to avoid financial decisions because they lack financial confidence.

The mistake most people make is that they think they need to know much more than they really need to know. You don’t have to be an expert in all things money. You just need to learn a few basic principles and you will be far ahead of the pack.I recently published my fourth personal finance book, Get Money Smart: Simple Lessons to Kickstart Your Financial Confidence & Grow Your Wealth.What makes this interesting is that I didn’t even want to write it. A couple of years ago I was working with a 22-year-old client who received a large lawsuit settlement. He admitted that he didn’t know very much about money, taxes, or investing and that he was nervous about being responsible for so much money. He was thirsty for knowledge and asked for a recommendation for a simple book that would give him a brief introduction to the world of personal finance. “No problem,” I said, assuming there were dozens of great options from which to choose.

Well, a week later I could still not find anything even remotely close to what I knew he needed. Instead, we decided to have weekly money coaching sessions where I would take a concept and do my best to explain it as simply as possible. I enjoyed doing this so much I decided to write Get Money Smart based on these lessons. If you want to increase your financial knowledge and confidence, this is a good place to start. Or if books aren’t your thing, sign up for a free Get Money Smart video course or take advantage of countless podcasts, audiobooks and webinars that will help get you money smart.


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