Saturday night I was at a party and while it was a good time, the great moment of the evening is when things are winding down and the discussions start getting pulled out. People are all in different states of inebriation and some of them accidentally let their guards down. There are others that purposely let their guards down, but pretend it’s accidental. Regardless of how it gets to that point, that is where some of the honest conversations come out of the evening.

There was a circle of us talking about careers, where we have been, and where we are going on. I went in the mode of just asking questions and there were three people at different spots in their life that had three different views on where they have been and where they are going. So while the conversations were anything but linear, I am going to do my best to make them that way.

I should preface this with the fact that I am anti-college in most scenarios. I didn’t make it past my first year in school and even if I had finished it wouldn’t have helped my career. There is a chance I could have made maybe 5% more then I do now, but saddled with student debt I don’t think it would have evened out in my lifetime. It does mean I had to work harder to get to where I am, but I have a respectable career with a respectable salary. I also spent a bit of time making the correct resume and choosing my jobs a bit (when I could) based on the résumé and the goal.

When I was around 24 I made a goal to reach a certain job with a certain income level by the time I was 30. Fudging numbers in a way I didn’t mean when I set the goal – I reached this by the time I was 29. I legitimately reached the same goal when I was 33. So depending on how you want to slice it I either reached it early or late. For those that are interested in the journey, I just ended up taking the longer path. I also got screwed over doing the same job for a bit less money working up through the ranks instead of getting hired from the outside. For those concerned about reaching the destination – I made it.

The first was someone who had recently gone back to school in his thirties. He is doing well and realizes that for him that school is more for the contacts than the direct learning. His contact list is growing and seems to be working out for him. He is going for film and realizes he is lucky to be at this point in history. If things don’t work out career-wise, he can still fulfill his dreams and do it online. He can do this and make supplemental or primary income. If he gets the big break and is pulled from the minors and into the majors, the world will be his oyster. He wants to create, he wants to grow, and he knows where he wants to be in 5-10 years. I also hope the best for him.

The next person was a guy in his twenties complaining that all companies care about is the paper. He doesn’t have a college degree (he doesn’t seem like going for it either). He is also in computers so I can speak with some authority that you do not need a degree if you want to get the work done. The confusing thing about it is that he is happy where he is. He wants more, but it’s in the abstract. He doesn’t know where he wants to be in 10 years – but he wants more. I explained to him the climbing through the ranks for compensation – he’s just stuck on the need for a degree that can be overcome.

He can volunteer and work on some online projects to pad out the résumé and get some legitimate experience. He can offer a non-profit to do work as needed. Anything to get that resume working in a way that will show any future he has the experience and doesn’t need the paper. All a degree can really get you is your first job, after that, a résumé is all that is required and can compensate. I also asked if he was happy where he worked. He said he loved it, he also was excited about a work conference he was being sent to.

I asked him if he was happy and why does he need to move. He didn’t know. Society has ingrained into us that we need to always be moving, to make more money, and to have bigger and better things. I’m working now and trying to slim down my life, but with better quality things. So less, but with roughly the same cost in the end. I explained to him that once you find where you are happy I wouldn’t look further until you truly didn’t enjoy your job. Don’t give in to the pressure. If you find something you enjoy (and your job isn’t in danger), keep at it and enjoy it.

The last person was the youngest and she wasn’t sure. I asked her what she wanted to do in ten years and she said she wanted to be a pirate. I asked her what was stopping her. She didn’t know where to begin. I immediately offered up that learning to sail might be a good start. At this point, she admitted to now being serious and said she wanted to be a forensic scientist. So I asked what is she doing toward that goal. She didn’t know where to start. I said that is definitely a career you need to go to school for, so I would at least enroll and get the starter stuff out of the way.

This highlights the point that this piece was leading to. She hasn’t started, because she doesn’t want to start the wrong way. There is no wrong way. It is either about the journey or the destination. The journey is what truly makes you. The destination is just the top of the mountain where there is nothing left to do. You can see the clouds below you – but what do you do next? You are not going to sit on the mountaintop forever. Eventually, you need to start the journey again by climbing down and back up again. It should never end until you die. To keep with the analogy – the first person is on his way to the top, the second one likes the party going on at the encampment part way up the mountain, and the last is looking for a sherpa and doesn’t know if she wants to leave the base camp party yet.

Too many people are worried about success. Society has taught us if you don’t do something well you are a failure. That failure is a bad thing. Just ignore him, he’s a failure. What is wrong with that? You learn from failure, and the only true success in life is constantly learning. He who knows the most is the one that truly wins. Once you stop learning you better enjoy where you’ve stopped – there is no going forward from that.

There are two types of failure in my mind. The first is failing big. You fail big when you have invested so much of your life/time/money into something that it absolutely destroys you for a bit. You feel like you can’t go on. You do. You have fallen down the mountain and you’ve learned which path not to take. You may have quickly made it to the top, but sometimes you have to take a big risk to get the big reward. This is truly something that gives you a setback that you can and will recover from.

The second type of failure is failing often. You take little risks that if they don’t work out will only knock you back a bit. This is the failure I prefer. My livelihood would suck if I failed big – but I’m at the point I don’t need to take a big risk. I can save the big risks now for side projects that I need to start working on again. Once I fail at something I put it behind me and don’t worry about it. I iterate it to the next attempt at something else. Failing is how you learn your limits. If you are not failing at all , you are not trying at all.

I’m a very laid-back guy for the most part. When I was twenty I heard something that would never change my life and I would do my best to live by:

There are two things to worry about:

• Things you can do nothing about
• Things you can do something about

For the things you can do nothing about, accept it and realize no matter what you put into it – you can do nothing about it, so stop worrying about it.

For the things you can do something about – do what needs to get done as quickly as possible, once it is done you can stop worrying about it.

So fail often or fail big – your life is too short to worry or fear failing.