For instance, I’ve been working at very small startups since around 2007 (after I decided pro photography wasn’t the career for me). And at one point in 2008 I explored working for a more established, profitable and growing technology company. I interviewed with them for the position of Software Architect which would have been a leadership position in the company, reporting directly to the CTO and taking over direction of two product development teams. It would have been an opportunity for me to shape the future of the company and how they used technology to achieve their goals.

The email I just noticed was the offer letter.

I had completely forgotten about this company and the offer they made me, so when I opened the email to take a peek, it really gave me a weird feeling. The kind of feeling that isn’t quite regret for turning it down, but certainly wasn’t the “I’m glad I didn’t accept that” feeling. It was a very good offer, for a position which I would have enjoyed. But when I talked to my boss at the time about it, he didn’t particularly try to dissuade me from accepting, but rather posed an interesting question:

“Is this one of those once-in-a-lifetime opportunities? If so, you should take it. If not, then why change jobs when another similar or better offer could come along in the future?”

I pondered on it for a day, and then turned down the offer.

About 3 months later, the startup I was working for at the time went out of business. I went to work for another startup, and that one too went into hibernation mode late last year. Whereas the company who made me that offer is still going strong. If I had taken the offer, I would probably still be working there. I would have significantly more money in the bank. I would probably be working fewer hours every week. And I would probably own a swank loft in downtown LA.

But I wouldn’t have met many of my current good friends. I wouldn’t have probably been able to spend two months working from Berlin, a trip which introduced me to my girlfriend. I wouldn’t have created a few cool products which are getting used around the world. And I wouldn’t be working with a group of crazy guys right now, trying to disrupt the entire music industry. No way to say whether my life would have been “better”, but it surely would have been much different. It’s interesting looking back.

There are probably a ton more forgotten moments and life events hidden away within my 12,390 sent and 102,189 received messages. I can’t wait for the rest of this email export to finish so I can do some analytics on them.

And there really is no room for running off half-cocked and spending your life savings starting an “ice cream for dogs” business because you love ice cream and you love dogs and someone told you that you could accomplish anything you put your mind to.

I always enjoy reading fiction–also known as 90 percent of all start-up how-to guides and articles. The dreamscapes they paint always seem to I’ve a knack for happy endings.

Follow your dreams.

Turn your passion into profits.

Do what makes you happy.

This is lovey-dovey utopian nonsense. This sort of advice would have you believe that if you simply put your all into something you will be successful. Bottom line: if the start-up idea your passionate about isn’t capable of generating revenue, your passion will bankrupt you

via Why ‘Be Passionate’ Is Awful Advice.

Worth a read, would love to hear what other people think about this.  Seems like it’s the “trophies for everyone!” mentality transferring into expectations of business as the young adults become entrepreneurs.  Everyone thinks they’re going to be the next Facebook or Google…

I can’t remember where I saw this, but the truth of it really struck me.

This is what I have come to recognize as the cause of my current state of discontent.  I have been doing a lot of self-reflection lately, which of course only happens when I have too much time for self-reflection.  My preference is to occupy myself with exciting (read: cutting edge, innovative) projects rather than silly introspection.

Now, it’s true that I have done several things this year with which I’m quite satisfied.  I’ve started making some good friends here in LA as the two-year anniversary of my moving west has come and gone.  We added the Atlanta Braves as yet another flagship Photocore client. I was involved in launching a free career assessment aimed at helping young people understand themselves and find their ideal job (more about that later).  But none of these satisfy my basal thirst for innovation.

I’ve had a handful of ideas germinating for a while, some of which have made it to concept or design phases.  And except for the one idea was pre-empted by Google (damn them!), they are viable business ideas and with enough effort they might be profitable.  But while “profitability” is on my list of positive adjectives for a a crazy idea, “fun”, “interesting” and “innovative” are higher on that list.

I would rather be involved in something unique than something profitable.

The two full-time jobs that I’ve worked since graduation were both companies that I chose for other than monetary reasons.  In the first case, I turned down an offer for a significantly higher salary to work at a promising small company that was doing very cool things in the area of IPTV and social networking.  Then, when I decided to leave that company, I happily took a cut to work with a company who had grand ideas about how to revolutionize their market.  I saw the opportunity to help the company take those great ideas from concept to execution and that really got me excited.

People who are smarter than me probably already are intimately familiar with what motivates them.  For me, I had some sort of mental block on the whole thing.  So I, rather accidently, went another route.

Recently, I took two very different career/personality assessments.

The first was the Lipson-Shiu Corporate Type Test – a spoof on that Myers-Briggs personality test.  After twelve questions it announced that I was ICIG (the Entrepreneur) which is defined as

“A bubbling energetic type often with boundless energy and a short attention span. Has a pattern of getting enthused about a project, starting it up and leaving the rest to others.”

I think it totally pegged me – surprisingly for a test written as a spoof – as a person who likes to start something big and leave the details to someone else while I start on something else.  I could never work at a large company maintaining software.  Running naked from an axe murderer in a room full of cacti would be a preferable fate.  This assessment gets an “A” for accuracy and a gold star in the plays-well-with-others column.

The second assessment I took was the YSN Self-Assessment.  This is a seriously serious assessment build by a crack team of authors, recruiters, scientists and engineers (including me!)  It didn’t tell me anything that I didn’t already know, but it did distill a few things for me that I hadn’t characterized so simply.  Among other things, the assessment measures your “values” which are evidently the things that motivate you to do what you do.  Based on a 30 minute Q&A session on the website, it tells you how your values stack up.  My strongest value? Uniqueness.  Next? Knowledge.  Ok, next? Anti-Structure.  Money is 5th out of 6. And I think that pretty much explains exactly what makes me tick.

Here are a few choice snippets from the premium version of my report:

• Your creativity is not constrained by criticism from others.
• You have a high energy level and work hard at meeting goals.
• You have a knack for creating solutions sometimes more through personal attempts, calculated risks, and creativity than in the book or established procedures.

Yes – I don’t care what other people thing about my ideas or opinions. Yes – when I’m excited about a goal I will hit it with no equivocation.  Yes – I can’t stand doing things by-the-book.  “A” for accuracy here too, and I can’t take any of that credit because I didn’t invent the science, I just automated it.

So how did both of these assessments actually help me?

Well, I can’t honestly say that they helped me in any concrete way, but they did get me thinking in different terms. They confirmed that for the remaining 209 days of this year I need to be working on things that excite me.  It means no more watching a season or two of some TV show over the weekend.  No more busywork. No more laziness. No more sleeping unless absolutely necessary.

Oh, and maybe I’ll write more blog posts too.

UPDATE: It has come to my attention that I may have given the impression that I work for peanuts just so that I can do cool things. That’s not true, I get what I would consider an industry-standard salary for my position.  What I was trying to impart is that there are things more important to me than money when making career and project decisions.  When you have just enough money to live the lifestyle that you desire, then you can really focus on choosing things that make you happy.  I’ve been fortunate enough to have more employement options than some, so I have been able to be picky about what I choose to do.  Money can’t buy you love, and at least in my case, money can’t buy me job satisfaction.