Being your own boss

In addition to the Spanish classes, cooking practice and blog writing, I’ve also been busy experimenting with online commerce and working on a start-up with a few friends.  And wow, it has been a lot of work (both the e-business and the start-up).

As a former corporate employee, I had no concept of what it’s like to be your own boss.  It is much harder than I expected.  You need to be extremely self motivated.  The peer reviews, evaluations, and performance appraisals were all a bit of a pain as an employee but from the outside looking in, I understand more clearly now that they served as very powerful motivational tools for individual performance.  Human beings need structure.  We need roadmaps, goals and guidelines.  We need systems of support and praise.  And even though many self-help books profile entrepreneurs as individuals who thrive on ambiguity, I strongly believe that the most successful entrepreneurs are those who create their own systems of structure.

Being your own boss literally means just that: being a boss to yourself.  This means getting up at a reasonable hour, earning your day’s keep (albeit nonexistent, small or potential) and answering to goals and targets that you’ve thought through and established for the foreseeable future.  It is so not about coffee dates in the mid-afternoon, getting your nails done sometime after that and then doing a few hour’s work here and there.  It is so much harder than that.

This kind of self discipline is tough work.  I’m only starting to get a feel for how to best manage myself.  I have to be my own mentor, advisor, boss, peer, employee.  I have to learn how to ensure that I’m performing at my best.  The most successful managers I’ve had (in my short career) are those who’ve not only pushed hard for successful individual performance, but who’ve also recognized my unique skills and passions and taken advantage of them.  Now it’s up to me to sift through and figure out what I’m best at, how I best work and how to garner the greatest output for my efforts.  This is a mind-bending exercise that takes time, energy and so much patience.

And as so often happens in the minds of writers, marketers, strategists, students or anyone with a deadline, my mind is an expert at finding many paths to distraction.  There are some days when I’ll motor through a task like a machine and other days when it feels like my productive output totaled only an hour’s worth of work (and oh the frustration that days like these bring).  It has all been a process of learning to learn, of learning to work, and learning how best to do both.

The process is long and sloooooow.  Learning about yourself and learning how to be your best self doesn’t happen overnight.  It takes concerted effort, deliberate time and a whole lot of forgiveness.  But here are the few things I’ve learned in the last year of being my own boat’s captain.

Be mindful of your fears
Our fears are a reflection of the things most important to us.  Instead of running from a fear, instead ask why you might be feeling the way you do.  Running away from things most important to us only because we fear facing them is counterproductive and keep us from growing.

Set daily routines

Wake at a decent hour each day.  Allot times for study, work, creative time.  Get on a gym schedule if possible.  Create a routine so that your mind and body know that it’s time to get down to business.


Be mindful of your most productive hours

Part of being your own boss is getting to know your own strengths and weaknesses.  It will help a huge deal if you recognize early how and where you’re most productive.  Do you work best in the mornings?  If so, rise early.  Do you work best with natural light, at a desk, sitting on the couch, in a coffee shop?  Do you need music, silence, ambient noise?  Are you most creative with pen & paper in hand or at your keyboard?  Recognizing your personal quirks can do wonders for your productivity.

Create a personal Board of Directors

Great companies enlist the guidance of a board of directors.  Create a Board of your own.  Garner the support and feedback of trusted friends, family members, old professors, mentors and maybe even relatives/cousins younger than you.  You should be comfortable enough with each member of your board to go to them for personal, professional or business advice.


Learn how to make decisions in ambiguous situations

Sometimes, the more choice we have, the less satisfied we are with whatever path we choose.  Oh, the paradox of choice.  Decision making becomes much easier when you start to look at your choices and your priorities in a silo.  Quit comparing your choices with those of others and start identifying priorities that are most significant to you personally.  Here is a great guide on how to do this.

Forgive yourself

It has taken me a long time to learn that I don’t have to be so perfect all the time.  As a recovering overachiever, I’ve learned to give myself time to discover the things most important to me.  When I traveled around the world last year, I regularly felt guilty for having left a stable job, for cutting ties to all things permanent in my life, for enjoying so much free time during the worst economic recession since the Depression.  I’ve realized that I needed the total distance and change to be able to tap the potential of what lies ahead.

Trust the wisdom of the moment

Surrendering to the moment and trusting in its wisdom is not an easy task.  We’re mostly control freaks, needing to know why, when, how we’ll get to the next big thing.  Sometimes big things will be inspired by the small things.  A chance meeting with a friend of a friend.  A light bulb idea at a coffee shop.  A casual discussion in an elevator.  These moments have the power to reap amazing results if you let them.  Surrender and believe.

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