I keep running around saying “Go Big or Go Home”…. a lot of times appropriate, sometimes maybe not..

It almost sounds like the stupid “YOLO” trend that went around the internet.  YOLO: You only live once.  This mantra was used to justify doing stupid.  Drugs, Party, Lottery, Not Saving for Retirement… a plethora of stupid.

Today, I wanted to talk about risk tolerance, and when is it appropriate to Go Big or Go Home.

What’s the balance between risk and reward?

  • Personal Finances
  • Career
  • Specific Job
  • Technology Choices
  • Marketing
  • etc

I’ve spoken with many colleagues about leaving the ‘saf’e corporate world to go to a startup.  I’ve done it a few times ( new one can be found @ http://perchsecurity.com ).   I get a lot of comments like:

  • “Oh man, I’m so jealous, I wish I could do that..”
  • “Don’t you worry about stability?”
  • “Going without my 401k is blasphemous, there’s no way!”
  • “My job is stable, I’m not interested..”


I get it.  It’s hard to jump into the unknown.  It’s hard to leave a role, or a company that you’ve been with for 10 years (people still do that??).  It always comes down to fear.  Now, I’m not saying if you don’t go to a startup then you’re scared.  I’m saying, if you WANT to go to a startup, if you WANT to try something new, but you’re scared, that’s when there’s a problem.

The majority of jobs in the US are for small companies.  If you find the right company, solving the right problem for the right people, take faith in your ability to problem solve.

For me, I’ve gotten myself into a level of confidence around my employment abilities that I’m not too worried.  If I lose my job,  I’m confident I’ll be able to find a new one.  Heck, THAT role could be even better.   I tend not to be all ‘doom and gloom’, (unless I’m going through a serious case of the “impostor syndrome”  https://en.wikipedia.org/wiki/Impostor_syndrome …. seriously, that’s for REAL), but I’m confident that I have knowledge, skills, experience etc, that will be valuable to another employer.

Because of these traits that I’ve internalized, I can accept a higher level of risk in employment.   Start ups are my jam.  I can work well in any environment, but I find passion building something new. There’s an excitement in a tiny company that’s unrivaled. Think about it.. if you’re at a large mega bank (no insult to mega banks, I may want a consulting gig some day), but if your project is late by a month. Meh, you’ll get yelled at.. You might get a bad review, might lose some of your bonus. That sucks. but , at a startup, if you piss off your biggest (and only?) customer, and they stop ordering. You’re done. The game is over.

Don’t hear that as “I like risk! I’m a glutton for punishment!”. It just shows the level of excitement… because now, imagine you pull an all-nighter, and get the updated code to a customer BARELY in time, and then they double their order. YES! You win! THAT’s the excitement. (True story, I’ll tell you over a beer, because it was fun.. and scary)

Here’s a list of books that are wonderful, and can really help:

This one is my current read.. blowing my mind:

**Referral links at amazon…. gotta buy my starbucks, yo!

And for fun: