I loved your post! I have two comments:

1. I think that the greatest barrier towards following a different path than the default (apart from ignorance) is fear of other people’s judgement/fear of shame. Taking responsibility for your own actions by not following the default route may lead you into failure. In that case you will have no excuse to use for your failure, since it was 100% your own choice and idea. Shame on you to have such bad ideas! How can you be so stupid?

2. I really liked what you said in a comment above above about watching older people to see what you should or should not do now, so that you end up (or not) like them. I think that several people think they do something similar, but they do not actually DO something about it. For example, even though they observe other people that have taken the same route as them and have ended up being unhappy and bored, they believe that this *magically* won’t happen to them! Or at least this is how they delude themselves. So I will quote Einstein -> Insanity: doing the same thing over and over again and expecting different results!

Cheers!

This is great stuff… I wish I had this advice when I graduated, it might have made a difference. But this attitude can be extended throughout your career, especially if you are in the midst of a change.

This is a great addition to some thoughts that Paul Graham has – check out http://paulgraham.com/hiring.html – the ideas there may not be AS relevent today due to the market, but they hightlight a very different way of thinking about making a living.

Thanks for the fantastic comment! I’m thrilled to hear you were able to get some use out of my response to Susan’s questions.

It’s interesting because you bring up a very good point: we all feel overwhelmed when we ask ourselves, “Where do I even start?” Same thing can be said about personal finance. We all want to be rich and get a good financial infrastructure, but most people don’t know where to begin so they just put it off indefinitely. Instead, you have to start small and build up traction along the way. It’s better to start saving $5/week for ten weeks (start small) then it is to try and save $500 in one fell swoop.

Starting small means that, if you fail, you’ll fail small. And you can pick yourself back up again quickly, learn where you went wrong, and then keep going. You can move up the ladder in literally any field if you just start small, realize that you’re in it for the long haul, and keep working on advancing yourself to the next level.

The more I read on blogs about working for yourself, the more excited I become but the more confused I also get. But, your response to Susan about your experiences was very helpful. This is the type of detailed experiential information that seems to be lacking and that I have been desperately searching for in the blogs I’ve read. Who knew it was as simple as:
“You do something small. Literally anything. It could be trying to set up your own ebay store, or spending a day outdoors with your friend’s high-end camera, experimenting with the various settings.”

I have such a variety of interests and skills that I feel like I’m a jack of many trades but master of none. Therefore, I’ve felt I’m not qualified in any of them at least enough to put them to use. Not knowing where to start has been a handicap to me until now. I see now it is not so much the what but just do and see where it takes me! Thanks so much for your insight!

The stuff I’m working on now has happened within the course of a year, but the things that lead up to that work (and enabled my career path) have happened over the course of the last 8 years. The main thing that I think separates me from most people is that I’ll try anything that looks interesting, and then I’ll keep going further down the rabbit hole. You know those random ideas you’ll talk about with your friends, the ones where you’ll all say, “That’s such a great idea, we should do that.” Well, I actually DO it when I feel strongly enough that it’s a good idea. And I don’t quit after two days — I see it through or quit when I realize the idea is fundamentally flawed (this used to happen to me all the time, but I’ve learned from each failure). I honestly think that’s a huge distinguishing trait, because it’s easy to talk about an idea but it’s exhausting to execute. I’ve learned skills, built relationships, and gotten interesting offers just from being curious and trying different things. Curiosity + Execution + Not being afraid to look stupid or fail = Every personal success I’ve had.

So how do you start? You do something small. Literally anything. It could be trying to set up your own ebay store, or spending a day outdoors with your friend’s high-end camera, experimenting with the various settings. People get into comfort zones as they get older, and that’s the problem. They’re mentally stuck because they hinder their own self-growth. And they’re unremarkable because they have no skills to speak of, and never cultivated a passion on the side.

How did I set goals? Well, I actually only had one career goal last year: do work for Tim Ferriss. I set that because I knew it’d be a challenge and would require a decent amount of strategy just to build up enough credibility before I approached him. And while I worked hard towards this goal, other opportunities would arise along the way and I’d jump at ALL of them. Every single door that opened for me, I’d walk through. I had nothing to lose, and could always turn around.

As far as benchmarks go… it’s really hard to say. It sounds horrible, but I just didn’t want to end up like some of my older friends in their late-20′s or early-30′s, who are really talented and awesome people with unfulfilling jobs and unremarkable lives. I paid REALLY close attention to their lifestyles and listened intently when they described how they got there, because I had a rough idea of what I wanted my life to look like within a couple years. And I knew if I emulated what they did, I’d probably end up with similar results. Not good.

I largely ignored what people my age were doing. There’s no point in watching what 22-years old are doing with their lives when you’re 22. It’s more important to end up (or not end up) like certain people who are years ahead of you. They’ve been through the same stuff you are about to go through, so I’d rather learn from their successes and failures. Most people my age (and I’m including myself in this statement) have very little to offer in terms of experience.

Honestly, the thing that’s been different from ALL of my peers regarding my career was my selection process. These were my requirements for people I’d work with:

— They were entrepreneurs.
— Their lifestyle, or parts of it, were things I wanted to have one day.
— They were smarter than me in some way, and it was clear that I could learn a lot from them.
— They were underrated.

That’s it. Most people will work for anyone that gives them a decent paycheck, but that can lead to a dead-end job that zombifies your brain. I sought out employers like a trader looks for stocks: I searched for people who I thought were undervalued that were also doing great things that interested me. Even though some of the people I work for have had a lot of success, I still feel that all of them are on the upswing — they have not reached their full potential. And because I had skills of my own to bring to the table, and had specific goals or things I wanted to learn, they were more willing to take me on.

I LOVE this post, and I’m going to have to whip the gender card out on you.

I’m three years older than you, and most of my female friends who are my age or older are STILL trying to duck under the cover of grad school, ‘safety’ jobs where they stare (hatefully) at foundation donor spreadsheets while simultaneously checking Facebook, or dreams of a beach vacation.

The question for them, I think, is this:
How do I start?

You set goals.
-How did you set goals?
-How did you know where / how to benchmark yourself?
-How did you translate the things you knew about your wishes, talents and own personality into a career vision?

It’s my observation that these exercises are harder for young women than young men, maybe due to ingrained rule-following and attitudes toward risk.

How can you train someone to think like you did? (Reading a blog post is certainly inspirational, but not entirely actionable)

-Susan