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Why happiness beats money when choosing a tech career

Rob Enderle | July 13, 2015
With a career spanning 40 years, columnist Rob Enderle has some advice to offer and explains why the one with the most toys in the end doesn’t necessarily win.

Over the years I've seen people go from jobs they were really happy at to jobs they absolutely hated and watched them get destroyed. Steve Ballmer at Microsoft (they are a long-time client) was the most painful to watch. For the most part, when I saw him in the late 1990s he seemed pretty happy and full of energy. In the last meeting we had back then I actually thought of him as a friend and I'll never forget the grin on his face when he passed me in his limo smiling and waving after the meeting. That was literally the last time I saw him with a sincere smile. When he became the CEO he just seemed angry all the time. He was driven to be CEO, but he seemed to absolutely hate the job and while he clearly worked his butt off at it, he wasn't successful.  

Eventually I learned I hated filling out forms, really didn't like to have to deal with employee drama (what finally pushed me over the edge was an affair between two of my direct reports), and corporate backstabbing politics. The stuff that really drives me postal is folks who intentionally do stupid things to make someone else look bad. As a manager or executive I had to deal with all of that crap so I got off that path and went in a very different direction.    

Figure out what size and kind of company you want to work for

If you want security and institutionalized upward mobility, you may get that more at a larger firm, if you want a lot of action and job breadth and are willing to tolerate a regular dose of crazy then a smaller firm will be your cup of tea. For me, it was working for firms that tended to value their employees highly because they picked the best and wanted to hold on to them. I couldn't stand working for a firm that treated employees like trash, discarding them regularly to manipulate non-sustainable short-term stock swings. It amazes me how many CEOs have no clue how layoffs actually work.  

In order to get to know a firm read about it, find current and ex-employees to chat to about it, and observe how well it takes care of its executives and employees. From that you can generally form an idea of whether the place is right for you, but only if you've first determined what kind of traits you admire and enjoy in a company.  

Firms tend to vary between polar opposites, on one end you have lots of granularity between highly volatile companies often with relatively clueless executives providing lots of potential for the politically astute sociopath. And on the other end you have firms that are historically well managed, mentor and promote from within where movement is more measured and loyalty is valued highly. I tend to prefer the latter type of company myself, but folks that like a lot of drama and politics would enjoy and likely do better in the former type firm.


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