How often have you uttered the envious phrase, “I’ve always wanted to do that!”? It could have been in response to a story told by a friend who just returned from a month-long trip to Australia, or a buddy who just brought the house down at an open mic night. Maybe it’s as trivial as a co-worker of yours standing up to the boss and telling him or her to go to hell. But, oh, how you wish you would have had it in you to pull off what they just did!

I’ve got news for you - you do have “it”. You absolutely have the ability to make any number of things happen. I bet you could even take a trip to a better place than Australia, one that would be rewarding for you on countless levels. The point is, whether it’s a trip to a revered location, a desire to do something creative, or something you want to do simply for the experience, if you ever want to start enjoying life in the way that you find best then you have to stop “wanting” and start “doing”.

Start that business you’ve been thinking about for years. Ask out that gorgeous guy or girl from the coffee shop. Grab the wife and kids and take them to Florida. No matter what your flight of fancy may be, know that even if the experience turns out to be only 1/10th as exciting or successful as you had originally hoped, you’ll never look back and wish you hadn’t given it a shot.

Life is too short, and your opportunities too few and far between, to wonder “what if?”. Every “what if?” in your mind should be directly followed by a concerted effort to decide when and how you could answer that very question. Every “I’ve always wanted to do that” should now be followed by a “and here’s how I will pull it off” thought in your head. You’re guaranteed to be a happier, more content person.

Of course, I understand that there are a lot of perfectly good reasons why the things on your “To Do in Life” list haven’t all been checked off yet. Some require money, some require excessive free time, and yet others go against what your circle of family and friends believe is a smart and acceptable way to live.

As we’ve all heard, if something in life is worth doing, then chances are it’s not going to be easy to do. Different types of obstacles exist no matter what sort of worthwhile, “I’ve always wanted to do that” activity or experience one can conjure up.

I think, then, the first step in moving from “I’ve always wanted to do that” to being a person that does those envious things is to get over any fears or misgivings you may have particular to each situation. Fear of failure, fear of “what other people will think”. Those need to be addressed, because they are incredibly common thoughts/emotions and they are limiting.

Generally, there are three types of obstacles that keep people from making the decision to do something like start a company, learn to speak Italian, or try a new food: Practical, Personal, and Social Obstacles.

Practical Obstacles - Practical obstacles are the limitations created by simple, matter-of-fact truths. You may really want to visit Paris, but don’t have the money on hand yet. Perhaps you have a young child to take care of and that is getting in the way of your dream to tour with a band. Practical obstacles are generally very evident reasons as to why you can’t do something.

At the same time, they are things that you can work around. Save money. Wait a year or two for your son or daughter to get a bit older and have everything else together to pursue your dream. If you think I’m oversimplifying these types of situations you may be right, but I’m a firm believer that if there’s a will, there’s a way. You can get around practical obstacles with some creativity and motivation. Trust me, you’re going to need those qualities to live exceptionally, so it’s best to start practicing them now.

Personal Obstacles - What I mean by personal obstacles are those internal battles you have within yourself when it comes to deciding if something is a “good” idea or not. This is where self-doubt usually sets in and destroys our desire to do things well before we can even consider if an idea is worth pursuing. Questions like “Am I really capable of that?” “Am I smart enough?” “What if I fail?” abound. To be honest, this very dilemma has been talked about to death. But you don’t need a motivational speaker to bring out feelings of belief in yourself. You just need courage. Have the guts to take that step, because even if you fall it will be worth it.

At some point in your line of decision making, no matter what you’re pondering, you have to have a little piece of you that tosses caution aside and says, “Screw it. This is my life and I’m doing this.” Find that within yourself and hold onto it for all time.

Social Obstacles - Social obstacles show up the second you let the dreaded “what will other people think?” pop up into your stream of consciousness. First of all, “other people” are always going to think something. Humans are social creatures and (particularly if you are American) seem to be overly-interested in the lives of other’s. Your friends, your family members and your co-workers are always going to have an opinion. And generally their opinions will vary from positive to negative depending on what the subject is.

Plus, they will rarely collectively lean more one way (positive) than another (negative). Your 19-year-old cousin will really admire you for camping outside the stadium to get playoff tickets, but probably doesn’t think (or care) too much about you whisking away your wife for a long-deserved romantic weekend in Napa. Grandma and Grandpa would think you’re a damn fool for dropping $250 on those same tickets, but a great husband for spending quality time with your wife.

What about your friend who just got back from Australia, that you envied so for doing something you’ve “always wanted to do”? Her boss is royally upset that she just missed a month of work, and her parents think it was a huge waste of money.

Your friend’s admirable decision to take a trip was met with just as many Practical, Personal, and Social obstacles as any other worthwhile decision. But it was her decision, and I doubt she regrets it. Next time, hopefully you won’t either.