Self-direction: the importance and challenges

Yesterday marked one month since my last day working at GE and beginning the next chapter of my life.  I’ve spent a lot of time reflecting on how this entrepreneurial lifestyle is different from a corporate job – in this post I will share my first important discovery.

It is absolutely imperative to be self-directed.  Of course corporate jobs offer a degree of autonomy, but you have a manager.  You have defined goals.  You have an office where you’re expected to work.  And you receive a regular paycheck in exchange for your work.  The same holds true in college (and all of education).  You have instructors, grades, examinations, assessments, and class sessions.  The “system” provides a structure which exists to keep you on track.

As an entrepreneur, you have none of these things for the most part.  I no longer have a specific place I have to go each day.  I don’t have a regular paycheck – I make money incrementally as I complete work.  To hold me accountable, I have only myself and my own systems and structure.  This level of flexibility and autonomy is one of the core reasons I wanted to start this journey – but that doesn’t mean it’s easy.

It’s very enticing to feel like I’m on summer vacation right now.  Stay up until 4am watching Netflix and wake up at 11am?  Sure!  Catch up with an old friend for 3 hours in the middle of the afternoon?  Why not?  It has only been a month, so I’m still in the process of figuring out how to avoid these pitfalls and remain productive and efficient.  Of course, I haven’t squandered away the last month: I’ve definitely worked hard and accomplished many of my goals.  But I’ve also fallen into the trap of enjoying my new flexible lifestyle too much and spent some of my time inefficiently.

In the process, I’ve picked up a few strategies which seem to be working well for me.  This is a journey and I’m still learning more each week, but here’s what I’ve gathered so far:

  • Set daily goals and deliver on them.  I’m acting as though I’m my own manager, and I have to meet deadlines and requirements each day just like in a traditional job.  I really enjoyed this post about being more productive – the gist is to determine at the end of each day 6 items you need to complete the next day and to work on only one item at a time.  I think this discipline helps a lot… we’re really not as great at multitasking as we think we are.  I use GQueues to keep track of tasks, always ensuring to assign due dates so I have a convenient view each day of what needs to get done.  (A great alternative is Wunderlist.  Either way, I highly suggest finding a task manager you like and using it!)
  • Ask friends and collaborators to hold me accountable.  I’ll tell the others involved with Ignitus what I intend to do each day so they can point out if I fail to deliver what I promise.  I chat with my dad every day about what we want to get done in the next few days for Harrison Event Center (which we hope to open in early September).  This constant feedback loop is an excellent support system.
  • Keep an intentional schedule.  At first, I simply set daily goals with the intention of accomplishing them “at some point in the day.”  This resulted in procrastination and delaying tasks until the next day.  Now, I establish specific work times, e.g. “5pm-7pm is Ignitus work time, 7pm-10pm is Advantum work.”  I wish I used this strategy more frequently in college!  I put all of this in my Google Calendar, which has been my best friend for several years now.
  • Leverage downtime strategically.  I’m bartending at my dad’s current location in Fairfield 3-4 days per week, and often in the afternoon I have free time during the slower periods of the day.  Rather than spending this time watching TV or playing darts, I opt to bring my laptop and get work done.  Likewise, if I show up early or have an hour between meetings, I’ll knock some easy tasks off my to-do list and stay on top of email rather than catching up on Reddit.  I’ve gotten a lot of work done by fully capitalizing on my downtime.

These are really simple strategies, but I’ve found they’re critical as I’m adjusting to being my own manager.  Please let me know in the comments if you have any other suggestions or observations about how you leverage these same strategies!