A few weeks back at BSidesATL, I sent out a Tweet that kind of summed up my view of things. It was prompted by an email from a fitness company with the subject line “Embrace Discomfort.” Of course they were talking about the pain of whatever fitness regimen you follow. Not me. To me, comfort is uncomfortable.

I guess I have always been this way. Taking risks isn’t risky from where I sit. In fact playing it safe feels dangerous. Of course I don’t take stupid risks and put myself in harm’s way. At least I don’t any more – now I have a family who depends on me. But people ask me how I have the courage to start new businesses and try things. I don’t know – I just do. I couldn’t really play it safe it I tried.
Not that playing it safe is bad. To the contrary, it’s a yin-yang thing. Society needs risk-takers and non-risk-takers. However you see yourself, make sure you understand and accept it, or it will not end well.
For instance some folks dream of being a swashbuckling entrepreneur, jumping into the great unknown with an idea and a credit card to float some expenses. If you are risk-averse that path will be brutal and disappointing. Even if the venture is successful it won’t feel that way because the roller coaster of building a business will be agonizing for someone who craves stability.

Similarly if you put an entrepreneur into a big stable company, they will get into trouble. A lot of trouble. Been there, done that. That’s why it is rare to see true entrepreneurs stay with the huge companies that acquire them, after the retention bonuses are paid and the stock is vested. It’s just soul-crushing for swashbucklers to work in place with subsidized cafeterias and large HR departments.
I joked that it was time to leave META Group back in the mid-90s, when we got big enough that there were people specifically tasked with making my job harder. They called it process and financial controls. I called it bureaucracy and stupid paperwork. It didn’t work for me so I started my own company. With neither a subsidized cafeteria nor an HR department. Just the way I like it.
–Mike
Photo credit: “2012_05_050006 Road to Risk Takers Select Committees” originally uploaded by Gwydion M. Williams
Have you registered for Disaster Recovery Breakfast VII yet? What are you waiting for. Check out the invite and then RSVP to rsvp (at) securosis.com, so we know how much food to get…
The fine folks at the RSA Conference posted the talk Jennifer Minella and I did on mindfulness at the 2014 conference. You can check it out on YouTube. Take an hour and check it out. Your emails, alerts and Twitter timeline will be there when you get back.
Have you checked out our new video podcast? Rich, Adrian, and Mike get into a Google Hangout and.. hang out. We talk a bit about security as well. We try to keep these to 15 minutes or less, and usually fail.
We are back at work on a variety of blog series, so here is a list of the research currently underway. Remember you can get our Heavy Feed via RSS, with our content in all its unabridged glory. And you can get all our research papers too.