Career advice for my younger self

First off, let me be clear here.  I’m not some big shot super-successful business guru that you should model your life on.  These are rules that I’ve learned or made for myself over the last decade or so, often from bitter failure.  If I had the opportunity to go back in time and give 20 year old me career advice it would be a long conversation, but these points would form the core of it.    So do yourself a favor and learn from my mistakes!  Or don’t, I’m not your supervisor after all.

not my supervisor
1.  Kick ass. 
“Good Enough” is never good enough.  Whether you’re a student, a wage slave stuck in some retail hellhole, or a white-color knowledge worker; make sure that when you do something you do it better then anyone else in the room could have.

The only part of this gigantically huge universe that any of us has real control over is ourselves.  I have failed over and over again and expect to continue to do so.  There’s always someone smarter, better looking, who came from a wealthier background or is better at something.  But no matter how many excuses I’ve made there was always something I could have done better, somewhere I could have improved.  Excuses don’t change anything, hard work does.

2.  Look Good.  This is particularly true in the business world but applies everywhere.  When you walk into a room make sure heads turn.

This is true in both the literal and figurative sense.  When I was freelance I used to always wear a Kilt, no one forgot the web developer in a kilt and being memorable was a huge boon for my business.   It also applies to the level of polish you apply to your work.  A great product that looks unimpressive won’t sell as well as a mediocre product that’s pretty – just ask the folks at Apple computers!  Humans are shallow small minded creatures who will happily forget about war, poverty, and the subjugation of their fellow man in the pursuit of shiny objects. As far as I can tell, there’s no way to change that. But if you’re smart, you can use it!  Be shiny, and make sure your work is shiny too.

3. Reinvent Everything.  It’s really easy to get attached to things, habits, and ideas and hold onto them long past their actual usefulness.

As that endlessly repeated Ghandi quote reminds us, changing the world requires changing yourself.  It’s trite, but it’s also true.  Doing so requires being willing to subject yourself, your beliefs, and behavior to intense and regular scrutiny.  Is this habit helping me achieve my goals? Does this way of looking at the world really fit with new information?  What can I do differently to get where I’m trying to go?   This is just about the hardest thing in the world but it’s necessary .  A person who can’t change can’t grow.  That doesn’t mean throwing away your core values and spinning on a dime whenever it’s convenient, it does mean identifying what’s important to you and what values you hold dear and constantly learning and iterating in support of those values.

4. Stay Positive. Life can be hard and unkind.  As far as I can tell, the universe doesn’t give a damn about any of us. So what? Being negative is a great way to end up unemployed, and then the world gets even harder and less kind.  So suck it up and deal!  Very few people care how you feel, they care how you make them feel.* Yes, I realize the irony of framing this in such a negative way, but that doesn’t make it any less true.

The fact is, if I want people to want me around, I need to stay positive.  So when people ask how I am and I’m tired and irritable I tell them “the world is a beautiful place”. Which is true even if it’s not really an answer; and oddly enough it usually makes me feel better.  I have a tendency to see the problems in everything – the flaws in every system. In the past that’s been a liability but some time in the last couple years I realized it’s an asset as long as I can come up with a solution and an actionable plan to implement it. Suddenly instead of being negative I’m a problem solver! That’s a win for me, and my career.  Weaponize your cynicism and wrap it in a smile.

*And on those rare occasions when you find folks who do genuinely give a damn, hold onto those people!

5.   You work for you.  Always remember this – a job is just a job.  The more you can learn and the more connections you can make the better, but don’t expect permanence or security.

The days of lifetime employment are gone.  The odds of any of us getting a job at one company and working up through the ranks over the course of decades is minimal.  Most of us are going to change careers – not just jobs but careers – at least 3 times before retirement.   That means that the only constant in my professional journey is me and it’s fundamentally up to me whether and how I’m going to succeed.  So when I go to interview for a job I’m evaluating my potential employer and team mates as much as they’re evaluating me.  If you see me looking across that desk I’m asking myself what I can learn from you, whether this position will challenge me, how and how much I can grow my skill set. And if I don’t like the answers I’m going to keep moving.

What would you add to this list?