The year was 1989. I was 22 years old, fresh out of college and ready to take on the world. That’s what I did, but not in the same way I would now if I could go back and do it again.

Thanks to my parents I was always encouraged to work for myself. Besides a few jobs during high-school and college, I’ve never had to work for anyone except for my customers. Right out of college I started a service related business. Did that for 10 years. Sold it, and went on to internet related businesses starting in 1999. Since that, the internet is where I’ve been. Starting with affiliate marketing, eBay and PPC arbitrage and now eCommerce and consulting.

While I’ve accomplished a lot, there are many things I would like to go back and tell my 22 year old self. Below are the top 5.

1. Take More Risks! The biggest risks usually have the largest payoffs. Not only monetary, but in all areas of business. When you’re young you don’t have a mortgage to pay, kids to worry about and other debts that may hold you back. You can afford to fail and learn from failure. I’m not saying you should take stupid risks, but risks that are calculated and have big potential. Think smart, plan and take risks that you’ll be happy you took while you’re young.
2. Don’t listen to negative opinions of others. Like many new business owners fresh from college, I listened to the opinions of everyone around me. While it’s smart to listen, the negative opinions will sometimes hold back your growth as a company. I was fairly good a filtering negativity, but I’d tell my 22 year old self to filter even more. The best entrepreneurial ideas usually come from the creative mind of one. The most successful and creative companies didn’t get started by the founder listening to people saying the idea can’t be done. Try your ideas no matter how crazy other people say they are.
3. Go with your gut instincts. There are many times I can remember that I had a gut instinct about something but didn’t go with it because of #1 and #2 above. This is why #1 and #2 are so important. Not taking risks and listening to others can severely hinder your potential. If you’re starting a new business you’ll be filled with ideas. Don’t let others tell you your ideas are wrong or not the “safe” option. Your idea could be the next Facebook. Go with your gut instincts, they’re usually right.
4. Get help in areas you know you’re weak. Like many new entrepreneurs just starting a new business, I thought I could do it all. I was wrong. I did hire an accountant, but I should have also hired an ad agency and PR firm. Sure, I knew textbook knowledge in these areas, but nothing of the real world and making things happen as fast as they could have. I took the slow path and did all my advertising and PR work myself. If I would have hired professionals in the areas I was weak, I could have had much greater success in a much faster time.
5. Think outside the box and have fun! Many new business owners, including myself back in ’89, think inside the box. It’s safe and comfortable in the box. You can follow others and do as they do. Don’t do it! Think WAY outside the box. Think creatively. It’s much more fun and it provides much greater reward when your crazy ideas are successful.

If you’re young, just out of college or just starting out in business… take my advice and the advice of other “positive thinking” business people around you. Entrepreneurs that have already been through the process of starting and growing a business can teach you a lot!

Do you have some lessons and things you would like to go back and tell yourself? Share them below in a comment.