As an entrepreneur for the past 12 years, I haven't collected a paycheck from any employer other than a company I own.  In theory this sounds great, but there are few things in life that apply more pressure than being responsible for not only your paycheck, but the paychecks of employees.  Most of these companies have done well, but some haven't.  It's also quite taboo to talk openly about the emotional and mental stress that startups create, but privately almost every CEO I've spent time with has shared similar feelings with me.  When Sebastian and I discussed posting on each other's blogs, I figured this was a great opportunity to open up about what it's like to be the CEO of a technology startup along with several previous companies, and specifically to discuss the self discipline that's required to successfully navigate the stresses of startups, because these same lessons apply in anyone's daily life.  As you can tell by the title, I liken it to having the self discipline of a Buddhist monk.

But first, some background:  When I was 22, I graduated from college with an offer from General Electric to work in their Technical Leadership Program.  It was a sweet offer -- a fast-track to management role where a select set of college graduates were rotated through various parts of the company.  It gave me the opportunity to work in Latin America.  I was sent to GE's Crotonville leadership campus, where I'd see Jack Welch, GE's CEO at the time, fly in and out on his helicopter, and senior GE executives would train us in leadership seminars.  It was like being a golden child, a chosen one.  We knew that we were being groomed to be the next generation of leaders at GE, and GE did everything it could to foster that confidence in us.  

This leadership program was just two years long.  It was going very well, but something was nagging at me:  Growing up, I had to be very entrepreneurial out of necessity.  I had to pay for college myself. I'd always been very independent and self sufficient.  Suddenly, I was part of a huge machine.  Although I was being treated very well, I felt that I wasn't being true to myself and my entrepreneurial spirit.  I knew that I could do more, and that if I didn't quit then, I would get sucked into the trappings of corporate life.  So I quit GE six months before I was supposed to graduate from the leadership program.  It was 1999 and the tech bubble was going in full swing.  I felt that staying even six more months would be too long.

Going from GE's leadership program to a startup company is a bit like going from the comfy cigar chair at country club to washing dishes in the back.  It's a jarring experience, but one that I was thirsty for.  I soaked it up, and quickly learned my first lesson in startups:  If you're not really, really passionate about what you're doing, then don't do it.  Although being an entrepreneur is romanticized in popular culture, the road is so long, and the pain is so great, that unless you're really passionate about it, you'll be crushed by the pressure.

Passion for what you're doing in life applies beyond startups.  It's easy for any of us to become trapped in the constructs we create.  We feel like we have responsibilities to those around us to be risk averse.  Maybe you have a mortgage.  Or kids in school.  Or a spouse depending on your income.  But I'm here to tell you that you are not trapped by your environment.  You are never a victim of your circumstances, and you have not only a right, but a responsibility to live your life in a way that inspires passion inside of you.  Those around you will benefit far more from that passion than from your fear of pursuing it, and they will be inspired themselves to seek out the things that they are passionate about.  You only live once.  No, seriously, you only live once.  If you're not doing something today that you're passionate about, then quit.  Take that scary plunge into the unknown.  You will be so happy that you did.  It won't be easy at first, but it well be better immediately.  

My next lesson from the startup world is about juggling priorities.  A startup is basically a black hole that wants to completely pwn you.  Think about it like this:  You're trying to accomplish something that's never been done before in the history of humankind.  People around you think you're crazy, because if they didn't, they'd be doing it themselves already.  You have to somehow get a group of people to understand your vision, then believe in it, and then get them to all work towards a singular goal to achieve it.  But that goal has never been defined by anyone before, and it's not entirely clear if it's the right goal to be aiming for.  The chances are astronomically high that you'll fail and you have to shield all of that risk from your employees so they can focus on making the small chance that you won't fail a reality.  Add in the friction that humans create and you'll start to understand how there's never enough time to execute on all the things that need to be done.  Oh, and that's just the startup.  If you have a significant other, or a family, or other obligations, you'd better hope they are all incredibly understanding, because if left unchecked, you won't be seeing much of them.  And I don't just mean once in a while.  I mean all the time.  For years.  But that's not all.  Since this startup is what you're so passionate about, it's all you'll think about.  You'll think about the startup's problems in the shower in the morning.  While you're headed into work.  You'll be thinking about some vexing work issue that's been nagging at you when you're sitting across from your wife at the only romantic dinner you've been able to get away for in three months.  You'll leave all the lights on when you leave the house because your mind will be focused on the startup.  You'll run red lights, you'll function on very little sleep, then you'll miss a 7am call because you overslept.  Not just once in a while, but all the time.  For years.  A startup is all-consuming.

There is a way to manage all of this, though.  It revolves around relentless prioritization.  And that starts with accepting that you simply will not have time to do everything that's important.  There is no "later."  Later never, ever comes.  Later is when there are a dozen other things vying for your attention.  There is always only "now."  The best way I've found to prioritize around these constraints is with a very specific software development methodology called "scrum".  I wrote an entire blog about scrum, but here are the cliff's notes:  Break everything down into the smallest units of value you can.  Define each unit as either a "feature" or a "chore".  A feature is something that truly adds value to your day.  A chore is something that you just have to get done but does not itself add value.  For example, writing this blog would be a "feature" but the process of actually posting and formatting it would be a "chore".   Then -- and here's the key part -- always prioritize and focus on the most important unit of work at any given point in time.  This sounds so obvious, but here's why it's not:  People often confuse time for priority.  For example, saying "I want to get this done by Friday" is much, much different from saying "right now, I'm going to focus on the most important thing I have to do."  The idea behind scrum is that if you're always focusing on the most important thing, then Friday doesn't matter.  It might get done by Friday, or it might take longer.  But if it's the most important thing, then it's what you should be working on right now, no matter how long it takes.  And the way you keep things from taking too long is by relentlessly breaking them down into smaller and smaller units of work, so you're always producing value (known as "velocity" in the scrum world).  

I even use scrum in my personal life.  In the past year, I've been endeavoring to draw a clear line between my professional and personal life.  I define blocks of time that will be either "work" or "personal" and then I apply a scrum methodology to either.  This means that when I'm not in work mode, I'm still focused on doing whatever is most important right now.  That might be relaxing with friends over drinks.  Just getting into the habit of relentless prioritization-- even when it's to prioritize relaxation or fun-- is a life changer.  

As you can imagine, taking a scrum approach to life requires an enormous amount of self discipline.  I'm not perfect at it.  It's often very tempting to do what you want to be doing instead of what's most important to be doing at any given point in time.  It's especially hard in my personal life.  I love photography, and sometimes I'll want to be learning about the latest HDR trick.  But what's most important at that moment might be connecting with a loved one in my life.  I have to really focus on prioritizing based on my own personal set of values, even if I might be tempted to do something else in that moment.  Think of the self discipline of a Buddhist monk practicing monastic silence for years next time you're tempted to stray from prioritizing successfully.

I have a number of other thoughts on being an entrepreneur that I've written about in previous posts, including my zeal for efficiency and how to build a strong personal brand (important in this digital age).  I also invite anyone who's currently an entrepreneur, or aspires to be one, to join the conversation in the community section of my blog.

The last thing I'll mention is how meaningful it is to enjoy yourself and those around you.  That's one reason I love Sebastian's and Tynan's blogs.  They both share this ridiculously awe inspired view of the world and how magical a place it is.  They're both focused on what they're passionate about and that's why they enjoy life so much.  

It's been a pleasure to guest post.  If you have questions, thoughts or experiences to share, I'd love to hear about them in the comments section below.